ES2243462T3 - Decahidro-isoquinolinas. - Google Patents
Decahidro-isoquinolinas.Info
- Publication number
- ES2243462T3 ES2243462T3 ES01913896T ES01913896T ES2243462T3 ES 2243462 T3 ES2243462 T3 ES 2243462T3 ES 01913896 T ES01913896 T ES 01913896T ES 01913896 T ES01913896 T ES 01913896T ES 2243462 T3 ES2243462 T3 ES 2243462T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- compound
- free base
- addition salt
- alkyl
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 239000002253 acid Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 239000012458 free base Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 10
- 201000000980 schizophrenia Diseases 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
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- 238000000034 method Methods 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 229940127557 pharmaceutical product Drugs 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- RDSAUPRYZCQORM-BJTUFNSYSA-N [(4s,4as,8ar)-2-[(2s)-3-(6-methoxypyridin-3-yl)-2-methylpropyl]-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-4-yl]-[4-(3,4-difluorophenyl)piperazin-1-yl]methanone Chemical compound C1=NC(OC)=CC=C1C[C@H](C)CN1C[C@@H](C(=O)N2CCN(CC2)C=2C=C(F)C(F)=CC=2)[C@H]2CCCC[C@H]2C1 RDSAUPRYZCQORM-BJTUFNSYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 28
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- 239000003795 chemical substances by application Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- 235000019439 ethyl acetate Nutrition 0.000 description 12
- 239000012071 phase Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
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- NFPMGIHGKCNKNA-VIFPVBQESA-N (2s)-2-methyl-3-quinoxalin-6-ylpropanal Chemical compound N1=CC=NC2=CC(C[C@H](C)C=O)=CC=C21 NFPMGIHGKCNKNA-VIFPVBQESA-N 0.000 description 3
- LGRGXMSVDFWJQL-ZETCQYMHSA-N (2s)-3-(2,1,3-benzothiadiazol-5-yl)-2-methylpropan-1-ol Chemical compound C1=C(C[C@@H](CO)C)C=CC2=NSN=C21 LGRGXMSVDFWJQL-ZETCQYMHSA-N 0.000 description 3
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- 241001465754 Metazoa Species 0.000 description 3
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- 208000019022 Mood disease Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- 150000002148 esters Chemical class 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- MCVMLYSLPCECGO-UHFFFAOYSA-N isoquinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CN=CC2=C1 MCVMLYSLPCECGO-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
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- BGQSOXANJRWNAC-KSMMKXTCSA-N (2s)-3-(2,1,3-benzothiadiazol-5-yl)-n-[(1r,2r)-1-hydroxy-1-phenylpropan-2-yl]-n,2-dimethylpropanamide Chemical compound C1([C@@H](O)[C@@H](C)N(C)C(=O)[C@H](CC2=CC3=NSN=C3C=C2)C)=CC=CC=C1 BGQSOXANJRWNAC-KSMMKXTCSA-N 0.000 description 2
- RLPVPYVIDWONQA-XHNCKOQMSA-N (4s,4as,8ar)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-4-carboxylic acid Chemical compound C1CCC[C@@H]2[C@H](C(=O)O)CNC[C@@H]21 RLPVPYVIDWONQA-XHNCKOQMSA-N 0.000 description 2
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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- NENLYAQPNATJSU-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline Chemical class C1NCCC2CCCCC21 NENLYAQPNATJSU-UHFFFAOYSA-N 0.000 description 1
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- ZAIIUFWBKFPTGD-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxycarbonyl]-1,2,3,4,4a,5,6,7-octahydroisoquinoline-4-carboxylic acid Chemical compound C1CCC=C2C(C(=O)OC(C)(C)C)NCC(C(O)=O)C21 ZAIIUFWBKFPTGD-UHFFFAOYSA-N 0.000 description 1
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- 238000012552 review Methods 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 230000004037 social stress Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 1
- NHXLMOGPVYXJNR-UHFFFAOYSA-N srif Chemical compound N1C(=O)C(C(C)O)NC(=O)C(CCCCN)NC(=O)C(CC=2C3=CC=CC=C3NC=2)NC(=O)C(CC=2C=CC=CC=2)NC(=O)C(CC=2C=CC=CC=2)NC(=O)C(CC(N)=O)NC(=O)C(CCCCN)NC(=O)C(NC(=O)CNC(=O)C(C)N)CSSCC(C(O)=O)NC(=O)C(CO)NC(=O)C(C(O)C)NC(=O)C1CC1=CC=CC=C1 NHXLMOGPVYXJNR-UHFFFAOYSA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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- 229940102566 valproate Drugs 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 238000002424 x-ray crystallography Methods 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/22—Anxiolytics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0007108.4A GB0007108D0 (en) | 2000-03-23 | 2000-03-23 | Organic compounds |
| GB0007108 | 2000-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2243462T3 true ES2243462T3 (es) | 2005-12-01 |
Family
ID=9888307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES01913896T Expired - Lifetime ES2243462T3 (es) | 2000-03-23 | 2001-03-21 | Decahidro-isoquinolinas. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6635647B2 (enExample) |
| EP (1) | EP1268466B1 (enExample) |
| JP (1) | JP4118565B2 (enExample) |
| AR (1) | AR029821A1 (enExample) |
| AT (1) | ATE298332T1 (enExample) |
| AU (1) | AU2001239310A1 (enExample) |
| CA (1) | CA2402751C (enExample) |
| CO (1) | CO5271675A1 (enExample) |
| DE (1) | DE60111621T2 (enExample) |
| DK (1) | DK1268466T3 (enExample) |
| ES (1) | ES2243462T3 (enExample) |
| GB (1) | GB0007108D0 (enExample) |
| PE (1) | PE20011114A1 (enExample) |
| PT (1) | PT1268466E (enExample) |
| WO (1) | WO2001070731A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB0128996D0 (en) | 2001-12-04 | 2002-01-23 | Novartis Ag | Organic compounds |
| GB0420722D0 (en) | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| WO2007085651A1 (en) * | 2006-01-30 | 2007-08-02 | Speedel Experimenta Ag | Process for the stereoselective preparation of alcohols from alpha, beta- insaturated compounds |
| AR059898A1 (es) | 2006-03-15 | 2008-05-07 | Janssen Pharmaceutica Nv | Derivados de 3-ciano-piridona 1,4-disustituida y su uso como moduladores alostericos de los receptores mglur2 |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| CA2697399C (en) | 2007-09-14 | 2016-01-19 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | 1,3-disubstituted 4-(aryl-x-phenyl)-1h-pyridin-2-ones |
| MX2010002536A (es) | 2007-09-14 | 2010-08-10 | Ortho Mcneil Janssen Pharm | 4-fenil-3,4,5,6-tetrahidro-2h, 1'h-[1,4]bipiridinil-2'-onas 1',3'-disubstituidas. |
| BRPI0918055A2 (pt) | 2008-09-02 | 2015-12-01 | Addex Pharmaceuticals Sa | derivados de 3-azabiciclo[3,1,0]hexila como moduladores de receptores metabotrópicos de glutamato. |
| CA2744138C (en) | 2008-11-28 | 2015-08-11 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| SG176021A1 (en) | 2009-05-12 | 2011-12-29 | Janssen Pharmaceuticals Inc | 1,2,4-triazolo [4,3-a] pyridine derivatives and their use for the treatment or prevention of neurological and psychiatric disorders |
| ES2409006T3 (es) | 2009-05-12 | 2013-06-24 | Janssen Pharmaceuticals Inc. | Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de los receptores mGluR2 |
| US8343977B2 (en) | 2009-12-30 | 2013-01-01 | Arqule, Inc. | Substituted triazolo-pyrimidine compounds |
| PL2649069T3 (pl) | 2010-11-08 | 2016-01-29 | Janssen Pharmaceuticals Inc | Pochodne 1,2,4-triazolo[4,3-a]pirydyny i ich zastosowanie jako dodatnich allosterycznych modulatorów receptorów mGluR2 |
| WO2012062759A1 (en) | 2010-11-08 | 2012-05-18 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| US9012448B2 (en) | 2010-11-08 | 2015-04-21 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| PT3096790T (pt) | 2014-01-21 | 2019-10-15 | Janssen Pharmaceutica Nv | Combinações compreendendo moduladores alostéricos positivos ou agonistas ortostéricos do recetor glutamatérgico metabotrópico do subtipo 2 e seu uso |
| EA202192105A3 (ru) | 2014-02-04 | 2022-02-28 | Янссен Фармацевтика Нв | Комбинации, содержащие положительные аллостерические модуляторы или ортостерические агонисты метаботропного глутаматергического рецептора 2 подтипа, и их применение |
| KR20200035035A (ko) | 2017-07-31 | 2020-04-01 | 노파르티스 아게 | 코카인 사용 감소 또는 코카인 사용 재발 예방에 있어서 마보글루란트의 용도 |
| CN111108105B (zh) | 2017-09-22 | 2023-03-31 | 朱比兰特埃皮帕德有限公司 | 作为pad抑制剂的杂环化合物 |
| KR102782563B1 (ko) | 2017-10-18 | 2025-03-14 | 주빌런트 에피파드 엘엘씨 | Pad 억제제로서의 이미다조-피리딘 화합물 |
| AU2018362046B2 (en) | 2017-11-06 | 2023-04-13 | Jubilant Prodel LLC | Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation |
| HUE067265T2 (hu) | 2017-11-24 | 2024-10-28 | Jubilant Episcribe Llc | Heterociklusos vegyületek mint PRMT5 inhibitorok |
| EP3765453A1 (en) | 2018-03-13 | 2021-01-20 | Jubilant Prodel LLC | Bicyclic compounds as inhibitors of pd1/pd-l1 interaction/activation |
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| US6329389B1 (en) * | 1998-04-08 | 2001-12-11 | Takeda Chemical Industries, Ltd. | Amine compounds, their production and use |
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2000
- 2000-03-23 GB GBGB0007108.4A patent/GB0007108D0/en not_active Ceased
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2001
- 2001-03-21 WO PCT/EP2001/003211 patent/WO2001070731A1/en not_active Ceased
- 2001-03-21 PE PE2001000262A patent/PE20011114A1/es not_active Application Discontinuation
- 2001-03-21 EP EP01913896A patent/EP1268466B1/en not_active Expired - Lifetime
- 2001-03-21 DE DE60111621T patent/DE60111621T2/de not_active Expired - Lifetime
- 2001-03-21 AR ARP010101320A patent/AR029821A1/es unknown
- 2001-03-21 ES ES01913896T patent/ES2243462T3/es not_active Expired - Lifetime
- 2001-03-21 PT PT01913896T patent/PT1268466E/pt unknown
- 2001-03-21 JP JP2001568934A patent/JP4118565B2/ja not_active Expired - Fee Related
- 2001-03-21 DK DK01913896T patent/DK1268466T3/da active
- 2001-03-21 US US10/221,983 patent/US6635647B2/en not_active Expired - Fee Related
- 2001-03-21 CO CO01022539A patent/CO5271675A1/es not_active Application Discontinuation
- 2001-03-21 AT AT01913896T patent/ATE298332T1/de not_active IP Right Cessation
- 2001-03-21 AU AU2001239310A patent/AU2001239310A1/en not_active Abandoned
- 2001-03-21 CA CA002402751A patent/CA2402751C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1268466B1 (en) | 2005-06-22 |
| US20030120072A1 (en) | 2003-06-26 |
| EP1268466A1 (en) | 2003-01-02 |
| ATE298332T1 (de) | 2005-07-15 |
| PE20011114A1 (es) | 2001-11-30 |
| DE60111621T2 (de) | 2006-05-18 |
| PT1268466E (pt) | 2005-10-31 |
| GB0007108D0 (en) | 2000-05-17 |
| WO2001070731A1 (en) | 2001-09-27 |
| CO5271675A1 (es) | 2003-04-30 |
| JP2003528096A (ja) | 2003-09-24 |
| AR029821A1 (es) | 2003-07-16 |
| DK1268466T3 (da) | 2005-10-10 |
| CA2402751C (en) | 2010-01-19 |
| JP4118565B2 (ja) | 2008-07-16 |
| AU2001239310A1 (en) | 2001-10-03 |
| CA2402751A1 (en) | 2001-09-27 |
| DE60111621D1 (de) | 2005-07-28 |
| US6635647B2 (en) | 2003-10-21 |
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