CA2017193A1 - N-(aryloxyalkyl) heteroarylpiperidines et -heteroarylpiperazines, procede de preparation et leur utilisation comme medicaments - Google Patents
N-(aryloxyalkyl) heteroarylpiperidines et -heteroarylpiperazines, procede de preparation et leur utilisation comme medicamentsInfo
- Publication number
- CA2017193A1 CA2017193A1 CA2017193A CA2017193A CA2017193A1 CA 2017193 A1 CA2017193 A1 CA 2017193A1 CA 2017193 A CA2017193 A CA 2017193A CA 2017193 A CA2017193 A CA 2017193A CA 2017193 A1 CA2017193 A1 CA 2017193A1
- Authority
- CA
- Canada
- Prior art keywords
- lower alkyl
- alkyl
- chem
- alkoxy
- hydrogen
- 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.)
- Granted
Links
- 239000003814 drug Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 230000008569 process Effects 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 1
- -1 C1 - C6-alkoxy Chemical group 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000000561 anti-psychotic effect Effects 0.000 abstract 1
- 125000003435 aroyl group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002284569A CA2284569A1 (fr) | 1989-05-19 | 1990-05-18 | N-(aryloxyalkyl) heteroarylpiperidines et -heteroarylpiperazines, procede de preparation et leur utilisation comme medicaments |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35441189A | 1989-05-19 | 1989-05-19 | |
| US354,411 | 1989-05-19 | ||
| US45679089A | 1989-12-29 | 1989-12-29 | |
| US456,790 | 1989-12-29 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002284569A Division CA2284569A1 (fr) | 1989-05-19 | 1990-05-18 | N-(aryloxyalkyl) heteroarylpiperidines et -heteroarylpiperazines, procede de preparation et leur utilisation comme medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2017193A1 true CA2017193A1 (fr) | 1990-11-19 |
| CA2017193C CA2017193C (fr) | 2000-06-27 |
Family
ID=26998389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002017193A Expired - Lifetime CA2017193C (fr) | 1989-05-19 | 1990-05-18 | N-(aryloxyalkyl) heteroarylpiperidines et -heteroarylpiperazines, procede de preparation et leur utilisation comme medicaments |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0402644B1 (fr) |
| JP (1) | JPH0662580B2 (fr) |
| KR (1) | KR0157308B1 (fr) |
| CN (2) | CN1086387C (fr) |
| AT (1) | ATE126512T1 (fr) |
| AU (1) | AU640653B2 (fr) |
| CA (1) | CA2017193C (fr) |
| CZ (1) | CZ282385B6 (fr) |
| DD (1) | DD300433A5 (fr) |
| DE (1) | DE69021645T2 (fr) |
| DK (1) | DK0402644T3 (fr) |
| ES (1) | ES2076253T3 (fr) |
| FI (2) | FI104072B1 (fr) |
| GR (1) | GR3017447T3 (fr) |
| HK (2) | HK1006710A1 (fr) |
| HU (2) | HU218200B (fr) |
| IE (1) | IE68431B1 (fr) |
| IL (1) | IL94425A (fr) |
| NO (1) | NO177301C (fr) |
| NZ (1) | NZ233710A (fr) |
| PL (1) | PL163965B1 (fr) |
| PT (1) | PT94084B (fr) |
| RU (3) | RU2062776C1 (fr) |
| SK (1) | SK242590A3 (fr) |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5561128A (en) * | 1989-05-19 | 1996-10-01 | Hoechst-Roussel Pharmaceuticals, Inc. | N-[(4-(heteroaryl)-1-piperidinyl)alkyl]-10,11-dihydro-5H-dibenz[B,F]azepines and related compounds and their therapeutic utility |
| US5364866A (en) * | 1989-05-19 | 1994-11-15 | Hoechst-Roussel Pharmaceuticals, Inc. | Heteroarylpiperidines, pyrrolidines and piperazines and their use as antipsychotics and analetics |
| US5776963A (en) * | 1989-05-19 | 1998-07-07 | Hoechst Marion Roussel, Inc. | 3-(heteroaryl)-1- (2,3-dihydro-1h-isoindol-2-yl)alkyl!pyrrolidines and 3-(heteroaryl)-1- (2,3-dihydro-1h-indol-1-yl)alkyl!pyrrolidines and related compounds and their therapeutic untility |
| DK203990D0 (da) * | 1990-08-24 | 1990-08-24 | Novo Nordisk As | Piperazinylderivater |
| US5328920A (en) * | 1991-04-17 | 1994-07-12 | Hoechst-Roussel Pharmaceuticals Incorporated | Substituted (pyridinylamino)-indoles |
| US5177088A (en) * | 1991-04-17 | 1993-01-05 | Hoechst-Roussel Pharmaceuticals Incorporated | Substituted 3-(pyridinylamino)-indoles |
| TW241263B (fr) * | 1991-08-22 | 1995-02-21 | Hoechst Roussel Pharma | |
| NZ240863A (en) * | 1991-09-11 | 1995-04-27 | Mcneilab Inc | Substituted 4-aryl piperidine and 4-aryl piperazine derivatives, preparation and pharmaceutical compositions thereof |
| US5378714A (en) * | 1991-11-27 | 1995-01-03 | Novo Nordisk A/S | Antipsychotic piperidine derivatives |
| WO1993010742A2 (fr) * | 1991-11-27 | 1993-06-10 | Novo Nordisk A/S | Composes chimiques, leur preparation et leur utilisation |
| WO1993013068A1 (fr) * | 1991-12-25 | 1993-07-08 | Zeria Pharmaceutical Co., Ltd. | Compose tricyclique et medicament renfermant ce compose |
| AU678186B2 (en) * | 1992-10-23 | 1997-05-22 | Merck Sharp & Dohme Limited | Dopamine receptor subtype ligands |
| CA2146018A1 (fr) * | 1992-10-23 | 1994-05-11 | Paul David Leeson | Ligands de sous-types de recepteurs dopaminergiques |
| DK60793D0 (da) * | 1993-05-26 | 1993-05-26 | Novo Nordisk As | Kemiske forbindelser, deres fremstilling og anvendelse |
| DK60593D0 (da) * | 1993-05-26 | 1993-05-26 | Novo Nordisk As | Kemiske forbindelser, deres fremstilling og anvendelse |
| GB9318691D0 (en) * | 1993-09-09 | 1993-10-27 | Merck Sharp & Dohme | Therapeutic agents |
| WO1995007893A1 (fr) * | 1993-09-15 | 1995-03-23 | Merck Sharp & Dohme Limited | Derives heteroaromatiques tricycliques fusionnes en tant que ligands pour les sous-types de recepteurs dopaminergiques |
| JP3274579B2 (ja) * | 1995-01-12 | 2002-04-15 | 住友製薬株式会社 | 脳血管障害に伴う精神症候治療剤 |
| ES2101646B1 (es) * | 1995-04-12 | 1998-04-01 | Ferrer Int | Nuevo compuesto derivado del cromeno. |
| US5668148A (en) * | 1995-04-20 | 1997-09-16 | Merck & Co., Inc. | Alpha1a adrenergic receptor antagonists |
| DE69611783T2 (de) * | 1995-06-06 | 2001-09-20 | Aventis Pharma Inc | Benzisoxazol- und indazol- derivate als antipsychotika |
| CA2241845C (fr) * | 1996-01-05 | 2002-10-01 | Hoechst Marion Roussel, Inc. | 4,5-dihydronaphth[1,2-c]isoxazoles et leurs derives ayant une activite au niveau du systeme nerveux central |
| US5880121A (en) * | 1996-01-05 | 1999-03-09 | Hoechst Marion Roussel Inc. | 4,5-dihydronaphth (1,2-c) isoxazoles and derivatives thereof |
| ES2144355B1 (es) * | 1997-12-30 | 2001-01-01 | Ferrer Int | Compuestos derivados del cromeno. |
| WO2001017993A1 (fr) * | 1999-09-09 | 2001-03-15 | EGIS Gyógyszergyár Rt. | Derives d'alkypiperidi nylbenzo [d] isoxazole presentant une activite psychotrope, compositions pharmaceutiques contenant ces derniers, et procede de preparation de l'ingredient actif |
| GB0102841D0 (en) * | 2001-02-05 | 2001-03-21 | Novartis Ag | Organic compounds |
| AU2006201188B2 (en) * | 2001-02-05 | 2007-11-15 | Novartis Ag | New use of iloperidone |
| EP2305656B1 (fr) * | 2001-08-31 | 2012-10-24 | Novartis AG | Isomeres optiques d'un metabolite d'iloperidone |
| ES2358416T3 (es) | 2001-10-30 | 2011-05-10 | Novartis Ag | Formulaciones de liberación prolongada de iloperidona y polímero en forma de estrella. |
| US6995144B2 (en) * | 2002-03-14 | 2006-02-07 | Eisai Co., Ltd. | Nitrogen containing heterocyclic compounds and medicines containing the same |
| GB0216416D0 (en) | 2002-07-15 | 2002-08-21 | Novartis Ag | Organic compounds |
| MXPA05002007A (es) * | 2002-09-17 | 2005-04-28 | Warner Lambert Co | Piperazinas heterociclicas sustituidas para el tratamiento de la esquizofrenia. |
| CA2505397A1 (fr) * | 2002-11-08 | 2004-05-21 | Warner-Lambert Company Llc | Derives de piperazine phenylalkyles et pyridylalkyles |
| US7160888B2 (en) | 2003-08-22 | 2007-01-09 | Warner Lambert Company Llc | [1,8]naphthyridin-2-ones and related compounds for the treatment of schizophrenia |
| GB0322994D0 (en) * | 2003-10-01 | 2003-11-05 | Novartis Ag | Organic compounds |
| CA2637531A1 (fr) | 2006-02-17 | 2007-08-30 | Memory Pharmaceuticals Corporation | Composes ayant une affinite pour le recepteur 5-ht6 |
| JP2010510314A (ja) | 2006-11-22 | 2010-04-02 | シーサイド セラピューティクス，エルエルシー | 精神遅滞、ダウン症候群、脆弱ｘ症候群および自閉症の治療方法 |
| WO2008128166A1 (fr) * | 2007-04-13 | 2008-10-23 | Concert Pharmaceuticals Inc. | Dérivés deutériés de composés 4-(6-fluoro-1,2-benzisoxazol-3-yl) pipéridine |
| CN101824030B (zh) * | 2009-03-04 | 2014-06-18 | 北京德众万全药物技术开发有限公司 | 一种伊潘立酮的制备方法 |
| EP3309151A1 (fr) | 2009-06-25 | 2018-04-18 | Alkermes Pharma Ireland Limited | Composés hétérocycliques pour le traitement de troubles neurologiques et psychologiques |
| WO2011032404A1 (fr) * | 2009-09-19 | 2011-03-24 | 浙江华海药业股份有限公司 | Procédé pour la préparation d'ilopéridone et procédé de cristallisation de celui-ci |
| CN102030744B (zh) * | 2009-09-30 | 2013-04-17 | 天津药物研究院 | 伊潘立酮晶体、其制备方法及药物组合物 |
| US20120220776A1 (en) * | 2009-11-19 | 2012-08-30 | Symed Labs Limited | Process for the preparation of iloperidone using a novel intermediate |
| WO2011154860A1 (fr) * | 2010-06-08 | 2011-12-15 | Alembic Pharmaceuticals Limited | Procédé amélioré pour la préparation de l'ilopéridone |
| CN102311430A (zh) * | 2010-06-29 | 2012-01-11 | 大道隆达（北京）医药科技发展有限公司 | 伊潘立酮的新晶态及其制备方法 |
| ITMI20101294A1 (it) * | 2010-07-14 | 2012-01-15 | Dipharma Francis Srl | Procedimento per la preparazione di iloperidone |
| WO2012032532A1 (fr) * | 2010-09-07 | 2012-03-15 | Symed Labs Limited | "procédés de fabrication de 4'-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)pipéridino]propoxy]-3'-methoxyacétophénone et de ses intermédiaires |
| WO2012063269A2 (fr) | 2010-11-12 | 2012-05-18 | Cadila Healthcare Limited | Procédé de préparation d'iloperidone |
| EP2640391B1 (fr) | 2010-11-15 | 2015-11-11 | Agenebio, Inc. | Dérivés de pyridazine, compositions et méthodes de traitement d'une déficience cognitive |
| WO2012123963A2 (fr) | 2011-02-24 | 2012-09-20 | Megafine Pharma (P) Ltd. | Procédé pour la préparation d'ilopéridone et de coprécipité amorphe d'ilopéridone avec un excipient pharmaceutiquement acceptable |
| WO2012153341A1 (fr) | 2011-05-12 | 2012-11-15 | Arch Pharmalabs Limited | Procédé pour la préparation d'iopéridone et sels pharmaceutiquement acceptables de celle-ci |
| WO2012164516A1 (fr) | 2011-06-03 | 2012-12-06 | Lupin Limited | Procédé pour la préparation d'ilopéridone |
| ITMI20120511A1 (it) * | 2012-03-29 | 2013-09-30 | Procos Spa | Processo one-pot per la sintesi di iloperidone |
| CA2891122C (fr) | 2012-11-14 | 2021-07-20 | The Johns Hopkins University | Methodes et compositions pour le traitement de la schizophrenie |
| WO2015095783A1 (fr) | 2013-12-20 | 2015-06-25 | Agenebio, Inc. | Dérivés de benzodiazépine, compositions et procédés de traitement de la déficience cognitive |
| JP6987384B2 (ja) | 2015-06-19 | 2021-12-22 | エージンバイオ， インコーポレイテッド | ベンゾジアゼピン誘導体、組成物、および認知障害を処置するための方法 |
| US20180170941A1 (en) | 2016-12-19 | 2018-06-21 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| US11505555B2 (en) | 2016-12-19 | 2022-11-22 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| BR112020026062B1 (pt) | 2018-06-19 | 2023-04-04 | Agenebio, Inc | Compostos derivados de benzodiazepina ou um sal farmaceuticamente aceitavel, isômero ou combinação dos mesmos, composição farmacêutica compreendendo os mesmos e usos dos mesmos para o tratamento de comprometimento cognitivo, câncer cerebral e psicose da doença de parkinson |
| WO2024039886A1 (fr) | 2022-08-19 | 2024-02-22 | Agenebio, Inc. | Dérivés de benzoazépine, compositions et méthodes de traitement de déficience cognitive |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4355037A (en) * | 1981-11-12 | 1982-10-19 | Hoechst-Roussel Pharmaceuticals | 3-(4-Piperidyl)-1,2-benzisoxales |
| US4458076A (en) * | 1983-05-31 | 1984-07-03 | Hoechst-Roussel Pharmaceuticals | 3-(4-Piperidinyl)-1,2-benzisothiazoles |
| HU198036B (en) * | 1983-08-22 | 1989-07-28 | Hoechst Roussel Pharma | Process for production of derivatives of 3-piperidil-/1h/-indasole and medical preparatives containing them |
| US4590196A (en) * | 1984-08-23 | 1986-05-20 | Bristol-Myers Company | Analgesic 1,2-benzisothiazol-3-ylpiperazine derivatives |
-
1990
- 1990-05-16 ES ES90109208T patent/ES2076253T3/es not_active Expired - Lifetime
- 1990-05-16 DE DE69021645T patent/DE69021645T2/de not_active Expired - Lifetime
- 1990-05-16 DK DK90109208.0T patent/DK0402644T3/da active
- 1990-05-16 AT AT90109208T patent/ATE126512T1/de not_active IP Right Cessation
- 1990-05-16 EP EP90109208A patent/EP0402644B1/fr not_active Expired - Lifetime
- 1990-05-17 FI FI902449A patent/FI104072B1/fi active IP Right Grant
- 1990-05-17 DD DD340772A patent/DD300433A5/de unknown
- 1990-05-17 NZ NZ233710A patent/NZ233710A/en unknown
- 1990-05-17 CZ CS902425A patent/CZ282385B6/cs not_active IP Right Cessation
- 1990-05-17 SK SK2425-90A patent/SK242590A3/sk not_active IP Right Cessation
- 1990-05-17 IL IL9442590A patent/IL94425A/en not_active IP Right Cessation
- 1990-05-18 RU SU904743876A patent/RU2062776C1/ru active
- 1990-05-18 IE IE180990A patent/IE68431B1/en not_active IP Right Cessation
- 1990-05-18 CA CA002017193A patent/CA2017193C/fr not_active Expired - Lifetime
- 1990-05-18 PT PT94084A patent/PT94084B/pt not_active IP Right Cessation
- 1990-05-18 RU RU95115403A patent/RU2147583C1/ru active
- 1990-05-18 KR KR1019900007102A patent/KR0157308B1/ko not_active IP Right Cessation
- 1990-05-18 PL PL90285247A patent/PL163965B1/pl unknown
- 1990-05-18 HU HU090/90A patent/HU218200B/hu unknown
- 1990-05-18 NO NO902214A patent/NO177301C/no not_active IP Right Cessation
- 1990-05-18 JP JP2127090A patent/JPH0662580B2/ja not_active Expired - Lifetime
- 1990-05-19 CN CN90103721A patent/CN1086387C/zh not_active Expired - Lifetime
- 1990-05-23 AU AU55770/90A patent/AU640653B2/en not_active Expired
-
1995
- 1995-06-29 HU HU95P/P00576P patent/HU211853A9/hu unknown
- 1995-09-20 GR GR950402573T patent/GR3017447T3/el unknown
-
1998
- 1998-06-22 HK HK98105870A patent/HK1006710A1/xx not_active IP Right Cessation
-
1999
- 1999-09-02 FI FI991869A patent/FI19991869A/fi unknown
- 1999-12-20 RU RU99126501/15A patent/RU2239434C2/ru active
-
2000
- 2000-11-06 CN CNB00130979XA patent/CN1223348C/zh not_active Expired - Lifetime
-
2001
- 2001-12-27 HK HK01109127A patent/HK1038316A1/xx not_active IP Right Cessation
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