JP2003512370A5 - - Google Patents
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- Publication number
- JP2003512370A5 JP2003512370A5 JP2001531826A JP2001531826A JP2003512370A5 JP 2003512370 A5 JP2003512370 A5 JP 2003512370A5 JP 2001531826 A JP2001531826 A JP 2001531826A JP 2001531826 A JP2001531826 A JP 2001531826A JP 2003512370 A5 JP2003512370 A5 JP 2003512370A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- trifluoromethylphenyl
- isoquinoline
- hydrochloride
- oxide
- 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
- -1 3-trifluoromethylphenyl Chemical group 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- TYLZBRGUMHEPMR-UHFFFAOYSA-N 2-isoquinolin-7-ylacetaldehyde Chemical compound C1=CN=CC2=CC(CC=O)=CC=C21 TYLZBRGUMHEPMR-UHFFFAOYSA-N 0.000 description 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- ZXXHOPNSTZKWRI-UHFFFAOYSA-N 7-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]isoquinoline Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C4C=NC=CC4=CC=3)CC=2)=C1 ZXXHOPNSTZKWRI-UHFFFAOYSA-N 0.000 description 1
- RZIAABRFQASVSW-UHFFFAOYSA-N Isoquinoline N-oxide Chemical compound C1=CC=CC2=C[N+]([O-])=CC=C21 RZIAABRFQASVSW-UHFFFAOYSA-N 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9913206A FR2800071B1 (fr) | 1999-10-22 | 1999-10-22 | Tetrahydropyridines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| FR99/13206 | 1999-10-22 | ||
| FR00/08328 | 2000-06-28 | ||
| FR0008328A FR2810984B1 (fr) | 2000-06-28 | 2000-06-28 | Pyridyl-tetrahydropyridines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| PCT/FR2000/002910 WO2001029026A1 (fr) | 1999-10-22 | 2000-10-19 | Phenyl- et pyridyl-tetrahydro-pyridines possedant une activite inhibitrice de fnt |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003512370A JP2003512370A (ja) | 2003-04-02 |
| JP2003512370A5 true JP2003512370A5 (https=) | 2007-12-06 |
| JP4831908B2 JP4831908B2 (ja) | 2011-12-07 |
Family
ID=26212500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001531826A Expired - Fee Related JP4831908B2 (ja) | 1999-10-22 | 2000-10-19 | Ｔｎｆ阻害活性を有するフェニル−およびピリジル−テトラヒドロピリジン類 |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US6509351B1 (https=) |
| EP (1) | EP1226137B8 (https=) |
| JP (1) | JP4831908B2 (https=) |
| KR (1) | KR100755115B1 (https=) |
| CN (1) | CN1158276C (https=) |
| AR (1) | AR026188A1 (https=) |
| AT (1) | ATE271554T1 (https=) |
| AU (1) | AU778306B2 (https=) |
| BG (1) | BG65564B1 (https=) |
| BR (1) | BR0014871A (https=) |
| CA (1) | CA2386417C (https=) |
| CZ (1) | CZ301566B6 (https=) |
| DE (1) | DE60012355T2 (https=) |
| DK (1) | DK1226137T3 (https=) |
| EA (1) | EA004508B1 (https=) |
| EE (1) | EE05055B1 (https=) |
| ES (1) | ES2223594T3 (https=) |
| HK (1) | HK1046532B (https=) |
| HR (1) | HRP20020347B1 (https=) |
| HU (1) | HUP0204444A3 (https=) |
| IL (2) | IL149250A0 (https=) |
| IS (1) | IS2308B (https=) |
| ME (1) | MEP25108A (https=) |
| MX (1) | MXPA02003979A (https=) |
| NO (1) | NO322596B1 (https=) |
| NZ (1) | NZ518112A (https=) |
| PL (1) | PL198421B1 (https=) |
| PT (1) | PT1226137E (https=) |
| RS (1) | RS50399B (https=) |
| SI (1) | SI1226137T1 (https=) |
| SK (1) | SK287098B6 (https=) |
| TR (1) | TR200201075T2 (https=) |
| TW (1) | TWI224097B (https=) |
| UA (1) | UA72934C2 (https=) |
| WO (1) | WO2001029026A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2823748B1 (fr) * | 2001-04-20 | 2004-02-20 | Sanofi Synthelabo | Tetrahydropyridyl-alkyl-benzodiazines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| FR2831166B1 (fr) * | 2001-10-18 | 2004-02-27 | Sanofi Synthelabo | Aralkyl-tetrahydro-pyridines, leur preparation et compositions pharmaceutiques les contenant |
| FR2832405B1 (fr) * | 2001-11-19 | 2004-12-10 | Sanofi Synthelabo | Tetrahydropyridyl-alkyl-heterocycles azotes, procede pour leur preparation et compositions pharmaceutiques les contenant |
| FR2840896B1 (fr) * | 2002-06-18 | 2005-04-08 | Sanofi Synthelabo | Phenyl-et pyridyl-piperazines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| JP4866610B2 (ja) | 2003-08-18 | 2012-02-01 | 富士フイルムファインケミカルズ株式会社 | ピリジルテトラヒドロピリジン類およびピリジルピペリジン類 |
| FR2883285B1 (fr) * | 2005-03-17 | 2007-05-18 | Sanofi Aventis Sa | Sel besylate de la 7-(2-(4-(3-trifluoromethyl-phenyl) -1,2,3,6-tetrahudro-pyrid-1-yl)ethyl) isoquinoleine, sa preparation et son utilisation en therapeutique |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3991061A (en) | 1975-07-16 | 1976-11-09 | G. D. Searle & Co. | Azanaphthaleneacetic acid derivatives |
| US4704390A (en) * | 1986-02-13 | 1987-11-03 | Warner-Lambert Company | Phenyl and heterocyclic tetrahydropyridyl alkoxy-benzheterocyclic compounds as antipsychotic agents |
| US5118691A (en) * | 1990-09-20 | 1992-06-02 | Warner-Lambert Co. | Substituted tetrahydropyridines as central nervous system agents |
| US5045550A (en) * | 1990-09-20 | 1991-09-03 | Warner-Lambert Co. | Substituted tetrahydropyridines as central nervous system agents |
| US5273977A (en) * | 1990-11-05 | 1993-12-28 | Warner-Lambert Company | Substituted tetrahydropyridines and hydroxypiperidines as central nervous system agents |
| JP2001511764A (ja) * | 1996-04-12 | 2001-08-14 | 住友製薬株式会社 | ピペリジニルピリミジン誘導体 |
| US5776939A (en) * | 1997-06-12 | 1998-07-07 | Eli Lilly And Company | Drug resistance and multidrug resistance modulators |
| US6281216B1 (en) * | 1998-02-09 | 2001-08-28 | Duphar International Research B.V. | 2-aminoquinoline derivatives having d4-agonistic activity |
| FR2803593B1 (fr) * | 2000-01-06 | 2002-02-15 | Sanofi Synthelabo | Nouvelles tetrahydropyridines, procede pour leur preparation et compositions pharmaceutiques les contenant |
-
2000
- 2000-10-19 HK HK02108188.3A patent/HK1046532B/zh not_active IP Right Cessation
- 2000-10-19 EA EA200200352A patent/EA004508B1/ru not_active IP Right Cessation
- 2000-10-19 AU AU79313/00A patent/AU778306B2/en not_active Ceased
- 2000-10-19 EE EEP200200210A patent/EE05055B1/xx not_active IP Right Cessation
- 2000-10-19 SI SI200030499T patent/SI1226137T1/xx unknown
- 2000-10-19 SK SK528-2002A patent/SK287098B6/sk not_active IP Right Cessation
- 2000-10-19 CA CA2386417A patent/CA2386417C/en not_active Expired - Fee Related
- 2000-10-19 AT AT00969646T patent/ATE271554T1/de active
- 2000-10-19 CZ CZ20021382A patent/CZ301566B6/cs not_active IP Right Cessation
- 2000-10-19 RS YUP-289/02A patent/RS50399B/sr unknown
- 2000-10-19 PT PT00969646T patent/PT1226137E/pt unknown
- 2000-10-19 DK DK00969646T patent/DK1226137T3/da active
- 2000-10-19 EP EP00969646A patent/EP1226137B8/fr not_active Expired - Lifetime
- 2000-10-19 IL IL14925000A patent/IL149250A0/xx active IP Right Grant
- 2000-10-19 WO PCT/FR2000/002910 patent/WO2001029026A1/fr not_active Ceased
- 2000-10-19 NZ NZ518112A patent/NZ518112A/en not_active IP Right Cessation
- 2000-10-19 CN CNB008160759A patent/CN1158276C/zh not_active Expired - Fee Related
- 2000-10-19 DE DE60012355T patent/DE60012355T2/de not_active Expired - Lifetime
- 2000-10-19 KR KR1020027005110A patent/KR100755115B1/ko not_active Expired - Fee Related
- 2000-10-19 HR HR20020347A patent/HRP20020347B1/xx not_active IP Right Cessation
- 2000-10-19 US US10/111,045 patent/US6509351B1/en not_active Expired - Lifetime
- 2000-10-19 JP JP2001531826A patent/JP4831908B2/ja not_active Expired - Fee Related
- 2000-10-19 UA UA2002043167A patent/UA72934C2/uk unknown
- 2000-10-19 ME MEP-251/08A patent/MEP25108A/xx unknown
- 2000-10-19 BR BR0014871-7A patent/BR0014871A/pt active Search and Examination
- 2000-10-19 TR TR2002/01075T patent/TR200201075T2/xx unknown
- 2000-10-19 PL PL354922A patent/PL198421B1/pl unknown
- 2000-10-19 HU HU0204444A patent/HUP0204444A3/hu unknown
- 2000-10-19 ES ES00969646T patent/ES2223594T3/es not_active Expired - Lifetime
- 2000-10-19 MX MXPA02003979A patent/MXPA02003979A/es active IP Right Grant
- 2000-10-20 AR ARP000105527A patent/AR026188A1/es not_active Application Discontinuation
- 2000-10-23 TW TW089122181A patent/TWI224097B/zh not_active IP Right Cessation
-
2002
- 2002-04-09 IS IS6336A patent/IS2308B/is unknown
- 2002-04-15 BG BG106613A patent/BG65564B1/bg unknown
- 2002-04-19 NO NO20021872A patent/NO322596B1/no not_active IP Right Cessation
- 2002-04-21 IL IL149250A patent/IL149250A/en not_active IP Right Cessation
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