JP2005509678A5 - - Google Patents
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- Publication number
- JP2005509678A5 JP2005509678A5 JP2003545647A JP2003545647A JP2005509678A5 JP 2005509678 A5 JP2005509678 A5 JP 2005509678A5 JP 2003545647 A JP2003545647 A JP 2003545647A JP 2003545647 A JP2003545647 A JP 2003545647A JP 2005509678 A5 JP2005509678 A5 JP 2005509678A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- tetrahydropyridine
- ethyl
- trifluoromethyl
- pyridyl
- 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
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 150000001204 N-oxides Chemical class 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- FYDQCGJHRQKPKM-UHFFFAOYSA-N 2-[1-[2-(3-pyridin-2-ylphenyl)ethyl]-3,6-dihydro-2h-pyridin-4-yl]-6-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C(C=CC=3)C=3N=CC=CC=3)CC=2)=N1 FYDQCGJHRQKPKM-UHFFFAOYSA-N 0.000 claims 1
- GGKLVYAFNZGPOP-UHFFFAOYSA-N 2-[3-[2-[4-(3-fluorophenyl)-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound FC1=CC=CC(C=2CCN(CCC=3C=C(C=CC=3)C=3N=CC=CC=3)CC=2)=C1 GGKLVYAFNZGPOP-UHFFFAOYSA-N 0.000 claims 1
- VBGFODYMECBXKE-UHFFFAOYSA-N 2-[3-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyrazine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C(C=CC=3)C=3N=CC=NC=3)CC=2)=C1 VBGFODYMECBXKE-UHFFFAOYSA-N 0.000 claims 1
- OMTLYGNWDBVLFE-UHFFFAOYSA-N 2-[3-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C(C=CC=3)C=3N=CC=CC=3)CC=2)=C1 OMTLYGNWDBVLFE-UHFFFAOYSA-N 0.000 claims 1
- BNJBITWHZTVRBT-UHFFFAOYSA-N 2-[3-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyrimidine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C(C=CC=3)C=3N=CC=CN=3)CC=2)=C1 BNJBITWHZTVRBT-UHFFFAOYSA-N 0.000 claims 1
- AVLSWKAQOQPIJX-UHFFFAOYSA-N 2-[4-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3N=CC=CC=3)CC=2)=C1 AVLSWKAQOQPIJX-UHFFFAOYSA-N 0.000 claims 1
- MVYFZCVMGBTQIE-UHFFFAOYSA-N 2-chloro-6-[1-[2-(3-pyridin-4-ylphenyl)ethyl]-3,6-dihydro-2h-pyridin-4-yl]pyridine Chemical compound ClC1=CC=CC(C=2CCN(CCC=3C=C(C=CC=3)C=3C=CN=CC=3)CC=2)=N1 MVYFZCVMGBTQIE-UHFFFAOYSA-N 0.000 claims 1
- UFZYFKMZPPOFND-UHFFFAOYSA-N 2-methyl-5-[3-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound C1=NC(C)=CC=C1C1=CC=CC(CCN2CC=C(CC2)C=2C=C(C=CC=2)C(F)(F)F)=C1 UFZYFKMZPPOFND-UHFFFAOYSA-N 0.000 claims 1
- GSZGXVFNJYIXSU-UHFFFAOYSA-N 2-methyl-5-[4-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound C1=NC(C)=CC=C1C(C=C1)=CC=C1CCN1CC=C(C=2C=C(C=CC=2)C(F)(F)F)CC1 GSZGXVFNJYIXSU-UHFFFAOYSA-N 0.000 claims 1
- WAGFDWFAMYQEPH-UHFFFAOYSA-N 3-[2-methyl-5-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound C1=C(C=2C=NC=CC=2)C(C)=CC=C1CCN(CC=1)CCC=1C1=CC=CC(C(F)(F)F)=C1 WAGFDWFAMYQEPH-UHFFFAOYSA-N 0.000 claims 1
- NERMPSYSZRPYAU-UHFFFAOYSA-N 3-[3-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridazine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C(C=CC=3)C=3N=NC=CC=3)CC=2)=C1 NERMPSYSZRPYAU-UHFFFAOYSA-N 0.000 claims 1
- VRVWULKTIUHPGX-UHFFFAOYSA-N 3-[3-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C(C=CC=3)C=3C=NC=CC=3)CC=2)=C1 VRVWULKTIUHPGX-UHFFFAOYSA-N 0.000 claims 1
- WQZHBVMNFSQWGI-UHFFFAOYSA-N 3-[4-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C=NC=CC=3)CC=2)=C1 WQZHBVMNFSQWGI-UHFFFAOYSA-N 0.000 claims 1
- IXYDBBSEBBTUDK-UHFFFAOYSA-N 4-[3-[2-[1-oxido-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-ium-1-yl]ethyl]phenyl]pyridine Chemical compound C1CC(C=2C=C(C=CC=2)C(F)(F)F)=CC[N+]1([O-])CCC(C=1)=CC=CC=1C1=CC=NC=C1 IXYDBBSEBBTUDK-UHFFFAOYSA-N 0.000 claims 1
- USRDGDMBBSRPAQ-UHFFFAOYSA-N 4-[3-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C(C=CC=3)C=3C=CN=CC=3)CC=2)=C1 USRDGDMBBSRPAQ-UHFFFAOYSA-N 0.000 claims 1
- UZZMVDOPBJYQBP-UHFFFAOYSA-N 4-[4-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C=CN=CC=3)CC=2)=C1 UZZMVDOPBJYQBP-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- PCBSZJZMHIUKIR-UHFFFAOYSA-N 5-[4-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyrimidine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C=NC=NC=3)CC=2)=C1 PCBSZJZMHIUKIR-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229940035676 analgesics Drugs 0.000 claims 1
- 239000000730 antalgic agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0114897A FR2832405B1 (fr) | 2001-11-19 | 2001-11-19 | Tetrahydropyridyl-alkyl-heterocycles azotes, procede pour leur preparation et compositions pharmaceutiques les contenant |
| PCT/FR2002/003929 WO2003044010A1 (fr) | 2001-11-19 | 2002-11-18 | Tetrahydropyridyl-alkyl-heterocycles azotes avec une activity du tnf______ |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005509678A JP2005509678A (ja) | 2005-04-14 |
| JP2005509678A5 true JP2005509678A5 (https=) | 2006-01-12 |
| JP4603794B2 JP4603794B2 (ja) | 2010-12-22 |
Family
ID=8869506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003545647A Expired - Fee Related JP4603794B2 (ja) | 2001-11-19 | 2002-11-18 | Ｔｎｆ活性を有する含窒素テトラヒドロピリジル−アルキル−ヘテロ環 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7211578B2 (https=) |
| EP (1) | EP1448550B1 (https=) |
| JP (1) | JP4603794B2 (https=) |
| AT (1) | ATE499359T1 (https=) |
| AU (1) | AU2002356244B2 (https=) |
| CA (1) | CA2464721C (https=) |
| DE (1) | DE60239284D1 (https=) |
| FR (1) | FR2832405B1 (https=) |
| HU (1) | HUP0402229A3 (https=) |
| MX (1) | MXPA04004760A (https=) |
| PL (1) | PL208647B1 (https=) |
| WO (1) | WO2003044010A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200840566A (en) * | 2006-12-22 | 2008-10-16 | Esteve Labor Dr | Heterocyclyl-substituted-ethylamino-phenyl derivatives, their preparation and use as medicaments |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4885572A (https=) * | 1972-02-17 | 1973-11-13 | ||
| JPS49100090A (https=) * | 1973-01-30 | 1974-09-20 | ||
| JPS49100089A (https=) * | 1973-01-30 | 1974-09-20 | ||
| JPS5236B2 (https=) * | 1973-03-28 | 1977-01-05 | ||
| JPS5046669A (https=) * | 1973-03-28 | 1975-04-25 | ||
| DE19517851A1 (de) * | 1995-05-16 | 1996-11-21 | Hoechst Ag | Organometallverbindung |
| FR2757160B1 (fr) | 1996-12-13 | 1999-03-12 | Sanofi Sa | 1-phenylalkyl-1,2,3,6-tetrahydropyridines |
| US6316466B1 (en) * | 1998-05-05 | 2001-11-13 | Syntex (U.S.A.) Llc | Pyrazole derivatives P-38 MAP kinase inhibitors |
| DZ2796A1 (fr) * | 1998-05-21 | 2003-12-01 | Smithkline Beecham Corp | Composés à fonction bis-aminométhyl-carbonyle nouveaux, procédé pour leur préparation et compositions pharmaceutiques les contenant. |
| HK1046532B (zh) * | 1999-10-22 | 2005-03-18 | Sanofi-Aventis | 具有抑制tnf活性的苯基-和吡啶基-四氫吡啶 |
| FR2803593B1 (fr) * | 2000-01-06 | 2002-02-15 | Sanofi Synthelabo | Nouvelles tetrahydropyridines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| SI1283839T1 (https=) * | 2000-05-26 | 2005-08-31 | Schering Corp |
-
2001
- 2001-11-19 FR FR0114897A patent/FR2832405B1/fr not_active Expired - Fee Related
-
2002
- 2002-11-18 JP JP2003545647A patent/JP4603794B2/ja not_active Expired - Fee Related
- 2002-11-18 US US10/495,890 patent/US7211578B2/en not_active Expired - Fee Related
- 2002-11-18 MX MXPA04004760A patent/MXPA04004760A/es active IP Right Grant
- 2002-11-18 CA CA2464721A patent/CA2464721C/en not_active Expired - Fee Related
- 2002-11-18 EP EP02803433A patent/EP1448550B1/fr not_active Expired - Lifetime
- 2002-11-18 DE DE60239284T patent/DE60239284D1/de not_active Expired - Lifetime
- 2002-11-18 PL PL370832A patent/PL208647B1/pl not_active IP Right Cessation
- 2002-11-18 AU AU2002356244A patent/AU2002356244B2/en not_active Ceased
- 2002-11-18 WO PCT/FR2002/003929 patent/WO2003044010A1/fr not_active Ceased
- 2002-11-18 AT AT02803433T patent/ATE499359T1/de not_active IP Right Cessation
- 2002-11-18 HU HU0402229A patent/HUP0402229A3/hu unknown
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