PH27115A - 1,4-disubstituted-piperidinyl compounds - Google Patents
1,4-disubstituted-piperidinyl compounds Download PDFInfo
- Publication number
- PH27115A PH27115A PH38074A PH38074A PH27115A PH 27115 A PH27115 A PH 27115A PH 38074 A PH38074 A PH 38074A PH 38074 A PH38074 A PH 38074A PH 27115 A PH27115 A PH 27115A
- Authority
- PH
- Philippines
- Prior art keywords
- compound
- bad original
- formula
- piperidinyl
- ethanone
- Prior art date
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- -1 1,4-disubstituted-piperidinyl compounds Chemical class 0.000 title description 16
- 150000001875 compounds Chemical class 0.000 claims description 76
- 238000000034 method Methods 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 3
- 210000003205 muscle Anatomy 0.000 claims description 3
- NDYMQOUYJJXCKJ-UHFFFAOYSA-N (4-fluorophenyl)-morpholin-4-ylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CCOCC1 NDYMQOUYJJXCKJ-UHFFFAOYSA-N 0.000 claims description 2
- IPZDVJVNVGCCDS-UHFFFAOYSA-N 2-(2-phenylpiperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1C1=CC=CC=C1 IPZDVJVNVGCCDS-UHFFFAOYSA-N 0.000 claims 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 241000699670 Mus sp. Species 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 150000002009 diols Chemical class 0.000 description 16
- 239000002253 acid Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000000463 material Substances 0.000 description 8
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- 229940093499 ethyl acetate Drugs 0.000 description 7
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- 230000008018 melting Effects 0.000 description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 125000005594 diketone group Chemical group 0.000 description 6
- 230000000717 retained effect Effects 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 125000003386 piperidinyl group Chemical group 0.000 description 5
- 230000001603 reducing effect Effects 0.000 description 5
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- 229960005181 morphine Drugs 0.000 description 4
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- 238000001953 recrystallisation Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000007864 suspending Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
Classifications
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14664788A | 1988-01-21 | 1988-01-21 | |
| US07/279,900 US5064838A (en) | 1988-01-21 | 1988-12-07 | 1,4-disubstituted-piperidinyl compounds as pain relievers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH27115A true PH27115A (en) | 1993-03-16 |
Family
ID=48782796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH38074A PH27115A (en) | 1988-01-21 | 1989-01-20 | 1,4-disubstituted-piperidinyl compounds |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5064838A (xx) |
| EP (1) | EP0325268B1 (xx) |
| JP (1) | JP2967990B2 (xx) |
| KR (1) | KR0131377B1 (xx) |
| CN (1) | CN1035823A (xx) |
| AR (2) | AR247385A1 (xx) |
| AT (1) | ATE90077T1 (xx) |
| AU (1) | AU615713B2 (xx) |
| CA (1) | CA1330087C (xx) |
| DE (1) | DE68906801T2 (xx) |
| DK (1) | DK26389A (xx) |
| ES (1) | ES2058346T3 (xx) |
| FI (1) | FI90534C (xx) |
| HU (2) | HU202494B (xx) |
| NO (1) | NO174505B (xx) |
| NZ (1) | NZ227643A (xx) |
| PH (1) | PH27115A (xx) |
| PT (1) | PT89497B (xx) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR910006138B1 (ko) * | 1986-09-30 | 1991-08-16 | 에자이 가부시끼가이샤 | 환상아민 유도체 |
| NZ236501A (en) * | 1989-12-21 | 1992-12-23 | Merrell Dow Pharma | Piperidine derivatives and antithrombotic compositions |
| US5292752A (en) * | 1989-12-21 | 1994-03-08 | Merrell Dow Pharmaceuticals Inc. | Antithrombotic compounds |
| AU652759B2 (en) * | 1990-06-01 | 1994-09-08 | Aventisub Ii Inc. | (+)-alpha-(2,3-dimethoxyphenyl)-1-(2-(4-fluorophenyl)ethyl)- 4-piperidinemethanol |
| DE69123052T2 (de) * | 1990-06-07 | 1997-03-06 | Merrell Pharmaceuticals Inc., Cincinnati, Ohio | Derivate des 1-piperidinyl-alkanoylarylsulfonamids |
| FR2672286B1 (fr) * | 1991-01-31 | 1994-11-18 | Synthelabo | Derives de 1-(4-chlorophenyl)-2-[4-(phenylmethyl)piperidin-1-yl]ethanol, leur preparation et leur application en therapeutique. |
| WO1992020661A1 (en) * | 1991-05-22 | 1992-11-26 | Merck & Co., Inc. | N, n-diacylpiperazines |
| FR2678269B1 (fr) * | 1991-06-27 | 1995-01-13 | Synthelabo | Derives de 1-(4-chlorophenyl)-2-[4-(2-phenylethyl)piperidin-1-yl]ethanol, leur application et leur preparation en therapeutique. |
| US5637699A (en) * | 1992-06-29 | 1997-06-10 | Merck & Co., Inc. | Process for preparing morpholine tachykinin receptor antagonists |
| US5719147A (en) * | 1992-06-29 | 1998-02-17 | Merck & Co., Inc. | Morpholine and thiomorpholine tachykinin receptor antagonists |
| US6048859A (en) * | 1992-06-29 | 2000-04-11 | Merck & Co., Inc. | Morpholine and thiomorpholine tachykinin receptor antagonists |
| US5387595A (en) * | 1992-08-26 | 1995-02-07 | Merck & Co., Inc. | Alicyclic compounds as tachykinin receptor antagonists |
| FR2696741B1 (fr) * | 1992-10-12 | 1994-11-25 | Synthelabo | Dérivés de 1-(4-chlorophényl)-2-[4-[(4-fluorophényl)méthyl]piperidin-1-yl] éthanol, leur préparation et leur application en thérapeutique. |
| US5344830A (en) * | 1992-12-10 | 1994-09-06 | Merck & Co., Inc. | N,N-diacylpiperazine tachykinin antagonists |
| US5348955A (en) * | 1993-06-22 | 1994-09-20 | Merck & Co., Inc. | N,N-diacylpiperazines |
| US5610165A (en) * | 1994-02-17 | 1997-03-11 | Merck & Co., Inc. | N-acylpiperidine tachykinin antagonists |
| TW385308B (en) * | 1994-03-04 | 2000-03-21 | Merck & Co Inc | Prodrugs of morpholine tachykinin receptor antagonists |
| EP0796619A1 (en) | 1996-03-21 | 1997-09-24 | Merrell Pharmaceuticals Inc. | Use of (+)-alpha-(2,3-dimethoxyphenyl)-1-(2-(4-fluorophenyl)ethyl)-4-piperidinemethanol in treating depressive disorders and bipolar disorders |
| US6028083A (en) * | 1997-07-25 | 2000-02-22 | Hoechst Marion Roussel, Inc. | Esters of (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol |
| DE69830045T2 (de) | 1997-10-31 | 2006-01-12 | Daiichi Suntory Pharma Co., Ltd. | Arylpiperidinopropanol und Arylpiperazinopropanol Derivate und dieselbe ent- haltende Pharmazeutika |
| US20050261341A1 (en) * | 1998-03-13 | 2005-11-24 | Aventis Pharmaceuticals Inc. | Novel processes for the preparation of (R)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol |
| US6713627B2 (en) * | 1998-03-13 | 2004-03-30 | Aventis Pharmaceuticals Inc. | Processes for the preparation of (R)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol |
| US6939879B2 (en) * | 1998-08-28 | 2005-09-06 | Aventis Pharmaceuticals Inc. | Use of R (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol for the treatment of substance induced insomnia |
| US6277864B1 (en) | 1998-08-28 | 2001-08-21 | Aventis Pharmaceuticals Inc. | Use of R- +)-α-(2,3-dimethoxyphenyl-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol for the treatment of sleep disorders |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3576810A (en) * | 1968-06-20 | 1971-04-27 | Robins Co Inc A H | 1-substituted-3-(-4)-aroylpiperidines |
| GB1402889A (en) * | 1973-02-03 | 1975-08-13 | Ciba Geigy Ag | Piperidine derivatives |
| FR2581993B1 (fr) * | 1985-05-14 | 1988-03-18 | Synthelabo | Derives de (benzoyl-4 piperidino)-2 phenyl-1 alcanols, leur preparation et leur application en therapeutique |
| KR910006138B1 (ko) * | 1986-09-30 | 1991-08-16 | 에자이 가부시끼가이샤 | 환상아민 유도체 |
-
1988
- 1988-12-07 US US07/279,900 patent/US5064838A/en not_active Expired - Fee Related
-
1989
- 1989-01-16 CA CA000588352A patent/CA1330087C/en not_active Expired - Fee Related
- 1989-01-17 FI FI890245A patent/FI90534C/fi not_active IP Right Cessation
- 1989-01-17 NZ NZ227643A patent/NZ227643A/xx unknown
- 1989-01-18 HU HU89189A patent/HU202494B/hu not_active IP Right Cessation
- 1989-01-18 HU HU90238A patent/HU205073B/hu not_active IP Right Cessation
- 1989-01-19 AR AR89313027A patent/AR247385A1/es active
- 1989-01-20 JP JP1013022A patent/JP2967990B2/ja not_active Expired - Fee Related
- 1989-01-20 NO NO890269A patent/NO174505B/no unknown
- 1989-01-20 AU AU28687/89A patent/AU615713B2/en not_active Ceased
- 1989-01-20 KR KR1019890000597A patent/KR0131377B1/ko not_active IP Right Cessation
- 1989-01-20 AT AT89100955T patent/ATE90077T1/de not_active IP Right Cessation
- 1989-01-20 PH PH38074A patent/PH27115A/en unknown
- 1989-01-20 ES ES89100955T patent/ES2058346T3/es not_active Expired - Lifetime
- 1989-01-20 EP EP89100955A patent/EP0325268B1/en not_active Expired - Lifetime
- 1989-01-20 DK DK026389A patent/DK26389A/da not_active Application Discontinuation
- 1989-01-20 DE DE8989100955T patent/DE68906801T2/de not_active Expired - Fee Related
- 1989-01-20 PT PT89497A patent/PT89497B/pt not_active IP Right Cessation
- 1989-01-21 CN CN89100339A patent/CN1035823A/zh active Pending
- 1989-05-09 AR AR89313868A patent/AR244666A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01224360A (ja) | 1989-09-07 |
| FI890245A (fi) | 1989-07-22 |
| HUT52050A (en) | 1990-06-28 |
| JP2967990B2 (ja) | 1999-10-25 |
| CA1330087C (en) | 1994-06-07 |
| DE68906801D1 (de) | 1993-07-08 |
| PT89497B (pt) | 1994-03-31 |
| KR890011840A (ko) | 1989-08-22 |
| AR244666A1 (es) | 1993-11-30 |
| HU900238D0 (en) | 1990-03-28 |
| ES2058346T3 (es) | 1994-11-01 |
| US5064838A (en) | 1991-11-12 |
| EP0325268B1 (en) | 1993-06-02 |
| HU202494B (en) | 1991-03-28 |
| DK26389D0 (da) | 1989-01-20 |
| HU205073B (en) | 1992-03-30 |
| FI90534B (fi) | 1993-11-15 |
| CN1035823A (zh) | 1989-09-27 |
| KR0131377B1 (ko) | 1998-04-17 |
| AR247385A1 (es) | 1994-12-29 |
| ATE90077T1 (de) | 1993-06-15 |
| DE68906801T2 (de) | 1993-09-23 |
| NZ227643A (en) | 1991-01-29 |
| EP0325268A1 (en) | 1989-07-26 |
| AU615713B2 (en) | 1991-10-10 |
| FI890245A0 (fi) | 1989-01-17 |
| NO174505C (xx) | 1994-05-18 |
| NO890269D0 (no) | 1989-01-20 |
| PT89497A (pt) | 1989-10-04 |
| DK26389A (da) | 1989-07-22 |
| NO174505B (no) | 1994-02-07 |
| NO890269L (no) | 1989-07-24 |
| AU2868789A (en) | 1989-07-27 |
| FI90534C (fi) | 1994-02-25 |
| HUT53871A (en) | 1990-12-28 |
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