NO324074B1 - Anvendelse av 4-substituerte tetrahydropyridiner for fremstilling av farmasoytiske preparater som virker pa TGF-<beta>1, samt en forbindelse - Google Patents
Anvendelse av 4-substituerte tetrahydropyridiner for fremstilling av farmasoytiske preparater som virker pa TGF-<beta>1, samt en forbindelse Download PDFInfo
- Publication number
- NO324074B1 NO324074B1 NO19995821A NO995821A NO324074B1 NO 324074 B1 NO324074 B1 NO 324074B1 NO 19995821 A NO19995821 A NO 19995821A NO 995821 A NO995821 A NO 995821A NO 324074 B1 NO324074 B1 NO 324074B1
- Authority
- NO
- Norway
- Prior art keywords
- tetrahydropyridine
- ethyl
- group
- trifluoromethylphenyl
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 93
- -1 4-substituted tetrahydropyridines Chemical class 0.000 title claims description 44
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title abstract description 36
- 102000004887 Transforming Growth Factor beta Human genes 0.000 title 1
- 108090001012 Transforming Growth Factor beta Proteins 0.000 title 1
- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 43
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
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- 239000001257 hydrogen Substances 0.000 claims description 19
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- WJJYZXPHLSLMGE-UHFFFAOYSA-N xaliproden Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C4C=CC=CC4=CC=3)CC=2)=C1 WJJYZXPHLSLMGE-UHFFFAOYSA-N 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 14
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- 125000000217 alkyl group Chemical group 0.000 claims description 12
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 4
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- CPNOPIRQIVSHKK-UHFFFAOYSA-N 1-[2-[4-(cyclohexen-1-yl)phenyl]ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3CCCCC=3)CC=2)=C1 CPNOPIRQIVSHKK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- FMGSTXSBZFEKMC-UHFFFAOYSA-N 1-(2-benzo[f][1,3]benzodioxol-6-ylethyl)-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical group FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C4C=C5OCOC5=CC4=CC=3)CC=2)=C1 FMGSTXSBZFEKMC-UHFFFAOYSA-N 0.000 claims description 3
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- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
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- 125000005504 styryl group Chemical group 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
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- 239000011737 fluorine Substances 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
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Landscapes
- Health & Medical Sciences (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9706522A FR2763847B1 (fr) | 1997-05-28 | 1997-05-28 | Utilisation de tetrahydropyridines 4-substituees pour fabriquer des medicaments agissant sur le tgf-beta-1 |
| PCT/FR1998/001000 WO1998053821A1 (fr) | 1997-05-28 | 1998-05-20 | Utilisation de tetrahydropyridines 4-substituees pour fabriquer des medicaments agissant sur le tgf-beta1 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO995821D0 NO995821D0 (no) | 1999-11-26 |
| NO995821L NO995821L (no) | 2000-01-28 |
| NO324074B1 true NO324074B1 (no) | 2007-08-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19995821A NO324074B1 (no) | 1997-05-28 | 1999-11-26 | Anvendelse av 4-substituerte tetrahydropyridiner for fremstilling av farmasoytiske preparater som virker pa TGF-<beta>1, samt en forbindelse |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US6342505B1 (ja) |
| EP (1) | EP1017385B1 (ja) |
| JP (1) | JP2002511855A (ja) |
| AR (1) | AR012856A1 (ja) |
| AT (1) | ATE245027T1 (ja) |
| AU (1) | AU7774898A (ja) |
| BR (1) | BR9809444A (ja) |
| CA (1) | CA2290557C (ja) |
| DE (1) | DE69816456T2 (ja) |
| DK (1) | DK1017385T3 (ja) |
| ES (1) | ES2201502T3 (ja) |
| FR (1) | FR2763847B1 (ja) |
| NO (1) | NO324074B1 (ja) |
| PT (1) | PT1017385E (ja) |
| WO (1) | WO1998053821A1 (ja) |
| ZA (1) | ZA984564B (ja) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2757510B1 (fr) * | 1996-12-23 | 2000-01-07 | Sanofi Sa | Forme microparticulaire d'un derive de tetrahydropyridine |
| FR2763847B1 (fr) * | 1997-05-28 | 2003-06-06 | Sanofi Sa | Utilisation de tetrahydropyridines 4-substituees pour fabriquer des medicaments agissant sur le tgf-beta-1 |
| FR2831166B1 (fr) * | 2001-10-18 | 2004-02-27 | Sanofi Synthelabo | Aralkyl-tetrahydro-pyridines, leur preparation et compositions pharmaceutiques les contenant |
| GB0226930D0 (en) * | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
| US20090076048A1 (en) * | 2007-09-19 | 2009-03-19 | Protia, Llc | Deuterium-enriched xaliproden |
| DE102008060549A1 (de) | 2008-12-04 | 2010-06-10 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Wirkstoff-Peptid-Konstrukt zur extrazellulären Anreicherung |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2531707A1 (fr) | 1982-08-16 | 1984-02-17 | Midy Spa | Trifluoromethylphenyltetrahydropyridines substituees a activite anorexigene, un procede de preparation et compositions pharmaceutiques |
| FR2662355B1 (fr) * | 1990-05-22 | 1994-11-10 | Sanofi Sa | Utilisation de la 1-[2-(2-naphtyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine pour la preparation de medicaments destines au traitement de troubles cerebraux et neuronaux. |
| FR2662442A1 (fr) | 1990-05-23 | 1991-11-29 | Midy Spa | Trifluoromethylphenyltetrahydropyridines n-substituees procede pour leur preparation, intermediaires du procede et compositions pharmaceutiques les contenant. |
| US5618822A (en) | 1990-05-23 | 1997-04-08 | Sanofi | N-substituted trifluoromethylphenyltetrahydropyridines, process for the preparation thereof, intermediates in said process and pharmaceutical compositions containing them |
| FR2672213B1 (fr) | 1991-02-05 | 1995-03-10 | Sanofi Sa | Utilisation de derives 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridiniques comme capteurs de radicaux libres. |
| HU211019B (en) | 1991-12-02 | 1995-09-28 | Richter Gedeon Vegyeszet | Process for producing new 1,2,3,6-tetrahydropyridine and piperidine derivatives substituted with n-(hydroxylalkyl) group and compositions comprising such compounds |
| US5522011A (en) * | 1993-09-27 | 1996-05-28 | International Business Machines Corporation | Speech coding apparatus and method using classification rules |
| MX9603868A (es) | 1995-01-11 | 1997-03-29 | Otsuka Pharma Co Ltd | Composicion farmaceutica de derivados de indeno para la regulacion de la apoptosis. |
| FR2736053B1 (fr) * | 1995-06-28 | 1997-09-19 | Sanofi Sa | Nouvelles 1-phenylalkyl-1,2,3,6-tetrahydropyridines |
| FR2757160B1 (fr) * | 1996-12-13 | 1999-03-12 | Sanofi Sa | 1-phenylalkyl-1,2,3,6-tetrahydropyridines |
| FR2757161B1 (fr) * | 1996-12-13 | 1999-03-12 | Sanofi Sa | Diphenylalkyl-tetrahydropyridines |
| FR2762514B1 (fr) * | 1997-04-29 | 1999-10-22 | Sanofi Sa | Utilisation de derives de la tetrahydropyridine pour la preparation de medicaments pour le traitement des maladies entrainant une demyelinisation |
| FR2763847B1 (fr) * | 1997-05-28 | 2003-06-06 | Sanofi Sa | Utilisation de tetrahydropyridines 4-substituees pour fabriquer des medicaments agissant sur le tgf-beta-1 |
-
1997
- 1997-05-28 FR FR9706522A patent/FR2763847B1/fr not_active Expired - Fee Related
-
1998
- 1998-05-20 DE DE69816456T patent/DE69816456T2/de not_active Expired - Fee Related
- 1998-05-20 ES ES98925747T patent/ES2201502T3/es not_active Expired - Lifetime
- 1998-05-20 AT AT98925747T patent/ATE245027T1/de not_active IP Right Cessation
- 1998-05-20 EP EP98925747A patent/EP1017385B1/fr not_active Expired - Lifetime
- 1998-05-20 BR BR9809444-0A patent/BR9809444A/pt not_active Application Discontinuation
- 1998-05-20 US US09/423,884 patent/US6342505B1/en not_active Expired - Fee Related
- 1998-05-20 CA CA002290557A patent/CA2290557C/en not_active Expired - Fee Related
- 1998-05-20 JP JP50030999A patent/JP2002511855A/ja not_active Withdrawn
- 1998-05-20 DK DK98925747T patent/DK1017385T3/da active
- 1998-05-20 WO PCT/FR1998/001000 patent/WO1998053821A1/fr active IP Right Grant
- 1998-05-20 PT PT98925747T patent/PT1017385E/pt unknown
- 1998-05-20 AU AU77748/98A patent/AU7774898A/en not_active Abandoned
- 1998-05-26 AR ARP980102423A patent/AR012856A1/es unknown
- 1998-05-28 ZA ZA984564A patent/ZA984564B/xx unknown
-
1999
- 1999-11-26 NO NO19995821A patent/NO324074B1/no unknown
-
2001
- 2001-11-20 US US10/044,223 patent/US6693118B2/en not_active Expired - Fee Related
-
2004
- 2004-02-05 US US10/773,073 patent/US7320982B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PT1017385E (pt) | 2003-10-31 |
| WO1998053821A1 (fr) | 1998-12-03 |
| DE69816456T2 (de) | 2004-04-15 |
| FR2763847A1 (fr) | 1998-12-04 |
| NO995821L (no) | 2000-01-28 |
| NO995821D0 (no) | 1999-11-26 |
| US20040157868A1 (en) | 2004-08-12 |
| JP2002511855A (ja) | 2002-04-16 |
| EP1017385B1 (fr) | 2003-07-16 |
| ATE245027T1 (de) | 2003-08-15 |
| CA2290557A1 (en) | 1998-12-03 |
| US6342505B1 (en) | 2002-01-29 |
| CA2290557C (en) | 2007-11-27 |
| FR2763847B1 (fr) | 2003-06-06 |
| EP1017385A1 (fr) | 2000-07-12 |
| ES2201502T3 (es) | 2004-03-16 |
| BR9809444A (pt) | 2000-06-13 |
| US20020091143A1 (en) | 2002-07-11 |
| ZA984564B (en) | 1998-12-03 |
| AR012856A1 (es) | 2000-11-22 |
| DK1017385T3 (da) | 2003-10-27 |
| AU7774898A (en) | 1998-12-30 |
| US7320982B2 (en) | 2008-01-22 |
| US6693118B2 (en) | 2004-02-17 |
| DE69816456D1 (de) | 2003-08-21 |
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