DD155615A5 - Verfahren zur herstellung von derivaten des cis-4-phenyl-1,2,3,4-tetrahydro-1-nahtalinamins - Google Patents

Verfahren zur herstellung von derivaten des cis-4-phenyl-1,2,3,4-tetrahydro-1-nahtalinamins Download PDF

Info

Publication number: DD155615A5
Authority: DD; German Democratic Republic
Prior art keywords: cis; hydrogen; meaning; tetrahydro; methyl
Prior art date: 1979-11-01

Application number

DD80224840A

Other languages

German (de)

English (en)

Inventor

Williard 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

1982-06-23

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=DD155615(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

1982-06-23 Publication of DD155615A5 publication Critical patent/DD155615A5/de

Links

238000004519 manufacturing process Methods 0.000 title 1
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-1 3-trifluoromethylphenyl Chemical group 0.000 claims description 17
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101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 9
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238000007918 intramuscular administration Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
238000005567 liquid scintillation counting Methods 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
XPLZAZCGEUUFJL-UHFFFAOYSA-N n-benzyl-3-[2-(pyridine-4-carbonyl)hydrazinyl]propanamide;hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C[NH2+]C(=O)CCNNC(=O)C1=CC=NC=C1 XPLZAZCGEUUFJL-UHFFFAOYSA-N 0.000 description 1
FOKKJVHTXPJHEN-UHFFFAOYSA-N naphthalen-1-ylazanium;chloride Chemical compound Cl.C1=CC=C2C(N)=CC=CC2=C1 FOKKJVHTXPJHEN-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
239000002547 new drug Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
IOXDAYKKVHAKSX-UHFFFAOYSA-N phenyl-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 IOXDAYKKVHAKSX-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000012056 semi-solid material Substances 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000009182 swimming Effects 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000018405 transmission of nerve impulse Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229960002791 zimeldine Drugs 0.000 description 1
OYPPVKRFBIWMSX-SXGWCWSVSA-N zimeldine Chemical compound C=1C=CN=CC=1C(=C/CN(C)C)\C1=CC=C(Br)C=C1 OYPPVKRFBIWMSX-SXGWCWSVSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- 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
- C—CHEMISTRY; METALLURGY
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- 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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Chemical & Material Sciences (AREA)
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Pain & Pain Management (AREA)
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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DD80224840A 1979-11-01 1980-10-30 Verfahren zur herstellung von derivaten des cis-4-phenyl-1,2,3,4-tetrahydro-1-nahtalinamins DD155615A5 (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
DD155615A5 true DD155615A5 (de)	1982-06-23

Family

ID=22221931

Family Applications (2)

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
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

Family Applications After (1)

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

Country Status (38)

Country	Link
US (1)	US4536518A (es)
EP (1)	EP0030081B1 (es)
JP (1)	JPS605584B2 (es)
KR (2)	KR840002001B1 (es)
AT (1)	ATE2668T1 (es)
AU (1)	AU517357B2 (es)
BA (2)	BA97149B1 (es)
BG (1)	BG60333B2 (es)
CA (1)	CA1130815A (es)
CS (4)	CS238609B2 (es)
DD (2)	DD155615A5 (es)
DE (2)	DE3062225D1 (es)
DK (1)	DK153390C (es)
EG (1)	EG15527A (es)
ES (2)	ES496443A0 (es)
FI (1)	FI68806C (es)
GR (1)	GR70781B (es)
HK (1)	HK82284A (es)
HR (2)	HRP930199B1 (es)
HU (1)	HU182224B (es)
IE (1)	IE50395B1 (es)
IL (1)	IL61374A (es)
IN (2)	IN159643B (es)
LU (1)	LU88330I2 (es)
LV (2)	LV5457A3 (es)
MX (1)	MX5980E (es)
MY (1)	MY8500326A (es)
NL (1)	NL940018I1 (es)
NO (2)	NO148996C (es)
NZ (1)	NZ195407A (es)
PH (1)	PH17319A (es)
PT (1)	PT72004B (es)
SG (1)	SG56584G (es)
SI (2)	SI8012798A8 (es)
SU (2)	SU1014467A3 (es)
UA (2)	UA6301A1 (es)
YU (2)	YU41951B (es)
ZA (1)	ZA806726B (es)

Families Citing this family (172)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE8004002L (sv) *	1980-05-29	1981-11-30	Arvidsson Folke Lars Erik	Terapeutiskt anvendbara tetralinderivat
US4839104A (en) *	1987-06-11	1989-06-13	Pfizer, Inc.	Process for preparing sertraline intermediates
US4777288A (en) *	1987-06-11	1988-10-11	Pfizer Inc.	Process for preparing a 4,4-diphenylbutanoic acid derivative
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
EP0415612B1 (en) *	1989-08-30	1993-11-10	Pfizer Inc.	Use of sertraline for the treatment of chemical dependencies
US5130338A (en) *	1989-08-30	1992-07-14	Pfizer Inc.	Method of treating chemical dependencies using sertraline
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
CA2176500C (en) *	1993-11-30	1999-09-28	George J. Quallich	Process for preparing a chiral tetralone
US5597826A (en)	1994-09-14	1997-01-28	Pfizer Inc.	Compositions containing sertraline and a 5-HT1D receptor agonist or antagonist
US6455736B1 (en)	1994-12-16	2002-09-24	Uop Llc	Process for preparation of pharmaceutically desired sertraline and sertraline analogs
US6410794B1 (en)	1994-12-16	2002-06-25	Uop Llc	Process for preparation of pharmaceutically desired chiral tetralone from tetralones
AU5966196A (en) *	1995-06-08	1997-01-09	Eli Lilly And Company	Methods of treating cold and allergic rhinitis
US6548084B2 (en) *	1995-07-20	2003-04-15	Smithkline Beecham Plc	Controlled release compositions
WO1997006792A1 (en) *	1995-08-16	1997-02-27	Eli Lilly And Company	Potentiation of serotonin response
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
TW526195B (en) *	1997-06-10	2003-04-01	Novartis Ag	Crystal modifications of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide and their use
US20030133974A1 (en) *	1997-07-01	2003-07-17	Curatolo William John	Encapsulated solution dosage forms of sertraline
US20040208926A1 (en) *	1997-07-01	2004-10-21	Pfizer Inc	Solubilized sertraline compositions
NZ513456A (en) *	1997-07-01	2003-02-28	Pfizer	Sertraline acetate, L-lactate and L-aspartate, processes for their preparation and their uses in psychotic disorders
DE69713353D1 (de) *	1997-12-11	2002-07-18	Torcan Chemical Ltd	Sertralin-Polymorph mit verbesserter Wasserlöslichkeit
IN191358B (es)	1998-01-16	2003-11-29	Pfizer Prod Inc
WO1999046233A1 (en) *	1998-03-09	1999-09-16	Sumika Fine Chemicals Co., Ltd.	Benzyl alcohol derivatives
EP1064250B1 (en) *	1998-03-18	2004-04-21	Ciba SC Holding AG	Process for the cis-selective catalytic hydrogenation of cyclohexylidenamines
FR2777000B1 (fr) *	1998-04-01	2002-09-27	Catalys	Procede de preparation de la sertraline racemique
ATE228119T1 (de) *	1998-04-15	2002-12-15	Pfizer Prod Inc	Heterocyclische carboxamide
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
HU226424B1 (en) *	1998-05-05	2008-12-29	Egis Gyogyszergyar Nyrt	Process for producing enantiomer mixture for preparation of sertraline
HU226423B1 (en) *	1998-05-05	2008-12-29	Egis Gyogyszergyar Nyrt	Process for producing a 1(2h)-naphtalene-1-ylidene derivative
IN182588B (es) *	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
AP2001002119A0 (en) *	1998-10-13	2001-03-22	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
EP1637516A1 (en) *	1998-11-27	2006-03-22	Teva Pharmaceutical Industries Ltd	Sertraline hydrochloride polymorphs
AU1633600A (en) *	1998-11-27	2000-06-19	Teva Pharmaceutical Industries Ltd.	Sertraline hydrochloride polymorphs
US6500987B1 (en) *	1998-11-27	2002-12-31	Teva Pharmaceutical Industries Ltd.	Sertraline hydrochloride polymorphs
AU2315400A (en) *	1999-03-01	2000-09-21	Middleton, Donald Stuart	1,2,3,4-tetrahydro-1-naphthalenamine compounds useful in therapy
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
DK1200387T3 (da) *	1999-07-29	2004-07-19	Ciba Sc Holding Ag	Fremgangsmåde til den cis-selektive katalytiske hydrogenering af cyclohexylidenaminer
US6495721B1 (en) *	1999-08-09	2002-12-17	Teva Pharmaceutical Industries Ltd.	Sertraline hydrochloride Form II and methods for the preparation thereof
IN185109B (es) *	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
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
TWI260315B (en) *	1999-10-29	2006-08-21	Ciba Sc Holding Ag	Polymorphic forms of sertraline hydrochloride
DE60021410T2 (de)	1999-11-16	2006-05-24	Ciba Speciality Chemicals Holding Inc.	Verfahren zur herstellung von ketiminen
JP2003514794A (ja)	1999-11-16	2003-04-22	チバスペシャルティケミカルズホールディングインコーポレーテッド	ケトイミンの調製方法
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
SK8872002A3 (en) *	1999-12-21	2002-12-03	Teva Pharma	Novel sertraline hydrochloride polymorphs, processes for preparing them, compositions containing them and methods of using them
EP1239839A2 (en)	1999-12-23	2002-09-18	Pfizer Products Inc.	Hydrogel-driven layered drug dosage form comprising sertraline
IN187170B (es)	2000-01-04	2002-02-23	Sun Pharmaceutical Ind Ltd
AU4363401A (en) *	2000-03-14	2001-09-24	Teva Pharma	Novel process for preparing (+)-cis-sertraline
WO2001078721A1 (en) *	2000-04-13	2001-10-25	Mayo Foundation For Medical Education And Research	Aβ42 LOWERING AGENTS
IN192343B (es) *	2000-05-26	2004-04-10	Ranbaxy Lab Ltd
ATE324365T1 (de) *	2000-08-31	2006-05-15	Pfizer	Phenoxyphenylheterozyklen als serotonin- wiederaufnahmehemmer
US6630504B2 (en)	2000-08-31	2003-10-07	Pfizer Inc.	Phenoxyphenylheterocyclyl derivatives as SSRIs
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
US6723878B2 (en)	2001-06-15	2004-04-20	Orion Corporation Fermion	Method for preparing sertraline
EP1401800A1 (en) *	2001-06-15	2004-03-31	Orion Corporation Fermion	A novel process for the preparation of (is-cis) -4-(3, 4-dichlorophenyl) -1, 2, 3, 4 - tetrahydro-n-methyl-1-naphthalenamine
CA2462903C (en) *	2001-10-12	2011-09-20	Serenix Pharmaceuticals, Llc	Beta-lactamyl vasopressin v1a antagonists
EP2316469A1 (en)	2002-02-22	2011-05-04	Shire LLC	Delivery system and methods for protecting and administering dextroamphetamine
WO2003093217A1 (en) *	2002-04-29	2003-11-13	Teva Pharmaceutical Industries Ltd.	Process for preparation of polymorphic form ii of sertraline hydrochloride, pharmaceutical formulations and methods of administration thereof
WO2004011413A1 (en) *	2002-07-29	2004-02-05	Cipla Limited	Sertraline
BR0316032A (pt) *	2002-11-07	2005-09-27	Torrent Pharmaceuticals Ltd	Processo para a preparação da forma polimórfica do cloridrato de sertralina
US20040131672A1 (en) *	2003-01-07	2004-07-08	Nilobon Podhipleux	Direct compression pharmaceutical composition containing a pharmaceutically active ingredient with poor flowing properties
EP1603548A4 (en) *	2003-02-05	2007-10-10	Myriad Genetics Inc	METHOD AND COMPOSITION FOR THE TREATMENT OF NEURODEEGENERATIVE DISEASES
WO2004087732A2 (en) *	2003-03-11	2004-10-14	Sun Pharmaceutical Industries Limited	Process for the preparation of (1s, 4s)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-n-methyl-1-naphthylamine
TW200503991A (en) *	2003-04-14	2005-02-01	Teva Pharma	Hydrogenation of imine intermediates of sertraline with catalysts
JP2007502329A (ja) *	2003-05-23	2007-02-08	トランスフォーム・ファーマシューティカルズ・インコーポレイテッド	セルトラリン組成物
US20050070577A1 (en) *	2003-07-03	2005-03-31	Pfizer Inc.	Compositions containing a serotonin selective reuptake inhibitor and a 5-HT2A receptor antagonist
WO2005065069A2 (en) *	2003-07-11	2005-07-21	Myriad Genetics, Inc.	Pharmaceutical methods, dosing regimes and dosage forms for the treatment of alzheimer's disease
EP1646605A1 (en) *	2003-07-15	2006-04-19	Recordati Industria Chimica e Farmaceutica S.p.A.	Sertraline hydrochloride form ii and methods for the preparation thereof
EP1648854A1 (en) *	2003-07-15	2006-04-26	RECORDATI INDUSTRIA CHIMICA E FARMACEUTICA S.p.a.	Methods for preparing sertraline hydrochloride polymorphs
HU227495B1 (en) *	2003-07-21	2011-07-28	Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag	Process for producing of imine intermediate
CA2537804A1 (en) *	2003-09-05	2005-03-17	Teva Pharmaceutical Industries Ltd	A recycling process for preparing sertraline
BRPI0414347A (pt) *	2003-09-12	2006-11-07	Warner Lambert Co	associação compreendendo um ligando de alfa-2-delta e um ssri e/ou snri para tratamento de depressão e distúrbios da ansiedade
DE602004024317D1 (de)	2003-09-12	2010-01-07	Pfizer	Kombinationen aus alpha-2-delta liganden und serotonin / noradrenalin-wiederaufnahmehemmern
PL1668014T3 (pl) *	2003-09-17	2009-06-30	Janssen Pharmaceutica Nv	Skondensowane związki heterocykliczne jako modulatory receptora serotoninowego
ATE469119T1 (de) *	2003-11-04	2010-06-15	Cipla Ltd	Verfahren zur herstellung von polymorphen von sertralin hydrochlorid
DE602004028150D1 (de) *	2003-11-26	2010-08-26	Pfizer Prod Inc	Aminopyrazolderivate als gsk-3-inhibitoren
US20050250803A1 (en) *	2003-11-26	2005-11-10	Pfizer Inc	Combination of dopamine agonists and monoamine reuptake inhibitors
DK1691811T3 (da)	2003-12-11	2014-10-20	Sunovion Pharmaceuticals Inc	Kombination af et sedativ og en neurotransmittermodulator og fremgangsmåder til forbedring af søvnkvaliteten og behandling af depression
WO2006001877A2 (en) *	2004-04-13	2006-01-05	Myriad Genetics, Inc.	Combination treatment for neurodegenerative disorders comprising r-flurbiprofen
US20050233010A1 (en) *	2004-04-19	2005-10-20	Satow Philip M	Lithium combinations, and uses related thereto
EP1742535A4 (en) *	2004-05-06	2008-10-15	Cydex Pharmaceuticals Inc	MASTER TASTE PREPARATIONS CONTAINING SERTRALINE AND SULFOALKYLETHER CYCLODEXTRIN
AR049401A1 (es)	2004-06-18	2006-07-26	Novartis Ag	Aza-biciclononanos
GB0415746D0 (en)	2004-07-14	2004-08-18	Novartis Ag	Organic compounds
WO2006020850A2 (en) *	2004-08-11	2006-02-23	Myriad Genetics, Inc.	Pharmaceutical composition and method for treating neurodegenerative disorders
BRPI0514303A (pt) *	2004-08-11	2008-06-10	Myriad Genetics Inc	composição farmacêutica e método para tratar distúrbios neurodegenerativos
WO2006020852A2 (en) *	2004-08-11	2006-02-23	Myriad Genetics, Inc.	Pharmaceutical composition and method for treating neurodegenerative disorders
TW200640836A (en) *	2005-02-23	2006-12-01	Teva Pharma	Processes for preparing sertraline
WO2006102283A2 (en)	2005-03-22	2006-09-28	Azevan Pharmaceuticals, Inc.	Beta-lactamylalkanoic acids for treating premenstrual disorders
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
JP2008538581A (ja) *	2005-04-22	2008-10-30	ワイス	｛［（２ｒ）−７−（２，６−ジクロロフェニル）−５−フルオロ−２，３−ジヒドロ−１−ベンゾフラン−２−イル］メチル｝アミン塩酸塩の結晶形態
JP2008538577A (ja) *	2005-04-22	2008-10-30	ワイス	ジヒドロベンゾフラン誘導体およびその使用
PE20061298A1 (es)	2005-04-22	2006-12-24	Wyeth Corp	Compuestos derivados de dihidrobenzofurano como agonistas del receptor de serotonina 5-ht2c
RU2007139541A (ru) *	2005-04-22	2009-05-27	Вайет (Us)	Производные хромана и хромена и их применение
WO2006116151A1 (en) *	2005-04-22	2006-11-02	Wyeth	Benzofuranyl alkanamine derivatives and uses thereof as 5-ht2c agonists
EP1885683A2 (en) *	2005-06-03	2008-02-13	Hetero Drugs Limited	A highly stereoselective synthesis of sertraline
US20070100165A1 (en) *	2005-06-09	2007-05-03	Ronen Borochovitz	Process for preparation of sertraline hydrochloride form I
RU2408368C2 (ru) *	2005-06-27	2011-01-10	Биовэйл Лэборэториз Интернэшнл С.Р.Л.	Препараты соли бупропиона с модифицированным высвобождением
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
EP1910346B1 (en) *	2005-07-19	2019-02-27	Azevan Pharmaceuticals, Inc.	Beta-lactamyl phenylalanine, cysteine, and serine vasopressin antagonist
US7598255B2 (en) *	2005-08-04	2009-10-06	Janssen Pharmaceutica Nv	Pyrimidine compounds as serotonin receptor modulators
EP1940389A2 (en)	2005-10-21	2008-07-09	Braincells, Inc.	Modulation of neurogenesis by pde inhibition
JP2009513672A (ja)	2005-10-31	2009-04-02	ブレインセルス，インコーポレイティド	神経発生のｇａｂａ受容体媒介調節
GB0525673D0 (en)	2005-12-16	2006-01-25	Novartis Ag	Organic compounds
GB0525672D0 (en)	2005-12-16	2006-01-25	Novartis Ag	Organic compounds
KR101381768B1 (ko) *	2006-01-06	2014-04-07	선오비온 파마슈티컬스 인코포레이티드	테트랄론-기재 모노아민 재흡수 저해제
EP1858838A1 (en) *	2006-01-23	2007-11-28	Teva Pharmaceutical Industries Ltd.	A recycling process for preparing 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
CN101410112A (zh) *	2006-03-24	2009-04-15	惠氏公司	治疗抑郁症的新治疗组合
WO2007119247A2 (en) *	2006-04-17	2007-10-25	Unichem Laboratories Limited	Improved manufacturing procedure for the preparation of polymorphic form ii of cis-(1s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthleneamine hydrochloride (sertraline hydrochloride)
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
CA2651862A1 (en)	2006-05-09	2007-11-22	Braincells, Inc.	5 ht receptor mediated neurogenesis
EP2382975A3 (en)	2006-05-09	2012-02-29	Braincells, Inc.	Neurogenesis by modulating angiotensin
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
EP2046119A2 (en) *	2006-07-07	2009-04-15	Myriad Genetics, Inc.	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
KR20090064418A (ko)	2006-09-08	2009-06-18	브레인셀즈 인코퍼레이션	4-아실아미노피리딘 유도체 포함 조합물
WO2008034032A2 (en) *	2006-09-14	2008-03-20	Azevan Pharmaceuticals, Inc.	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
US20080167363A1 (en) *	2006-12-28	2008-07-10	Braincells, Inc	Modulation of Neurogenesis By Melatoninergic Agents
EP2125017A2 (en) *	2007-01-11	2009-12-02	Braincells, Inc.	Modulation of neurogenesis with use of modafinil
CA2594198A1 (en) *	2007-07-20	2009-01-20	Apotex Pharmachem Inc.	A novel process for the preparation of sertraline hydrochloride form ii
US20090062399A1 (en) *	2007-08-29	2009-03-05	Protia, Llc	Deuterium-enriched sertraline
EP2288345B1 (en)	2008-04-18	2015-06-10	University College Dublin National University Of Ireland, Dublin	Psycho-pharmaceuticals
EP2291181B9 (en)	2008-04-18	2013-09-11	University College Dublin National University Of Ireland, Dublin	Captodiamine for the treatment of depression symptoms
WO2010099217A1 (en)	2009-02-25	2010-09-02	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 (en)	2010-04-19	2011-10-26	Nlife Therapeutics S.L.	Compositions and methods for selective delivery of oligonucleotide molecules to specific neuron types
WO2011163231A2 (en)	2010-06-21	2011-12-29	Theracos, Inc.	Combination therapy for the treatment of diabetes
CN107007596A (zh)	2010-07-01	2017-08-04	阿泽凡药物公司	用于治疗创伤后应激障碍的方法
PH12013501900A1 (en)	2011-03-17	2017-08-23	Lupin Ltd	Controlled release pharmaceutical compositions of selective serotonin reuptake inhibitor
KR101340270B1 (ko) *	2011-11-10	2013-12-10	보령제약 주식회사	(+)-시스-서트랄린의 선택적인 제조방법
WO2014060384A1 (en) *	2012-10-18	2014-04-24	F. Hoffmann-La Roche Ag	Ethynyl derivatives as modulators of mglur5 receptor activity
WO2015148962A1 (en)	2014-03-28	2015-10-01	Azevan Pharmaceuticals, Inc.	Compositions and methods for treating neurodegenerative diseases
WO2015193921A1 (en)	2014-06-20	2015-12-23	Council Of Scientific And Industrial Research	An organocatalytic asymmetric synthesis of antidepressants
EP3180340B1 (en) *	2014-08-11	2018-10-10	Hydra Biosciences, Inc.	Pyrido[2,3-d]pyrimidine-2,4(1h,3h)-dione derivatives
JP6667092B2 (ja) *	2014-08-11	2020-03-18	ハイドラ・バイオサイエンシーズ・リミテッド・ライアビリティ・カンパニーＨｙｄｒａＢｉｏｓｃｉｅｎｃｅｓ，ＬＬＣ	ピロロ［３，２−ｄ］ピリミジン−２，４（３Ｈ，５Ｈ）−ジオン誘導体
EP3180337B1 (en) *	2014-08-11	2018-10-10	Hydra Biosciences, Inc.	Pyrido[3,4-d]pyrimidine-2,4(1h,3h)-dione derivatives
WO2016023832A1 (en) *	2014-08-11	2016-02-18	Hydra Biosciences, Inc.	Thieno- and furo[2,3-d]pyrimidine-2,4[1h,3h]-dione derivatives as trpc5 modulators for the treatment of neuropsychiatric disorders
AU2016326442B2 (en)	2015-09-21	2022-05-12	S.C. Johnson & Son, Inc.	System for mixing and dispensing
JP2020534274A (ja)	2017-09-15	2020-11-26	アゼヴァンファーマシューティカルズ，インコーポレイテッド	脳損傷を治療するための組成物及び方法
WO2020043716A1 (en)	2018-08-27	2020-03-05	Katholieke Universiteit Leuven	Pharmacological targeting of de novo serine/glycine synthesis
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
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- 1980-10-28 SU SU802999197A patent/SU1014467A3/ru active
- 1980-10-28 DE DE8080303809T patent/DE3062225D1/de not_active Expired
- 1980-10-28 UA UA2999197A patent/UA6301A1/uk unknown
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- 1980-10-28 AT AT80303809T patent/ATE2668T1/de active
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- 1980-10-29 CS CS807314A patent/CS238609B2/cs unknown
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- 1980-10-31 ES ES496443A patent/ES496443A0/es active Granted
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1981
- 1981-08-28 SU SU813325759A patent/SU1034602A3/ru active
- 1981-11-05 ES ES506892A patent/ES8207123A1/es not_active Expired
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1983
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1984
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1985
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1991
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1992
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1993
- 1993-02-18 HR HR930199A patent/HRP930199B1/xx not_active IP Right Cessation
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1994
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1996
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Also Published As

Publication number	Publication date
NO148996B (no)	1983-10-17
BA97150B1 (bs)	1998-12-28
US4536518A (en)	1985-08-20
ATE2668T1 (de)	1986-03-15
JPS605584B2 (ja)	1985-02-12
CS238609B2 (en)	1985-12-16
JPS5686137A (en)	1981-07-13
EP0030081A1 (en)	1981-06-10
IN159643B (es)	1987-05-30
SI8310672A8 (en)	1996-04-30
IL61374A (en)	1983-10-31
HK82284A (en)	1984-11-09
DK153390C (da)	1988-12-05
YU42846B (en)	1988-12-31
SG56584G (en)	1985-03-08
LU88330I2 (fr)	1994-05-04
YU67283A (en)	1983-10-31
NZ195407A (en)	1984-05-31
PT72004A (en)	1980-11-01
SU1034602A3 (ru)	1983-08-07
ES8201949A1 (es)	1982-01-16
HRP931527B1 (en)	1996-04-30
ES506892A0 (es)	1982-09-01
HRP930199B1 (en)	1996-02-29
GR70781B (es)	1983-03-23
IE50395B1 (en)	1986-04-16
CS238617B2 (en)	1985-12-16
FI803398L (fi)	1981-05-02
UA6301A1 (uk)	1994-12-29
IL61374A0 (en)	1980-12-31
ES8207123A1 (es)	1982-09-01
LV5456A3 (lv)	1994-03-10
BG60333B2 (bg)	1994-11-30
IE802259L (en)	1981-05-01
DE19775012I2 (de)	2001-02-08
YU41951B (en)	1988-02-29
EG15527A (en)	1987-04-30
CA1130815A (en)	1982-08-31
MX5980E (es)	1984-09-12
IN159644B (es)	1987-05-30
FI68806C (fi)	1985-11-11
SI8012798A8 (sl)	1994-12-31
NO148996C (no)	1984-01-25
BA97149B1 (bs)	1998-12-28
EP0030081B1 (en)	1983-03-02
LV5457A3 (lv)	1994-03-10
MY8500326A (en)	1985-12-31
KR840002000B1 (ko)	1984-10-27
NO803258L (no)	1981-05-04
DK153390B (da)	1988-07-11
YU279880A (en)	1983-09-30
SU1014467A3 (ru)	1983-04-23
NL940018I1 (nl)	1994-10-17
NO1996011I1 (no)	1996-09-24
UA6311A1 (uk)	1994-12-29
ZA806726B (en)	1981-10-28
AU517357B2 (en)	1981-07-23
AU6389780A (en)	1981-05-07
DD203045A5 (de)	1983-10-12
DK395280A (da)	1981-05-02
HU182224B (en)	1983-12-28
DE3062225D1 (en)	1983-04-07
FI68806B (fi)	1985-07-31
ES496443A0 (es)	1982-01-16
PT72004B (en)	1981-08-31
KR840002001B1 (ko)	1984-10-27
CS354291A3 (en)	1992-12-16
KR830004202A (ko)	1983-07-06
PH17319A (en)	1984-07-20
CS238618B2 (en)	1985-12-16

Publication	Publication Date	Title
DD155615A5 (de)	1982-06-23	Verfahren zur herstellung von derivaten des cis-4-phenyl-1,2,3,4-tetrahydro-1-nahtalinamins
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
DE2018135A1 (de)	1970-10-22	Neue 1-Aminobenzocycloalkanderivate
CH621115A5 (es)	1981-01-15
DE2048555A1 (de)	1971-04-15	Substituierte Phenathanolamine und Verfahren zu ihrer Herstellung
DE1795132A1 (de)	1972-01-05	Verfahren zur Herstellung eines neuen Tetrahydroazepinderivates
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
DE2812578A1 (de)	1978-10-05	1-aminoindane und verfahren zu ihrer herstellung
DD147537A5 (de)	1981-04-08	Verfahren zur herstellung von 1,2,4,5-tetra-alkyl-4-aryl-piperidinen
DE2657978B2 (de)	1980-06-04	Linksdrehende Enantiomere und Racemate von Trifluormethylthio(und -sulfonyl)cyproheptadinderivaten, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
CH622769A5 (es)	1981-04-30
DE3402060A1 (de)	1985-08-01	Substituierte 5,11-dihydro-6h-dibenz(b,e)azepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2656088A1 (de)	1977-06-23	Neues benzylalkoholderivat und verfahren zu seiner herstellung
DE2507429C2 (de)	1982-10-07	Aminosäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2348577C2 (de)	1982-06-03	1-Amino-4-phenyl-1,2,3,4-tetrahydronaphthaline, deren pharmakologisch verträglichen Salze und diese enthaltende pharmazeutische Zubereitungen
DE2633931A1 (de)	1977-02-17	Pyrazolderivate, deren salze mit saeuren, verfahren zu ihrer herstellung und arzneipraeparate
DE1643123A1 (de)	1971-01-14	Verfahren zur Herstellung neuer 1,1-Diphenyl-2-methyl-3-(benzylidenamino)-propanolen
DE2440734A1 (de)	1975-03-13	Amphetaminderivate, verfahren zu deren herstellung und sie enthaltende arzneimittel
DE2756852A1 (de)	1978-06-22	1-amino-niedrig-alkyl-3,4-diphenyl- 1h-pyrazole
CH660004A5 (de)	1987-03-13	Basische oximaether.
DE2313625C2 (de)	1986-03-13	&alpha;-(Aminoalkyl)-4-hydroxy-3-(methylsulfonylmethyl)-benzylalkohole, ihre Salze, Verfahren zu ihrer Herstellung und ihre Verwendung
DD149664A5 (de)	1981-07-22	Verfahren zur herstellung von 1,1'-biphenyl-2-yl-alkylamin-derivaten
EP0280290A2 (de)	1988-08-31	Mittel mit antidepressiver Wirkung
CH635095A5 (en)	1983-03-15	(+,-)-cis-alpha-(3-(2,6-Dimethyl-1-piperidinyl)propyl)-alpha-pheny l-2-pyridylmethanol compounds

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1994-04-14	NPV	Change in the person, the name or the address of the representative (addendum to changes before extension act)