ZA200502928B - Novel compounds. - Google Patents

Novel compounds. Download PDF

Info

Publication number: ZA200502928B
Authority: ZA; South Africa
Prior art keywords: substituted; methyl; trifluoroethyl; bis; alkyl
Prior art date: 2002-10-16

Application number

ZA200502928A

Other languages

English (en)

Inventor

Daniel Page

Hua Yang

Christopher Walpole

Original Assignee

Astrazeneca Ab

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-10-16

Filing date

2005-04-11

Publication date

2006-02-22

2005-04-11 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2006-02-22 Publication of ZA200502928B publication Critical patent/ZA200502928B/en

Links

150000001875 compounds Chemical class 0.000 title claims description 134
-1 cyano, acetoxymethyl Chemical group 0.000 claims description 176
125000000217 alkyl group Chemical group 0.000 claims description 83
238000000034 method Methods 0.000 claims description 62
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 55
125000003118 aryl group Chemical group 0.000 claims description 41
229910052736 halogen Inorganic materials 0.000 claims description 36
150000002367 halogens Chemical class 0.000 claims description 36
208000002193 Pain Diseases 0.000 claims description 31
239000000203 mixture Substances 0.000 claims description 28
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
230000036407 pain Effects 0.000 claims description 24
125000004429 atom Chemical group 0.000 claims description 22
229910052799 carbon Inorganic materials 0.000 claims description 20
238000002560 therapeutic procedure Methods 0.000 claims description 20
125000001072 heteroaryl group Chemical group 0.000 claims description 18
239000000126 substance Substances 0.000 claims description 18
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
125000003342 alkenyl group Chemical group 0.000 claims description 13
125000004093 cyano group Chemical group *C#N 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
125000000304 alkynyl group Chemical group 0.000 claims description 12
239000003814 drug Substances 0.000 claims description 12
125000001309 chloro group Chemical group Cl* 0.000 claims description 11
229910052731 fluorine Inorganic materials 0.000 claims description 11
125000006575 electron-withdrawing group Chemical group 0.000 claims description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
241001465754 Metazoa Species 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
239000011737 fluorine Substances 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
125000003107 substituted aryl group Chemical group 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 8
208000024827 Alzheimer disease Diseases 0.000 claims description 7
208000023105 Huntington disease Diseases 0.000 claims description 7
208000018737 Parkinson disease Diseases 0.000 claims description 7
125000000732 arylene group Chemical group 0.000 claims description 7
201000010099 disease Diseases 0.000 claims description 7
125000005549 heteroarylene group Chemical group 0.000 claims description 7
201000006417 multiple sclerosis Diseases 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 6
206010028980 Neoplasm Diseases 0.000 claims description 5
206010052779 Transplant rejections Diseases 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 3
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
AGROOURTVBEEML-IBGZPJMESA-N 2-[(4-ethoxyphenyl)methyl]-1-[[(2s)-pyrrolidin-2-yl]methyl]-n,n-bis(2,2,2-trifluoroethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(OCC)=CC=C1CC1=NC2=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C2N1C[C@H]1NCCC1 AGROOURTVBEEML-IBGZPJMESA-N 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
125000006224 2-tetrahydrofuranylmethyl group Chemical group [H]C([H])(*)C1([H])OC([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
FNLQDVXHDNFXIY-UHFFFAOYSA-N 3h-benzimidazole-5-carboxamide Chemical compound NC(=O)C1=CC=C2NC=NC2=C1 FNLQDVXHDNFXIY-UHFFFAOYSA-N 0.000 claims description 2
DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
ONIOHLBIZBGVBM-UHFFFAOYSA-N 1,2-bis(2,2,2-trifluoroethyl)benzimidazole-5-carboxamide Chemical compound NC(=O)C1=CC=C2N(CC(F)(F)F)C(CC(F)(F)F)=NC2=C1 ONIOHLBIZBGVBM-UHFFFAOYSA-N 0.000 claims 1
KXUMHFGYWDKZSU-UHFFFAOYSA-N 1-(cyclobutylmethyl)-2-[(4-ethoxyphenyl)methyl]-n,n-bis(2,2,2-trifluoroethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(OCC)=CC=C1CC1=NC2=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C2N1CC1CCC1 KXUMHFGYWDKZSU-UHFFFAOYSA-N 0.000 claims 1
NIKRJWCSBDCYRW-UHFFFAOYSA-N 1-(cyclopropylmethyl)-2-[(4-ethoxyphenyl)methyl]-n,n-bis(2,2,2-trifluoroethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(OCC)=CC=C1CC1=NC2=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C2N1CC1CC1 NIKRJWCSBDCYRW-UHFFFAOYSA-N 0.000 claims 1
GLANOPXXGUFGBY-UHFFFAOYSA-N 2-[(4-ethoxyphenyl)methyl]-1-(3-methylbutyl)-n,n-bis(2,2,2-trifluoroethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(OCC)=CC=C1CC1=NC2=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C2N1CCC(C)C GLANOPXXGUFGBY-UHFFFAOYSA-N 0.000 claims 1
ZZDOQQCFPYLFOZ-UHFFFAOYSA-N 2-[(4-ethoxyphenyl)methyl]-1-(furan-2-ylmethyl)-n,n-bis(2,2,2-trifluoroethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(OCC)=CC=C1CC1=NC2=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C2N1CC1=CC=CO1 ZZDOQQCFPYLFOZ-UHFFFAOYSA-N 0.000 claims 1
ZSWLGGNYIPGHJN-UHFFFAOYSA-N 2-[(4-ethoxyphenyl)methyl]-1-(oxan-2-ylmethyl)-n,n-bis(2,2,2-trifluoroethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(OCC)=CC=C1CC1=NC2=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C2N1CC1OCCCC1 ZSWLGGNYIPGHJN-UHFFFAOYSA-N 0.000 claims 1
DYAGQKIGXLRUMA-UHFFFAOYSA-N 2-[(4-ethoxyphenyl)methyl]-1-(oxan-4-ylmethyl)-n,n-bis(2,2,2-trifluoroethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(OCC)=CC=C1CC1=NC2=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C2N1CC1CCOCC1 DYAGQKIGXLRUMA-UHFFFAOYSA-N 0.000 claims 1
NGQVVOCBTFNYFP-HXUWFJFHSA-N 2-[(4-ethoxyphenyl)methyl]-1-[[(2r)-piperidin-2-yl]methyl]-n,n-bis(2,2,2-trifluoroethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(OCC)=CC=C1CC1=NC2=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C2N1C[C@@H]1NCCCC1 NGQVVOCBTFNYFP-HXUWFJFHSA-N 0.000 claims 1
NGQVVOCBTFNYFP-FQEVSTJZSA-N 2-[(4-ethoxyphenyl)methyl]-1-[[(2s)-piperidin-2-yl]methyl]-n,n-bis(2,2,2-trifluoroethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(OCC)=CC=C1CC1=NC2=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C2N1C[C@H]1NCCCC1 NGQVVOCBTFNYFP-FQEVSTJZSA-N 0.000 claims 1
ASRUWUVTMPICIQ-UHFFFAOYSA-N 2-[(5-ethoxypyridin-2-yl)methyl]-1-(3-methylbutyl)-n,n-bis(2,2,2-trifluoroethyl)benzimidazole-5-carboxamide Chemical compound N1=CC(OCC)=CC=C1CC1=NC2=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C2N1CCC(C)C ASRUWUVTMPICIQ-UHFFFAOYSA-N 0.000 claims 1
XCXIDUYEGMTXAC-UHFFFAOYSA-N 2-[(5-ethoxypyridin-2-yl)methyl]-1-(oxan-4-ylmethyl)-n,n-bis(2,2,2-trifluoroethyl)benzimidazole-5-carboxamide Chemical compound N1=CC(OCC)=CC=C1CC1=NC2=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C2N1CC1CCOCC1 XCXIDUYEGMTXAC-UHFFFAOYSA-N 0.000 claims 1
KSMDOAOQYUCUEZ-UHFFFAOYSA-N 2-[(5-ethoxypyridin-2-yl)methyl]-1-(thiophen-3-ylmethyl)-n,n-bis(2,2,2-trifluoroethyl)benzimidazole-5-carboxamide Chemical compound N1=CC(OCC)=CC=C1CC1=NC2=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C2N1CC1=CSC=C1 KSMDOAOQYUCUEZ-UHFFFAOYSA-N 0.000 claims 1
PNYLMORCPFAPGI-UHFFFAOYSA-N 2-[1-(4-ethoxyphenyl)ethyl]-1-(pyridin-4-ylmethyl)-n,n-bis(2,2,2-trifluoroethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(OCC)=CC=C1C(C)C1=NC2=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C2N1CC1=CC=NC=C1 PNYLMORCPFAPGI-UHFFFAOYSA-N 0.000 claims 1
125000002877 alkyl aryl group Chemical group 0.000 claims 1
208000035475 disorder Diseases 0.000 claims 1
JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 claims 1
ROWMQJJMCWDJDT-UHFFFAOYSA-N tribromomethane Chemical compound Br[C](Br)Br ROWMQJJMCWDJDT-UHFFFAOYSA-N 0.000 claims 1
239000000543 intermediate Substances 0.000 description 77
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
102000005962 receptors Human genes 0.000 description 45
108020003175 receptors Proteins 0.000 description 45
239000000047 product Substances 0.000 description 41
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
125000000623 heterocyclic group Chemical group 0.000 description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
235000019439 ethyl acetate Nutrition 0.000 description 30
239000000243 solution Substances 0.000 description 30
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 19
238000003818 flash chromatography Methods 0.000 description 19
239000000741 silica gel Substances 0.000 description 19
229910002027 silica gel Inorganic materials 0.000 description 19
239000003480 eluent Substances 0.000 description 18
238000004007 reversed phase HPLC Methods 0.000 description 18
239000002904 solvent Substances 0.000 description 18
ABUBCIQFGIBKHX-UHFFFAOYSA-N 4-fluoro-3-nitro-n,n-bis(2,2,2-trifluoroethyl)benzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C1F ABUBCIQFGIBKHX-UHFFFAOYSA-N 0.000 description 17
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 16
230000000694 effects Effects 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 15
239000004215 Carbon black (E152) Substances 0.000 description 14
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
229930195733 hydrocarbon Natural products 0.000 description 14
239000003446 ligand Substances 0.000 description 14
229910052760 oxygen Inorganic materials 0.000 description 14
239000000018 receptor agonist Substances 0.000 description 14
229940044601 receptor agonist Drugs 0.000 description 14
DOJYHQGYPJKSPT-UHFFFAOYSA-N 2-(4-ethoxyphenyl)acetyl chloride Chemical compound CCOC1=CC=C(CC(Cl)=O)C=C1 DOJYHQGYPJKSPT-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 12
239000012267 brine Substances 0.000 description 12
125000004432 carbon atom Chemical group C* 0.000 description 12
229920006395 saturated elastomer Polymers 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
150000003254 radicals Chemical class 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000000556 agonist Substances 0.000 description 10
150000001721 carbon Chemical class 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
125000006413 ring segment Chemical group 0.000 description 8
239000011734 sodium Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
239000007821 HATU Substances 0.000 description 7
229910052717 sulfur Inorganic materials 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
125000003636 chemical group Chemical group 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000005557 antagonist Substances 0.000 description 5
230000027455 binding Effects 0.000 description 5
239000011575 calcium Substances 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
210000003169 central nervous system Anatomy 0.000 description 5
125000005842 heteroatom Chemical group 0.000 description 5
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 4
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 4
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
208000005298 acute pain Diseases 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
231100000673 dose–response relationship Toxicity 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
125000004585 polycyclic heterocycle group Chemical group 0.000 description 4
239000007787 solid Substances 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
JTAORGBESRGYTR-UHFFFAOYSA-N 2-(5-ethoxypyridin-2-yl)acetic acid Chemical compound CCOC1=CC=C(CC(O)=O)N=C1 JTAORGBESRGYTR-UHFFFAOYSA-N 0.000 description 3
208000008035 Back Pain Diseases 0.000 description 3
206010058019 Cancer Pain Diseases 0.000 description 3
208000000094 Chronic Pain Diseases 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000007983 Tris buffer Substances 0.000 description 3
238000003556 assay Methods 0.000 description 3
XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229930003827 cannabinoid Natural products 0.000 description 3
239000003557 cannabinoid Substances 0.000 description 3
239000002775 capsule Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000010494 dissociation reaction Methods 0.000 description 3
230000005593 dissociations Effects 0.000 description 3
230000004927 fusion Effects 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000012528 membrane Substances 0.000 description 3
208000004296 neuralgia Diseases 0.000 description 3
208000021722 neuropathic pain Diseases 0.000 description 3
230000002093 peripheral effect Effects 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
230000002285 radioactive effect Effects 0.000 description 3
239000012453 solvate Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
208000009935 visceral pain Diseases 0.000 description 3
125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 2
125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 2
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 2
125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 2
125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 2
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 2
125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 2
125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 2
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
VMUXSMXIQBNMGZ-UHFFFAOYSA-N 3,4-dihydrocoumarin Chemical compound C1=CC=C2OC(=O)CCC2=C1 VMUXSMXIQBNMGZ-UHFFFAOYSA-N 0.000 description 2
GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 2
BQNKEAFVSRZTIS-UHFFFAOYSA-N 4-(furan-3-ylmethylamino)-3-nitro-n,n-bis(2,2,2-trifluoroethyl)benzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C1NCC1=COC=C1 BQNKEAFVSRZTIS-UHFFFAOYSA-N 0.000 description 2
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
208000000884 Airway Obstruction Diseases 0.000 description 2
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
208000011231 Crohn disease Diseases 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
208000032612 Glial tumor Diseases 0.000 description 2
206010018338 Glioma Diseases 0.000 description 2
241000282412 Homo Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
208000004454 Hyperalgesia Diseases 0.000 description 2
206010020751 Hypersensitivity Diseases 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
201000004681 Psoriasis Diseases 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 2
201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
208000026935 allergic disease Diseases 0.000 description 2
230000007815 allergy Effects 0.000 description 2
230000003502 anti-nociceptive effect Effects 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
238000004774 atomic orbital Methods 0.000 description 2
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 description 2
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
239000012148 binding buffer Substances 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
206010006451 bronchitis Diseases 0.000 description 2
201000011510 cancer Diseases 0.000 description 2
229940065144 cannabinoids Drugs 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
230000001684 chronic effect Effects 0.000 description 2
229940110456 cocoa butter Drugs 0.000 description 2
235000019868 cocoa butter Nutrition 0.000 description 2
CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
DMSHWWDRAYHEBS-UHFFFAOYSA-N dihydrocoumarin Natural products C1CC(=O)OC2=C1C=C(OC)C(OC)=C2 DMSHWWDRAYHEBS-UHFFFAOYSA-N 0.000 description 2
238000006073 displacement reaction Methods 0.000 description 2
229960004242 dronabinol Drugs 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000009396 hybridization Methods 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
125000002883 imidazolyl group Chemical group 0.000 description 2
230000002519 immonomodulatory effect Effects 0.000 description 2
238000000099 in vitro assay Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 2
BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
125000001786 isothiazolyl group Chemical group 0.000 description 2
125000000842 isoxazolyl group Chemical group 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
125000006501 nitrophenyl group Chemical group 0.000 description 2
229940127240 opiate Drugs 0.000 description 2
125000002971 oxazolyl group Chemical group 0.000 description 2
RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
125000003373 pyrazinyl group Chemical group 0.000 description 2
125000003226 pyrazolyl group Chemical group 0.000 description 2
125000002098 pyridazinyl group Chemical group 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
125000000168 pyrrolyl group Chemical group 0.000 description 2
LJPZHJUSICYOIX-UHFFFAOYSA-N quinolizidine Chemical compound C1CCCC2CCCCN21 LJPZHJUSICYOIX-UHFFFAOYSA-N 0.000 description 2
230000002441 reversible effect Effects 0.000 description 2
206010039073 rheumatoid arthritis Diseases 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
LPQZERIRKRYGGM-UHFFFAOYSA-N tert-butyl pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1 LPQZERIRKRYGGM-UHFFFAOYSA-N 0.000 description 2
125000003831 tetrazolyl group Chemical group 0.000 description 2
125000000335 thiazolyl group Chemical group 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
125000005500 uronium group Chemical group 0.000 description 2
239000011534 wash buffer Substances 0.000 description 2
239000011701 zinc Substances 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
AVGHIQUXSVAJBC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.1]heptane Chemical compound C1C2CCN1NC2 AVGHIQUXSVAJBC-UHFFFAOYSA-N 0.000 description 1
FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 description 1
CZLMRJZAHXYRIX-UHFFFAOYSA-N 1,3-dioxepane Chemical compound C1CCOCOC1 CZLMRJZAHXYRIX-UHFFFAOYSA-N 0.000 description 1
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
125000005877 1,4-benzodioxanyl group Chemical group 0.000 description 1
FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
AAQTWLBJPNLKHT-UHFFFAOYSA-N 1H-perimidine Chemical compound N1C=NC2=CC=CC3=CC=CC1=C32 AAQTWLBJPNLKHT-UHFFFAOYSA-N 0.000 description 1
YHCUZRJTNSWYCY-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1h-azepine Chemical compound C1CNCC=CC1 YHCUZRJTNSWYCY-UHFFFAOYSA-N 0.000 description 1
OZIJESHLNXSUNE-UHFFFAOYSA-N 2,3-dihydrofuran;thiolane 1,1-dioxide Chemical compound C1CC=CO1.O=S1(=O)CCCC1 OZIJESHLNXSUNE-UHFFFAOYSA-N 0.000 description 1
VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
GSUPYHWEFVSXBA-UHFFFAOYSA-N 2,5-dihydrofuran;oxolane Chemical compound C1CCOC1.C1OCC=C1 GSUPYHWEFVSXBA-UHFFFAOYSA-N 0.000 description 1
JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
XFODSSNTSYDZSH-UHFFFAOYSA-N 2-(5-ethoxypyridin-2-yl)acetic acid;hydrochloride Chemical compound Cl.CCOC1=CC=C(CC(O)=O)N=C1 XFODSSNTSYDZSH-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
GJKIQEHDDXDBLW-UHFFFAOYSA-N 3-amino-4-(3-methylbutylamino)-n,n-bis(2,2,2-trifluoroethyl)benzamide Chemical compound CC(C)CCNC1=CC=C(C(=O)N(CC(F)(F)F)CC(F)(F)F)C=C1N GJKIQEHDDXDBLW-UHFFFAOYSA-N 0.000 description 1
BDACNNIDQIXILN-UHFFFAOYSA-N 3-nitro-4-(oxan-4-ylmethylamino)-n,n-bis(2,2,2-trifluoroethyl)benzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C1NCC1CCOCC1 BDACNNIDQIXILN-UHFFFAOYSA-N 0.000 description 1
BMKNZQPMGFZZLW-UHFFFAOYSA-N 3-nitro-4-(thiophen-3-ylmethylamino)-n,n-bis(2,2,2-trifluoroethyl)benzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C1NCC1=CSC=C1 BMKNZQPMGFZZLW-UHFFFAOYSA-N 0.000 description 1
YXXMDOIUOWUKIU-NSHDSACASA-N 3-nitro-4-[[(2s)-oxolan-2-yl]methylamino]-n,n-bis(2,2,2-trifluoroethyl)benzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C1NC[C@H]1OCCC1 YXXMDOIUOWUKIU-NSHDSACASA-N 0.000 description 1
FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 description 1
BAKUAUDFCNFLBX-UHFFFAOYSA-N 4,7-dihydro-1,3-dioxepine Chemical compound C1OCC=CCO1 BAKUAUDFCNFLBX-UHFFFAOYSA-N 0.000 description 1
HRMSWLBWFXPBQW-UHFFFAOYSA-N 4-(3-methylbutylamino)-3-nitro-n,n-bis(2,2,2-trifluoroethyl)benzamide Chemical compound CC(C)CCNC1=CC=C(C(=O)N(CC(F)(F)F)CC(F)(F)F)C=C1[N+]([O-])=O HRMSWLBWFXPBQW-UHFFFAOYSA-N 0.000 description 1
PYGDBYLZTJJMSC-UHFFFAOYSA-N 4-(cyclobutylmethylamino)-3-nitro-n,n-bis(2,2,2-trifluoroethyl)benzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C1NCC1CCC1 PYGDBYLZTJJMSC-UHFFFAOYSA-N 0.000 description 1
PACKAMUWVSIGFT-UHFFFAOYSA-N 4-(cyclohexylmethylamino)-3-nitro-n,n-bis(2,2,2-trifluoroethyl)benzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C1NCC1CCCCC1 PACKAMUWVSIGFT-UHFFFAOYSA-N 0.000 description 1
ZDKRHIOBLDKCJQ-UHFFFAOYSA-N 4-(cyclopropylmethylamino)-3-nitro-n,n-bis(2,2,2-trifluoroethyl)benzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)N(CC(F)(F)F)CC(F)(F)F)=CC=C1NCC1CC1 ZDKRHIOBLDKCJQ-UHFFFAOYSA-N 0.000 description 1
BOJWTAQWPVBIPG-UHFFFAOYSA-N 4-fluoro-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C([N+]([O-])=O)=C1 BOJWTAQWPVBIPG-UHFFFAOYSA-N 0.000 description 1
YPWFNLSXQIGJCK-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1O2 YPWFNLSXQIGJCK-UHFFFAOYSA-N 0.000 description 1
125000005941 7-oxabicyclo[2.2.1]heptyl group Chemical group 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
206010006187 Breast cancer Diseases 0.000 description 1
208000026310 Breast neoplasm Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
102000009135 CB2 Cannabinoid Receptor Human genes 0.000 description 1
108010073376 CB2 Cannabinoid Receptor Proteins 0.000 description 1
125000006414 CCl Chemical group ClC* 0.000 description 1
208000031968 Cadaver Diseases 0.000 description 1
102000018208 Cannabinoid Receptor Human genes 0.000 description 1
108050007331 Cannabinoid receptor Proteins 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
208000017667 Chronic Disease Diseases 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
206010012335 Dependence Diseases 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
108010084680 Heterogeneous-Nuclear Ribonucleoprotein K Proteins 0.000 description 1
101000831942 Homo sapiens Stomatin-like protein 3 Proteins 0.000 description 1
101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
208000035154 Hyperesthesia Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
206010065390 Inflammatory pain Diseases 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
108010052285 Membrane Proteins Proteins 0.000 description 1
102000018697 Membrane Proteins Human genes 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
102100023482 Mitogen-activated protein kinase 14 Human genes 0.000 description 1
XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
108010025020 Nerve Growth Factor Proteins 0.000 description 1
102000015336 Nerve Growth Factor Human genes 0.000 description 1
208000028389 Nerve injury Diseases 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920002873 Polyethylenimine Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000023146 Pre-existing disease Diseases 0.000 description 1
206010060862 Prostate cancer Diseases 0.000 description 1
208000000236 Prostatic Neoplasms Diseases 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
102100029645 UBX domain-containing protein 11 Human genes 0.000 description 1
240000003864 Ulex europaeus Species 0.000 description 1
YNOGYQAEJGADFJ-RXMQYKEDSA-N [(2r)-oxolan-2-yl]methanamine Chemical compound NC[C@H]1CCCO1 YNOGYQAEJGADFJ-RXMQYKEDSA-N 0.000 description 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000005336 allyloxy group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000036592 analgesia Effects 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
238000010171 animal model Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000001028 anti-proliverative effect Effects 0.000 description 1
230000006907 apoptotic process Effects 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
125000002393 azetidinyl group Chemical group 0.000 description 1
125000004069 aziridinyl group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
239000012964 benzotriazole Substances 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000012925 biological evaluation Methods 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
150000001669 calcium Chemical class 0.000 description 1
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
125000004623 carbolinyl group Chemical group 0.000 description 1
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 1
125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
239000003086 colorant Substances 0.000 description 1
125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000392 cycloalkenyl group Chemical group 0.000 description 1
UBLYEVLMRSPMOG-UHFFFAOYSA-N cyclopentylmethanamine Chemical compound NCC1CCCC1 UBLYEVLMRSPMOG-UHFFFAOYSA-N 0.000 description 1
IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 1
230000007850 degeneration Effects 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000000532 dioxanyl group Chemical group 0.000 description 1
125000005879 dioxolanyl group Chemical group 0.000 description 1
238000009826 distribution Methods 0.000 description 1
230000004064 dysfunction Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
XNABHFLZYMCJHE-UHFFFAOYSA-N furan-3-ylmethanamine Chemical compound NCC=1C=COC=1 XNABHFLZYMCJHE-UHFFFAOYSA-N 0.000 description 1
JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
125000003838 furazanyl group Chemical group 0.000 description 1
DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000004404 heteroalkyl group Chemical group 0.000 description 1
125000005553 heteroaryloxy group Chemical group 0.000 description 1
125000006588 heterocycloalkylene group Chemical group 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
210000003630 histaminocyte Anatomy 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
230000005931 immune cell recruitment Effects 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
210000004969 inflammatory cell Anatomy 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229940125425 inverse agonist Drugs 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 description 1
125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 description 1
GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000002540 macrophage Anatomy 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
229960003194 meglumine Drugs 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
230000008764 nerve damage Effects 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
IPBPLHNLRKRLPJ-UHFFFAOYSA-N oxan-4-ylmethanamine Chemical compound NCC1CCOCC1 IPBPLHNLRKRLPJ-UHFFFAOYSA-N 0.000 description 1
FQROAMAHRSNCHM-UHFFFAOYSA-N oxane;hydrochloride Chemical compound Cl.C1CCOCC1 FQROAMAHRSNCHM-UHFFFAOYSA-N 0.000 description 1
UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 description 1
AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
125000003566 oxetanyl group Chemical group 0.000 description 1
125000005646 oximino group Chemical group 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000004031 partial agonist Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
229950000688 phenothiazine Drugs 0.000 description 1
125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 1
125000005954 phenoxathiinyl group Chemical group 0.000 description 1
125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000009117 preventive therapy Methods 0.000 description 1
ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
238000005956 quaternization reaction Methods 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
238000011552 rat model Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000004044 response Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
SREOWIJUADGCQP-SECBINFHSA-N tert-butyl (2r)-2-(methylamino)piperidine-1-carboxylate Chemical compound CN[C@H]1CCCCN1C(=O)OC(C)(C)C SREOWIJUADGCQP-SECBINFHSA-N 0.000 description 1
ACNKKWLAQZIYGF-CQSZACIVSA-N tert-butyl (2r)-2-[[2-amino-4-[bis(2,2,2-trifluoroethyl)carbamoyl]anilino]methyl]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@@H]1CNC1=CC=C(C(=O)N(CC(F)(F)F)CC(F)(F)F)C=C1N ACNKKWLAQZIYGF-CQSZACIVSA-N 0.000 description 1
GRROEHMIBHYUMU-CQSZACIVSA-N tert-butyl (2r)-2-[[4-[bis(2,2,2-trifluoroethyl)carbamoyl]-2-nitroanilino]methyl]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@@H]1CNC1=CC=C(C(=O)N(CC(F)(F)F)CC(F)(F)F)C=C1[N+]([O-])=O GRROEHMIBHYUMU-CQSZACIVSA-N 0.000 description 1
IRSSIQNSBCQILH-UHFFFAOYSA-N tert-butyl 3-(aminomethyl)morpholine-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCOCC1CN IRSSIQNSBCQILH-UHFFFAOYSA-N 0.000 description 1
ZSVCOWAIWVDKIJ-UHFFFAOYSA-N tert-butyl 3-[[4-[bis(2,2,2-trifluoroethyl)carbamoyl]-2-nitroanilino]methyl]morpholine-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCOCC1CNC1=CC=C(C(=O)N(CC(F)(F)F)CC(F)(F)F)C=C1[N+]([O-])=O ZSVCOWAIWVDKIJ-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
125000002053 thietanyl group Chemical group 0.000 description 1
VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
125000001730 thiiranyl group Chemical group 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
DUDAKCCDHRNMDJ-UHFFFAOYSA-N thiophen-3-ylmethanamine Chemical compound NCC=1C=CSC=1 DUDAKCCDHRNMDJ-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
230000005760 tumorsuppression Effects 0.000 description 1
125000004417 unsaturated alkyl group Chemical group 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
HQVHOQAKMCMIIM-UHFFFAOYSA-N win 55,212-2 Chemical compound C=12N3C(C)=C(C(=O)C=4C5=CC=CC=C5C=CC=4)C2=CC=CC=1OCC3CN1CCOCC1 HQVHOQAKMCMIIM-UHFFFAOYSA-N 0.000 description 1
125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Immunology (AREA)
Psychology (AREA)
Transplantation (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Hydrogenated Pyridines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

ZA200502928A 2002-10-16 2005-04-11 Novel compounds. ZA200502928B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE0203070A SE0203070D0 (en)	2002-10-16	2002-10-16	Novel compounds

Publications (1)

Publication Number	Publication Date
ZA200502928B true ZA200502928B (en)	2006-02-22

Family

ID=20289294

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200502928A ZA200502928B (en)	2002-10-16	2005-04-11	Novel compounds.

Country Status (20)

Country	Link
US (1)	US7407968B2 (is)
EP (1)	EP1554254A1 (is)
JP (1)	JP2006505568A (is)
KR (1)	KR20050049551A (is)
CN (1)	CN100349874C (is)
AR (1)	AR041626A1 (is)
AU (1)	AU2003269775B2 (is)
BR (1)	BR0315320A (is)
CA (1)	CA2501418A1 (is)
IS (1)	IS7827A (is)
MX (1)	MXPA05003901A (is)
NO (1)	NO20052182L (is)
NZ (1)	NZ539079A (is)
PL (1)	PL376564A1 (is)
RU (1)	RU2323211C2 (is)
SE (1)	SE0203070D0 (is)
TW (1)	TWI285638B (is)
UA (1)	UA81919C2 (is)
WO (1)	WO2004035548A1 (is)
ZA (1)	ZA200502928B (is)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE0101387D0 (sv) *	2001-04-20	2001-04-20	Astrazeneca Ab	Novel compounds
SE0203070D0 (en)	2002-10-16	2002-10-16	Astrazeneca Ab	Novel compounds
SE0301701D0 (sv) *	2003-06-10	2003-06-10	Astrazeneca Ab	Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof
SE0301698D0 (sv) *	2003-06-10	2003-06-10	Astrazeneca Ab	Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof
SE0301699D0 (sv) *	2003-06-10	2003-06-10	Astrazeneca Ab	Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof
DE602005011844D1 (de) *	2004-11-02	2009-01-29	Pfizer	Sulfonylbenzimidazolderivate
WO2007091950A1 (en) *	2006-02-07	2007-08-16	Astrazeneca Ab	Benzimidazoles and imidazopyridines useful in the treatment of diseases or disorders associated with cannabinoid receptor 2 (cb2) such as pain
CN101511796B (zh)	2006-09-05	2012-05-09	协和发酵麒麟株式会社	咪唑衍生物
WO2008032764A1 (fr)	2006-09-13	2008-03-20	Kyowa Hakko Kirin Co., Ltd.	Dérivé hétérocyclique fusionné
JP5485148B2 (ja) *	2007-06-21	2014-05-07	カラセラピューティクスインコーポレイテッド	置換イミダゾ複素環
WO2009025785A2 (en) *	2007-08-21	2009-02-26	Merck & Co., Inc.	Cb2 receptor ligands for the treatment of pain
KR101837759B1 (ko)	2010-02-18	2018-04-26	브이티브이 테라퓨틱스 엘엘씨	치환된 융합 이미다졸 유도체, 약학적 조성물, 및 그것의 사용 방법
US8759535B2 (en)	2010-02-18	2014-06-24	High Point Pharmaceuticals, Llc	Substituted fused imidazole derivatives, pharmaceutical compositions, and methods of use thereof
AU2012284184B2 (en)	2011-07-18	2017-03-09	Merck Patent Gmbh	Benzamides
US10835521B2 (en) *	2012-07-13	2020-11-17	The Cleveland Clinic Foundation	Neuroprotective CB2 receptor agonists
WO2016089648A1 (en)	2014-12-01	2016-06-09	Vtv Therapeutics Llc	Bach 1 inhibitors in combination with nrf2 activators and pharmaceutical compositions thereof
CN111658644B (zh) *	2020-03-31	2021-05-14	中山大学	一种小分子stat3抑制剂wz-2-033及其在制备治疗乳腺癌和胃癌药物中的应用

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2945044A (en) *	1957-07-12	1960-07-12	Ciba Pharm Prod Inc	Certain 1-(diethyl-aminoethyl), 5-amino, 2-benzyl or substituted benzyl, benzimidazoles
FR1481049A (fr) *	1965-11-25	1967-05-19	France Ministre Des Armees	Nouveaux dialkylaminoalkyl-1 p-alkoxyphényl alkyl-2 benzimidazoles 5-substitués
CA2036307C (en)	1990-03-08	2002-07-09	Susan Jean Ward	3-arylcarbonyl-1-aminoalkyl-1h-indole-containing antiglaucoma compositions and method
FR2741621B1 (fr) *	1995-11-23	1998-02-13	Sanofi Sa	Nouveaux derives de pyrazole, procede pour leur preparation et compositions pharmaceutiques en contenant
FR2789079B3 (fr) *	1999-02-01	2001-03-02	Sanofi Synthelabo	Derive d'acide pyrazolecarboxylique, sa preparation, les compositions pharmaceutiques en contenant
AUPR118000A0 (en) *	2000-11-02	2000-11-23	Amrad Operations Pty. Limited	Therapeutic molecules and methods
CA2436133A1 (en) *	2001-01-29	2002-08-08	University Of Connecticut	Receptor selective cannabimimetic aminoalkylindoles
SE0101387D0 (sv) *	2001-04-20	2001-04-20	Astrazeneca Ab	Novel compounds
AU2002347022A1 (en) *	2001-12-20	2003-07-09	Novo Nordisk A/S	Benzimidazols and indols as glucagon receptor antagonists/inverse agonisten
SE0203070D0 (en)	2002-10-16	2002-10-16	Astrazeneca Ab	Novel compounds

2002
- 2002-10-16 SE SE0203070A patent/SE0203070D0/xx unknown
2003
- 2003-10-09 TW TW092128115A patent/TWI285638B/zh not_active IP Right Cessation
- 2003-10-15 CN CNB2003801059214A patent/CN100349874C/zh not_active Expired - Fee Related
- 2003-10-15 AU AU2003269775A patent/AU2003269775B2/en not_active Ceased
- 2003-10-15 PL PL376564A patent/PL376564A1/pl not_active Application Discontinuation
- 2003-10-15 RU RU2005109156/04A patent/RU2323211C2/ru not_active IP Right Cessation
- 2003-10-15 MX MXPA05003901A patent/MXPA05003901A/es not_active Application Discontinuation
- 2003-10-15 JP JP2004545139A patent/JP2006505568A/ja active Pending
- 2003-10-15 US US10/530,499 patent/US7407968B2/en not_active Expired - Fee Related
- 2003-10-15 UA UAA200502658A patent/UA81919C2/uk unknown
- 2003-10-15 AR ARP030103753A patent/AR041626A1/es unknown
- 2003-10-15 WO PCT/SE2003/001604 patent/WO2004035548A1/en active IP Right Grant
- 2003-10-15 CA CA002501418A patent/CA2501418A1/en not_active Abandoned
- 2003-10-15 BR BR0315320-7A patent/BR0315320A/pt not_active IP Right Cessation
- 2003-10-15 EP EP03751705A patent/EP1554254A1/en not_active Withdrawn
- 2003-10-15 KR KR1020057006538A patent/KR20050049551A/ko not_active Application Discontinuation
- 2003-10-15 NZ NZ539079A patent/NZ539079A/en unknown
2005
- 2005-04-11 ZA ZA200502928A patent/ZA200502928B/en unknown
- 2005-04-27 IS IS7827A patent/IS7827A/is unknown
- 2005-05-03 NO NO20052182A patent/NO20052182L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
RU2323211C2 (ru)	2008-04-27
WO2004035548A1 (en)	2004-04-29
US20070105893A1 (en)	2007-05-10
AU2003269775A1 (en)	2004-05-04
JP2006505568A (ja)	2006-02-16
MXPA05003901A (es)	2005-06-22
TW200410944A (en)	2004-07-01
CA2501418A1 (en)	2004-04-29
CN1726194A (zh)	2006-01-25
SE0203070D0 (en)	2002-10-16
TWI285638B (en)	2007-08-21
UA81919C2 (uk)	2008-02-25
KR20050049551A (ko)	2005-05-25
RU2005109156A (ru)	2006-01-20
US7407968B2 (en)	2008-08-05
IS7827A (is)	2005-04-27
AU2003269775B2 (en)	2007-05-03
EP1554254A1 (en)	2005-07-20
BR0315320A (pt)	2005-08-16
NO20052182L (no)	2005-05-03
AR041626A1 (es)	2005-05-26
CN100349874C (zh)	2007-11-21
NZ539079A (en)	2007-11-30
PL376564A1 (pl)	2006-01-09

Publication	Publication Date	Title
US20090111865A1 (en)	2009-04-30	Benzimidazole Derivatives, Compositions Containing Them, Preparation Thereof and Uses Thereof
US7407968B2 (en)	2008-08-05	Compounds
ZA200602446B (en)	2007-09-26	Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof
US7384955B2 (en)	2008-06-10	Azaindole derivatives, preparations thereof, uses thereof and compositions containing them
US20080004288A1 (en)	2008-01-03	Indazole Sulphonamide Derivatives
US7517898B2 (en)	2009-04-14	Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof
US20070072853A1 (en)	2007-03-29	Benzimidazole derivatives compositions containing them, preparation thereof and uses thereof
EP1670790B1 (en)	2008-08-20	Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof
EP1670770B1 (en)	2008-08-20	Benzimidazole derivatives, compositions containing them, preparation therof and uses thereof
US7244850B2 (en)	2007-07-17	Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof
US20070265325A1 (en)	2007-11-15	Nitro Indazole Derivatives