NO831678L - Fremgangsmaate for fremstilling av terapeutisk aktive pyrazolopyridin-derivater. - Google Patents

Fremgangsmaate for fremstilling av terapeutisk aktive pyrazolopyridin-derivater.

Info

Publication number: NO831678L
Authority: NO; Norway
Prior art keywords: formula; alkyl; give; hydrogen; compound
Prior art date: 1982-05-12

Application number

NO831678A

Other languages

English (en)

Norwegian (no)

Inventor

Thomas Michael Bare

James Boniface Campbell

Anthony Frederick Heald

Original Assignee

Ici America Inc

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.)

1982-05-12

Filing date

1983-05-11

Publication date

1983-11-14

1983-01-21 Priority claimed from GB838301676A external-priority patent/GB8301676D0/en

1983-05-11 Application filed by Ici America Inc filed Critical Ici America Inc

1983-11-14 Publication of NO831678L publication Critical patent/NO831678L/no

Links

238000000034 method Methods 0.000 title claims description 37
238000002360 preparation method Methods 0.000 title claims description 7
150000005229 pyrazolopyridines Chemical class 0.000 title claims description 3
230000001225 therapeutic effect Effects 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 134
229910052739 hydrogen Inorganic materials 0.000 claims description 106
125000000217 alkyl group Chemical group 0.000 claims description 91
239000001257 hydrogen Substances 0.000 claims description 74
150000002431 hydrogen Chemical class 0.000 claims description 39
125000003118 aryl group Chemical group 0.000 claims description 33
125000003107 substituted aryl group Chemical group 0.000 claims description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
150000001412 amines Chemical class 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 17
125000003710 aryl alkyl group Chemical group 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
125000003342 alkenyl group Chemical group 0.000 claims description 15
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
239000001301 oxygen Substances 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
125000000304 alkynyl group Chemical group 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
229910052794 bromium Chemical group 0.000 claims description 11
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 7
125000000547 substituted alkyl group Chemical group 0.000 claims description 7
125000001589 carboacyl group Chemical group 0.000 claims description 6
238000007363 ring formation reaction Methods 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 5
150000008065 acid anhydrides Chemical class 0.000 claims description 2
150000001266 acyl halides Chemical class 0.000 claims description 2
125000003435 aroyl group Chemical group 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 375
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 219
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 181
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 174
239000007787 solid Substances 0.000 description 156
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 119
239000000741 silica gel Substances 0.000 description 118
229910002027 silica gel Inorganic materials 0.000 description 118
125000004432 carbon atom Chemical group C* 0.000 description 91
239000000243 solution Substances 0.000 description 90
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
238000001819 mass spectrum Methods 0.000 description 71
239000000047 product Substances 0.000 description 71
-1 pyrazolo[3,4-b]-pyridine lactones Chemical class 0.000 description 70
239000000203 mixture Substances 0.000 description 68
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 67
239000003921 oil Substances 0.000 description 64
235000019198 oils Nutrition 0.000 description 64
238000000921 elemental analysis Methods 0.000 description 56
150000002596 lactones Chemical class 0.000 description 56
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 55
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
150000003951 lactams Chemical class 0.000 description 44
238000006243 chemical reaction Methods 0.000 description 43
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
239000002904 solvent Substances 0.000 description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
239000003480 eluent Substances 0.000 description 34
239000013078 crystal Substances 0.000 description 33
229910001220 stainless steel Inorganic materials 0.000 description 32
239000010935 stainless steel Substances 0.000 description 32
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
238000010992 reflux Methods 0.000 description 22
239000007858 starting material Substances 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 21
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
150000001204 N-oxides Chemical class 0.000 description 16
125000003545 alkoxy group Chemical group 0.000 description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
238000001953 recrystallisation Methods 0.000 description 14
238000012360 testing method Methods 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
229910000041 hydrogen chloride Inorganic materials 0.000 description 13
239000010410 layer Substances 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
241000700159 Rattus Species 0.000 description 12
235000011089 carbon dioxide Nutrition 0.000 description 12
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 12
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
125000005843 halogen group Chemical group 0.000 description 11
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 description 10
229910000104 sodium hydride Inorganic materials 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000007788 liquid Substances 0.000 description 9
239000000463 material Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
238000004821 distillation Methods 0.000 description 8
230000000694 effects Effects 0.000 description 8
229960002200 flunitrazepam Drugs 0.000 description 8
229910052744 lithium Inorganic materials 0.000 description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
239000011734 sodium Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 7
150000001299 aldehydes Chemical group 0.000 description 7
229910021529 ammonia Inorganic materials 0.000 description 7
230000027455 binding Effects 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
230000035939 shock Effects 0.000 description 7
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000012259 ether extract Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
125000004043 oxo group Chemical group O=* 0.000 description 6
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
238000006467 substitution reaction Methods 0.000 description 6
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
241000124008 Mammalia Species 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
230000000949 anxiolytic effect Effects 0.000 description 5
239000002585 base Substances 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000012267 brine Substances 0.000 description 5
150000002081 enamines Chemical class 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000000284 extract Substances 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 4
JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 4
XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 4
YBPLPFYORGKPKX-UHFFFAOYSA-N 2-pentylpyrazol-3-amine Chemical compound CCCCCN1N=CC=C1N YBPLPFYORGKPKX-UHFFFAOYSA-N 0.000 description 4
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
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 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
VVJKKWFAADXIJK-UHFFFAOYSA-N allylamine Natural products NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
150000001450 anions Chemical class 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
125000001246 bromo group Chemical group Br* 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002366 halogen compounds Chemical class 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
150000003141 primary amines Chemical class 0.000 description 4
230000009467 reduction Effects 0.000 description 4
102220007331 rs111033633 Human genes 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
NUGZBVBZIDWZAD-UHFFFAOYSA-N 1h-pyrazole-4-carbonitrile Chemical compound N#CC=1C=NNC=1 NUGZBVBZIDWZAD-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
IPOVOSHRRIJKBR-UHFFFAOYSA-N 2-ethylpropanedioyl dichloride Chemical compound CCC(C(Cl)=O)C(Cl)=O IPOVOSHRRIJKBR-UHFFFAOYSA-N 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
CECDJGIKIJVDLE-UHFFFAOYSA-N 8-amino-4-pentyl-11-propyl-2,4,5,11-tetrazatricyclo[7.3.0.03,7]dodeca-1(9),2,5,7-tetraen-10-one Chemical compound N1=C2N(CCCCC)N=CC2=C(N)C2=C1CN(CCC)C2=O CECDJGIKIJVDLE-UHFFFAOYSA-N 0.000 description 3
208000019901 Anxiety disease Diseases 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
239000002249 anxiolytic agent Substances 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
150000007942 carboxylates Chemical class 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
150000007857 hydrazones Chemical class 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
125000000468 ketone group Chemical group 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
230000004044 response Effects 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
239000011592 zinc chloride Substances 0.000 description 3
235000005074 zinc chloride Nutrition 0.000 description 3
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 2
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
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QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
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241000282693 Cercopithecidae Species 0.000 description 1
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241000282326 Felis catus Species 0.000 description 1
101000933374 Gallus gallus Brain-specific homeobox/POU domain protein 3 Proteins 0.000 description 1
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238000000023 Kugelrohr distillation Methods 0.000 description 1
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BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
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CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
229920002359 Tetronic® Chemical class 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
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239000012346 acetyl chloride Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
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239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
238000007083 alkoxycarbonylation reaction Methods 0.000 description 1
150000001347 alkyl bromides Chemical class 0.000 description 1
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230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
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239000007864 aqueous solution Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
DLGYNVMUCSTYDQ-UHFFFAOYSA-N azane;pyridine Chemical compound N.C1=CC=NC=C1 DLGYNVMUCSTYDQ-UHFFFAOYSA-N 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
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239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
IQNQAOGGWGCROX-UHFFFAOYSA-N cartazolate Chemical compound CCCCNC1=C(C(=O)OCC)C=NC2=C1C=NN2CC IQNQAOGGWGCROX-UHFFFAOYSA-N 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
210000003710 cerebral cortex Anatomy 0.000 description 1
230000008859 change Effects 0.000 description 1
YZECYWIRJYJOEX-UHFFFAOYSA-N chembl313035 Chemical compound CCOC(=O)C1=C(C)N=C2N(CCCCC)N=CC2=C1O YZECYWIRJYJOEX-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
DGBIGWXXNGSACT-UHFFFAOYSA-N clonazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl DGBIGWXXNGSACT-UHFFFAOYSA-N 0.000 description 1
229960003120 clonazepam Drugs 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
HXSNGAHNYZBZTH-UHFFFAOYSA-N cyclopropylmethanamine;hydrochloride Chemical compound Cl.NCC1CC1 HXSNGAHNYZBZTH-UHFFFAOYSA-N 0.000 description 1
238000011161 development Methods 0.000 description 1
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
229960003529 diazepam Drugs 0.000 description 1
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SQAUUQRBOCJRCW-UHFFFAOYSA-N diethyl 2-acetylpropanedioate Chemical compound CCOC(=O)C(C(C)=O)C(=O)OCC SQAUUQRBOCJRCW-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
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OCJKUQIPRNZDTK-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)(F)F OCJKUQIPRNZDTK-UHFFFAOYSA-N 0.000 description 1
ZKRJCMKLCDWROR-UHFFFAOYSA-N ethyl 4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)C=CC(F)(F)F ZKRJCMKLCDWROR-UHFFFAOYSA-N 0.000 description 1
FUTJWGAFYCKALV-UHFFFAOYSA-N ethyl 4-chloro-1-ethyl-6-methylpyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C2N(CC)N=CC2=C1Cl FUTJWGAFYCKALV-UHFFFAOYSA-N 0.000 description 1
BICHVFVJNWILFV-UHFFFAOYSA-N ethyl 4-chloro-6-methyl-1-(3-methylbutyl)pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C2N(CCC(C)C)N=CC2=C1Cl BICHVFVJNWILFV-UHFFFAOYSA-N 0.000 description 1
JUMISPXPPLKMGY-UHFFFAOYSA-N ethyl 4-chloro-6-methyl-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C2NN=CC2=C1Cl JUMISPXPPLKMGY-UHFFFAOYSA-N 0.000 description 1
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JKYQDLMQSFWIMU-UHFFFAOYSA-N ethyl 6-(acetyloxymethyl)-4-chloro-1-(4,4,4-trifluorobutyl)pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(COC(C)=O)N=C2N(CCCC(F)(F)F)N=CC2=C1Cl JKYQDLMQSFWIMU-UHFFFAOYSA-N 0.000 description 1
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125000000623 heterocyclic group Chemical group 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
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239000005457 ice water Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
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229910052740 iodine Chemical group 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
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238000002955 isolation Methods 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
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238000004519 manufacturing process Methods 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
238000006198 methoxylation reaction Methods 0.000 description 1
230000002438 mitochondrial effect Effects 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
WPQSESLBDJWWHA-UHFFFAOYSA-N n,n-dichloro-1-phenylmethanamine Chemical compound ClN(Cl)CC1=CC=CC=C1 WPQSESLBDJWWHA-UHFFFAOYSA-N 0.000 description 1
USEMRPYUFJNFQN-UHFFFAOYSA-N n-cyclohexyl-2-(3,5-dimethylpyrazol-1-yl)-6-methylpyrimidin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(C)=CC(NC2CCCCC2)=N1 USEMRPYUFJNFQN-UHFFFAOYSA-N 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
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238000007254 oxidation reaction Methods 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000006201 parenteral dosage form Substances 0.000 description 1
230000037361 pathway Effects 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
YVZACCLFRNQBNO-UHFFFAOYSA-N pentylhydrazine Chemical compound CCCCCNN YVZACCLFRNQBNO-UHFFFAOYSA-N 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
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150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000013641 positive control Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 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
238000000746 purification Methods 0.000 description 1
QGKLPGKXAVVPOJ-UHFFFAOYSA-N pyrrolidin-3-one Chemical compound O=C1CCNC1 QGKLPGKXAVVPOJ-UHFFFAOYSA-N 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
238000006462 rearrangement reaction Methods 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
102220012898 rs397516346 Human genes 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
238000000526 short-path distillation Methods 0.000 description 1
231100000161 signs of toxicity Toxicity 0.000 description 1
210000002027 skeletal muscle Anatomy 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
230000001629 suppression Effects 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000012353 t test Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical class C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
- C07C53/21—Acids containing three or more carbon atoms containing fluorine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO831678A 1982-05-12 1983-05-11 Fremgangsmaate for fremstilling av terapeutisk aktive pyrazolopyridin-derivater. NO831678L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8213700		1982-05-12
GB838301676A GB8301676D0 (en)	1983-01-21	1983-01-21	Nitrogen containing heterocycles

Publications (1)

Publication Number	Publication Date
NO831678L true NO831678L (no)	1983-11-14

Family

ID=26282806

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO831678A NO831678L (no)	1982-05-12	1983-05-11	Fremgangsmaate for fremstilling av terapeutisk aktive pyrazolopyridin-derivater.

Country Status (17)

Country	Link
US (2)	US4511568A (es)
EP (1)	EP0094175B1 (es)
KR (1)	KR840004750A (es)
AU (1)	AU1425983A (es)
DD (1)	DD210456A5 (es)
DE (1)	DE3367217D1 (es)
DK (1)	DK211783A (es)
ES (1)	ES522325A0 (es)
FI (1)	FI831646L (es)
GB (1)	GB8310266D0 (es)
GR (1)	GR78856B (es)
IL (1)	IL68571A0 (es)
IN (1)	IN159825B (es)
NO (1)	NO831678L (es)
NZ (1)	NZ204203A (es)
PT (1)	PT76678B (es)
ZW (1)	ZW10983A1 (es)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8329531D0 (en) *	1983-11-04	1983-12-07	Ici America Inc	Pyrazolopyridine cycloalkanones
DE3520390A1 (de) *	1984-07-07	1986-02-06	Bayer Ag, 5090 Leverkusen	Imidazo-pyrrolo-pyridin-derivate
GB8421116D0 (en) *	1984-08-20	1984-09-26	Ici America Inc	Alkynyl derivatives
GB8425104D0 (en) *	1984-10-04	1984-11-07	Ici America Inc	Amide derivatives
GB8610980D0 (en) *	1986-05-06	1986-06-11	Ici America Inc	Heterocyclic fused tricyclic compounds
GB8610981D0 (en) *	1986-05-06	1986-06-11	Ici America Inc	Quinoline amides
DE19944332A1 (de) *	1999-09-16	2001-03-22	Dresden Arzneimittel	Antikonvulsiv und anxiolytisch wirkende 4-Amino-1-aryl-1,5-dihydro-pyrrol-2-one und Verfahren zu deren Herstellung
US20030220646A1 (en) *	2002-05-23	2003-11-27	Thelen Sarah L.	Method and apparatus for reducing femoral fractures
KR20080080206A (ko) *	2005-12-20	2008-09-02	아스트라제네카 아베	Ｇａｂａａ-수용체 조절제로서의 치환된 신놀린 유도체 및그의 합성 방법
US7465795B2 (en) *	2005-12-20	2008-12-16	Astrazeneca Ab	Compounds and uses thereof
TW200911760A (en) *	2007-06-19	2009-03-16	Astrazeneca Ab	Compounds and uses thereof

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1514010A (fr) *	1966-03-14	1968-02-16	American Home Prod	Procédé de préparation de benzonaphtyridines
BE787249A (fr) *	1971-08-05	1973-02-05	Squibb & Sons Inc	Derives amino d'acides pyrazolopyridine carboxyliques, leurs esters et les sels de ces composes, ainsi que leurs procedes de preparation
US3850940A (en) *	1972-11-24	1974-11-26	Squibb & Sons Inc	Intermediate pyrazolopyridine carbonitriles
US4051236A (en) *	1973-02-15	1977-09-27	E. R. Squibb & Sons, Inc.	Inhibition of blood platelet aggregation
US4038281A (en) *	1975-10-16	1977-07-26	E. R. Squibb & Sons, Inc.	Certain 2,7-dihydro-4H-pyrazolo[3,4-b]pyridine-5-ketones
US4018779A (en) *	1976-03-25	1977-04-19	E. R. Squibb & Sons, Inc.	Derivatives of 10,11-dihydrobenzo[4,5]cyclohepta[1,2-b]-pyrazolo[4,3-e]pyridine-5(1H)ones
US4072681A (en) *	1977-03-02	1978-02-07	E. R. Squibb & Sons, Inc.	3,7-Dihydro- and 1,7-dihydro-4H-pyrazolo[4',3':5,6]pyrido[4,3-d]pyrimidin-4-ones
US4329349A (en) *	1979-07-25	1982-05-11	Sandoz, Inc.	6-C1-4 Alkyl-7-phenyl or substituted phenyl-1,6-naphthyridine-5(6H)-ones
US4364948A (en) *	1981-09-28	1982-12-21	Ici Americas Inc.	Pyrazolo[3,4-b]pyridine compounds

1983
- 1983-04-15 US US06/485,191 patent/US4511568A/en not_active Expired - Fee Related
- 1983-04-15 GB GB838310266A patent/GB8310266D0/en active Pending
- 1983-04-27 DE DE8383302389T patent/DE3367217D1/de not_active Expired
- 1983-04-27 EP EP83302389A patent/EP0094175B1/en not_active Expired
- 1983-04-27 GR GR71229A patent/GR78856B/el unknown
- 1983-05-04 IN IN281/DEL/83A patent/IN159825B/en unknown
- 1983-05-04 IL IL68571A patent/IL68571A0/xx unknown
- 1983-05-05 AU AU14259/83A patent/AU1425983A/en not_active Abandoned
- 1983-05-09 ZW ZW109/83A patent/ZW10983A1/xx unknown
- 1983-05-11 NO NO831678A patent/NO831678L/no unknown
- 1983-05-11 NZ NZ204203A patent/NZ204203A/en unknown
- 1983-05-11 FI FI831646A patent/FI831646L/fi not_active Application Discontinuation
- 1983-05-11 DK DK211783A patent/DK211783A/da not_active Application Discontinuation
- 1983-05-11 PT PT76678A patent/PT76678B/pt unknown
- 1983-05-12 KR KR1019830002044A patent/KR840004750A/ko not_active Application Discontinuation
- 1983-05-12 ES ES522325A patent/ES522325A0/es active Granted
- 1983-05-12 DD DD83250875A patent/DD210456A5/de unknown
1984
- 1984-06-25 US US06/624,530 patent/US4645838A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
KR840004750A (ko)	1984-10-24
AU1425983A (en)	1983-11-17
ZW10983A1 (en)	1984-12-05
GR78856B (es)	1984-10-02
DK211783D0 (da)	1983-05-11
FI831646A0 (fi)	1983-05-11
DD210456A5 (de)	1984-06-13
EP0094175B1 (en)	1986-10-29
DK211783A (da)	1983-11-13
IL68571A0 (en)	1983-09-30
ES8502116A1 (es)	1984-12-16
NZ204203A (en)	1986-01-24
US4511568A (en)	1985-04-16
GB8310266D0 (en)	1983-05-18
FI831646L (fi)	1983-11-13
IN159825B (es)	1987-06-06
EP0094175A1 (en)	1983-11-16
PT76678A (en)	1983-06-01
US4645838A (en)	1987-02-24
DE3367217D1 (en)	1986-12-04
ES522325A0 (es)	1984-12-16
PT76678B (en)	1986-01-14

Publication	Publication Date	Title
US4563525A (en)	1986-01-07	Process for preparing pyrazolopyridine compounds
ES2273369T3 (es)	2007-05-01	Derivados 6,5 heterobiciclicos sustituidos.
NL1026029C2 (nl)	2005-07-05	Cannabinoïdreceptorliganden en toepassingen daarvan.
DE69826518T2 (de)	2005-09-22	Imidazonaphthyridinderivate und ihre verwendung zur induzierung von biosythese von cytokin
EP0263071B1 (en)	1992-08-12	2-Substituted-e-fused-[1,2,4]-triazolo[1,5-c] pyrimidines, pharmaceutical compositions, and uses thereof
TW202200575A (zh)	2022-01-01	一種免疫抑制劑、其製備方法和應用
CA2351724A1 (en)	2000-07-06	1h-imidazo¬4,5-d\|pyridazin-7-ones, 3h-imidazo¬4,5-c\|pyridin-4-ones and corresponding thiones as corticotropin releasing factor (crf) receptor ligands
NO831678L (no)	1983-11-14	Fremgangsmaate for fremstilling av terapeutisk aktive pyrazolopyridin-derivater.
JP2004526769A (ja)	2004-09-02	子宮収縮抑制オキシトシン受容体拮抗薬としての新規三環系ピリジルベンズアゼピンカルボキサミドおよびその誘導体
KR20170003521A (ko)	2017-01-09	3 고리성 화합물 및 jak 저해제
JP2004527537A (ja)	2004-09-09	子宮収縮抑制オキシトシン受容体拮抗薬としての新規三環系ヒドロキシカルボキシアミド及びその誘導体
DE60001138T2 (de)	2003-10-23	Polycyclische Azaindolderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
US4552883A (en)	1985-11-12	Pyrazolo[3,4-b]pyridine carboxylic acid esters and their pharmaceutical use
DE60218646T2 (de)	2007-11-22	N-biphenylcarbonyl- und n-phenylpyridylcarbonyl substituierte bi- und tricyclische azepine und diazepine als vasopressin-agonisten
US5968946A (en)	1999-10-19	Heterocyclic derivatives useful in treating central nervous system disorders
US4602014A (en)	1986-07-22	Ring-fused pyrazolo[3,4-d]-pyridin-3-one derivatives as benzodiazepine receptor modulators
NO971687L (no)	1997-06-13	Diazepinoindoler som forsfodiesterase IV-inhibitorer
EP0360621B1 (en)	1994-01-19	Substituted thienopyrans as antihypertensive agents
NO853923L (no)	1986-04-07	Fremgangsm¨te for fremstilling av terapeutisk aktive amid- derivater.
JPS61112076A (ja)	1986-05-30	ベンゼン縮合複素環化合物
JPH0322390B2 (es)	1991-03-26
KR20060092219A (ko)	2006-08-22	유도성 ｎｏ-합성효소 억제제로서의 아미노피리딘-유도체
CZ9394A3 (en)	1994-08-17	9H-IMIDAZO/1,2-a/BENZIMIDAZOL-3-ACETAMIDO DERIVATIVES, PROCESS OF THEIR PREPARATION AND PHARMACEUTICAL PREPARATIONS IN WHICH THEY ARE COMPRISED
US4705793A (en)	1987-11-10	Pyrazolo[3,4-b]pyrrolo[3,4-e]pyridine-5(1H)-one and 1-H-pyrazolo[3,4-b][1,6]naphthyridine-5(6H)-one derivations, useful as anti-anxiety agents
CS114291A3 (en)	1992-01-15	Benzothieno-[2,3-b] pyrazine-2,3-(1h,4h) diones, processes for their preparation and a pharmaceutical comprising them