RU2128653C1 - Производные пиперазина, способ их получения и фармацевтическая композиция - Google Patents
Производные пиперазина, способ их получения и фармацевтическая композиция Download PDFInfo
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- RU2128653C1 RU2128653C1 RU94039542A RU94039542A RU2128653C1 RU 2128653 C1 RU2128653 C1 RU 2128653C1 RU 94039542 A RU94039542 A RU 94039542A RU 94039542 A RU94039542 A RU 94039542A RU 2128653 C1 RU2128653 C1 RU 2128653C1
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- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
- 150000004885 piperazines Chemical class 0.000 title claims abstract description 4
- 230000015572 biosynthetic process Effects 0.000 title abstract 3
- 238000003786 synthesis reaction Methods 0.000 title abstract 3
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 239000002168 alkylating agent Substances 0.000 claims abstract description 4
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- -1 o-methoxyphenyl Chemical group 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 230000003042 antagnostic effect Effects 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- WLAUUBQPEYNCHF-UHFFFAOYSA-N n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-n-phenylcyclohexanecarboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCN(C(=O)C2CCCCC2)C=2C=CC=CC=2)CC1 WLAUUBQPEYNCHF-UHFFFAOYSA-N 0.000 claims description 2
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MUSOMUXTQGJZKD-UHFFFAOYSA-N 1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCN(CCCl)CC1 MUSOMUXTQGJZKD-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- MUXVCSNTPQZCTF-UHFFFAOYSA-N C1(CCCCC1)C(=O)Cl.C1(CCCCC1)C(=O)NC1=CC=CC=C1 Chemical compound C1(CCCCC1)C(=O)Cl.C1(CCCCC1)C(=O)NC1=CC=CC=C1 MUXVCSNTPQZCTF-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
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- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
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- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
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- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
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- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
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- 150000001805 chlorine compounds Chemical class 0.000 description 1
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
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- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
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- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
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- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
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- 235000021400 peanut butter Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000009519 pharmacological trial Methods 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000036299 sexual function Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000008454 sleep-wake cycle Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Child & Adolescent Psychology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9200293.0 | 1992-01-08 | ||
| GB929200293A GB9200293D0 (en) | 1992-01-08 | 1992-01-08 | Piperazine derivatives |
| PCT/GB1992/002399 WO1993014076A1 (en) | 1992-01-08 | 1992-12-24 | Piperazine derivatives as 5-ht receptors antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU94039542A RU94039542A (ru) | 1996-08-10 |
| RU2128653C1 true RU2128653C1 (ru) | 1999-04-10 |
Family
ID=10708249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU94039542A RU2128653C1 (ru) | 1992-01-08 | 1992-12-24 | Производные пиперазина, способ их получения и фармацевтическая композиция |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5532242A (index.php) |
| EP (1) | EP0620817B1 (index.php) |
| JP (1) | JP3274865B2 (index.php) |
| KR (1) | KR100283345B1 (index.php) |
| AT (1) | ATE183504T1 (index.php) |
| AU (1) | AU668901B2 (index.php) |
| BR (1) | BR9207030A (index.php) |
| CA (1) | CA2125182A1 (index.php) |
| DE (1) | DE69229834T2 (index.php) |
| ES (1) | ES2134835T3 (index.php) |
| FI (1) | FI106200B (index.php) |
| GB (2) | GB9200293D0 (index.php) |
| HU (1) | HUT70513A (index.php) |
| IL (1) | IL104305A (index.php) |
| MX (1) | MX9300031A (index.php) |
| NZ (1) | NZ246205A (index.php) |
| PH (1) | PH30268A (index.php) |
| RU (1) | RU2128653C1 (index.php) |
| TW (1) | TW265337B (index.php) |
| WO (1) | WO1993014076A1 (index.php) |
| ZA (1) | ZA93141B (index.php) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2366428C2 (ru) * | 2002-12-20 | 2009-09-10 | Дзе Маклин Хоспитал Корпорейшн | Соединения для нормализации цикла сна/бодрствования |
| US7863254B2 (en) | 2000-03-16 | 2011-01-04 | The Mclean Hospital Corporation | Compounds for the treatment of psychiatric or substance abuse disorders |
| US7947661B2 (en) | 2004-08-11 | 2011-05-24 | The Mclean Hospital Corporation | Compounds for the treatment of marihuana dependence, withdrawal, and usage |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69332860T2 (de) * | 1992-12-21 | 2004-03-11 | Smithkline Beecham Corp. | Bicyklische fibrinogen antagoniste |
| US5609849A (en) * | 1994-03-11 | 1997-03-11 | The Trustees Of The University Of Pennsylvania | Serotonin (5-HT1A) receptor ligands and imaging agents |
| US5451584A (en) * | 1994-11-10 | 1995-09-19 | American Home Products Corporation | N-alkynyl carboxamides as sertonergic agents |
| US5541179A (en) * | 1995-05-02 | 1996-07-30 | American Home Products Corporation | Tropon-2-one piperazine carboxamides as serotonergic agents |
| ATE229946T1 (de) | 1996-04-05 | 2003-01-15 | Sod Conseils Rech Applic | Alpha-1 adrenergischer rezeptor antagonisten |
| US5610164A (en) * | 1996-07-24 | 1997-03-11 | American Home Products Corporation | (Thiophen-2-yl)-piperidin or tetrahydropyridin azabicyclocarboxamides |
| IT1293804B1 (it) | 1997-08-01 | 1999-03-10 | Recordati Chem Pharm | Diarilalchilpiperazine attive sulle basse vie urinarie |
| IT1293807B1 (it) * | 1997-08-01 | 1999-03-10 | Recordati Chem Pharm | Derivati 1- (n-fenilaminoalchil) piperazinici sostituiti alla posizione 2 dell'anello fenilico |
| US6399614B1 (en) | 1997-08-01 | 2002-06-04 | Recordati S.A. Chemical And Pharmaceutical Company | 1-(N-phenylaminoalkyl)piperazine derivatives substituted at position 2 of the phenyl ring |
| RU2161614C2 (ru) * | 1998-03-17 | 2001-01-10 | Тульский государственный педагогический университет им. Л.Н. Толстого | Способ получения динатриевой соли n,n,-бис-(4-амино-2-сульфофенил)пиперазина |
| JP2002532481A (ja) * | 1998-12-17 | 2002-10-02 | アメリカン・ホーム・プロダクツ・コーポレイション | ５−ｈｔ１ａ受容体活性を有するピペラジンエチルアミド誘導体 |
| US6344458B1 (en) | 1998-12-17 | 2002-02-05 | American Home Products Corporation | Piperazine ethylamide derivatives |
| EA200500087A1 (ru) * | 2000-06-27 | 2005-06-30 | Тайсо Фармасьютикал Ко., Лтд. | Производные пиперазина |
| AR034206A1 (es) * | 2001-02-16 | 2004-02-04 | Solvay Pharm Bv | Un procedimiento para la preparacion de mesilatos de derivados de piperazina y dichos mesilatos |
| EP1765075A4 (en) | 2004-06-10 | 2010-11-10 | Mclean Hospital Corp | PYRIMIDINES, AS FORM. uridine; IN THE TREATMENT OF PATIENTS WITH MANIC-DEPRESSIVE PSYCHOSIS |
| US7731940B2 (en) | 2006-01-25 | 2010-06-08 | The Regents Of The University Of California | Compositions and methods related to serotonin 5-HT1A receptors |
| 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 |
| TW200845978A (en) * | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| WO2009033703A1 (en) * | 2007-09-14 | 2009-03-19 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | 1,3-disubstituted-4-phenyl-1 h-pyridin-2-ones |
| ES2365966T3 (es) | 2007-09-14 | 2011-10-14 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | 4-(aril-x-fenil)-1h-piridin-2-onas 1,3-disustituidas. |
| BRPI0816767B8 (pt) | 2007-09-14 | 2021-05-25 | Addex Pharmaceuticals Sa | composto 4-fenil-3,4,5,6-tetra-hidro-2h,1'h-[1,4']bipiridi¬nil-2'-onas 1',3'-dissubstituídas, composição farmacêutica e uso dos mesmos |
| ES2637794T3 (es) * | 2007-11-14 | 2017-10-17 | Janssen Pharmaceuticals, Inc. | Derivados de imidazo[1,2-A]piridina y su uso como moduladores alostéricos positivos de receptores MGLUR2 |
| JP5547194B2 (ja) | 2008-09-02 | 2014-07-09 | ジャンセン ファーマシューティカルズ， インコーポレイテッド． | 代謝型グルタミン酸受容体の調節因子としての３−アザビシクロ［３．１．０］ヘキシル誘導体 |
| BRPI0920354A2 (pt) | 2008-10-16 | 2017-06-27 | Addex Pharmaceuticals Sa | derivados de indol e benzomorfolina como moduladores de receptores de glutamato metabotrópicos |
| CN102232074B (zh) | 2008-11-28 | 2014-12-03 | 奥梅-杨森制药有限公司 | 作为代谢性谷氨酸盐受体调节剂的吲哚和苯并噁嗪衍生物 |
| 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 |
| BRPI1010831A2 (pt) | 2009-05-12 | 2016-04-05 | Addex Pharmaceuticals Sa | derivados de 1,2,4-triazolo[4,3-a]piridina e seu como moduladores alostéricos positivos de receptores de mglur2 |
| 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 |
| WO2011027656A1 (en) | 2009-09-04 | 2011-03-10 | Semiconductor Energy Laboratory Co., Ltd. | Transistor and display device |
| PT2649069E (pt) | 2010-11-08 | 2015-11-20 | Janssen Pharmaceuticals Inc | Derivados de 1,2,4-triazolo[4,3-a]piridina e sua utilização como moduladores alostéricos positivos de recetores mglur2 |
| CN103261195B (zh) | 2010-11-08 | 2015-09-02 | 杨森制药公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
| AU2011328203B2 (en) | 2010-11-08 | 2015-03-19 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| CN103360342B (zh) * | 2012-04-09 | 2015-12-16 | 江苏恩华药业股份有限公司 | 3-氰基苯胺烷基芳基哌嗪衍生物及在制备药物中的应用 |
| 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 |
| HUE045610T2 (hu) | 2014-01-21 | 2020-01-28 | Janssen Pharmaceutica Nv | 2-es altípusú metabotróp glutamáterg receptor pozitív allosztérikus modulátorait vagy ortosztérikus agonistáit tartalmazó kombinációk és alkalmazásuk |
| PH12021552653A1 (en) | 2014-01-21 | 2023-07-17 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU534071A1 (ru) * | 1974-03-26 | 1980-04-30 | Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латвийской Сср | -Замещенные пиперазины,обладающие психотропной активностью |
| GB2230780B (en) * | 1989-04-22 | 1992-10-21 | American Home Prod | Tertiary alkyl functionalized piperazine derivatives |
| GB2230781B (en) * | 1989-04-22 | 1993-04-28 | Wyeth John & Brother Ltd | Piperazine derivatives |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3037982A (en) * | 1959-08-12 | 1962-06-05 | Miles Lab | Phenylpiperazinylalkyl propionanilides |
| AU532411B2 (en) * | 1979-03-01 | 1983-09-29 | Duphar International Research B.V. | Phenyl piperazine derivatives |
| NL8005133A (nl) * | 1980-09-12 | 1982-04-01 | Duphar Int Res | Fenylpiperazinederivaten met antiagressieve werking. |
| NL8005131A (nl) * | 1980-09-12 | 1982-04-01 | Duphar Int Res | Fenylpiperazinederivaten met analgetische werking. |
| DE3571436D1 (en) * | 1984-12-21 | 1989-08-17 | Duphar Int Res | New pharmaceutical compositions having anti-psychotic properties |
| US5010078A (en) * | 1988-05-24 | 1991-04-23 | American Home Products Corporation | Aryl- and heteroaryl piperazinyl carboxamides having central nervous system activity |
| CA1340113C (en) * | 1988-05-24 | 1998-11-03 | Magid A. Abou-Gharbia | Aryl-and heteroaryl piperazinyl carboxamides having central nervous system activity |
| GB8909209D0 (en) * | 1989-04-22 | 1989-06-07 | Wyeth John & Brother Ltd | Piperazine derivatives |
| US5340812A (en) * | 1989-04-22 | 1994-08-23 | John Wyeth & Brother, Limited | Piperazine derivatives |
| FR2655988B1 (fr) * | 1989-12-20 | 1994-05-20 | Adir Cie | Nouveaux derives de la napht-1-yl piperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| DK178590D0 (da) * | 1990-07-26 | 1990-07-26 | Novo Nordisk As | 1,4-disubstituerede piperaziner |
| ES2027898A6 (es) * | 1991-01-24 | 1992-06-16 | Espanola Prod Quimicos | Procedimiento de preparacion de nuevos derivados de la 2-metoxifenilpiperacina. |
-
1992
- 1992-01-08 GB GB929200293A patent/GB9200293D0/en active Pending
- 1992-12-24 JP JP51221993A patent/JP3274865B2/ja not_active Expired - Fee Related
- 1992-12-24 CA CA002125182A patent/CA2125182A1/en not_active Abandoned
- 1992-12-24 KR KR1019940702344A patent/KR100283345B1/ko not_active Expired - Fee Related
- 1992-12-24 EP EP93900365A patent/EP0620817B1/en not_active Expired - Lifetime
- 1992-12-24 HU HU9402042A patent/HUT70513A/hu not_active IP Right Cessation
- 1992-12-24 RU RU94039542A patent/RU2128653C1/ru active
- 1992-12-24 DE DE69229834T patent/DE69229834T2/de not_active Expired - Fee Related
- 1992-12-24 GB GB9227001A patent/GB2263110B/en not_active Expired - Fee Related
- 1992-12-24 NZ NZ246205A patent/NZ246205A/en unknown
- 1992-12-24 US US08/256,330 patent/US5532242A/en not_active Expired - Lifetime
- 1992-12-24 WO PCT/GB1992/002399 patent/WO1993014076A1/en not_active Ceased
- 1992-12-24 ES ES93900365T patent/ES2134835T3/es not_active Expired - Lifetime
- 1992-12-24 AT AT93900365T patent/ATE183504T1/de not_active IP Right Cessation
- 1992-12-24 AU AU31697/93A patent/AU668901B2/en not_active Ceased
- 1992-12-24 BR BR9207030A patent/BR9207030A/pt not_active Application Discontinuation
-
1993
- 1993-01-05 IL IL104305A patent/IL104305A/en not_active IP Right Cessation
- 1993-01-06 TW TW082100059A patent/TW265337B/zh active
- 1993-01-07 PH PH45533A patent/PH30268A/en unknown
- 1993-01-07 MX MX9300031A patent/MX9300031A/es not_active IP Right Cessation
- 1993-01-08 ZA ZA93141A patent/ZA93141B/xx unknown
-
1994
- 1994-07-07 FI FI943247A patent/FI106200B/fi active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU534071A1 (ru) * | 1974-03-26 | 1980-04-30 | Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латвийской Сср | -Замещенные пиперазины,обладающие психотропной активностью |
| GB2230780B (en) * | 1989-04-22 | 1992-10-21 | American Home Prod | Tertiary alkyl functionalized piperazine derivatives |
| GB2230781B (en) * | 1989-04-22 | 1993-04-28 | Wyeth John & Brother Ltd | Piperazine derivatives |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7863254B2 (en) | 2000-03-16 | 2011-01-04 | The Mclean Hospital Corporation | Compounds for the treatment of psychiatric or substance abuse disorders |
| US8030294B2 (en) | 2000-03-16 | 2011-10-04 | The Mclean Hospital Corporation | Compounds for the treatment of psychiatric or substance abuse disorders |
| US8575219B2 (en) | 2000-03-16 | 2013-11-05 | The Mclean Hospital | Compounds for the treatment of psychiatric or substance abuse disorders |
| RU2366428C2 (ru) * | 2002-12-20 | 2009-09-10 | Дзе Маклин Хоспитал Корпорейшн | Соединения для нормализации цикла сна/бодрствования |
| US7947661B2 (en) | 2004-08-11 | 2011-05-24 | The Mclean Hospital Corporation | Compounds for the treatment of marihuana dependence, withdrawal, and usage |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2263110B (en) | 1995-08-09 |
| BR9207030A (pt) | 1995-12-05 |
| DE69229834T2 (de) | 2000-01-13 |
| AU3169793A (en) | 1993-08-03 |
| IL104305A (en) | 1998-04-05 |
| WO1993014076A1 (en) | 1993-07-22 |
| EP0620817A1 (en) | 1994-10-26 |
| FI106200B (fi) | 2000-12-15 |
| CA2125182A1 (en) | 1993-07-22 |
| PH30268A (en) | 1997-02-20 |
| JPH07502739A (ja) | 1995-03-23 |
| ES2134835T3 (es) | 1999-10-16 |
| GB2263110A (en) | 1993-07-14 |
| IL104305A0 (en) | 1993-05-13 |
| DE69229834D1 (de) | 1999-09-23 |
| TW265337B (index.php) | 1995-12-11 |
| US5532242A (en) | 1996-07-02 |
| GB9227001D0 (en) | 1993-02-17 |
| HUT70513A (en) | 1995-10-30 |
| HU9402042D0 (en) | 1994-09-28 |
| JP3274865B2 (ja) | 2002-04-15 |
| ATE183504T1 (de) | 1999-09-15 |
| ZA93141B (en) | 1994-07-08 |
| NZ246205A (en) | 1996-12-20 |
| KR100283345B1 (ko) | 2001-03-02 |
| EP0620817B1 (en) | 1999-08-18 |
| AU668901B2 (en) | 1996-05-23 |
| MX9300031A (es) | 1993-07-01 |
| FI943247L (fi) | 1994-07-07 |
| FI943247A0 (fi) | 1994-07-07 |
| GB9200293D0 (en) | 1992-02-26 |
| RU94039542A (ru) | 1996-08-10 |
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