UA7589A1 - METHOD OF OBTAINING (1-ARYLCYCLOBUTYL) -ALKYLAMINES OR THEIR PHARMACOLOGICALLY IMPROVED SALTS - Google Patents
METHOD OF OBTAINING (1-ARYLCYCLOBUTYL) -ALKYLAMINES OR THEIR PHARMACOLOGICALLY IMPROVED SALTSInfo
- Publication number
- UA7589A1 UA7589A1 UA3834158A UA3834158A UA7589A1 UA 7589 A1 UA7589 A1 UA 7589A1 UA 3834158 A UA3834158 A UA 3834158A UA 3834158 A UA3834158 A UA 3834158A UA 7589 A1 UA7589 A1 UA 7589A1
- Authority
- UA
- Ukraine
- Prior art keywords
- chloro
- phenyl
- arylcyclobutyl
- alkylamines
- nmgbr
- Prior art date
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- 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
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/50—Halogenated unsaturated alcohols containing six-membered aromatic rings and other 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
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- 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
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
-
- 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
- C07C45/44—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reduction and hydrolysis of nitriles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/227—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
- C07C49/237—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/567—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Изобретение касается замещенных аминов, в частности (1-арилциклобутил)-алкиламинов общей формулы: или 1; а) n=0; R1 – C1-С4-алкил; C3-циклоалкил или фенил; б) n=1; R1 - Н; R5 и R6 вместе с фенилом образуют 4-хлорфенил; 3-хлор-5-метилфенил; 3,4-дихлорфенил; 4-хлор-3-трифторметилфенил; 4-метоксифенил; 4-бромфенил; 3-хлор-4-метил-фенил; 2-нафтил; 4-фторфенил или 4-бифенилил; R7 – С1-С2-алкил, или их фармакологически приемлемых солей, обладающих антидепрессивной активностью, что может быть использовано в медицине. Цель - создание новых активных веществ указанного класса без побочных действий. Синтез ведут обработкой соответствующего карбонитрила реактивом Гриньяра: R1MgBr или R7MgBr, где R1 и R7 - см. выше, в среде эфира (толуола) при температуре до кипения. Полученный продукт, содержащий группу CR1-NMgBr или CHR1-CR7-NMgBr, с R1 и R7, указанными выше, подвергают восстановлению с помощью боргидрида натрия в среде этанола, метанола или диэтиленгликольдиметилового эфира. Выделение целевого продукта ведут в свободном виде или в виде фармакологически приемлемой соли. Новые вещества обладают антидепрессивной активностью при дозе ED50=30мг/кг без признаков тираминазного ингибирования, наблюдающегося с известным 1-фенил-2-аминоциклопропаном.The invention relates to substituted amines, in particular (1-arylcyclobutyl) -alkylamines of the general formula: or 1; a) n = 0; R1 is C1 -C4 alkyl; C3 cycloalkyl or phenyl; b) n = 1; R1 is H; R5 and R6 together with phenyl form 4-chlorophenyl; 3-chloro-5-methylphenyl; 3,4-dichlorophenyl; 4-chloro-3-trifluoromethylphenyl; 4-methoxyphenyl; 4-bromophenyl; 3-chloro-4-methylphenyl; 2-naphthyl; 4-fluorophenyl or 4-biphenylyl; R7 - C1-C2-alkyl, or their pharmacologically acceptable salts with antidepressant activity, which can be used in medicine. The goal is to create new active substances of the specified class without side effects. The synthesis is carried out by treating the corresponding carbonitrile with a Grignard reagent: R1MgBr or R7MgBr, where R1 and R7 - see above, in an ether (toluene) medium at a temperature to boiling. The resulting product containing the CR1-NMgBr or CHR1-CR7-NMgBr group with R1 and R7 as indicated above is subjected to reduction with sodium borohydride in ethanol, methanol or diethylene glycol dimethyl ether. Isolation of the target product is carried out in free form or in the form of a pharmacologically acceptable salt. The new substances have antidepressant activity at a dose of ED50 = 30mg / kg without signs of tyraminase inhibition observed with the known 1-phenyl-2-aminocyclopropane.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8110710 | 1981-04-06 | ||
GB8110709 | 1981-04-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
UA7589A1 true UA7589A1 (en) | 1995-09-29 |
Family
ID=26279045
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA3834158A UA7589A1 (en) | 1981-04-06 | 1982-04-05 | METHOD OF OBTAINING (1-ARYLCYCLOBUTYL) -ALKYLAMINES OR THEIR PHARMACOLOGICALLY IMPROVED SALTS |
UA3426748A UA7838A1 (en) | 1981-04-06 | 1982-04-05 | METHOD OF OBTAINING SUBSTITUTED 1- (1-PHENYLYCYCLOBUTYL) -ALKYLAMINES OR THEIR PHARMACOLOGICALLY IMPROVED SALTS |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA3426748A UA7838A1 (en) | 1981-04-06 | 1982-04-05 | METHOD OF OBTAINING SUBSTITUTED 1- (1-PHENYLYCYCLOBUTYL) -ALKYLAMINES OR THEIR PHARMACOLOGICALLY IMPROVED SALTS |
Country Status (40)
Country | Link |
---|---|
KR (1) | KR900000274B1 (en) |
AT (1) | AT382612B (en) |
AU (1) | AU545595B2 (en) |
BG (2) | BG40652A3 (en) |
CA (1) | CA1248955A (en) |
CH (1) | CH652117A5 (en) |
CS (1) | CS244672B2 (en) |
CY (1) | CY1408A (en) |
DD (1) | DD208348A5 (en) |
DE (1) | DE3212682A1 (en) |
DK (1) | DK161770C (en) |
ES (5) | ES511152A0 (en) |
FI (1) | FI77223C (en) |
FR (1) | FR2504920B1 (en) |
GB (1) | GB2098602B (en) |
GE (1) | GEP19970661B (en) |
GR (1) | GR76697B (en) |
HK (1) | HK13888A (en) |
HU (1) | HU186582B (en) |
IE (1) | IE52768B1 (en) |
IL (1) | IL65257A0 (en) |
IN (1) | IN155773B (en) |
IT (1) | IT1235758B (en) |
JO (1) | JO1184B1 (en) |
KE (1) | KE3753A (en) |
LU (1) | LU84070A1 (en) |
MY (1) | MY8800048A (en) |
NL (1) | NL192201C (en) |
NO (1) | NO156785C (en) |
NZ (1) | NZ200178A (en) |
PH (1) | PH22762A (en) |
PL (2) | PL139120B1 (en) |
PT (1) | PT74580B (en) |
RO (2) | RO89436A2 (en) |
SE (1) | SE452611B (en) |
SG (1) | SG67287G (en) |
SU (2) | SU1482522A3 (en) |
UA (2) | UA7589A1 (en) |
YU (2) | YU44336B (en) |
ZW (1) | ZW4982A1 (en) |
Families Citing this family (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IE56001B1 (en) * | 1982-09-30 | 1991-03-13 | Boots Co Plc | 1-arylcyclobutylmethylamine compounds |
IE56000B1 (en) * | 1982-09-30 | 1991-03-13 | Boots Co Plc | 1-arylcyclobutylalkylamine compounds |
GB8412480D0 (en) * | 1984-05-16 | 1984-06-20 | Elliott M | Pesticides |
DK58285D0 (en) * | 1984-05-30 | 1985-02-08 | Novo Industri As | PEPTIDES AND MANUFACTURING AND USING THEREOF |
GB8501192D0 (en) * | 1985-01-17 | 1985-02-20 | Boots Co Plc | Therapeutic agents |
DK119785D0 (en) * | 1985-03-15 | 1985-03-15 | Nordisk Gentofte | INSULIN PREPARATION |
US5157021A (en) * | 1985-03-15 | 1992-10-20 | Novo Nordisk A/S | Insulin derivatives and pharmaceutical preparations containing these derivatives |
GB8531071D0 (en) * | 1985-12-17 | 1986-01-29 | Boots Co Plc | Therapeutic compound |
GB2184122B (en) * | 1985-12-17 | 1989-10-18 | Boots Co Plc | N,n-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methyl butylamine hydrochloride monohydrate |
GB8704777D0 (en) * | 1987-02-28 | 1987-04-01 | Boots Co Plc | Medical treatment |
JP2675573B2 (en) * | 1988-03-31 | 1997-11-12 | 科研製薬株式会社 | Brain function improver |
AU4542893A (en) * | 1992-06-23 | 1994-01-24 | Sepracor, Inc. | Methods and compositions for treating depression and other disorders using optically pure (-) sibutramine |
GB9309749D0 (en) * | 1993-05-12 | 1993-06-23 | Boots Co Plc | Therapeutic agents |
US5459164A (en) * | 1994-02-03 | 1995-10-17 | Boots Pharmaceuticals, Inc. | Medical treatment |
DE19518988A1 (en) * | 1995-05-29 | 1996-12-05 | Basf Ag | Use of aryl substituted cyclobutylalkylamines to treat obesity |
GB9524681D0 (en) | 1995-12-02 | 1996-01-31 | Knoll Ag | Chemical process |
GB9619757D0 (en) * | 1996-09-21 | 1996-11-06 | Knoll Ag | Chemical process |
GB9619961D0 (en) * | 1996-09-25 | 1996-11-13 | Knoll Ag | Medical treatment |
GB9619962D0 (en) * | 1996-09-25 | 1996-11-13 | Knoll Ag | Medical treatment |
GB9727131D0 (en) | 1997-12-24 | 1998-02-25 | Knoll Ag | Therapeutic agents |
AU2007200334B8 (en) * | 1998-08-24 | 2010-10-21 | Sepracor, Inc. | Methods of using and compositions comprising dopamine reuptake inhibitors |
US6331571B1 (en) * | 1998-08-24 | 2001-12-18 | Sepracor, Inc. | Methods of treating and preventing attention deficit disorders |
US6476078B2 (en) | 1999-08-11 | 2002-11-05 | Sepracor, Inc. | Methods of using sibutramine metabolites in combination with a phosphodiesterase inhibitor to treat sexual dysfunction |
US6339106B1 (en) | 1999-08-11 | 2002-01-15 | Sepracor, Inc. | Methods and compositions for the treatment and prevention of sexual dysfunction |
US6974838B2 (en) | 1998-08-24 | 2005-12-13 | Sepracor Inc. | Methods of treating or preventing pain using sibutramine metabolites |
BG65170B1 (en) * | 1999-03-17 | 2007-05-31 | Knoll Gmbh | Use of n-substituted derivatives of 1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine for the production of a medicine for treating eating disorders |
US6552087B1 (en) | 1999-03-19 | 2003-04-22 | Abbott Gmbh & Co. Kg | Therapeutic agent comprising (+)-sibutramine |
GB9915617D0 (en) | 1999-07-05 | 1999-09-01 | Knoll Ag | Therapeutic agents |
US6399826B1 (en) | 1999-08-11 | 2002-06-04 | Sepracor Inc. | Salts of sibutramine metabolites, methods of making sibutramine metabolites and intermediates useful in the same, and methods of treating pain |
AU2002210816A1 (en) * | 2000-11-02 | 2002-05-15 | Torrent Pharmaceuticals Ltd | Process for preparation of beta-phenethylamine derivative |
WO2002083631A1 (en) | 2001-04-13 | 2002-10-24 | Sepracor Inc. | Methods of preparing didesmethylsibutramine and other sibutramine derivatives |
KR100536750B1 (en) * | 2002-10-05 | 2005-12-16 | 한미약품 주식회사 | Pharmaceutical composition comprising crystalline hemihydrate of sibutramine methanesulfonate |
FR2870537A1 (en) * | 2004-05-19 | 2005-11-25 | Servier Lab | NOVEL PROCESS FOR SYNTHESIZING (1S) -4,5-DIMETHOXY-1- (METHYL AMINOMETHYL) BENZOCYCLOBUTANE AND ITS ADDITION SALTS AND APPLICATION TO THE SYNTHESIS OF IVABRADINE AND ITS ADDITION SALTS PHARMACEUTICALLY ACCEPTABLE ACID |
KR100606533B1 (en) | 2004-08-27 | 2006-08-01 | 한올제약주식회사 | An improved synthetic method of sibutramine |
KR100606534B1 (en) | 2004-11-01 | 2006-08-01 | 한올제약주식회사 | An improved synthetic method of sibutramine |
KR100618176B1 (en) * | 2004-12-02 | 2006-09-01 | 휴먼팜 주식회사 | Sibutramine tartrate, its preparation process and phamaceutical composition comprising it |
EP1846359A4 (en) | 2005-01-06 | 2010-03-31 | Cj Cheiljedang Corp | Inorganic acid salts of sibutramine |
BRPI0716952A2 (en) * | 2006-09-15 | 2013-10-29 | Reviva Pharmaceuticals Inc | COMPOUND, METHODS FOR TREATING AND / OR PREVENTING OBESITY OR CO-MORBID INDICATION RELATED TO OBESITY, AND FOR SYNTHESIZING CYCLOalkylmethylamine Derivatives |
US8604244B2 (en) | 2010-07-02 | 2013-12-10 | Reviva Pharmaceuticals, Inc. | Compositions, synthesis, and methods of using cycloalkylmethylamine derivatives |
CN101555214B (en) * | 2008-04-08 | 2012-07-11 | 北京嘉事联博医药科技有限公司 | Phenylcyclobutylacylamide derivative as well as optical isomer, preparation method and application thereof |
FR2935381B1 (en) * | 2008-08-29 | 2010-12-17 | Servier Lab | NOVEL METHOD FOR THE RESOLUTION OF ENANTIOMERES OF (3,4-DIMETHOXY-BICYCLOO-4.2.0-OCTA-1,3,5-TRIEN-7-YL) NITRILE AND APPLICATION TO THE SYNTHESIS OF IVABRADINE |
WO2010082216A2 (en) * | 2008-12-08 | 2010-07-22 | Matrix Laboratories Ltd | Novel salts of sibutramine and their crystal forms |
AP3099A (en) | 2009-11-02 | 2015-01-31 | Pfizer | Dioxa-bicyclo[3.2.1]octane-2,3,4-triol de derivatives |
EP2797870B1 (en) * | 2011-12-30 | 2019-02-20 | Reviva Pharmaceuticals, Inc. | Compositions, synthesis, and methods of using 1-[1-phenyl-cyclobutyl]isobutylamine derivatives |
FR2993561B1 (en) * | 2012-07-17 | 2014-10-31 | Servier Lab | PROCESS FOR ENZYMATIC SYNTHESIS OF (7S) -1- (3,4-DIMETHOXY BICYCLO [4.2.0] OCTA-1,3,5-TRIENE 7-YL) N-METHYL METHANAMINE, AND APPLICATION TO THE SYNTHESIS OF THE IVABRADINE AND ITS SALTS |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1124485B (en) * | 1960-02-12 | 1962-03-01 | Hoechst Ag | Process for the preparation of analeptically active phenylcycloalkylmethylamines |
US3526656A (en) * | 1967-05-25 | 1970-09-01 | Parke Davis & Co | (1-arylcyclobutyl)carbonyl carbamic acid derivatives |
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1982
- 1982-03-03 IE IE481/82A patent/IE52768B1/en active Protection Beyond IP Right Term
- 1982-03-15 PT PT74580A patent/PT74580B/en unknown
- 1982-03-15 IL IL65257A patent/IL65257A0/en unknown
- 1982-03-16 ZW ZW49/82A patent/ZW4982A1/en unknown
- 1982-03-16 PH PH27003A patent/PH22762A/en unknown
- 1982-03-30 NZ NZ200178A patent/NZ200178A/en unknown
- 1982-03-31 AU AU82213/82A patent/AU545595B2/en not_active Expired
- 1982-03-31 NO NO821087A patent/NO156785C/en not_active IP Right Cessation
- 1982-03-31 DK DK146482A patent/DK161770C/en not_active IP Right Cessation
- 1982-03-31 NL NL8201347A patent/NL192201C/en not_active IP Right Cessation
- 1982-03-31 CA CA000400146A patent/CA1248955A/en not_active Expired
- 1982-04-01 FR FR8205634A patent/FR2504920B1/en not_active Expired
- 1982-04-01 RO RO82114421A patent/RO89436A2/en unknown
- 1982-04-01 CY CY140882A patent/CY1408A/en unknown
- 1982-04-01 GB GB8209591A patent/GB2098602B/en not_active Expired
- 1982-04-01 CH CH2020/82A patent/CH652117A5/en not_active IP Right Cessation
- 1982-04-01 RO RO107119A patent/RO84802B/en unknown
- 1982-04-02 IT IT8248157A patent/IT1235758B/en active
- 1982-04-02 YU YU750/82A patent/YU44336B/en unknown
- 1982-04-02 AT AT0132582A patent/AT382612B/en not_active IP Right Cessation
- 1982-04-05 HU HU821040A patent/HU186582B/en unknown
- 1982-04-05 DE DE19823212682 patent/DE3212682A1/en active Granted
- 1982-04-05 GR GR67812A patent/GR76697B/el unknown
- 1982-04-05 UA UA3834158A patent/UA7589A1/en unknown
- 1982-04-05 LU LU84070A patent/LU84070A1/en unknown
- 1982-04-05 JO JO19821184A patent/JO1184B1/en active
- 1982-04-05 UA UA3426748A patent/UA7838A1/en unknown
- 1982-04-05 FI FI821197A patent/FI77223C/en not_active IP Right Cessation
- 1982-04-05 ES ES511152A patent/ES511152A0/en active Granted
- 1982-04-05 SU SU823426748A patent/SU1482522A3/en active
- 1982-04-05 IN IN383/CAL/82A patent/IN155773B/en unknown
- 1982-04-05 SE SE8202166A patent/SE452611B/en not_active IP Right Cessation
- 1982-04-06 CS CS822457A patent/CS244672B2/en unknown
- 1982-04-06 PL PL1982235832A patent/PL139120B1/en unknown
- 1982-04-06 KR KR828201506A patent/KR900000274B1/en active
- 1982-04-06 BG BG8360417A patent/BG40652A3/en unknown
- 1982-04-06 BG BG8256100A patent/BG40651A3/en unknown
- 1982-04-06 DD DD82238787A patent/DD208348A5/en not_active IP Right Cessation
- 1982-04-06 PL PL1982240079A patent/PL136242B1/en unknown
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1983
- 1983-01-17 ES ES519029A patent/ES8406413A1/en not_active Expired
- 1983-01-17 ES ES519031A patent/ES8407002A1/en not_active Expired
- 1983-01-17 ES ES519032A patent/ES8403097A1/en not_active Expired
- 1983-01-17 ES ES519030A patent/ES519030A0/en active Granted
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1985
- 1985-01-09 SU SU853834158A patent/SU1461372A3/en active
- 1985-01-17 YU YU63/85A patent/YU44253B/en unknown
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1987
- 1987-08-19 SG SG67287A patent/SG67287G/en unknown
- 1987-08-20 KE KE3753A patent/KE3753A/en unknown
-
1988
- 1988-02-15 HK HK138/88A patent/HK13888A/en not_active IP Right Cessation
- 1988-12-30 MY MY48/88A patent/MY8800048A/en unknown
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1994
- 1994-09-07 GE GEAP19942156A patent/GEP19970661B/en unknown
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