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GB1086191A - Phenylcyclopropane derivatives - Google Patents

Phenylcyclopropane derivatives

Info

Publication number
GB1086191A
GB1086191A GB43626/63A GB4362663A GB1086191A GB 1086191 A GB1086191 A GB 1086191A GB 43626/63 A GB43626/63 A GB 43626/63A GB 4362663 A GB4362663 A GB 4362663A GB 1086191 A GB1086191 A GB 1086191A
Authority
GB
United Kingdom
Prior art keywords
phenylcyclopropane
activity
prepared
radical
reacting
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
Application number
GB43626/63A
Inventor
Uberto Maria Teotino
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.)
Whitefin Holding SA
Original Assignee
Whitefin Holding SA
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
Priority to NL128365D priority Critical patent/NL128365C/xx
Application filed by Whitefin Holding SA filed Critical Whitefin Holding SA
Priority to GB43626/63A priority patent/GB1086191A/en
Priority to GB49345/66A priority patent/GB1086192A/en
Priority to IL22302A priority patent/IL22302A/en
Priority to NL6412766A priority patent/NL6412766A/xx
Priority to CH1426464A priority patent/CH482648A/en
Priority to CH507369A priority patent/CH485645A/en
Priority to DE19641518207 priority patent/DE1518207B1/en
Priority to BE655245D priority patent/BE655245A/xx
Priority to ES0305661A priority patent/ES305661A1/en
Priority to CH1678269A priority patent/CH490335A/en
Priority to FR993776A priority patent/FR1415997A/en
Priority to BR164004/64A priority patent/BR6464004D0/en
Priority to DK546064AA priority patent/DK127726B/en
Priority to AT586167A priority patent/AT273066B/en
Priority to SE13334/64A priority patent/SE317669B/xx
Priority to FI2317/64A priority patent/FI43069B/fi
Priority to AT586267A priority patent/AT266812B/en
Priority to LU47291D priority patent/LU47291A1/xx
Priority to AT938664A priority patent/AT269832B/en
Priority to JP39062253A priority patent/JPS4821102B1/ja
Priority to FR4380A priority patent/FR4555M/fr
Priority to FR4379A priority patent/FR4217M/fr
Priority to FR4377A priority patent/FR4282M/fr
Priority to FR4378A priority patent/FR4554M/fr
Priority to JP42012912A priority patent/JPS507598B1/ja
Priority to NO16771767A priority patent/NO123719B/no
Publication of GB1086191A publication Critical patent/GB1086191A/en
Priority to NL6901128A priority patent/NL6901128A/xx
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/03—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pain & Pain Management (AREA)
  • Anesthesiology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Novel compounds of formula <FORM:1086191/C2/1> in which R is hydrogen, hydroxyl, halogen, nitro, amino or alkoxy, R1 is a straight or branched alxyl radical having at least 2 carbon atoms, or cycloalkyl, aralkyl, arylcycloalky-alkyl, hydroxy-alkyl or a carboxylic acyl radical, R2 is hydrogen, a straight or branched alkyl radical, or hydroxyalkyl radical, or the grouping -NR1R2 represents a heterocyclic ring, and, with the exception of the compounds in which R1 is a carboxylic acyl radical, the acid addition and quaternary ammonium salts thereof, and the separated cis- and trans-iso mers as well as the cis-trans mixture, are prepared (a) when R1 is not a carboxylic acyl radical (1) by reducing the corresponding 2 - phenylcyclopropane - 1 - carbonamide or (2) by reacting the appropriate 2-phenylcyclo-propane-1-halomethyl compound with an amine of formula HNR1R2 in the presence of an acid-binding agent, or (b) when R1 is as first defined, by reacting a 2-phenylcyclopropane-1-amino-methyl derivative with a compound R1Y where Y is halogen, in the presence of an acid binding agent. Compounds in which R1 is a 2-phenyl-cyclopropyl-1-methyl group may also be prepared by reduction of the corresponding compounds in which R1 is a 2-phenylcyclopropane-1-carbonamide group. 1 - (N,N - Hydroxyethyl)-aminomethyl-2-phenylcyclopropane may be prepared by reacting ethyl phenylcyclopropane-carboxylate with diethanolamine and reducing the product. The 2-phenylcyclopropane-1-halomethyl starting materials are prepared by reacting thionyl chloride with 1-hydroxymethyl-2-phenylcyclo-propane which may itself be made by reducing a 2-phenylcyclopropane-1-carboxylate. Therapeutic compositions having the properties of stimulating the central nervous system and/or affecting the peripheral neuro-vegetative section and/or providing uterus-stimulating action and/or anti-exudative activity and/or anti-inflammatory activity, and/or appetite-depressing activity and/or antimicotic activity and/or antimicrobic activity, and which may be administered orally, subcutaneously or intravenously, contain as active ingredient a compound of Formula I above.
GB43626/63A 1963-11-05 1963-11-05 Phenylcyclopropane derivatives Expired GB1086191A (en)

Priority Applications (28)

Application Number Priority Date Filing Date Title
NL128365D NL128365C (en) 1963-11-05
GB43626/63A GB1086191A (en) 1963-11-05 1963-11-05 Phenylcyclopropane derivatives
GB49345/66A GB1086192A (en) 1963-11-05 1963-11-05 Phenylcyclopropane derivatives
IL22302A IL22302A (en) 1963-11-05 1964-10-21 Phenylcyclopropane derivatives
NL6412766A NL6412766A (en) 1963-11-05 1964-11-03
CH1426464A CH482648A (en) 1963-11-05 1964-11-04 Process for the preparation of new phenylcyclopropane compounds
CH507369A CH485645A (en) 1963-11-05 1964-11-04 Process for the preparation of new phenylcyclopropane compounds
DE19641518207 DE1518207B1 (en) 1963-11-05 1964-11-04 Process for the production of new phenylcyclopropane derivatives or their salts and quaternary ammonium compounds
BE655245D BE655245A (en) 1963-11-05 1964-11-04
ES0305661A ES305661A1 (en) 1963-11-05 1964-11-04 Procedure for the production of fenilciclopropan derivatives. (Machine-translation by Google Translate, not legally binding)
CH1678269A CH490335A (en) 1963-11-05 1964-11-04 Process for the preparation of new phenylcyclopropane compounds
FR993776A FR1415997A (en) 1963-11-05 1964-11-04 Phenylcyclopropane derivatives and methods of preparation
DK546064AA DK127726B (en) 1963-11-05 1964-11-05 Analogous process for the preparation of 1-halobenzoylaminomethyl-2-phenyl-cyclopropane compounds.
BR164004/64A BR6464004D0 (en) 1963-11-05 1964-11-05 PROCESS FOR THE PREPARATION OF FENILCYCLOPROPAN DERIVATIVES
AT586167A AT273066B (en) 1963-11-05 1964-11-05 Process for the production of new phenylcyclopropane derivatives and their salts
SE13334/64A SE317669B (en) 1963-11-05 1964-11-05
FI2317/64A FI43069B (en) 1963-11-05 1964-11-05
AT586267A AT266812B (en) 1963-11-05 1964-11-05 Process for the preparation of new phenylcyclopropanecarboxamides
LU47291D LU47291A1 (en) 1963-11-05 1964-11-05
AT938664A AT269832B (en) 1963-11-05 1964-11-05 Process for the production of new phenylcyclopropane derivatives and their salts
JP39062253A JPS4821102B1 (en) 1963-11-05 1964-11-05
FR4380A FR4555M (en) 1963-11-05 1965-02-04
FR4379A FR4217M (en) 1963-11-05 1965-02-04
FR4377A FR4282M (en) 1963-11-05 1965-02-04
FR4378A FR4554M (en) 1963-11-05 1965-02-04
JP42012912A JPS507598B1 (en) 1963-11-05 1967-03-02
NO16771767A NO123719B (en) 1963-11-05 1967-04-13
NL6901128A NL6901128A (en) 1963-11-05 1969-01-23

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB43626/63A GB1086191A (en) 1963-11-05 1963-11-05 Phenylcyclopropane derivatives

Publications (1)

Publication Number Publication Date
GB1086191A true GB1086191A (en) 1967-10-04

Family

ID=10429612

Family Applications (2)

Application Number Title Priority Date Filing Date
GB49345/66A Expired GB1086192A (en) 1963-11-05 1963-11-05 Phenylcyclopropane derivatives
GB43626/63A Expired GB1086191A (en) 1963-11-05 1963-11-05 Phenylcyclopropane derivatives

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB49345/66A Expired GB1086192A (en) 1963-11-05 1963-11-05 Phenylcyclopropane derivatives

Country Status (15)

Country Link
JP (2) JPS4821102B1 (en)
AT (3) AT273066B (en)
BE (1) BE655245A (en)
BR (1) BR6464004D0 (en)
CH (1) CH482648A (en)
DE (1) DE1518207B1 (en)
DK (1) DK127726B (en)
ES (1) ES305661A1 (en)
FI (1) FI43069B (en)
FR (4) FR4554M (en)
GB (2) GB1086192A (en)
IL (1) IL22302A (en)
LU (1) LU47291A1 (en)
NL (3) NL6412766A (en)
SE (1) SE317669B (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4103030A (en) * 1974-12-11 1978-07-25 Sumitomo Chemical Company, Limited Novel cyclopropylmethylamine derivatives
GB2170197A (en) * 1985-01-17 1986-07-30 Ici Plc Cyclopropane-containing amine compounds
WO2007025144A1 (en) * 2005-08-24 2007-03-01 University Of Illinois - Chicago 5-ht2c receptor agonists as anorectic agents
US7622589B2 (en) 2005-03-17 2009-11-24 Pfizer Inc. Substituted sulfonylaminoarylmethyl cyclopropanecarboxamide as VR1 receptor antagonists
US8829041B2 (en) 2006-06-23 2014-09-09 Abbvie Inc. Cyclopropyl amine derivatives
US8853390B2 (en) 2010-09-16 2014-10-07 Abbvie Inc. Processes for preparing 1,2-substituted cyclopropyl derivatives
US9108948B2 (en) 2006-06-23 2015-08-18 Abbvie Inc. Cyclopropyl amine derivatives
US9186353B2 (en) 2009-04-27 2015-11-17 Abbvie Inc. Treatment of osteoarthritis pain

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4202902A (en) * 1979-03-05 1980-05-13 Shell Oil Company Lipogenesis control by cyclopropane-carboxylic acids, esters and amides
DE3582728D1 (en) * 1985-01-17 1991-06-06 Ici Plc TERTIAL AMINO CONNECTIONS.
GB8617377D0 (en) * 1986-07-16 1986-08-20 Ici Plc Tertiary amine compounds
WO1992001447A1 (en) * 1990-07-18 1992-02-06 Sandoz Ltd. 2-cyclopropylacetic acid derivatives
NZ584100A (en) 2007-08-22 2011-07-29 Astrazeneca Ab Cyclopropyl amide derivatives
TW201039825A (en) 2009-02-20 2010-11-16 Astrazeneca Ab Cyclopropyl amide derivatives 983
BR112012020782A2 (en) 2010-02-18 2016-05-03 Astrazeneca Ab compound and process for preparing a compound

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3081336A (en) * 1963-03-12 Carbamates
US3050559A (en) * 1962-08-21 Substituted phenylcyclopropylamjnes
US2997422A (en) * 1959-01-09 1961-08-22 Smith Kline French Lab Monoamine oxidase inhibition
US3106578A (en) * 1960-09-16 1963-10-08 Smith Kline French Lab Nu-phenethyl-2-phenylcyclopropylamine derivatives
US3079403A (en) * 1960-09-19 1963-02-26 Smith Kline French Lab Process for preparing amines

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4103030A (en) * 1974-12-11 1978-07-25 Sumitomo Chemical Company, Limited Novel cyclopropylmethylamine derivatives
GB2170197A (en) * 1985-01-17 1986-07-30 Ici Plc Cyclopropane-containing amine compounds
US7622589B2 (en) 2005-03-17 2009-11-24 Pfizer Inc. Substituted sulfonylaminoarylmethyl cyclopropanecarboxamide as VR1 receptor antagonists
US7915448B2 (en) * 2005-03-17 2011-03-29 Pfizer Inc. Substituted sulfonylaminoarylmethyl cyclopropanecarboxamide as VR1 receptor antagonists
WO2007025144A1 (en) * 2005-08-24 2007-03-01 University Of Illinois - Chicago 5-ht2c receptor agonists as anorectic agents
US8829041B2 (en) 2006-06-23 2014-09-09 Abbvie Inc. Cyclopropyl amine derivatives
US9108948B2 (en) 2006-06-23 2015-08-18 Abbvie Inc. Cyclopropyl amine derivatives
US9186353B2 (en) 2009-04-27 2015-11-17 Abbvie Inc. Treatment of osteoarthritis pain
US8853390B2 (en) 2010-09-16 2014-10-07 Abbvie Inc. Processes for preparing 1,2-substituted cyclopropyl derivatives

Also Published As

Publication number Publication date
AT269832B (en) 1969-04-10
ES305661A1 (en) 1965-05-01
BR6464004D0 (en) 1973-08-09
FR4217M (en) 1966-06-13
IL22302A (en) 1968-10-24
NL6412766A (en) 1965-05-06
LU47291A1 (en) 1965-11-05
NL128365C (en)
FR4555M (en) 1966-11-02
AT266812B (en) 1968-12-10
FR4554M (en) 1966-11-02
JPS4821102B1 (en) 1973-06-26
AT273066B (en) 1969-07-25
CH482648A (en) 1969-12-15
BE655245A (en) 1965-05-04
GB1086192A (en) 1967-10-04
SE317669B (en) 1969-11-24
FR4282M (en) 1966-07-11
NL6901128A (en) 1969-04-25
DE1518207B1 (en) 1971-07-01
DK127726B (en) 1973-12-24
FI43069B (en) 1970-10-01
JPS507598B1 (en) 1975-03-27

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