DE69329231T2 - Pyrazolo(4,3-c)pyridine, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Inhibitoren der Serotonin-Wiederaufnahme - Google Patents

Pyrazolo(4,3-c)pyridine, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Inhibitoren der Serotonin-Wiederaufnahme

Info

Publication number: DE69329231T2
Authority: DE; Germany
Prior art keywords: compound; formula; pyrazole; hydrogen; pyridine
Prior art date: 1992-10-22
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.): Expired - Fee Related

Application number

DE69329231T

Other languages

German (de)

English (en)

Other versions

DE69329231D1 (de

Inventor

Kevin J. Kapples

Gregory Shutske

John Dick Tomer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Aventis Pharmaceuticals Inc

Original Assignee

Aventis Pharmaceuticals 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.)

1992-10-22

Filing date

1993-10-08

Publication date

2001-03-29

1993-10-08 Application filed by Aventis Pharmaceuticals Inc filed Critical Aventis Pharmaceuticals Inc

2000-09-21 Application granted granted Critical

2000-09-21 Publication of DE69329231D1 publication Critical patent/DE69329231D1/de

2001-03-29 Publication of DE69329231T2 publication Critical patent/DE69329231T2/de

2013-10-09 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

230000000697 serotonin reuptake Effects 0.000 title claims description 6
238000000034 method Methods 0.000 title abstract description 8
238000002360 preparation method Methods 0.000 title description 14
239000003112 inhibitor Substances 0.000 title description 5
WCXFPLXZZSWROM-UHFFFAOYSA-N 1h-pyrazolo[4,3-c]pyridine Chemical class C1=NC=C2C=NNC2=C1 WCXFPLXZZSWROM-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 61
239000000203 mixture Substances 0.000 claims abstract description 17
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
239000001257 hydrogen Substances 0.000 claims abstract description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 14
229910052736 halogen Inorganic materials 0.000 claims abstract description 11
150000002367 halogens Chemical class 0.000 claims abstract description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
230000003287 optical effect Effects 0.000 claims abstract description 4
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 40
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 20
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
239000004480 active ingredient Substances 0.000 claims description 7
230000000694 effects Effects 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
VMVNZNXAVJHNDJ-UHFFFAOYSA-N methyl 2,2,2-trifluoroacetate Chemical compound COC(=O)C(F)(F)F VMVNZNXAVJHNDJ-UHFFFAOYSA-N 0.000 claims description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
239000002168 alkylating agent Substances 0.000 claims description 2
229940100198 alkylating agent Drugs 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 claims 1
150000007529 inorganic bases Chemical class 0.000 claims 1
125000004076 pyridyl group Chemical group 0.000 abstract 1
239000003772 serotonin uptake inhibitor Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
DRTZAIDVOGUYSP-UHFFFAOYSA-N pyridin-1-ium;chloride;hydrochloride Chemical compound Cl.Cl.C1=CC=NC=C1 DRTZAIDVOGUYSP-UHFFFAOYSA-N 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
125000000217 alkyl group Chemical group 0.000 description 8
239000000243 solution Substances 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
239000000725 suspension Substances 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
229930006000 Sucrose Natural products 0.000 description 6
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 6
210000004556 brain Anatomy 0.000 description 6
239000003921 oil Substances 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000005720 sucrose Substances 0.000 description 6
210000003568 synaptosome Anatomy 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000000872 buffer Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
239000002775 capsule Substances 0.000 description 4
-1 dialkylaminoalkyl chloride Chemical compound 0.000 description 4
238000001914 filtration Methods 0.000 description 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
229940076279 serotonin Drugs 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 3
HOCPDSKONPQIQM-UHFFFAOYSA-N 4-(2-bromoethyl)isoindole-1,3-dione Chemical compound BrCCC1=CC=CC2=C1C(=O)NC2=O HOCPDSKONPQIQM-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
208000021384 Obsessive-Compulsive disease Diseases 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
239000000935 antidepressant agent Substances 0.000 description 3
229940005513 antidepressants Drugs 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
239000011976 maleic acid Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
235000015320 potassium carbonate Nutrition 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
OFCNTYBPPAQCRE-UHFFFAOYSA-N 3-(2-aminoethyl)-3h-indol-5-ol Chemical compound C1=C(O)C=C2C(CCN)C=NC2=C1 OFCNTYBPPAQCRE-UHFFFAOYSA-N 0.000 description 2
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 2
OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
208000020401 Depressive 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
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FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 2
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125000004432 carbon atom Chemical group C* 0.000 description 2
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239000003795 chemical substances by application Substances 0.000 description 2
DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
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MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
210000003016 hypothalamus Anatomy 0.000 description 2
239000007937 lozenge Substances 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
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
CSYNQJPENMOLHR-UHFFFAOYSA-N n,n-diethylethanamine;ethyl acetate Chemical compound CCOC(C)=O.CCN(CC)CC CSYNQJPENMOLHR-UHFFFAOYSA-N 0.000 description 2
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TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
150000003222 pyridines Chemical class 0.000 description 2
230000000862 serotonergic effect Effects 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000008174 sterile solution Substances 0.000 description 2
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229910052727 yttrium Inorganic materials 0.000 description 2
FMCAFXHLMUOIGG-JTJHWIPRSA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-JTJHWIPRSA-N 0.000 description 1
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MEVXSUZBFYZPHZ-UHFFFAOYSA-N 2-amino-3-methyl-4h-imidazol-5-one;sulfuric acid Chemical compound OS(O)(=O)=O.CN1CC(=O)N=C1N MEVXSUZBFYZPHZ-UHFFFAOYSA-N 0.000 description 1
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Classifications

- 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
- 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
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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
- A61P25/24—Antidepressants
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurosurgery (AREA)
Life Sciences & Earth Sciences (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Neurology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Silver Salt Photography Or Processing Solution Therefor (AREA)

DE69329231T 1992-10-22 1993-10-08 Pyrazolo(4,3-c)pyridine, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Inhibitoren der Serotonin-Wiederaufnahme Expired - Fee Related DE69329231T2 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/964,690 US5264576A (en)	1992-10-22	1992-10-22	Pyrazolo[4,3-c]pyridines which are intermediates

Publications (2)

Publication Number	Publication Date
DE69329231D1 DE69329231D1 (de)	2000-09-21
DE69329231T2 true DE69329231T2 (de)	2001-03-29

Family

ID=25508857

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE69329231T Expired - Fee Related DE69329231T2 (de)	1992-10-22	1993-10-08	Pyrazolo(4,3-c)pyridine, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Inhibitoren der Serotonin-Wiederaufnahme

Country Status (18)

Country	Link
US (4)	US5264576A (2)
EP (1)	EP0594001B1 (2)
JP (1)	JP2656211B2 (2)
KR (1)	KR100295026B1 (2)
CN (1)	CN1049658C (2)
AT (1)	ATE195522T1 (2)
AU (1)	AU671305B2 (2)
CA (1)	CA2108941A1 (2)
DE (1)	DE69329231T2 (2)
DK (1)	DK0594001T3 (2)
ES (1)	ES2152237T3 (2)
FI (1)	FI103890B1 (2)
GR (1)	GR3034819T3 (2)
MX (1)	MX9306552A (2)
NO (1)	NO300374B1 (2)
NZ (1)	NZ250003A (2)
PT (1)	PT594001E (2)
TW (1)	TW252114B (2)

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US5300498A (en) *	1993-06-04	1994-04-05	Hoechst-Roussel Pharmaceuticals Incorporated	6-piperazinyl-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acids, esters, amides and related compounds
US5618824A (en) *	1994-03-09	1997-04-08	Merrell Pharmaceuticals Inc.	Treatment of obsessive-compulsive disorders with 5-HT2 antagonists
US5565413A (en) *	1994-12-06	1996-10-15	Zeneca Limited	Substituted pyridyl phenyl ketone herbicides
US20050101587A9 (en) *	2000-08-14	2005-05-12	Butler Christopher R.	Method for treating allergies using substituted pyrazoles
RU2317988C2 (ru)	2000-08-14	2008-02-27	Орто-Макнейл Фармасьютикал, Инк.	Замещенные пиразолы, фармацевтическая композиция на их основе, применение фармацевтической композиции и способ ингибирования активности катепсина s
AU2001281255B2 (en)	2000-08-14	2006-07-20	Ortho-Mcneil Pharmaceutical, Inc.	Substituted pyrazoles
US7332494B2 (en)	2000-08-14	2008-02-19	Janssen Pharmaceutica, N.V.	Method for treating allergies using substituted pyrazoles
US20070117785A1 (en) *	2000-08-14	2007-05-24	Butler Christopher R	Substituted pyrazoles and methods of treatment with substituted pyrazoles
PT1309592E (pt) *	2000-08-14	2006-07-31	Ortho Mcneil Pharm Inc	Pirazoles substituidos
CN1642973A (zh)	2000-09-06	2005-07-20	奥索-麦克尼尔药品公司	治疗变态反应的方法
KR20050004214A (ko) *	2002-05-31	2005-01-12	에자이 가부시키가이샤	피라졸 화합물 및 이것을 포함하여 이루어지는 의약 조성물
EP2328895B1 (en) *	2008-09-16	2013-03-27	Proximagen Limited	Pyrazolo[4,3-c]pyridine compounds and their use as inhibitors of SSAO
CN102558174B (zh) *	2011-08-23	2014-03-19	天津市斯芬克司药物研发有限公司	一种全新吡唑并[4,3-c]吡啶化合物的发明及其合成方法
CA2871388A1 (en)	2012-06-27	2014-01-03	F. Hoffmann-La Roche Ag	5-azaindazole compounds and methods of use

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3994890A (en) *	1974-01-31	1976-11-30	Chugai Seiyaku Kabushiki Kaisha	1-Aminoalkyl, 3-phenyl indazoles
JPS5944314B2 (ja) *	1975-01-15	1984-10-29	中外製薬株式会社	インダゾ−ル誘導体の製法
JPS5936627B2 (ja) *	1975-07-25	1984-09-05	中外製薬株式会社	インダゾ−ル誘導体の製法
DK27383A (da) *	1982-02-17	1983-08-18	Lepetit Spa	Fremgangsmaade til fremstilling af pyrazol(4,3-c)pyridiner
JPH0615542B2 (ja) *	1986-07-22	1994-03-02	吉富製薬株式会社	ピラゾロピリジン化合物
EP0338087A4 (en) *	1987-10-13	1991-07-24	Yoshitomi Pharmaceutical Industries, Ltd.	Fused pyrazole compounds, process for their preparation, and their medicinal use
DK181190D0 (da) *	1990-07-30	1990-07-30	Lundbeck & Co As H	3-aryl-indol- eller 3-aryl-indazolderivater
EP0494774A1 (en) *	1991-01-11	1992-07-15	MERCK SHARP & DOHME LTD.	Indazole-substituted fivemembered heteroaromatic compounds
GB9216783D0 (en) *	1992-08-07	1992-09-23	Ici Plc	Heterocyclic derivatives
US5300478A (en) *	1993-01-28	1994-04-05	Zeneca Limited	Substituted fused pyrazolo compounds

1992
- 1992-10-22 US US07/964,690 patent/US5264576A/en not_active Expired - Fee Related
1993
- 1993-08-17 US US08/106,953 patent/US5296491A/en not_active Expired - Fee Related
- 1993-10-08 AT AT93116317T patent/ATE195522T1/de not_active IP Right Cessation
- 1993-10-08 EP EP93116317A patent/EP0594001B1/en not_active Expired - Lifetime
- 1993-10-08 DE DE69329231T patent/DE69329231T2/de not_active Expired - Fee Related
- 1993-10-08 PT PT93116317T patent/PT594001E/pt unknown
- 1993-10-08 ES ES93116317T patent/ES2152237T3/es not_active Expired - Lifetime
- 1993-10-08 DK DK93116317T patent/DK0594001T3/da active
- 1993-10-20 FI FI934621A patent/FI103890B1/fi active
- 1993-10-20 NZ NZ250003A patent/NZ250003A/en unknown
- 1993-10-21 AU AU49128/93A patent/AU671305B2/en not_active Ceased
- 1993-10-21 NO NO933784A patent/NO300374B1/no not_active IP Right Cessation
- 1993-10-21 CA CA002108941A patent/CA2108941A1/en not_active Abandoned
- 1993-10-21 MX MX9306552A patent/MX9306552A/es not_active IP Right Cessation
- 1993-10-22 KR KR1019930022006A patent/KR100295026B1/ko not_active Expired - Fee Related
- 1993-10-22 JP JP5265158A patent/JP2656211B2/ja not_active Expired - Fee Related
- 1993-10-22 CN CN93120396A patent/CN1049658C/zh not_active Expired - Fee Related
- 1993-10-22 TW TW082108790A patent/TW252114B/zh active
1994
- 1994-01-12 US US08/181,147 patent/US5380847A/en not_active Expired - Fee Related
- 1994-09-15 US US08/306,294 patent/US5428169A/en not_active Expired - Fee Related
2000
- 2000-11-10 GR GR20000402506T patent/GR3034819T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP0594001B1 (en)	2000-08-16
ES2152237T3 (es)	2001-02-01
MX9306552A (es)	1994-06-30
FI103890B (fi)	1999-10-15
AU4912893A (en)	1994-05-05
US5428169A (en)	1995-06-27
CN1049658C (zh)	2000-02-23
ATE195522T1 (de)	2000-09-15
EP0594001A1 (en)	1994-04-27
KR100295026B1 (ko)	2001-09-17
US5264576A (en)	1993-11-23
NO300374B1 (no)	1997-05-20
TW252114B (2)	1995-07-21
DK0594001T3 (da)	2000-10-30
FI934621A0 (fi)	1993-10-20
GR3034819T3 (en)	2001-02-28
DE69329231D1 (de)	2000-09-21
FI934621L (fi)	1994-04-23
KR940009185A (ko)	1994-05-20
NO933784L (no)	1994-04-25
NZ250003A (en)	1996-03-26
CA2108941A1 (en)	1994-04-23
FI103890B1 (fi)	1999-10-15
US5296491A (en)	1994-03-22
US5380847A (en)	1995-01-10
CN1099033A (zh)	1995-02-22
PT594001E (pt)	2001-01-31
AU671305B2 (en)	1996-08-22
NO933784D0 (no)	1993-10-21
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Publication	Publication Date	Title
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DE60213851T2 (de)	2007-09-13	Ringannelierte pyrazolderivate
DE69210849T2 (de)	1996-12-05	N-(Aryloxyalkyl)heteroaryl-8-Azabicyclo[3.2.1]Octan, Zwischenverbindungen und Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel
DE69205312T2 (de)	1996-03-14	Substituierte Imidazol-2-one Derivate und Verfahren zu deren Herstellung.
DE69415391T2 (de)	1999-08-26	Chinazolinonderivate
DE69116788T2 (de)	1996-07-18	4-substituierte Dihydropyrido [4,3-d] pyrimidine als Analgetika und entzündungshemmende Mittel zur topischen Anwendung bei der Behandlung von Hauterkrankungen
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DE68902386T2 (de)	1993-02-11	N-pyridinyl-9h-carbazol-9-amine, verfahren zu ihrer herstellung und ihre verwendung als medikamente.
DE69514315T2 (de)	2000-07-27	AZABICYCLOALKYLDERIVATE VON IMIDAZO[1,5-a]INDOL-3-ONE ALS 5HT3 ANTAGONISTEN
DE69405292T2 (de)	1998-02-12	6-Piperazinyl-1H-pyrazolo(3,4-b)pyridin-3-carbonsäuren, ihre Ester, Amide und verwandte Verbindungen, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
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