CN106132956A - 一类杂环化合物、其制备方法和用途 - Google Patents
一类杂环化合物、其制备方法和用途 Download PDFInfo
- Publication number
- CN106132956A CN106132956A CN201580008897.5A CN201580008897A CN106132956A CN 106132956 A CN106132956 A CN 106132956A CN 201580008897 A CN201580008897 A CN 201580008897A CN 106132956 A CN106132956 A CN 106132956A
- Authority
- CN
- China
- Prior art keywords
- piperazin
- alkyl
- group
- ethyl
- benzothien
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract 3
- -1 Heterocycle compound Chemical class 0.000 title claims 64
- 150000003839 salts Chemical class 0.000 claims abstract 25
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract 16
- 208000015114 central nervous system disease Diseases 0.000 claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- 239000003814 drug Substances 0.000 claims abstract 2
- 125000003545 alkoxy group Chemical group 0.000 claims 51
- 125000000217 alkyl group Chemical group 0.000 claims 49
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 28
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 25
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 17
- 125000000335 thiazolyl group Chemical group 0.000 claims 17
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 15
- 125000002098 pyridazinyl group Chemical group 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000002541 furyl group Chemical group 0.000 claims 13
- 125000001544 thienyl group Chemical group 0.000 claims 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 125000002971 oxazolyl group Chemical group 0.000 claims 12
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims 12
- 125000001425 triazolyl group Chemical group 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 125000003373 pyrazinyl group Chemical group 0.000 claims 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims 11
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 11
- 125000000168 pyrrolyl group Chemical group 0.000 claims 11
- 125000001589 carboacyl group Chemical group 0.000 claims 10
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 9
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 9
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 8
- 125000001786 isothiazolyl group Chemical group 0.000 claims 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 8
- 238000000034 method Methods 0.000 claims 7
- 125000004193 piperazinyl group Chemical group 0.000 claims 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- 125000003172 aldehyde group Chemical group 0.000 claims 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims 6
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 208000035475 disorder Diseases 0.000 claims 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims 5
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 5
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 5
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 5
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- 208000019022 Mood disease Diseases 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 claims 2
- FPVHORFNDSKMPV-UHFFFAOYSA-N 3-[2-[4-(1-benzothiophen-4-yl)piperazin-1-yl]ethyl]-9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound S1C2=C(C=C1)C(=CC=C2)N1CCN(CC1)CCC1=C(N=C2N(C1=O)CCCC2O)C FPVHORFNDSKMPV-UHFFFAOYSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 125000005256 alkoxyacyl group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 2
- 125000005605 benzo group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 125000005997 bromomethyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 2
- 125000005051 dihydropyrazinyl group Chemical group N1(CC=NC=C1)* 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 208000024714 major depressive disease Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 208000019906 panic disease Diseases 0.000 claims 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 2
- 125000005310 triazolidinyl group Chemical group N1(NNCC1)* 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims 1
- GJTQRHFCZWUPOH-UHFFFAOYSA-N 2-[2-[4-(1-benzothiophen-4-yl)piperazin-1-yl]ethyl]-4H-1,4-benzoxazin-3-one Chemical compound S1C2=C(C=C1)C(=CC=C2)N1CCN(CC1)CCC1C(NC2=C(O1)C=CC=C2)=O GJTQRHFCZWUPOH-UHFFFAOYSA-N 0.000 claims 1
- OHSHVZPWRGUHCW-UHFFFAOYSA-N 2-methyl-3-[2-(4-thieno[2,3-d]pyrimidin-4-ylpiperazin-1-yl)ethyl]-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound CC=1N=C2N(C(C=1CCN1CCN(CC1)C=1C3=C(N=CN=1)SC=C3)=O)CCCC2 OHSHVZPWRGUHCW-UHFFFAOYSA-N 0.000 claims 1
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- GNDSQXWHXQCRHF-UHFFFAOYSA-N 3-[2-[4-(1-benzothiophen-4-yl)piperidin-1-yl]ethyl]-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound S1C2=C(C=C1)C(=CC=C2)C1CCN(CC1)CCC1=C(N=C2N(C1=O)CCCC2)C GNDSQXWHXQCRHF-UHFFFAOYSA-N 0.000 claims 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- LPMALGBKIXQXQN-UHFFFAOYSA-N 5-[3-[4-(6-ethylthieno[2,3-d]pyrimidin-4-yl)piperazin-1-yl]propyl]-3-thiophen-2-yl-1,2,4-oxadiazole Chemical compound N1=CN=C2SC(CC)=CC2=C1N(CC1)CCN1CCCC(ON=1)=NC=1C1=CC=CS1 LPMALGBKIXQXQN-UHFFFAOYSA-N 0.000 claims 1
- XRWBBZODDQFRNH-UHFFFAOYSA-N 6-ethyl-4-[4-(2-thiophen-2-ylethyl)piperazin-1-yl]thieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SC(CC)=CC2=C1N(CC1)CCN1CCC1=CC=CS1 XRWBBZODDQFRNH-UHFFFAOYSA-N 0.000 claims 1
- LSWAIDPZAGTFNI-UHFFFAOYSA-N 9-hydroxy-2-methyl-3-[2-(4-thieno[2,3-c]pyridin-4-ylpiperazin-1-yl)ethyl]-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound OC1CCCN2C1=NC(=C(C2=O)CCN1CCN(CC1)C1=C2C(=CN=C1)SC=C2)C LSWAIDPZAGTFNI-UHFFFAOYSA-N 0.000 claims 1
- BVMHGNCIMARWAI-UHFFFAOYSA-N 9-hydroxy-2-methyl-3-[2-(4-thieno[2,3-d]pyrimidin-4-ylpiperazin-1-yl)ethyl]-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound OC1CCCN2C1=NC(=C(C2=O)CCN1CCN(CC1)C=1C2=C(N=CN=1)SC=C2)C BVMHGNCIMARWAI-UHFFFAOYSA-N 0.000 claims 1
- 208000017194 Affective disease Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 206010003805 Autism Diseases 0.000 claims 1
- 208000020706 Autistic disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- KCGVCOYGVSPQOS-UHFFFAOYSA-N C(C)(=O)N1C=C(C2=CC(=CC=C12)C#N)CCCCN1CCN(CC1)C1=CC=CC=2SC=CC=21 Chemical compound C(C)(=O)N1C=C(C2=CC(=CC=C12)C#N)CCCCN1CCN(CC1)C1=CC=CC=2SC=CC=21 KCGVCOYGVSPQOS-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- MPDQCQJPJRABDG-UHFFFAOYSA-N ClC1=C(C=C2CC(NC2=C1)=O)CCN1CCN(CC1)C1=C2C(=CN=C1)SC=C2 Chemical compound ClC1=C(C=C2CC(NC2=C1)=O)CCN1CCN(CC1)C1=C2C(=CN=C1)SC=C2 MPDQCQJPJRABDG-UHFFFAOYSA-N 0.000 claims 1
- ACOZVIRGPCYPPB-UHFFFAOYSA-N ClC1=C(C=C2CC(NC2=C1)=O)CCN1CCN(CC1)C1=CC=CC=2SCCC=21 Chemical compound ClC1=C(C=C2CC(NC2=C1)=O)CCN1CCN(CC1)C1=CC=CC=2SCCC=21 ACOZVIRGPCYPPB-UHFFFAOYSA-N 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000004356 Hysteria Diseases 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- MFCRSJJVXNJHME-UHFFFAOYSA-N O=C1CCC2CCC(CCN3CCN(CC3)c3cncc4sccc34)CC2N1 Chemical compound O=C1CCC2CCC(CCN3CCN(CC3)c3cncc4sccc34)CC2N1 MFCRSJJVXNJHME-UHFFFAOYSA-N 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- 206010033664 Panic attack Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- KWPJWBPLKDTBKU-UHFFFAOYSA-N S1C=CC2=C1C=CC=C2N1CCN(CC1)CCC1SC2=C(NC1=O)C=CC=C2 Chemical compound S1C=CC2=C1C=CC=C2N1CCN(CC1)CCC1SC2=C(NC1=O)C=CC=C2 KWPJWBPLKDTBKU-UHFFFAOYSA-N 0.000 claims 1
- KBHXMZSGJZPKNI-UHFFFAOYSA-N S1C=CC2=C1C=CC=C2N1CCN(CC1)CCCN1C(CCC2=CC=CC=C12)=O Chemical compound S1C=CC2=C1C=CC=C2N1CCN(CC1)CCCN1C(CCC2=CC=CC=C12)=O KBHXMZSGJZPKNI-UHFFFAOYSA-N 0.000 claims 1
- OJDITGPGUOMRTH-UHFFFAOYSA-N S1C=CC2=C1C=CC=C2N1CCN(CC1)CCN1C(SC2=C1C=CC=C2)=O Chemical compound S1C=CC2=C1C=CC=C2N1CCN(CC1)CCN1C(SC2=C1C=CC=C2)=O OJDITGPGUOMRTH-UHFFFAOYSA-N 0.000 claims 1
- 206010041250 Social phobia Diseases 0.000 claims 1
- 208000031674 Traumatic Acute Stress disease Diseases 0.000 claims 1
- 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 208000026345 acute stress disease Diseases 0.000 claims 1
- 230000003044 adaptive effect Effects 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 238000007112 amidation reaction Methods 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 208000012839 conversion disease Diseases 0.000 claims 1
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims 1
- 125000005048 dihydroisoxazolyl group Chemical group O1N(CC=C1)* 0.000 claims 1
- 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims 1
- 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 claims 1
- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims 1
- 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 claims 1
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims 1
- 125000005058 dihydrotriazolyl group Chemical group N1(NNC=C1)* 0.000 claims 1
- 208000024732 dysthymic disease Diseases 0.000 claims 1
- 201000003104 endogenous depression Diseases 0.000 claims 1
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000013403 hyperactivity Diseases 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 230000036651 mood Effects 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims 1
- 208000016686 tic disease Diseases 0.000 claims 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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Abstract
Description
Claims (14)
- PCT国内申请,权利要求书已公开。
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JP2018502157A (ja) * | 2015-01-12 | 2018-01-25 | レビバ ファーマシューティカルズ,インコーポレイティド | アルツハイマー病の治療方法 |
EP3244896B1 (en) * | 2015-01-12 | 2024-06-12 | Reviva Pharmaceuticals, Inc. | Methods for treating pulmonary hypertension |
EP3150591A1 (en) * | 2015-10-02 | 2017-04-05 | Crystal Pharma S.A.U | Process and intermediates for the preparation of benzo[b]thiophene compounds |
CN105461608B (zh) * | 2015-11-23 | 2017-11-28 | 东南大学 | 二氢吲哚‑2‑酮类d3受体配体及其制备方法和用途 |
US10464931B2 (en) | 2015-12-28 | 2019-11-05 | Honour (R&D) | Process for the preparation of Quinolin-2(1H)-one derivatives |
CN106478548A (zh) * | 2016-07-19 | 2017-03-08 | 贵州大学 | 一种6‑羟基灭草松的制备工艺 |
CN107098855A (zh) * | 2017-04-05 | 2017-08-29 | 上海诺星医药科技有限公司 | 一种制备7‑羟基‑2‑喹啉酮的方法 |
WO2019242717A1 (zh) * | 2018-06-21 | 2019-12-26 | 中国科学院上海药物研究所 | 一种苯并噻吩化合物的马来酸盐、其结晶形式及其用途 |
CN111004211B (zh) * | 2019-12-29 | 2021-04-02 | 苏州诚和医药化学有限公司 | 一种依匹哌唑中间体4-溴苯并[b]噻吩的合成方法 |
US20240208969A1 (en) * | 2021-04-12 | 2024-06-27 | Impact Therapeutics (Shanghai), Inc. | Substituted fused bicyclic compounds as parp inhibitors and the use thereof |
EP4382521A4 (en) * | 2021-08-05 | 2025-01-01 | Shujing Biopharma Co Ltd | REGULATOR CONTAINING A TRICYCLIC DERIVATIVE, ITS PREPARATION PROCESS AND ITS USE |
CN116425716A (zh) * | 2021-12-31 | 2023-07-14 | 南京艾德凯腾生物医药有限责任公司 | 一种依匹哌唑中间体的制备方法 |
US11851435B2 (en) * | 2022-03-07 | 2023-12-26 | National Health Research Institutes | PTGR2 inhibitors and their use |
EP4493551A1 (en) | 2022-03-14 | 2025-01-22 | Slap Pharmaceuticals LLC | Multicyclic compounds |
CN116891465A (zh) | 2022-03-30 | 2023-10-17 | 苏州旺山旺水生物医药有限公司 | 一类n-取代的喹啉酮化合物、其制备方法和用途 |
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EP3115361B1 (en) | 2019-10-23 |
JP2017508756A (ja) | 2017-03-30 |
US10174011B2 (en) | 2019-01-08 |
CN106132956B (zh) | 2019-12-10 |
RU2667498C2 (ru) | 2018-09-21 |
RU2016137169A (ru) | 2018-03-21 |
JP6395850B2 (ja) | 2018-09-26 |
EP3115361A4 (en) | 2017-04-26 |
KR101840249B1 (ko) | 2018-03-20 |
CN104892589A (zh) | 2015-09-09 |
AU2015226578B2 (en) | 2017-11-23 |
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