NO310144B1 - 4-Aryl-1-fenylalkyl-1,2,3,6-tetrahydropyridiner med neurotropisk og neurobeskyttende aktivitet, fremgangsmåte forfremstilling derav og farmasöytisk sammensetning - Google Patents
4-Aryl-1-fenylalkyl-1,2,3,6-tetrahydropyridiner med neurotropisk og neurobeskyttende aktivitet, fremgangsmåte forfremstilling derav og farmasöytisk sammensetning Download PDFInfo
- Publication number
- NO310144B1 NO310144B1 NO19976079A NO976079A NO310144B1 NO 310144 B1 NO310144 B1 NO 310144B1 NO 19976079 A NO19976079 A NO 19976079A NO 976079 A NO976079 A NO 976079A NO 310144 B1 NO310144 B1 NO 310144B1
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- Norway
- Prior art keywords
- mixture
- ethyl
- tetrahydropyridine
- mol
- formula
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 74
- 238000002360 preparation method Methods 0.000 title claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 230000000324 neuroprotective effect Effects 0.000 title description 3
- 230000002276 neurotropic effect Effects 0.000 title description 3
- -1 phenoxy, phenylamino Chemical group 0.000 claims abstract description 41
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 239000012453 solvate Substances 0.000 claims abstract description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 161
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 47
- 238000010992 reflux Methods 0.000 claims description 20
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- 238000006243 chemical reaction Methods 0.000 claims description 18
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 18
- 239000002585 base Substances 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 238000012546 transfer Methods 0.000 claims description 8
- 150000002940 palladium Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000012736 aqueous medium Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical group 0.000 claims description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 abstract 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000005504 styryl group Chemical group 0.000 abstract 1
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- 238000004587 chromatography analysis Methods 0.000 description 30
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
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- HAKSOKWVNPZVNM-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridine;hydrochloride Chemical compound Cl.C1CNC=CC1 HAKSOKWVNPZVNM-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 239000012047 saturated solution Substances 0.000 description 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 17
- 239000002253 acid Substances 0.000 description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
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- 239000012071 phase Substances 0.000 description 12
- 238000004809 thin layer chromatography Methods 0.000 description 12
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- IFYKRMQORZOMNY-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCNCC=2)=C1 IFYKRMQORZOMNY-UHFFFAOYSA-N 0.000 description 10
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
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- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- UEKQSLXYFDHEJR-UHFFFAOYSA-N tributylstannane;hydrochloride Chemical compound Cl.CCCC[SnH](CCCC)CCCC UEKQSLXYFDHEJR-UHFFFAOYSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 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 description 1
Classifications
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9507760A FR2736053B1 (fr) | 1995-06-28 | 1995-06-28 | Nouvelles 1-phenylalkyl-1,2,3,6-tetrahydropyridines |
| PCT/FR1996/000995 WO1997001536A1 (fr) | 1995-06-28 | 1996-06-26 | 4-aryl-1-phenylalkyl-1,2,3,6-tetrahydropyridines ayant une activite neurotrophique et neuroprotectrice |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO976079D0 NO976079D0 (no) | 1997-12-23 |
| NO976079L NO976079L (no) | 1997-12-23 |
| NO310144B1 true NO310144B1 (no) | 2001-05-28 |
Family
ID=9480466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19976079A NO310144B1 (no) | 1995-06-28 | 1997-12-23 | 4-Aryl-1-fenylalkyl-1,2,3,6-tetrahydropyridiner med neurotropisk og neurobeskyttende aktivitet, fremgangsmåte forfremstilling derav og farmasöytisk sammensetning |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US5981754A (cs) |
| EP (2) | EP0837848B1 (cs) |
| JP (2) | JP3147906B2 (cs) |
| KR (1) | KR100460581B1 (cs) |
| CN (1) | CN1153765C (cs) |
| AT (1) | ATE223897T1 (cs) |
| AU (1) | AU715090B2 (cs) |
| BR (1) | BR9608662A (cs) |
| CA (1) | CA2225746C (cs) |
| CY (1) | CY2312B1 (cs) |
| CZ (1) | CZ291075B6 (cs) |
| DE (1) | DE69623631T2 (cs) |
| DK (1) | DK0837848T3 (cs) |
| EE (1) | EE03870B1 (cs) |
| ES (1) | ES2183965T3 (cs) |
| FR (1) | FR2736053B1 (cs) |
| HK (1) | HK1014952A1 (cs) |
| HU (1) | HUP9900055A3 (cs) |
| IL (1) | IL122159A (cs) |
| IS (1) | IS1999B (cs) |
| NO (1) | NO310144B1 (cs) |
| NZ (1) | NZ312723A (cs) |
| PL (2) | PL192353B1 (cs) |
| PT (1) | PT837848E (cs) |
| RU (1) | RU2163237C2 (cs) |
| SK (2) | SK283707B6 (cs) |
| TR (1) | TR199701710T1 (cs) |
| UA (1) | UA62914C2 (cs) |
| WO (1) | WO1997001536A1 (cs) |
| ZA (1) | ZA965527B (cs) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| FR2771006B1 (fr) * | 1997-11-14 | 2000-12-01 | Sanofi Sa | Association de principes actifs pour le traitement de la demence senile du type alzheimer |
| FR2771007B1 (fr) * | 1997-11-14 | 2000-12-01 | Sanofi Sa | Association de principes actifs pour le traitement de la demence senile du type alzheimer |
| CO4980891A1 (es) * | 1997-11-14 | 2000-11-27 | Sanofi Sa | Asociacion de principios activos para el tratamiento de la demencia senil de tipo azheimer |
| WO1999065896A1 (en) * | 1998-06-19 | 1999-12-23 | Eli Lilly And Company | Preparation of heteroaryl compounds |
| FR2803593B1 (fr) * | 2000-01-06 | 2002-02-15 | Sanofi Synthelabo | Nouvelles tetrahydropyridines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| ATE365162T1 (de) | 2001-04-20 | 2007-07-15 | Sanofi Aventis | Tetrahydropyridyl-alkyl-heterozykle, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen die sie enthalten |
| FR2823748B1 (fr) * | 2001-04-20 | 2004-02-20 | Sanofi Synthelabo | Tetrahydropyridyl-alkyl-benzodiazines, 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 |
| EA009027B1 (ru) * | 2002-12-16 | 2007-10-26 | Мицубиси Фарма Корпорейшн | Производные 3-замещенного-4-пиримидона |
| EP1657240A4 (en) | 2003-08-18 | 2009-04-08 | Fujifilm Finechemicals Co Ltd | PYRIDYLTETRAHYDROPYRIDINE, PYRIDYLPIPERIDINE AND METHOD FOR THE PRODUCTION THEREOF |
| TWI350168B (en) * | 2004-05-07 | 2011-10-11 | Incyte Corp | Amido compounds and their use as pharmaceuticals |
| EA200700118A1 (ru) * | 2004-06-24 | 2007-08-31 | Инсайт Корпорейшн | Амидосоединения и их применение в качестве лекарственных средств |
| CA2584502A1 (en) * | 2004-06-24 | 2006-01-05 | Incyte Corporation | 2-methylpropanamides and their use as pharmaceuticals |
| EP1758882A4 (en) * | 2004-06-24 | 2008-01-23 | Incyte Corp | AMID COMPOUNDS AND THEIR USE AS MEDICAMENTS |
| US20060009491A1 (en) * | 2004-06-24 | 2006-01-12 | Incyte Corporation | Amido compounds and their use as pharmaceuticals |
| EP1758580A4 (en) | 2004-06-24 | 2008-01-16 | Incyte Corp | N-SUBSTITUTED PIPERIDINE AND ITS USE AS A MEDICAMENT |
| US20060122197A1 (en) * | 2004-08-10 | 2006-06-08 | Wenqing Yao | Amido compounds and their use as pharmaceuticals |
| GEP20125565B (en) * | 2004-11-10 | 2012-07-10 | Incyte Corp | Lactam compounds and their pharmaceutical use |
| US8110581B2 (en) | 2004-11-10 | 2012-02-07 | Incyte Corporation | Lactam compounds and their use as pharmaceuticals |
| CA2587153A1 (en) * | 2004-11-18 | 2006-05-26 | Incyte Corporation | Inhibitors of 11-.beta. hydroxyl steroid dehydrogenase type 1 and methods of using the same |
| 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 |
| JP4864342B2 (ja) * | 2005-04-27 | 2012-02-01 | 北興化学工業株式会社 | ビアリール化合物の製造方法 |
| US20070066584A1 (en) * | 2005-09-21 | 2007-03-22 | Wenqing Yao | Amido compounds and their use as pharmaceuticals |
| BRPI0619446A2 (pt) * | 2005-12-05 | 2011-10-04 | Incyte Corp | compostos de lactama, suas composições e método de modulação da atividade de 11bhsd1 |
| WO2007084314A2 (en) * | 2006-01-12 | 2007-07-26 | Incyte Corporation | MODULATORS OF 11-ß HYDROXYL STEROID DEHYDROGENASE TYPE 1, PHARMACEUTICAL COMPOSITIONS THEREOF, AND METHODS OF USING THE SAME |
| BRPI0707408A2 (pt) * | 2006-01-31 | 2011-05-03 | Incyte Corp | compostos de amido e seu uso como produtos farmacêuticos |
| WO2007101270A1 (en) * | 2006-03-02 | 2007-09-07 | Incyte Corporation | MODULATORS OF 11-β HYDROXYL STEROID DEHYDROGENASE TYPE 1, PHARMACEUTICAL COMPOSITIONS THEREOF, AND METHODS OF USING THE SAME |
| US20070208001A1 (en) * | 2006-03-03 | 2007-09-06 | Jincong Zhuo | Modulators of 11- beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same |
| US20070293529A1 (en) * | 2006-05-01 | 2007-12-20 | Yun-Long Li | Tetrasubstituted ureas as modulators of 11-beta hydroxyl steroid dehydrogenase type 1 |
| WO2007137066A2 (en) * | 2006-05-17 | 2007-11-29 | Incyte Corporation | HETEROCYCLIC INHIBITORS OF 11-β HYDROXYL STEROID DEHYDROGENASE TYPE I AND METHODS OF USING THE SAME |
| CL2008001839A1 (es) * | 2007-06-21 | 2009-01-16 | Incyte Holdings Corp | Compuestos derivados de 2,7-diazaespirociclos, inhibidores de 11-beta hidroxil esteroide deshidrogenasa tipo 1; composicion farmaceutica que comprende a dichos compuestos; utiles para tratar la obesidad, diabetes, intolerancia a la glucosa, diabetes tipo ii, entre otras enfermedades. |
| KR20100135711A (ko) | 2007-12-20 | 2010-12-27 | 엔비보 파마슈티칼즈, 인코퍼레이티드 | 사중치환된 벤젠 |
| JP5899119B2 (ja) * | 2010-01-19 | 2016-04-06 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | アリール酢酸誘導体及びヘテロアリール酢酸誘導体を製造する方法 |
| US10858351B2 (en) | 2017-04-26 | 2020-12-08 | Alberta Research Chemicals Inc. | Substituted tetrahydropyridine derivatives as IDO-1 inhibitors and uses thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2098248T3 (es) * | 1989-05-17 | 1997-05-01 | Pfizer | Derivados de 2-piperidino-1-alcanoles como agentes antiisquemicos. |
| FR2650505B1 (fr) * | 1989-08-07 | 1994-06-03 | Midy Spa | Utilisation de trifluoromethylphenyltetrahydropyridines pour la preparation de medicaments destines a combattre les troubles de la motricite intestinale |
| 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. |
| 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 |
| DE4325855A1 (de) * | 1993-08-02 | 1995-02-09 | Boehringer Ingelheim Kg | Neue Benzoesäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
-
1995
- 1995-06-28 FR FR9507760A patent/FR2736053B1/fr not_active Expired - Fee Related
-
1996
- 1996-06-26 EP EP96924023A patent/EP0837848B1/fr not_active Expired - Lifetime
- 1996-06-26 AU AU64619/96A patent/AU715090B2/en not_active Ceased
- 1996-06-26 NZ NZ312723A patent/NZ312723A/en unknown
- 1996-06-26 EE EE9700348A patent/EE03870B1/xx not_active IP Right Cessation
- 1996-06-26 HU HU9900055A patent/HUP9900055A3/hu unknown
- 1996-06-26 AT AT96924023T patent/ATE223897T1/de not_active IP Right Cessation
- 1996-06-26 KR KR1019970709747A patent/KR100460581B1/ko not_active IP Right Cessation
- 1996-06-26 WO PCT/FR1996/000995 patent/WO1997001536A1/fr active IP Right Grant
- 1996-06-26 US US08/973,712 patent/US5981754A/en not_active Expired - Fee Related
- 1996-06-26 EP EP02006482A patent/EP1216996A3/fr not_active Withdrawn
- 1996-06-26 DK DK96924023T patent/DK0837848T3/da active
- 1996-06-26 IL IL12215996A patent/IL122159A/en not_active IP Right Cessation
- 1996-06-26 RU RU98101492/04A patent/RU2163237C2/ru not_active IP Right Cessation
- 1996-06-26 PL PL357052A patent/PL192353B1/pl not_active IP Right Cessation
- 1996-06-26 JP JP50420697A patent/JP3147906B2/ja not_active Expired - Fee Related
- 1996-06-26 SK SK1781-97A patent/SK283707B6/sk unknown
- 1996-06-26 CA CA002225746A patent/CA2225746C/en not_active Expired - Fee Related
- 1996-06-26 TR TR97/01710T patent/TR199701710T1/xx unknown
- 1996-06-26 PT PT96924023T patent/PT837848E/pt unknown
- 1996-06-26 BR BR9608662A patent/BR9608662A/pt not_active IP Right Cessation
- 1996-06-26 CZ CZ19974222A patent/CZ291075B6/cs not_active IP Right Cessation
- 1996-06-26 DE DE69623631T patent/DE69623631T2/de not_active Expired - Fee Related
- 1996-06-26 UA UA97126360A patent/UA62914C2/uk unknown
- 1996-06-26 SK SK593-2003A patent/SK285433B6/sk unknown
- 1996-06-26 PL PL96324216A patent/PL187087B1/pl not_active IP Right Cessation
- 1996-06-26 ES ES96924023T patent/ES2183965T3/es not_active Expired - Lifetime
- 1996-06-26 CN CNB961950900A patent/CN1153765C/zh not_active Expired - Fee Related
- 1996-06-28 ZA ZA965527A patent/ZA965527B/xx unknown
-
1997
- 1997-12-23 NO NO19976079A patent/NO310144B1/no unknown
- 1997-12-23 IS IS4641A patent/IS1999B/is unknown
-
1999
- 1999-01-14 HK HK99100183A patent/HK1014952A1/xx not_active IP Right Cessation
-
2000
- 2000-07-31 JP JP2000231069A patent/JP3302351B2/ja not_active Expired - Fee Related
-
2003
- 2003-01-15 CY CY0300004A patent/CY2312B1/xx unknown
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