JP3274865B2 - ５−ｈｔレセプター拮抗物質としてのピペラジン誘導体 - Google Patents
５−ｈｔレセプター拮抗物質としてのピペラジン誘導体Info
- Publication number
- JP3274865B2 JP3274865B2 JP51221993A JP51221993A JP3274865B2 JP 3274865 B2 JP3274865 B2 JP 3274865B2 JP 51221993 A JP51221993 A JP 51221993A JP 51221993 A JP51221993 A JP 51221993A JP 3274865 B2 JP3274865 B2 JP 3274865B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- lower alkyl
- compounds
- pct
- monocyclic
- 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 - Fee Related
Links
- 150000004885 piperazines Chemical class 0.000 title description 2
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 2
- 229940127239 5 Hydroxytryptamine receptor antagonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 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
- 239000003727 serotonin 1A antagonist Substances 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- -1 heteroaryl radical Chemical class 0.000 abstract description 13
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
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- 210000003169 central nervous system Anatomy 0.000 description 2
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- 239000002552 dosage form Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 125000005843 halogen group Chemical group 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 102220240796 rs553605556 Human genes 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-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
- WKZLNEWVIAGNAW-UHFFFAOYSA-N 5-Carboxyamidotryptamine Chemical compound C1=C(C(N)=O)C=C2C(CCN)=CNC2=C1 WKZLNEWVIAGNAW-UHFFFAOYSA-N 0.000 description 1
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-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
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 102000014630 G protein-coupled serotonin receptor activity proteins Human genes 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
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- 150000001408 amides Chemical class 0.000 description 1
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- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 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
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- 125000006168 tricyclic group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (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)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929200293A GB9200293D0 (en) | 1992-01-08 | 1992-01-08 | Piperazine derivatives |
| GB9200293.0 | 1992-01-08 | ||
| PCT/GB1992/002399 WO1993014076A1 (en) | 1992-01-08 | 1992-12-24 | Piperazine derivatives as 5-ht receptors antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH07502739A JPH07502739A (ja) | 1995-03-23 |
| JP3274865B2 true JP3274865B2 (ja) | 2002-04-15 |
Family
ID=10708249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51221993A Expired - Fee Related JP3274865B2 (ja) | 1992-01-08 | 1992-12-24 | ５−ｈｔレセプター拮抗物質としてのピペラジン誘導体 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5532242A (enExample) |
| EP (1) | EP0620817B1 (enExample) |
| JP (1) | JP3274865B2 (enExample) |
| KR (1) | KR100283345B1 (enExample) |
| AT (1) | ATE183504T1 (enExample) |
| AU (1) | AU668901B2 (enExample) |
| BR (1) | BR9207030A (enExample) |
| CA (1) | CA2125182A1 (enExample) |
| DE (1) | DE69229834T2 (enExample) |
| ES (1) | ES2134835T3 (enExample) |
| FI (1) | FI106200B (enExample) |
| GB (2) | GB9200293D0 (enExample) |
| HU (1) | HUT70513A (enExample) |
| IL (1) | IL104305A (enExample) |
| MX (1) | MX9300031A (enExample) |
| NZ (1) | NZ246205A (enExample) |
| PH (1) | PH30268A (enExample) |
| RU (1) | RU2128653C1 (enExample) |
| TW (1) | TW265337B (enExample) |
| WO (1) | WO1993014076A1 (enExample) |
| ZA (1) | ZA93141B (enExample) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG63579A1 (en) * | 1992-12-21 | 1999-03-30 | Smithkline Beecham Corp | Bicyclic fibrinogen antagonists |
| 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 |
| JP3845452B2 (ja) | 1996-04-05 | 2006-11-15 | ソシエテ・ド・コンセイユ・ド・ルシエルシエ・エ・ダアツプリカーシヨン・シヤンテイフイツク・（エス．セー．エール．アー．エス） | α１―交感神経受容体拮抗薬 |
| US5610164A (en) * | 1996-07-24 | 1997-03-11 | American Home Products Corporation | (Thiophen-2-yl)-piperidin or tetrahydropyridin azabicyclocarboxamides |
| 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 |
| 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 |
| 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 |
| US6344458B1 (en) | 1998-12-17 | 2002-02-05 | American Home Products Corporation | Piperazine ethylamide derivatives |
| AU3124100A (en) * | 1998-12-17 | 2000-07-03 | American Home Products Corporation | Piperazine ethylamide derivatives with 5-ht1a receptor activity |
| WO2001068104A1 (en) | 2000-03-16 | 2001-09-20 | The Mclean Hospital Corporation | Compounds for the treatment of psychiatric or substance abuse disorders |
| HUP0301719A2 (hu) * | 2000-06-27 | 2003-09-29 | Taisho Pharmaceutical Co., Ltd. | Szorongásos neurózis vagy depresszió kezelésére szolgáló gyógyszerkészítmény és piperazinszármazékok |
| 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 |
| CA2508995A1 (en) * | 2002-12-20 | 2004-07-15 | The Mclean Hospital Corporation | Use of cytidine-, creatine-, and adenosine-containing compounds and adenosine-elevating compounds for normalizing sleep/wake cycle, treating a sleep disorder or improving cognitive function |
| US7737128B2 (en) | 2004-06-10 | 2010-06-15 | The Mclean Hospital Corporation | Pyrimidines, such as uridine, in treatments for patients with bipolar disorder |
| WO2006020703A1 (en) | 2004-08-11 | 2006-02-23 | The Mclean Hospital Corporation | Compounds for the treatment of marihuana dependence, withdrawal, and usage |
| US7731940B2 (en) | 2006-01-25 | 2010-06-08 | The Regents Of The University Of California | Compositions and methods related to serotonin 5-HT1A receptors |
| TWI417095B (zh) * | 2006-03-15 | 2013-12-01 | Janssen Pharmaceuticals Inc | １，４-二取代之３-氰基-吡啶酮衍生物及其作為ｍＧｌｕＲ２-受體之正向異位性調節劑之用途 |
| 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 |
| KR20100065191A (ko) | 2007-09-14 | 2010-06-15 | 오르토-맥닐-얀센 파마슈티칼스 인코포레이티드 | １,３-이치환된 ４-(아릴-ｘ-페닐)-１ｈ-피리딘-２-온 |
| CA2696948C (en) | 2007-09-14 | 2013-04-30 | Jose Maria Cid-Nunez | 1',3'-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2h,1'h-[1,4']bipyridinyl-2'-ones |
| KR20100080597A (ko) * | 2007-09-14 | 2010-07-09 | 오르토-맥닐-얀센 파마슈티칼스 인코포레이티드 | １,３-이치환된-４-페닐-1ｈ-피리딘-2-온 |
| EP2220083B1 (en) * | 2007-11-14 | 2017-07-19 | Janssen Pharmaceuticals, Inc. | Imidazo[1,2-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| CA2735764C (en) | 2008-09-02 | 2016-06-14 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
| AU2009304293B2 (en) | 2008-10-16 | 2012-04-26 | Addex Pharma S.A. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
| BRPI0921333A2 (pt) | 2008-11-28 | 2015-12-29 | Addex Pharmaceuticals Sa | derivados de indol e benzoxazina como moduladores de receptores de glutamato metabotrópicos |
| NZ596078A (en) | 2009-05-12 | 2013-06-28 | 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 |
| 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 |
| EA020671B1 (ru) | 2009-05-12 | 2014-12-30 | Янссен Фармасьютикалз, Инк. | ПРОИЗВОДНЫЕ 1,2,4-ТРИАЗОЛО[4,3-a]ПИРИДИНА И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ПОЛОЖИТЕЛЬНЫХ АЛЛОСТЕРИЧЕСКИХ МОДУЛЯТОРОВ РЕЦЕПТОРОВ mGluR2 |
| WO2011027656A1 (en) | 2009-09-04 | 2011-03-10 | Semiconductor Energy Laboratory Co., Ltd. | Transistor and display device |
| CA2815002C (en) | 2010-11-08 | 2019-10-22 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| CN103298810B (zh) | 2010-11-08 | 2016-03-16 | 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 |
| EP2643320B1 (en) | 2010-11-08 | 2015-03-04 | 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 |
| KR102414246B1 (ko) | 2014-01-21 | 2022-06-27 | 얀센 파마슈티카 엔.브이. | 대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도 |
| LT3431106T (lt) | 2014-01-21 | 2021-02-10 | Janssen Pharmaceutica Nv | Deriniai, apimantys 2 potipio metabotropinio glutamaterginio receptoriaus teigiamus alosterinius moduliatorius arba ortosterinius agonistus, ir jų panaudojimas |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3037982A (en) * | 1959-08-12 | 1962-06-05 | Miles Lab | Phenylpiperazinylalkyl propionanilides |
| SU534071A1 (ru) * | 1974-03-26 | 1980-04-30 | Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латвийской Сср | -Замещенные пиперазины,обладающие психотропной активностью |
| 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. |
| EP0190472B1 (en) * | 1984-12-21 | 1989-07-12 | Duphar International Research B.V | 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 |
| IL90279A (en) * | 1988-05-24 | 1995-03-30 | American Home Prod | Piperazinyl carboxamide derivatives, their preparation and pharmaceutical com¦ositions containing them |
| 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 |
| NZ233398A (en) * | 1989-04-22 | 1991-12-23 | American Home Prod | Aryl- or heteroaryl-substituted piperazine derivatives and pharmaceutical compositions |
| IE950248L (en) * | 1989-04-22 | 1990-10-22 | Wyeth John & Brother Ltd | 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 AU AU31697/93A patent/AU668901B2/en not_active Ceased
- 1992-12-24 AT AT93900365T patent/ATE183504T1/de not_active IP Right Cessation
- 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 BR BR9207030A patent/BR9207030A/pt not_active Application Discontinuation
- 1992-12-24 US US08/256,330 patent/US5532242A/en not_active Expired - Lifetime
- 1992-12-24 RU RU94039542A patent/RU2128653C1/ru active
- 1992-12-24 ES ES93900365T patent/ES2134835T3/es not_active Expired - Lifetime
- 1992-12-24 JP JP51221993A patent/JP3274865B2/ja not_active Expired - Fee Related
- 1992-12-24 DE DE69229834T patent/DE69229834T2/de not_active Expired - Fee Related
- 1992-12-24 NZ NZ246205A patent/NZ246205A/en unknown
- 1992-12-24 WO PCT/GB1992/002399 patent/WO1993014076A1/en not_active Ceased
- 1992-12-24 GB GB9227001A patent/GB2263110B/en not_active Expired - Fee Related
- 1992-12-24 HU HU9402042A patent/HUT70513A/hu not_active IP Right Cessation
-
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 MX MX9300031A patent/MX9300031A/es not_active IP Right Cessation
- 1993-01-07 PH PH45533A patent/PH30268A/en unknown
- 1993-01-08 ZA ZA93141A patent/ZA93141B/xx unknown
-
1994
- 1994-07-07 FI FI943247A patent/FI106200B/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| MX9300031A (es) | 1993-07-01 |
| FI106200B (fi) | 2000-12-15 |
| GB9200293D0 (en) | 1992-02-26 |
| IL104305A (en) | 1998-04-05 |
| ATE183504T1 (de) | 1999-09-15 |
| RU94039542A (ru) | 1996-08-10 |
| AU668901B2 (en) | 1996-05-23 |
| AU3169793A (en) | 1993-08-03 |
| ES2134835T3 (es) | 1999-10-16 |
| EP0620817B1 (en) | 1999-08-18 |
| ZA93141B (en) | 1994-07-08 |
| PH30268A (en) | 1997-02-20 |
| TW265337B (enExample) | 1995-12-11 |
| JPH07502739A (ja) | 1995-03-23 |
| KR100283345B1 (ko) | 2001-03-02 |
| BR9207030A (pt) | 1995-12-05 |
| DE69229834T2 (de) | 2000-01-13 |
| GB2263110A (en) | 1993-07-14 |
| CA2125182A1 (en) | 1993-07-22 |
| WO1993014076A1 (en) | 1993-07-22 |
| RU2128653C1 (ru) | 1999-04-10 |
| US5532242A (en) | 1996-07-02 |
| HUT70513A (en) | 1995-10-30 |
| DE69229834D1 (de) | 1999-09-23 |
| NZ246205A (en) | 1996-12-20 |
| FI943247A0 (fi) | 1994-07-07 |
| FI943247L (fi) | 1994-07-07 |
| EP0620817A1 (en) | 1994-10-26 |
| HU9402042D0 (en) | 1994-09-28 |
| GB9227001D0 (en) | 1993-02-17 |
| GB2263110B (en) | 1995-08-09 |
| IL104305A0 (en) | 1993-05-13 |
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