AU545595B2 - (phenylcyclobutyl)alkyl amines and amides as anti- depressants; intermediate ketones and nitriles - Google Patents

(phenylcyclobutyl)alkyl amines and amides as anti- depressants; intermediate ketones and nitriles

Info

Publication number
AU545595B2
AU545595B2 AU82213/82A AU8221382A AU545595B2 AU 545595 B2 AU545595 B2 AU 545595B2 AU 82213/82 A AU82213/82 A AU 82213/82A AU 8221382 A AU8221382 A AU 8221382A AU 545595 B2 AU545595 B2 AU 545595B2
Authority
AU
Australia
Prior art keywords
phenylcyclobutyl
depressants
nitriles
amides
alkyl amines
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired, expires
Application number
AU82213/82A
Other languages
English (en)
Other versions
AU8221382A (en
Inventor
James Edward Jeffery
Antonin Kozlik
Eric Charles Wilmshurst
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Abbott GmbH and Co KG
Original Assignee
Boots Co PLC
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.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26279045&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AU545595(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Boots Co PLC filed Critical Boots Co PLC
Publication of AU8221382A publication Critical patent/AU8221382A/en
Application granted granted Critical
Publication of AU545595B2 publication Critical patent/AU545595B2/en
Assigned to KNOLL AKTIENGESELLSCHAFT reassignment KNOLL AKTIENGESELLSCHAFT Alteration of Name(s) in Register under S187 Assignors: BOOTS COMPANY PLC, THE
Assigned to ABBOTT GMBH & CO. KG reassignment ABBOTT GMBH & CO. KG Request to Amend Deed and Register Assignors: KNOLL AKTIENGESELLSCHAFT
Adjusted expiration legal-status Critical
Expired legal-status Critical Current

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Classifications

    • 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
    • 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
    • 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)
AU82213/82A 1981-04-06 1982-03-31 (phenylcyclobutyl)alkyl amines and amides as anti- depressants; intermediate ketones and nitriles Expired AU545595B2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB8110710 1981-04-06
GB8110710 1981-04-06
GB8110709 1981-04-06
GB8110709 1981-04-06

Publications (2)

Publication Number Publication Date
AU8221382A AU8221382A (en) 1982-10-14
AU545595B2 true AU545595B2 (en) 1985-07-18

Family

ID=26279045

Family Applications (1)

Application Number Title Priority Date Filing Date
AU82213/82A Expired AU545595B2 (en) 1981-04-06 1982-03-31 (phenylcyclobutyl)alkyl amines and amides as anti- depressants; intermediate ketones and nitriles

Country Status (40)

Country Link
KR (1) KR900000274B1 (es)
AT (1) AT382612B (es)
AU (1) AU545595B2 (es)
BG (2) BG40652A3 (es)
CA (1) CA1248955A (es)
CH (1) CH652117A5 (es)
CS (1) CS244672B2 (es)
CY (1) CY1408A (es)
DD (1) DD208348A5 (es)
DE (1) DE3212682A1 (es)
DK (1) DK161770C (es)
ES (5) ES8305678A1 (es)
FI (1) FI77223C (es)
FR (1) FR2504920B1 (es)
GB (1) GB2098602B (es)
GE (1) GEP19970661B (es)
GR (1) GR76697B (es)
HK (1) HK13888A (es)
HU (1) HU186582B (es)
IE (1) IE52768B1 (es)
IL (1) IL65257A0 (es)
IN (1) IN155773B (es)
IT (1) IT1235758B (es)
JO (1) JO1184B1 (es)
KE (1) KE3753A (es)
LU (1) LU84070A1 (es)
MY (1) MY8800048A (es)
NL (1) NL192201C (es)
NO (1) NO156785C (es)
NZ (1) NZ200178A (es)
PH (1) PH22762A (es)
PL (2) PL139120B1 (es)
PT (1) PT74580B (es)
RO (2) RO89436A2 (es)
SE (1) SE452611B (es)
SG (1) SG67287G (es)
SU (2) SU1482522A3 (es)
UA (2) UA7589A1 (es)
YU (2) YU44336B (es)
ZW (1) ZW4982A1 (es)

Families Citing this family (45)

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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 (da) * 1984-05-30 1985-02-08 Novo Industri As Peptider samt fremstilling og anvendelse deraf
GB8501192D0 (en) * 1985-01-17 1985-02-20 Boots Co Plc Therapeutic agents
DK119785D0 (da) * 1985-03-15 1985-03-15 Nordisk Gentofte Insulinpraeparat
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 (ja) * 1988-03-31 1997-11-12 科研製薬株式会社 脳機能改善剤
WO1994000114A1 (en) * 1992-06-23 1994-01-06 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 (de) * 1995-05-29 1996-12-05 Basf Ag Verwendung arylsubstituierter Cyclobutylalkylamine zur Behandlung der Fettleibigkeit
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
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
US6331571B1 (en) 1998-08-24 2001-12-18 Sepracor, Inc. Methods of treating and preventing attention deficit disorders
US6974838B2 (en) 1998-08-24 2005-12-13 Sepracor Inc. Methods of treating or preventing pain using sibutramine metabolites
BG65170B1 (bg) * 1999-03-17 2007-05-31 Knoll Gmbh Използване на n-заместени производни на 1-[1-(4-хлорофенил)циклобутил]-3-метилбутиламин за производство на лекарство за лечение на разстройства при храненето
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
WO2002036540A2 (en) * 2000-11-02 2002-05-10 Torrent Pharmaceuticals Ltd PROCESS FOR PREPARATION OF β-PHENETHYLAMINE DERIVATIVE
WO2002083631A1 (en) 2001-04-13 2002-10-24 Sepracor Inc. Methods of preparing didesmethylsibutramine and other sibutramine derivatives
KR100536750B1 (ko) * 2002-10-05 2005-12-16 한미약품 주식회사 시부트라민 메탄술폰산염의 결정성 반수화물을 포함하는약학 조성물
FR2870537A1 (fr) * 2004-05-19 2005-11-25 Servier Lab Nouveau procede de synthese du (1s)-4,5-dimethoxy-1-(methyl aminomethyl-)-benzocyclobutane et de ses sels d'addition, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
KR100606533B1 (ko) 2004-08-27 2006-08-01 한올제약주식회사 시부트라민의 개선된 합성방법
KR100606534B1 (ko) 2004-11-01 2006-08-01 한올제약주식회사 생산성을 향상시킨 시부트라민의 개선된 합성방법
KR100618176B1 (ko) * 2004-12-02 2006-09-01 휴먼팜 주식회사 시부트라민 주석산염, 이의 제조 방법 및 이를 포함하는약학적 조성물
JP2008526836A (ja) 2005-01-06 2008-07-24 シージェー チェイルジェダン コーポレーション シブトラミンの無機酸塩
JP2010503709A (ja) 2006-09-15 2010-02-04 レビバ ファーマシューティカルズ，インコーポレーテッド シクロアルキルメチルアミンの合成、使用方法および組成物
CN101555214B (zh) * 2008-04-08 2012-07-11 北京嘉事联博医药科技有限公司 苯基环丁基酰胺衍生物及其光学异构体、制备方法和用途
FR2935381B1 (fr) * 2008-08-29 2010-12-17 Servier Lab Nouveau procede de resolution des enantiomerees du (3,4-dimethoxy-bicyclo°4.2.0!octa-1,3,5-trien-7-yl)nitrile et application a la synthese de l'ivabradine
WO2010082216A2 (en) * 2008-12-08 2010-07-22 Matrix Laboratories Ltd Novel salts of sibutramine and their crystal forms
US8669380B2 (en) 2009-11-02 2014-03-11 Pfizer Inc. Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives
WO2012003501A2 (en) 2010-07-02 2012-01-05 Reviva Pharmaceuticals, Inc. Compositions, synthesis, and methods of using cycloalkylmethylamine derivatives
US9238625B2 (en) * 2011-12-30 2016-01-19 Reviva Pharmaceuticals, Inc. Compositions, synthesis, and methods of using phenylcycloalkylmethylamine derivatives
FR2993561B1 (fr) * 2012-07-17 2014-10-31 Servier Lab Procede de synthese enzymatique de la (7s)-1-(3,4-dimethoxy bicyclo[4.2.0]octa-1,3,5-triene 7-yl) n-methyl methanamine, et application a la synthese de l'ivabradine et de ses sels

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DE1124485B (de) * 1960-02-12 1962-03-01 Hoechst Ag Verfahren zur Herstellung von analeptisch wirksamen Phenylcycloalkylmethylaminen
US3526656A (en) * 1967-05-25 1970-09-01 Parke Davis & Co (1-arylcyclobutyl)carbonyl carbamic acid derivatives

Also Published As

Publication number Publication date
PL240079A1 (en) 1983-09-12
GB2098602B (en) 1984-08-22
NL8201347A (nl) 1982-11-01
FI821197A0 (fi) 1982-04-05
PT74580A (en) 1982-04-01
YU6385A (en) 1985-08-31
PL139120B1 (en) 1986-12-31
RO89436A2 (ro) 1986-06-30
FR2504920A1 (fr) 1982-11-05
CS244672B2 (en) 1986-08-14
ATA132582A (de) 1986-08-15
SU1482522A3 (ru) 1989-05-23
IE52768B1 (en) 1988-02-17
FI821197L (fi) 1982-10-07
DK161770B (da) 1991-08-12
NL192201C (nl) 1997-03-04
IE820481L (en) 1982-10-06
ES519031A0 (es) 1984-08-16
YU44253B (en) 1990-04-30
AU8221382A (en) 1982-10-14
NO156785C (no) 1987-11-25
ES8406413A1 (es) 1984-08-01
LU84070A1 (fr) 1983-06-07
ES511152A0 (es) 1983-04-16
CS245782A2 (en) 1985-08-15
UA7838A1 (uk) 1995-12-26
IT1235758B (it) 1992-09-28
DE3212682A1 (de) 1982-10-21
IT8248157A0 (it) 1982-04-02
FR2504920B1 (fr) 1985-06-28
PL136242B1 (en) 1986-02-28
AT382612B (de) 1987-03-25
PH22762A (en) 1988-12-12
NL192201B (nl) 1996-11-01
DK161770C (da) 1992-02-10
NZ200178A (en) 1985-07-31
ES8403097A1 (es) 1984-03-01
UA7589A1 (uk) 1995-09-29
BG40651A3 (en) 1986-01-15
ES519029A0 (es) 1984-08-01
KE3753A (en) 1987-10-02
BG40652A3 (en) 1986-01-15
NO821087L (no) 1982-10-07
CY1408A (en) 1988-04-22
JO1184B1 (en) 1983-11-30
CH652117A5 (fr) 1985-10-31
YU75082A (en) 1985-08-31
FI77223C (fi) 1989-02-10
NO156785B (no) 1987-08-17
HU186582B (en) 1985-08-28
FI77223B (fi) 1988-10-31
DE3212682C2 (es) 1992-03-26
KR830010065A (ko) 1983-12-26
RO84802A (ro) 1984-09-29
GEP19970661B (en) 1997-01-04
SU1461372A3 (ru) 1989-02-23
HK13888A (en) 1988-02-26
ES519032A0 (es) 1984-03-01
GR76697B (es) 1984-08-28
SE8202166L (sv) 1982-11-25
PT74580B (en) 1983-12-23
SG67287G (en) 1988-02-19
DK146482A (da) 1982-10-07
CA1248955A (en) 1989-01-17
SE452611B (sv) 1987-12-07
ES8406414A1 (es) 1984-08-01
ZW4982A1 (en) 1982-11-03
MY8800048A (en) 1988-12-31
RO84802B (ro) 1984-10-30
IL65257A0 (en) 1983-12-30
GB2098602A (en) 1982-11-24
YU44336B (en) 1990-06-30
ES8407002A1 (es) 1984-08-16
ES519030A0 (es) 1984-08-01
PL235832A1 (en) 1983-09-12
IN155773B (es) 1985-03-09
ES8305678A1 (es) 1983-04-16
KR900000274B1 (ko) 1990-01-24
DD208348A5 (de) 1984-05-02

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