DD203045A5 - Verfahren zur herstellung von cis-4-phenyl-1,2,3,4-tetra-hydro-1-napthalinamin-derivaten - Google Patents

Verfahren zur herstellung von cis-4-phenyl-1,2,3,4-tetra-hydro-1-napthalinamin-derivaten Download PDF

Info

Publication number: DD203045A5
Authority: DD; German Democratic Republic
Prior art keywords: meaning; cis; hydrogen; methyl; formula
Prior art date: 1979-11-01

Application number

DD80240118A

Other languages

German (de)

English (en)

Inventor

Willard M Welch

Charles A Harbert

Billie K Koe

Allen R Kraska

Original Assignee

Pfizer

Priority date (The priority date 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 date listed.)

1979-11-01

Filing date

1980-10-30

Publication date

1983-10-12

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22221931&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DD203045(A5) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1980-10-30 Application filed by Pfizer filed Critical Pfizer

1983-10-12 Publication of DD203045A5 publication Critical patent/DD203045A5/de

Links

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Classifications

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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- 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
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/30—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by two rings
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- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
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- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
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- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings

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DD80240118A 1979-11-01 1980-10-30 Verfahren zur herstellung von cis-4-phenyl-1,2,3,4-tetra-hydro-1-napthalinamin-derivaten DD203045A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/090,240 US4536518A (en)	1979-11-01	1979-11-01	Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine

Publications (1)

Publication Number	Publication Date
DD203045A5 true DD203045A5 (de)	1983-10-12

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ID=22221931

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Application Number	Title	Priority Date	Filing Date
DD80240118A DD203045A5 (de)	1979-11-01	1980-10-30	Verfahren zur herstellung von cis-4-phenyl-1,2,3,4-tetra-hydro-1-napthalinamin-derivaten
DD80224840A DD155615A5 (de)	1979-11-01	1980-10-30	Verfahren zur herstellung von derivaten des cis-4-phenyl-1,2,3,4-tetrahydro-1-nahtalinamins

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD80224840A DD155615A5 (de)	1979-11-01	1980-10-30	Verfahren zur herstellung von derivaten des cis-4-phenyl-1,2,3,4-tetrahydro-1-nahtalinamins

Country Status (38)

Country	Link
US (1)	US4536518A (fr)
EP (1)	EP0030081B1 (fr)
JP (1)	JPS605584B2 (fr)
KR (2)	KR840002001B1 (fr)
AT (1)	ATE2668T1 (fr)
AU (1)	AU517357B2 (fr)
BA (2)	BA97150B1 (fr)
BG (1)	BG60333B2 (fr)
CA (1)	CA1130815A (fr)
CS (4)	CS238609B2 (fr)
DD (2)	DD203045A5 (fr)
DE (2)	DE19775012I2 (fr)
DK (1)	DK153390C (fr)
EG (1)	EG15527A (fr)
ES (2)	ES496443A0 (fr)
FI (1)	FI68806C (fr)
GR (1)	GR70781B (fr)
HK (1)	HK82284A (fr)
HR (2)	HRP930199B1 (fr)
HU (1)	HU182224B (fr)
IE (1)	IE50395B1 (fr)
IL (1)	IL61374A (fr)
IN (2)	IN159643B (fr)
LU (1)	LU88330I2 (fr)
LV (2)	LV5456A3 (fr)
MX (1)	MX5980E (fr)
MY (1)	MY8500326A (fr)
NL (1)	NL940018I1 (fr)
NO (2)	NO148996C (fr)
NZ (1)	NZ195407A (fr)
PH (1)	PH17319A (fr)
PT (1)	PT72004B (fr)
SG (1)	SG56584G (fr)
SI (2)	SI8012798A8 (fr)
SU (2)	SU1014467A3 (fr)
UA (2)	UA6301A1 (fr)
YU (2)	YU41951B (fr)
ZA (1)	ZA806726B (fr)

Families Citing this family (172)

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Publication number	Priority date	Publication date	Assignee	Title
SE8004002L (sv) *	1980-05-29	1981-11-30	Arvidsson Folke Lars Erik	Terapeutiskt anvendbara tetralinderivat
US4777288A (en) *	1987-06-11	1988-10-11	Pfizer Inc.	Process for preparing a 4,4-diphenylbutanoic acid derivative
US4839104A (en) *	1987-06-11	1989-06-13	Pfizer, Inc.	Process for preparing sertraline intermediates
FR2623802B1 (fr) *	1987-11-26	1990-05-04	Lucien Laboratoires	Derives d'amino-4 trifluoromethyl-1 tetralines. leur preparation et leur application en therapeutique
US4855500A (en) *	1988-05-04	1989-08-08	Pfizer Inc.	Process for preparing a ketimine
FR2632633B1 (fr) *	1988-06-08	1991-04-05	Delalande Sa	Procede de preparation de 4-aryl-1-tetralones
US4981870A (en) *	1989-03-07	1991-01-01	Pfizer Inc.	Use of 4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine derivatives in the treatment of psychosis, inflammation and as immunosuppressants
US4940731A (en) *	1989-08-30	1990-07-10	Pfizer Inc.	Method of treating premature ejaculation using sertraline
US5130338A (en) *	1989-08-30	1992-07-14	Pfizer Inc.	Method of treating chemical dependencies using sertraline
ATE96999T1 (de) *	1989-08-30	1993-11-15	Pfizer	Verwendung von sertralin zur behandlung von abhaengigkeiten von chemischen stoffen.
US4962128A (en) *	1989-11-02	1990-10-09	Pfizer Inc.	Method of treating anxiety-related disorders using sertraline
FR2665443B1 (fr) *	1990-08-03	1992-11-06	Lucien Laboratoires	Derives d'amino-4-methyl-1-tetralines, leur preparation et leur application en therapeutique.
US5082970A (en) *	1991-03-06	1992-01-21	Pfizer Inc.	Process for recycling amine isomer
GB9114947D0 (en) *	1991-07-11	1991-08-28	Pfizer Ltd	Process for preparing sertraline
GB9114948D0 (en) *	1991-07-11	1991-08-28	Pfizer Ltd	Process for preparing sertraline intermediates
US5196607A (en) *	1992-02-14	1993-03-23	Pfizer Inc.	Process for preparing ketone enantiomer
US5248699A (en) *	1992-08-13	1993-09-28	Pfizer Inc.	Sertraline polymorph
US5288916A (en) *	1993-03-25	1994-02-22	Bend Research, Inc.	Enantiomeric resolution of 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone
US5750794A (en) *	1993-11-30	1998-05-12	Pfizer Inc.	Process for preparing chiral tetralone
US5597826A (en)	1994-09-14	1997-01-28	Pfizer Inc.	Compositions containing sertraline and a 5-HT1D receptor agonist or antagonist
US6410794B1 (en)	1994-12-16	2002-06-25	Uop Llc	Process for preparation of pharmaceutically desired chiral tetralone from tetralones
US6455736B1 (en)	1994-12-16	2002-09-24	Uop Llc	Process for preparation of pharmaceutically desired sertraline and sertraline analogs
WO1996041633A1 (fr) *	1995-06-08	1996-12-27	Eli Lilly And Company	Methodes de traitement des rhumes et des rhinites allergiques
US6548084B2 (en) *	1995-07-20	2003-04-15	Smithkline Beecham Plc	Controlled release compositions
EP0759299B1 (fr) *	1995-08-16	2000-04-26	Eli Lilly And Company	Potentialisation de la sérotonine
US5734083A (en) *	1996-05-17	1998-03-31	Torcan Chemical Ltd.	Sertraline polymorph
HU222341B1 (hu) *	1996-12-18	2003-06-28	Richter Gedeon Vegyészeti Gyár Rt.	Eljárás sertralin előállítására és az eljárásban alkalmazott intermedier
TW403740B (en) *	1997-06-10	2000-09-01	Novartis Ag	Novel crystal modifications of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide
US20030133974A1 (en) *	1997-07-01	2003-07-17	Curatolo William John	Encapsulated solution dosage forms of sertraline
SK180499A3 (en)	1997-07-01	2001-08-06	Pfizer	Sertraline salts and sustained-release dosage forms of sertraline
US20040208926A1 (en) *	1997-07-01	2004-10-21	Pfizer Inc	Solubilized sertraline compositions
DE69713353D1 (de) *	1997-12-11	2002-07-18	Torcan Chemical Ltd	Sertralin-Polymorph mit verbesserter Wasserlöslichkeit
IN191358B (fr) *	1998-01-16	2003-11-29	Pfizer Prod Inc
WO1999046233A1 (fr) *	1998-03-09	1999-09-16	Sumika Fine Chemicals Co., Ltd.	Derives de l'alcool benzylique
ES2217748T3 (es)	1998-03-18	2004-11-01	Ciba Specialty Chemicals Holding Inc.	Procedimiento para la hidrogenacin catalitica cis-selectiva de ciclohexilidenaminas.
FR2777000B1 (fr) *	1998-04-01	2002-09-27	Catalys	Procede de preparation de la sertraline racemique
PT957099E (pt)	1998-04-15	2003-02-28	Pfizer Prod Inc	Carboxamidas heterociclicas
US6054614A (en) *	1998-04-23	2000-04-25	Ciba Specialty Chemicals Corporation	Process for the preparation of tetralone imines for the preparation of active pharmaceutical compounds
HU226423B1 (en) *	1998-05-05	2008-12-29	Egis Gyogyszergyar Nyrt	Process for producing a 1(2h)-naphtalene-1-ylidene derivative
HU226424B1 (en) *	1998-05-05	2008-12-29	Egis Gyogyszergyar Nyrt	Process for producing enantiomer mixture for preparation of sertraline
IN182588B (fr)	1998-05-12	1999-05-08	Sun Pharmaceutical Ind Ltd
DE19830201A1 (de) *	1998-07-07	2000-01-13	Boehringer Ingelheim Pharma	Mittel mit antidepressiver Wirkung
OA11662A (en) *	1998-10-13	2004-12-08	Pfizer Prod Inc	Sertraline oral concentrate.
US6727283B2 (en)	1998-10-13	2004-04-27	Pfizer Inc.	Sertraline oral concentrate
IL132500A0 (en)	1998-10-29	2001-03-19	Pfizer Prod Inc	Stereoselective microbial reduction of a racemic tetralone
AU1031500A (en) *	1998-11-03	2000-05-22	Dandy A/S	Sucrose fatty acid esters for use as increased release of active ingredients
US6518284B2 (en) *	1998-11-18	2003-02-11	Faes, Fabrica Espanola De Productos Quimicos Y Farmaceuticos S.A.	4-substituted piperidines
WO2000032551A1 (fr) *	1998-11-27	2000-06-08	Teva Pharmaceutical Industries Ltd.	Polymorphes de chlorhydrate de sertraline
US6500987B1 (en) *	1998-11-27	2002-12-31	Teva Pharmaceutical Industries Ltd.	Sertraline hydrochloride polymorphs
EP1632474A1 (fr) *	1998-11-27	2006-03-08	Teva Pharmaceutical Industries Ltd.	Polymorphes de chlorhydrate de Sertraline
DE60021859T2 (de) *	1999-03-01	2006-06-01	Pfizer Inc.	1, 2, 3, 4-tetrahydro-1-naphthalenamin verbindungen zur therapeutsichen verwendung
US6245782B1 (en)	1999-05-17	2001-06-12	Heartdrug Research L.L.C.	Methods of inhibiting platelet activation with selective serotonin reuptake inhibitors
YU32700A (sh)	1999-06-09	2002-03-18	Pfizer Products Inc.	Postupak za dobijanje sertralina iz hiralnog tetralona
TR200200110T2 (tr) *	1999-07-29	2002-06-21	Ciba Specialty Chemicals Holding Inc.	Sikloheksilidenaminlerin cis-selektif katalitik hidrojenasyonu için süreç
US6495721B1 (en)	1999-08-09	2002-12-17	Teva Pharmaceutical Industries Ltd.	Sertraline hydrochloride Form II and methods for the preparation thereof
IN185109B (fr) *	1999-09-01	2000-11-18	Torrent Pharmaceuticals Ltd
DK174219B1 (da) *	1999-10-27	2002-09-30	Gea Farmaceutisk Fabrik As	Forbedret syntese af racemisk sertralin
TWI260315B (en) *	1999-10-29	2006-08-21	Ciba Sc Holding Ag	Polymorphic forms of sertraline hydrochloride
US20050119351A1 (en) *	1999-10-29	2005-06-02	Van Der Schaaf Paul A.	Polymorphic forms of sertraline hydrochloride
US7442838B2 (en) *	1999-10-29	2008-10-28	Ciba Specialty Chemicals Corp.	Polymorphic forms of sertraline hydrochloride
DE60020153T2 (de)	1999-11-16	2006-01-26	Ciba Speciality Chemicals Holding Inc.	Verfahren zur herstellung von ketiminen
US6806386B1 (en) *	1999-11-16	2004-10-19	Ciba Specialty Chemicals Corporation	Process for the preparation of ketimines
US6380200B1 (en)	1999-12-07	2002-04-30	Pfizer, Inc.	Combination of aldose reductase inhibitors and selective serotonin reuptake inhibitors for the treatment of diabetic complications
PT1248605E (pt) *	1999-12-21	2007-03-30	Teva Pharma	Novos polimorfos de cloridrato de sertralina, processos para a sua preparação, composições que os contêm e métodos para a sua utilização
MXPA02006335A (es)	1999-12-23	2002-12-13	Pfizer Prod Inc	Forma de dosificacion de farmaco en capas impulsada por hidrogel.
IN187170B (fr)	2000-01-04	2002-02-23	Sun Pharmaceutical Ind Ltd
KR20070002101A (ko) *	2000-03-14	2007-01-04	테바 파마슈티컬 인더스트리즈 리미티드	(+)-시스-세르트랄린의 신규한 제조 방법
WO2001078721A1 (fr) *	2000-04-13	2001-10-25	Mayo Foundation For Medical Education And Research	Agents de reduction de a$g(b)42
IN192343B (fr) *	2000-05-26	2004-04-10	Ranbaxy Lab Ltd
US6630504B2 (en)	2000-08-31	2003-10-07	Pfizer Inc.	Phenoxyphenylheterocyclyl derivatives as SSRIs
DE60119047D1 (de) *	2000-08-31	2006-06-01	Pfizer	Phenoxyphenylheterozyklen als Serotonin-Wiederaufnahmehemmer
US6482440B2 (en)	2000-09-21	2002-11-19	Phase 2 Discovery, Inc.	Long acting antidepressant microparticles
US6645946B1 (en)	2001-03-27	2003-11-11	Pro-Pharmaceuticals, Inc.	Delivery of a therapeutic agent in a formulation for reduced toxicity
US7067700B2 (en) *	2001-05-31	2006-06-27	Fermion Oy	Process for preparing sertraline hydrochloride polymorphic form II
EP1401800A1 (fr) *	2001-06-15	2004-03-31	Orion Corporation Fermion	Nouveau procede pour la preparation de (is-cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-n-methyl-1-naphtalenamine
US6723878B2 (en)	2001-06-15	2004-04-20	Orion Corporation Fermion	Method for preparing sertraline
AU2002342045C1 (en) *	2001-10-12	2009-07-30	Azevan Pharmaceuticals, Inc.	Beta-lactamyl vasopressin Vla antagonists
IL163666A0 (en)	2002-02-22	2005-12-18	New River Pharmaceuticals Inc	Active agent delivery systems and methods for protecting and administering active agents
WO2003093217A1 (fr) *	2002-04-29	2003-11-13	Teva Pharmaceutical Industries Ltd.	Procedes pour preparer une forme ii polymorphe d'hydrochlorure de sertraline, preparations pharmaceutiques et procedes d'administration
AU2003254475A1 (en) *	2002-07-29	2004-02-16	Cipla Limited	Sertraline
WO2004041773A1 (fr) *	2002-11-07	2004-05-21	Sunil Sadanand Nadkarni	Procede de preparation de forme polymorphe chlorhydrate de sertraline
US20040131672A1 (en) *	2003-01-07	2004-07-08	Nilobon Podhipleux	Direct compression pharmaceutical composition containing a pharmaceutically active ingredient with poor flowing properties
WO2004071431A2 (fr) *	2003-02-05	2004-08-26	Myriad Genetics, Inc.	Composition et methode de traitement de troubles neurodegeneratifs
WO2004087732A2 (fr) *	2003-03-11	2004-10-14	Sun Pharmaceutical Industries Limited	Procede de preparation de (1s, 4s)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-n-methyl-1-naphtylamine
ES2242555T1 (es) *	2003-04-14	2005-11-16	Teva Pharmaceutical Industries Limited	Hidrogenacion de intermediarios de imina de sertralina con catalizadores.
EP1626950A4 (fr) *	2003-05-23	2007-05-23	Transform Pharmaceuticals Inc	Compositions de sertraline
US20050070577A1 (en) *	2003-07-03	2005-03-31	Pfizer Inc.	Compositions containing a serotonin selective reuptake inhibitor and a 5-HT2A receptor antagonist
EP1651195A4 (fr) *	2003-07-11	2007-10-03	Myriad Genetics Inc	Procedes pharmaceutiques, posologies et formes posologiques pour le traitement de la maladie d'alzheimer
EP1648854A1 (fr) *	2003-07-15	2006-04-26	RECORDATI INDUSTRIA CHIMICA E FARMACEUTICA S.p.a.	Procedes de preparation de polymorphes de chlorhydrate de sertraline
WO2005012224A1 (fr) *	2003-07-15	2005-02-10	Recordati Industria Chimica E Farmaceutica S.P.A.	Chlorhydrate de sertraline de forme ii et procedes de preparation associes
HU227495B1 (en) *	2003-07-21	2011-07-28	Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag	Process for producing of imine intermediate
CA2537804A1 (fr) *	2003-09-05	2005-03-17	Teva Pharmaceutical Industries Ltd	Procede de recyclage pour l'elaboration de sertraline
MXPA06002789A (es)	2003-09-12	2006-06-14	Pfizer	Combinaciones que comprenden ligandos alfa-2-delta.
AU2004271796A1 (en) *	2003-09-12	2005-03-24	Warner-Lambert Company Llc	Combination comprising an alpha-2-delta ligand and an SSRI and/or SNRI for treatment of depression and anxiety disorders
MXPA06003150A (es) *	2003-09-17	2006-08-31	Johnson & Johnson	Compuestos heterociclicos fusionados.
CA2544684A1 (fr) *	2003-11-04	2005-05-26	Cipla Limited	Procede de preparation de polymorphismes d'inhibiteur selectif de recaptage de serotonine
WO2005051488A1 (fr) *	2003-11-26	2005-06-09	Pfizer Products Inc.	Association d'agonistes de la dopamine et d'inhibiteurs de recaptage de la monoamine
EP1689721B1 (fr) *	2003-11-26	2010-07-14	Pfizer Products Inc.	Derives d'aminopyrazole en tant qu'inhibiteurs de la gsk-3
PL1691811T3 (pl)	2003-12-11	2014-12-31	Sunovion Pharmaceuticals Inc	Skojarzenie leku uspokajającego i modulatora neuroprzekaźnikowego oraz sposoby poprawy jakości snu i leczenia depresji
WO2006001877A2 (fr) *	2004-04-13	2006-01-05	Myriad Genetics, Inc.	Composition pharmaceutique et methode de traitement de troubles neurodegeneratifs
US20050233010A1 (en) *	2004-04-19	2005-10-20	Satow Philip M	Lithium combinations, and uses related thereto
EP1742535A4 (fr) *	2004-05-06	2008-10-15	Cydex Pharmaceuticals Inc	Preparations au gout masque contenant de la sertraline et de la sulfoalkylether cyclodextrine
PE20060437A1 (es)	2004-06-18	2006-06-08	Novartis Ag	COMPUESTOS AZA-BICICLONONANOS COMO LIGANDOS COLINERGICOS DE nAChR
GB0415746D0 (en)	2004-07-14	2004-08-18	Novartis Ag	Organic compounds
WO2006020850A2 (fr) *	2004-08-11	2006-02-23	Myriad Genetics, Inc.	Composition pharmaceutique et technique de traitement de troubles neurodegeneratifs
WO2006020853A2 (fr) *	2004-08-11	2006-02-23	Myriad Genetics, Inc.	Composition pharmaceutique et methode de traitement de troubles neurodegeneratifs
WO2006020852A2 (fr) *	2004-08-11	2006-02-23	Myriad Genetics, Inc.	Composition pharmaceutique et technique de traitement de troubles neurodegeneratifs
US7345201B2 (en) *	2005-02-23	2008-03-18	Teva Pharmaceutical Industries, Ltd.	Processes for preparing sertraline
WO2006102283A2 (fr)	2005-03-22	2006-09-28	Azevan Pharmaceuticals, Inc.	Acides beta-lactamylalcanoiques destines au traitement des troubles premenstruels
JP2006265169A (ja) *	2005-03-24	2006-10-05	Tokuyama Corp	アルキリデンコハク酸化合物の製造方法
GB0507090D0 (en) *	2005-04-07	2005-05-11	Sandoz Ag	Process for preparing polymorphic form ll of sertraline hydrochloride
GB0507298D0 (en)	2005-04-11	2005-05-18	Novartis Ag	Organic compounds
PE20061298A1 (es)	2005-04-22	2006-12-24	Wyeth Corp	Compuestos derivados de dihidrobenzofurano como agonistas del receptor de serotonina 5-ht2c
BRPI0610027A2 (pt) *	2005-04-22	2010-05-18	Wyeth Corp	derivados de cromano e cromeno e usos dos mesmos
CA2605554A1 (fr)	2005-04-22	2006-11-02	Wyeth	Derives d'alcanamine de benzofuranyle et leurs utilisations comme agonistes 5-ht2c
WO2006116170A1 (fr) *	2005-04-22	2006-11-02	Wyeth	Derives de dihydrobenzofurane et utilisations de ceux-ci
PE20061319A1 (es) *	2005-04-22	2006-12-28	Wyeth Corp	Cristales formados de clorhidrato de {[(2r)-7-(2,6-diclorofenil)-5-fluoro-2-3-dihidro-1-benzofurano-2-il]metil}amina
EP1885683A2 (fr) *	2005-06-03	2008-02-13	Hetero Drugs Limited	Synthese hautement stereoselective de sertraline
US20070100165A1 (en) *	2005-06-09	2007-05-03	Ronen Borochovitz	Process for preparation of sertraline hydrochloride form I
US7884136B2 (en)	2005-06-27	2011-02-08	Biovail Laboratories International S.R.L.	Modified-release formulations of a bupropion salt
AU2006269231A1 (en)	2005-07-08	2007-01-18	Braincells, Inc.	Methods for identifying agents and conditions that modulate neurogenesis
US20070015832A1 (en) *	2005-07-14	2007-01-18	Myriad Genetics, Incorporated	Methods of treating overactive bladder and urinary incontinence
PL1910346T3 (pl) *	2005-07-19	2019-09-30	Azevan Pharmaceuticals, Inc.	Beta-laktamowy antagonista wazopresyny fenyloalaniny, cysteiny i seryny
US7598255B2 (en) *	2005-08-04	2009-10-06	Janssen Pharmaceutica Nv	Pyrimidine compounds as serotonin receptor modulators
JP2009512711A (ja)	2005-10-21	2009-03-26	ブレインセルス，インコーポレイティド	Ｐｄｅ阻害による神経新生の調節
EP2314289A1 (fr)	2005-10-31	2011-04-27	Braincells, Inc.	Modulation de la neurogenese dont la médiation est assurée par récepteur gaba
GB0525672D0 (en)	2005-12-16	2006-01-25	Novartis Ag	Organic compounds
GB0525673D0 (en)	2005-12-16	2006-01-25	Novartis Ag	Organic compounds
US8053603B2 (en) *	2006-01-06	2011-11-08	Sunovion Pharmaceuticals Inc.	Tetralone-based monoamine reuptake inhibitors
WO2007087387A1 (fr) *	2006-01-23	2007-08-02	Teva Pharmaceutical Industries Ltd.	Procede de recyclage pour preparer la sertraline
FR2912057B1 (fr) *	2007-02-07	2009-04-17	Sanofi Aventis Sa	Composition pharmaceutique contenant en association le saredutant et un inhibiteur selectif de la recapture de la serotonine ou un inhibiteur de la recapture de la serotonine/norepinephrine
US20100216734A1 (en)	2006-03-08	2010-08-26	Braincells, Inc.	Modulation of neurogenesis by nootropic agents
TW200806300A (en) *	2006-03-24	2008-02-01	Wyeth Corp	New therapeutic combinations for the treatment of depression
WO2007119247A2 (fr) *	2006-04-17	2007-10-25	Unichem Laboratories Limited	Procédé de production amélioré destiné à la préparation de la forme polymorphe ii de l'hydrochlorure de cis-(1s)-n-methyl-4-(3,4-dichlorophényle)-1,2,3,4-tétrahydro-1-napthlèneamine (hydrochlorure de sertraline)
TR200808115T1 (tr) *	2006-04-28	2009-03-23	Sandoz Ag	4(S,R)-(3,4-diklorofenil)-3,4-dihidro-l(2H)-naftalin-l-ilid n]metilamin'ın Hazırlanması için Proses.@
US7858611B2 (en) *	2006-05-09	2010-12-28	Braincells Inc.	Neurogenesis by modulating angiotensin
AU2007249399A1 (en)	2006-05-09	2007-11-22	Braincells, Inc.	Neurogenesis by modulating angiotensin
CA2651862A1 (fr)	2006-05-09	2007-11-22	Braincells, Inc.	Neurogenese induite par le recepteur 5ht
US7518019B2 (en) *	2006-06-01	2009-04-14	Hetero Drugs Limited	Processes for preparing sertraline hydrochloride crystalline forms
US20100279990A1 (en) *	2006-06-13	2010-11-04	Ramot At Tel-Aviv University Ltd.	Antiproliferative compounds, compositions and methods of use
US7893053B2 (en) *	2006-06-16	2011-02-22	Theracos, Inc.	Treating psychological conditions using muscarinic receptor M1 antagonists
US20080033045A1 (en) *	2006-07-07	2008-02-07	Myriad Genetics, Incorporated	Treatment of psychiatric disorders
TW200817003A (en) *	2006-07-31	2008-04-16	Sanofi Aventis	Pharmaceutical composition comprising, in combination, saredutant and a selective serotonin peuptake inhibitor or a serotonin/norepinephrine reuptake inhibitor
US20060257475A1 (en) *	2006-08-17	2006-11-16	Boehringer Ingelheim International Gmbh	Stable Sertraline Hydrochloride Formulation and Method
WO2008030651A1 (fr)	2006-09-08	2008-03-13	Braincells, Inc.	Combinaisons contenant un dérivé de 4-acylaminopyridine
US20100016274A1 (en) *	2006-09-14	2010-01-21	Koppel Gary A	Beta-lactam cannabinoid receptor modulators
US20100184806A1 (en)	2006-09-19	2010-07-22	Braincells, Inc.	Modulation of neurogenesis by ppar agents
FR2909376A1 (fr) *	2006-11-30	2008-06-06	Cerep Sa	Procedes de preparation de la desmethulsertraline ou d'un de ses sels pharmaceutiquement acceptables
WO2008083204A2 (fr) *	2006-12-28	2008-07-10	Braincells, Inc.	Modulation de la neurogenèse par des ligands mélatoninergiques
EP2125017A2 (fr) *	2007-01-11	2009-12-02	Braincells, Inc.	Modulation de la neurogenèse en utilisant du modafinil
CA2594198A1 (fr) *	2007-07-20	2009-01-20	Apotex Pharmachem Inc.	Procede inedit de preparation d'hydrochlorure de sertraline de forme ii
US20090062399A1 (en) *	2007-08-29	2009-03-05	Protia, Llc	Deuterium-enriched sertraline
US8461389B2 (en)	2008-04-18	2013-06-11	University College Dublin, National University Of Ireland, Dublin	Psycho-pharmaceuticals
WO2009128058A1 (fr)	2008-04-18	2009-10-22	UNIVERSITY COLLEGE DUBLIN, NATIONAL UNIVERSITY OF IRELAND, DUBLIN et al	Produits psycho-pharmaceutiques
US20100216805A1 (en)	2009-02-25	2010-08-26	Braincells, Inc.	Modulation of neurogenesis using d-cycloserine combinations
US9260413B2 (en) *	2010-03-04	2016-02-16	Merck Sharp & Dohme Corp.	Inhibitors of catechol O-methyl transferase and their use in the treatment of psychotic disorders
EP2380595A1 (fr)	2010-04-19	2011-10-26	Nlife Therapeutics S.L.	Compositions et procédés pour la fourniture sélective de molécules d'oligonucléotides à des types de neurones spécifiques
WO2011163231A2 (fr)	2010-06-21	2011-12-29	Theracos, Inc.	Thérapie combinée pour le traitement du diabète
RU2623209C9 (ru)	2010-07-01	2018-01-22	Азеван Фармасьютикалз, Инк.	Способы лечения посттравматического стрессового расстройства
EP2685966A1 (fr)	2011-03-17	2014-01-22	Lupin Limited	Compositions pharmaceutiques à libération contrôlée d'un inhibiteur sélectif de la recapture de sérotonine
KR101340270B1 (ko) *	2011-11-10	2013-12-10	보령제약 주식회사	(+)-시스-서트랄린의 선택적인 제조방법
CN104603110B (zh) *	2012-10-18	2016-08-31	霍夫曼-拉罗奇有限公司	作为mGluR5受体活性的调节剂的乙炔基衍生物
BR112016022575A2 (pt)	2014-03-28	2017-08-15	Azevan Pharmaceuticals Inc	Composições e métodos para o tratamento de doenças neurodegenerativas
US10266481B2 (en)	2014-06-20	2019-04-23	Council Of Scientific & Industrial Research	Organocatalytic asymmetric synthesis of antidepressants
WO2016023825A1 (fr) *	2014-08-11	2016-02-18	Hydra Biosciences, Inc.	Dérivés de pyrido[3,4-d]pyrimidine-2,4(1h,3h)-dione
EP3180340B1 (fr) *	2014-08-11	2018-10-10	Hydra Biosciences, Inc.	Dérivés de pyrido[2,3-d]pyrimidine-2,4(1h,3h)-dione
WO2016023831A1 (fr) *	2014-08-11	2016-02-18	Hydra Biosciences, Inc.	Dérivés de pyrrolo[3,2-d]pyrimidine-2,4(3h,5h)-dione
EP3180345B1 (fr) *	2014-08-11	2018-10-10	Hydra Biosciences, Inc.	Dérivés thieno- et furo[2,3-d]pyrimidine-2,4[1h,3h]-dione en tant que modulateurs trpc5 pour le traitement de maladies neuropsychiatriques
WO2017053459A1 (fr)	2015-09-21	2017-03-30	S.C. Johnson & Son, Inc.	Système de mélange et de distribution
MX2020002762A (es)	2017-09-15	2020-09-17	Azevan Pharmaceuticals Inc	Composiciones y métodos para tratar una lesión cerebral.
WO2020043716A1 (fr)	2018-08-27	2020-03-05	Katholieke Universiteit Leuven	Ciblage pharmacologique de la synthèse de novo de sérine/glycine
GB2630572A (en)	2023-05-29	2024-12-04	Novumgen Ltd	An orally disintegrating tablet of sertraline and its process of preparation

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2887509A (en) *	1956-11-05	1959-05-19	Lilly Co Eli	Hydroxybenzoyl benzoate salt of beta-(o-chlorophenyl)-beta-hydroxyethyl isopropylamine
US3704323A (en) *	1969-12-23	1972-11-28	Squibb & Sons Inc	Indane derivatives
US4029731A (en) *	1974-11-06	1977-06-14	Pfizer Inc.	Aminophenyltetralin compounds
US4045488A (en) *	1974-11-06	1977-08-30	Pfizer Inc.	Aminophenyltetralin compounds

1979
- 1979-11-01 US US06/090,240 patent/US4536518A/en not_active Expired - Lifetime
1980
- 1980-09-18 DK DK395280A patent/DK153390C/da active
- 1980-09-27 IN IN699/DEL/80A patent/IN159643B/en unknown
- 1980-10-27 MX MX809122U patent/MX5980E/es unknown
- 1980-10-28 DE DE1997175012 patent/DE19775012I2/de active Active
- 1980-10-28 EP EP80303809A patent/EP0030081B1/fr not_active Expired
- 1980-10-28 HU HU802601A patent/HU182224B/hu unknown
- 1980-10-28 PH PH24780A patent/PH17319A/en unknown
- 1980-10-28 DE DE8080303809T patent/DE3062225D1/de not_active Expired
- 1980-10-28 SU SU802999197A patent/SU1014467A3/ru active
- 1980-10-28 UA UA2999197A patent/UA6301A1/uk unknown
- 1980-10-28 AT AT80303809T patent/ATE2668T1/de active
- 1980-10-28 UA UA3325759A patent/UA6311A1/uk unknown
- 1980-10-29 EG EG666/80A patent/EG15527A/xx active
- 1980-10-29 CS CS807314A patent/CS238609B2/cs unknown
- 1980-10-30 DD DD80240118A patent/DD203045A5/de unknown
- 1980-10-30 DD DD80224840A patent/DD155615A5/de unknown
- 1980-10-30 GR GR63247A patent/GR70781B/el unknown
- 1980-10-30 CA CA363,568A patent/CA1130815A/fr not_active Expired
- 1980-10-30 IL IL61374A patent/IL61374A/xx unknown
- 1980-10-30 FI FI803398A patent/FI68806C/fi not_active IP Right Cessation
- 1980-10-30 NZ NZ195407A patent/NZ195407A/en unknown
- 1980-10-31 SI SI8012798A patent/SI8012798A8/sl unknown
- 1980-10-31 JP JP55153698A patent/JPS605584B2/ja not_active Expired
- 1980-10-31 ES ES496443A patent/ES496443A0/es active Granted
- 1980-10-31 PT PT72004A patent/PT72004B/pt unknown
- 1980-10-31 KR KR1019800004176A patent/KR840002001B1/ko not_active Expired
- 1980-10-31 AU AU63897/80A patent/AU517357B2/en not_active Expired
- 1980-10-31 IE IE2259/80A patent/IE50395B1/en not_active IP Right Cessation
- 1980-10-31 ZA ZA00806726A patent/ZA806726B/xx unknown
- 1980-10-31 YU YU2798/80A patent/YU41951B/xx unknown
- 1980-10-31 NO NO803258A patent/NO148996C/no unknown
1981
- 1981-08-28 SU SU813325759A patent/SU1034602A3/ru active
- 1981-11-05 ES ES506892A patent/ES8207123A1/es not_active Expired
- 1981-11-11 CS CS818298A patent/CS238618B2/cs unknown
- 1981-11-11 CS CS818297A patent/CS238617B2/cs unknown
1983
- 1983-03-21 SI SI8310672A patent/SI8310672A8/sl unknown
- 1983-03-21 YU YU672/83A patent/YU42846B/xx unknown
1984
- 1984-01-20 IN IN060/DEL/84A patent/IN159644B/en unknown
- 1984-06-01 KR KR1019840003057A patent/KR840002000B1/ko not_active Expired
- 1984-08-13 SG SG565/84A patent/SG56584G/en unknown
- 1984-11-01 HK HK822/84A patent/HK82284A/en not_active IP Right Cessation
1985
- 1985-12-30 MY MY326/85A patent/MY8500326A/xx unknown
1991
- 1991-11-22 CS CS913542A patent/CS354291A3/cs unknown
1992
- 1992-03-16 BG BG096071A patent/BG60333B2/bg unknown
1993
- 1993-02-18 HR HR930199A patent/HRP930199B1/xx not_active IP Right Cessation
- 1993-06-24 LU LU88330C patent/LU88330I2/fr unknown
- 1993-11-15 LV LV931227A patent/LV5456A3/xx unknown
- 1993-11-15 LV LV931228A patent/LV5457A3/xx unknown
- 1993-12-30 HR HRP-672/83A patent/HRP931527B1/xx not_active IP Right Cessation
1994
- 1994-08-31 NL NL940018C patent/NL940018I1/nl unknown
1996
- 1996-09-24 NO NO1996011C patent/NO1996011I1/no unknown
1997
- 1997-03-28 BA BA970150A patent/BA97150B1/bs active
- 1997-03-28 BA BA970149A patent/BA97149B1/bs active

Also Published As

Publication number	Publication date
NZ195407A (en)	1984-05-31
PT72004A (en)	1980-11-01
HRP931527B1 (en)	1996-04-30
EP0030081B1 (fr)	1983-03-02
LV5456A3 (lv)	1994-03-10
NO1996011I1 (no)	1996-09-24
FI68806B (fi)	1985-07-31
ES8201949A1 (es)	1982-01-16
DD155615A5 (de)	1982-06-23
ES506892A0 (es)	1982-09-01
SI8012798A8 (sl)	1994-12-31
BA97149B1 (bs)	1998-12-28
CS238617B2 (en)	1985-12-16
DK395280A (da)	1981-05-02
UA6311A1 (uk)	1994-12-29
CS354291A3 (en)	1992-12-16
HRP930199B1 (en)	1996-02-29
SU1014467A3 (ru)	1983-04-23
YU41951B (en)	1988-02-29
AU6389780A (en)	1981-05-07
AU517357B2 (en)	1981-07-23
EP0030081A1 (fr)	1981-06-10
CS238618B2 (en)	1985-12-16
DE19775012I2 (de)	2001-02-08
IN159643B (fr)	1987-05-30
NL940018I1 (nl)	1994-10-17
JPS5686137A (en)	1981-07-13
BG60333B2 (bg)	1994-11-30
GR70781B (fr)	1983-03-23
PT72004B (en)	1981-08-31
DE3062225D1 (en)	1983-04-07
FI803398L (fi)	1981-05-02
UA6301A1 (uk)	1994-12-29
JPS605584B2 (ja)	1985-02-12
KR830004202A (ko)	1983-07-06
HK82284A (en)	1984-11-09
LU88330I2 (fr)	1994-05-04
CS238609B2 (en)	1985-12-16
BA97150B1 (bs)	1998-12-28
SI8310672A8 (en)	1996-04-30
YU42846B (en)	1988-12-31
MY8500326A (en)	1985-12-31
LV5457A3 (lv)	1994-03-10
KR840002000B1 (ko)	1984-10-27
US4536518A (en)	1985-08-20
IN159644B (fr)	1987-05-30
CA1130815A (fr)	1982-08-31
NO148996C (no)	1984-01-25
DK153390C (da)	1988-12-05
EG15527A (en)	1987-04-30
FI68806C (fi)	1985-11-11
SU1034602A3 (ru)	1983-08-07
IL61374A0 (en)	1980-12-31
ES496443A0 (es)	1982-01-16
HU182224B (en)	1983-12-28
ATE2668T1 (de)	1986-03-15
IE50395B1 (en)	1986-04-16
IL61374A (en)	1983-10-31
YU279880A (en)	1983-09-30
NO803258L (no)	1981-05-04
SG56584G (en)	1985-03-08
KR840002001B1 (ko)	1984-10-27
DK153390B (da)	1988-07-11
PH17319A (en)	1984-07-20
IE802259L (en)	1981-05-01
NO148996B (no)	1983-10-17
YU67283A (en)	1983-10-31
MX5980E (es)	1984-09-12
ES8207123A1 (es)	1982-09-01
ZA806726B (en)	1981-10-28

Publication	Publication Date	Title
DD203045A5 (de)	1983-10-12	Verfahren zur herstellung von cis-4-phenyl-1,2,3,4-tetra-hydro-1-napthalinamin-derivaten
US4556676A (en)	1985-12-03	Antidepressant derivatives of trans-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine
DE2657013A1 (de)	1977-07-28	Phthalanderivate und verfahren zu deren herstellung sowie diese enthaltende pharmazeutische mittel
EP0828484A1 (fr)	1998-03-18	Utilisation de cyclobutylalkylamines substituees par aryle pour le traitement de l'obesite
DE1593760A1 (de)	1972-06-08	Verfahren zur Herstellung neuer Benz-epinderivate
DD150457A5 (de)	1981-09-02	Verfahren zur herstellung der(r,r)optisch isomeren verbindungen von labetalol
DD235065A5 (de)	1986-04-23	Verfahren zur herstellung von n-(2-(4-fluorphenyl)-1-methyl)-n-methyl-n-propinylamin
DD149071A5 (de)	1981-06-24	Herstellung 2-substituierter trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido eckige klammer auf 4,3-b eckige klammer zu indole
DE2062001A1 (de)	1971-07-15	Isochinolin Derivate
DD147537A5 (de)	1981-04-08	Verfahren zur herstellung von 1,2,4,5-tetra-alkyl-4-aryl-piperidinen
DE2408476C2 (fr)	1990-12-06
EP0770082B1 (fr)	2000-03-08	Derives d'acide carboxylique de dioxo-thiopyrano-pyridine et leur utilisation comme medicaments
DE3320394A1 (de)	1983-12-08	Optisch aktive n-arylierte oxazolidinon-(2)-derivate, deren verwendung als spezifische und reversible inhibitoren von monoaminooxydase des b-typs sowie verfahren zu deren herstellung
DE2656088A1 (de)	1977-06-23	Neues benzylalkoholderivat und verfahren zu seiner herstellung
DE2355262C3 (de)	1982-05-27	1-Piperidinsulfonylharnstoffe, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
DE2348577C2 (de)	1982-06-03	1-Amino-4-phenyl-1,2,3,4-tetrahydronaphthaline, deren pharmakologisch verträglichen Salze und diese enthaltende pharmazeutische Zubereitungen
DE2708110A1 (de)	1977-09-08	Pyrrolbenzoxaaza-alkane
DE2507429C2 (de)	1982-10-07	Aminosäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2803688A1 (de)	1978-08-10	Neue benzolsulfonamid- und benzolcarboxamidderivate
DE1915230A1 (de)	1970-02-05	Hydroxyphenylalkylaminderivate und Verfahren zu deren Herstellung
DE2835536A1 (de)	1979-03-01	Verfahren zur erzielung eines antioestrogenen effekts bei warmbluetern, hierfuer geeignete zusammensetzungen und verbindungen sowie verfahren zur herstellung dieser verbindungen
DE1922280C3 (de)	1980-01-17	l-Methyl-5-(3'-dimethylaminopropyliden)-5Hdibenzo [a,d] -cyelohepten-N- oxid und dessen Säureadditionssalze, sowie Verfahren zu deren Herstellung und diese Verbindungen enthaltende Präparate
DE2440734A1 (de)	1975-03-13	Amphetaminderivate, verfahren zu deren herstellung und sie enthaltende arzneimittel
DE2738131A1 (de)	1978-03-09	Aminoketone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2513197A1 (de)	1975-10-09	Cyclische verbindungen