GB1493222A - Cycloalkanone oxime ethers and process for the preparation thereof - Google Patents

Cycloalkanone oxime ethers and process for the preparation thereof

Info

Publication number
GB1493222A
GB1493222A GB3176/76A GB317676A GB1493222A GB 1493222 A GB1493222 A GB 1493222A GB 3176/76 A GB3176/76 A GB 3176/76A GB 317676 A GB317676 A GB 317676A GB 1493222 A GB1493222 A GB 1493222A
Authority
GB
United Kingdom
Prior art keywords
hal
reacting
alkylene
oxime
cyclohexanethione
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
GB3176/76A
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.)
Egyt Gyogyszervegyeszeti Gyar
Original Assignee
Egyt Gyogyszervegyeszeti Gyar
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 claimed from US05/652,806 external-priority patent/US4083978A/en
Priority to US05/652,806 priority Critical patent/US4083978A/en
Priority to DK32576A priority patent/DK149043C/en
Priority to GB3176/76A priority patent/GB1493222A/en
Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar
Priority to FI760218A priority patent/FI65615C/en
Priority to SE7600969A priority patent/SE410733B/en
Priority to FR7602460A priority patent/FR2339397A1/en
Priority to NLAANVRAGE7600945,A priority patent/NL180585C/en
Priority to BE164044A priority patent/BE838213A/en
Priority to CA245,043A priority patent/CA1071201A/en
Priority to JP1273676A priority patent/JPS5295643A/en
Priority to AT125076A priority patent/AT339276B/en
Priority to AT813776A priority patent/AT342019B/en
Priority claimed from AT125076A external-priority patent/AT339276B/en
Priority to CH223676A priority patent/CH626058A5/en
Priority to DD191525A priority patent/DD125547A5/xx
Priority to DE2609017A priority patent/DE2609017C3/en
Priority to US05/749,399 priority patent/US4077999A/en
Publication of GB1493222A publication Critical patent/GB1493222A/en
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
    • C07D295/04—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
    • C07D295/08—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 singly bound oxygen or sulfur atoms
    • C07D295/084—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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

Landscapes

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

Abstract

1493222 Cycloalkanone-oxime ethers EGYT GYOGYSZERVEGYESZETI GYAR 27 Jan 1976 03176/76 Heading C2C Novel compounds I and acid addition and quarternary ammonium salts thereof in which R is phenyl optionally substituted by a halogen atom or by one or more, C 1-4 alkoxy OH, NO 2 or di C 1-3 alkylamine groups, R 1 and R 2 are H or together represent a bond, A is C 2-4 alkylene and B is NR<SP>3</SP>R<SP>4</SP> (where R<SP>3</SP> and R<SP>4</SP> are H or both C 1-4 alkyl or R<SP>3</SP> and R<SP>4</SP> together represent C 4-7 alkylene optionally interrupted by O, NH, N-C 1-3 alkyl or N-benzyl) and n is 3 to 10; are prepared by (1) reacting an oxime B-AONH 2 with (a) the corresponding ketone or thioketone or (b) a compound IV or (2) reacting the corresponding unsubstituted oxime with a compound B-A-Hal or with Hal-CH 2 -A<SP>1</SP>-Hal followed by aminating with NHR 3 R 4 (where Hal and Hal<SP>1</SP> are halogen and A<SP>1</SP> is C 1-3 alkylene); and, if desired, forming a salt thereof or treating a salt formed to produce the free base. 2-Benzylidene-cyclohexanethione is prepared by reacting cyclohexanethione with benzaldehyde. Compounds I have local analgesic, spasmolytic, nicotine-lethality inhibiting, tetrabenazine antagonistic and tetracor-spasm inhibiting properties and form with a carrier diluent and/or auxiliary agent a pharmaceutical composition which may be administered orally or parenterally.
GB3176/76A 1976-01-27 1976-01-27 Cycloalkanone oxime ethers and process for the preparation thereof Expired GB1493222A (en)

Priority Applications (16)

Application Number Priority Date Filing Date Title
US05/652,806 US4083978A (en) 1976-01-27 1976-01-27 Oxime ethers
DK32576A DK149043C (en) 1976-01-27 1976-01-27 METHOD OF ANALOGUE FOR THE PREPARATION OF 2-BENZAL OR 2-BENZYL-1- (AMINOALCOXYIMINO) -CYCLOALKANES OR SALTS OR QUATERNARY AMMONIUM DERIVATIVES THEREOF
GB3176/76A GB1493222A (en) 1976-01-27 1976-01-27 Cycloalkanone oxime ethers and process for the preparation thereof
FI760218A FI65615C (en) 1976-01-27 1976-01-29 OXIMETRY OF THE THERAPEUTIC FREQUENCY OF THERAPEUTIC EQUIPMENT
SE7600969A SE410733B (en) 1976-01-27 1976-01-29 WAY TO PRODUCE CERTAIN DETAILED OXIMETERS
FR7602460A FR2339397A1 (en) 1976-01-27 1976-01-29 NEW OXIMES ETHERS, PROCESS FOR THE PREPARATION OF THEM AND MEDICINAL PRODUCTS CONTAINING THEM
NLAANVRAGE7600945,A NL180585C (en) 1976-01-27 1976-01-30 PROCESS FOR THE PREPARATION OF OXIM ETHERS, AND PROCESS FOR THE PREPARATION OR MANUFACTURE OF PHARMACEUTICAL PREPARATIONS CONTAINING THE SAME
BE164044A BE838213A (en) 1976-01-27 1976-02-03 NEW OXIMES ETHERS, PROCESS FOR THE PREPARATION OF THEM AND MEDICINAL PRODUCTS CONTAINING THEM
CA245,043A CA1071201A (en) 1976-01-27 1976-02-04 Oxime ethers and process for the preparation thereof
JP1273676A JPS5295643A (en) 1976-01-27 1976-02-07 Oxim ether and process for preparing same
AT813776A AT342019B (en) 1976-01-27 1976-02-23 PROCESS FOR THE PREPARATION OF BASIC CYCLOAL CANONOXIMATHERS AND THEIR ACID ADDITION SALTS
AT125076A AT339276B (en) 1976-01-27 1976-02-23 PROCESS FOR THE PREPARATION OF BASIC CYCLOAL CANONOXIMATHERS AND THEIR ACID ADDITION SALTS
CH223676A CH626058A5 (en) 1976-01-27 1976-02-24 Process for the preparation of basic oxime ethers
DD191525A DD125547A5 (en) 1976-01-27 1976-02-26
DE2609017A DE2609017C3 (en) 1976-01-27 1976-03-04 Basic oxime ethers, processes for their preparation and medicinal products containing these compounds
US05/749,399 US4077999A (en) 1976-01-27 1976-12-10 Novel oxime ethers

Applications Claiming Priority (16)

Application Number Priority Date Filing Date Title
US05/652,806 US4083978A (en) 1976-01-27 1976-01-27 Oxime ethers
DK32576A DK149043C (en) 1976-01-27 1976-01-27 METHOD OF ANALOGUE FOR THE PREPARATION OF 2-BENZAL OR 2-BENZYL-1- (AMINOALCOXYIMINO) -CYCLOALKANES OR SALTS OR QUATERNARY AMMONIUM DERIVATIVES THEREOF
GB3176/76A GB1493222A (en) 1976-01-27 1976-01-27 Cycloalkanone oxime ethers and process for the preparation thereof
FI760218A FI65615C (en) 1976-01-27 1976-01-29 OXIMETRY OF THE THERAPEUTIC FREQUENCY OF THERAPEUTIC EQUIPMENT
SE7600969A SE410733B (en) 1976-01-27 1976-01-29 WAY TO PRODUCE CERTAIN DETAILED OXIMETERS
FR7602460A FR2339397A1 (en) 1976-01-27 1976-01-29 NEW OXIMES ETHERS, PROCESS FOR THE PREPARATION OF THEM AND MEDICINAL PRODUCTS CONTAINING THEM
NLAANVRAGE7600945,A NL180585C (en) 1976-01-27 1976-01-30 PROCESS FOR THE PREPARATION OF OXIM ETHERS, AND PROCESS FOR THE PREPARATION OR MANUFACTURE OF PHARMACEUTICAL PREPARATIONS CONTAINING THE SAME
BE164044A BE838213A (en) 1976-01-27 1976-02-03 NEW OXIMES ETHERS, PROCESS FOR THE PREPARATION OF THEM AND MEDICINAL PRODUCTS CONTAINING THEM
CA245,043A CA1071201A (en) 1976-01-27 1976-02-04 Oxime ethers and process for the preparation thereof
JP1273676A JPS5295643A (en) 1976-01-27 1976-02-07 Oxim ether and process for preparing same
AT813776A AT342019B (en) 1976-01-27 1976-02-23 PROCESS FOR THE PREPARATION OF BASIC CYCLOAL CANONOXIMATHERS AND THEIR ACID ADDITION SALTS
AT125076A AT339276B (en) 1976-01-27 1976-02-23 PROCESS FOR THE PREPARATION OF BASIC CYCLOAL CANONOXIMATHERS AND THEIR ACID ADDITION SALTS
CH223676A CH626058A5 (en) 1976-01-27 1976-02-24 Process for the preparation of basic oxime ethers
DD191525A DD125547A5 (en) 1976-01-27 1976-02-26
DE2609017A DE2609017C3 (en) 1976-01-27 1976-03-04 Basic oxime ethers, processes for their preparation and medicinal products containing these compounds
US05/749,399 US4077999A (en) 1976-01-27 1976-12-10 Novel oxime ethers

Publications (1)

Publication Number Publication Date
GB1493222A true GB1493222A (en) 1977-11-30

Family

ID=27585558

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3176/76A Expired GB1493222A (en) 1976-01-27 1976-01-27 Cycloalkanone oxime ethers and process for the preparation thereof

Country Status (13)

Country Link
JP (1) JPS5295643A (en)
AT (1) AT342019B (en)
BE (1) BE838213A (en)
CA (1) CA1071201A (en)
CH (1) CH626058A5 (en)
DD (1) DD125547A5 (en)
DE (1) DE2609017C3 (en)
DK (1) DK149043C (en)
FI (1) FI65615C (en)
FR (1) FR2339397A1 (en)
GB (1) GB1493222A (en)
NL (1) NL180585C (en)
SE (1) SE410733B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2134904A (en) * 1983-02-08 1984-08-22 Egyt Gyogyszervegyeszeti Gyar Basic oxime ethers
EP0168245A2 (en) * 1984-07-10 1986-01-15 Egis Gyogyszergyar Basic oxime ethers, pharmaceutical compositions possessing antianginal activityand the use of basic oxime ethers for manufactoring medicaments for the treatment of angina
EP0619298A2 (en) * 1993-04-09 1994-10-12 Egis Gyogyszergyar Rt. (Phenylmethylene)-2-(alkyl)-1- omega-(amino)-alkoxyimino -cycloalkane derivatives, a process for preparing them as well as medicaments containing them and the use of them

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2658938A1 (en) * 1976-12-24 1978-07-06 Hoechst Ag NEW BASICLY SUBSTITUTED 0-PROPYLOXIME, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A MEDICINAL PRODUCT
HU180739B (en) * 1979-07-03 1983-04-29 Egyt Gyogyszervegyeszeti Gyar Process for producing basic oxime-ethers
FR2518090A1 (en) * 1981-12-11 1983-06-17 Univablot OXIMES A-B UNSATURATED ETHERS, PROCESS FOR THEIR PREPARATION AND THEIR USE AS A MEDICINAL PRODUCT
HU190387B (en) * 1982-05-25 1986-08-28 Egyt Gyogyszervegyeszeti Gyar,Hu Process for producing 2-bracket-z-bracket closed-phenyl-methylene-cycloheptane derivatives
HU189226B (en) * 1983-02-08 1986-06-30 Egyt Gyogyszervegyeszeti Gyar,Hu Process for producing basic oxime-ethers
HU202195B (en) * 1987-12-31 1991-02-28 Egyt Gyogyszervegyeszeti Gyar Process for producing new substituted styrene derivatives and medical compositions comprising such compounds
CA2006309C (en) * 1988-12-29 2001-12-18 Jean Hutt Azolylmethylcyclopentane benzylidene fungicide
HU212415B (en) * 1989-08-25 1996-06-28 Egyt Gyogyszervegyeszeti Gyar Process for producing new cyclic oxym derivatives and pharmaceutical compositions containing them as active components

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3262975A (en) 1963-02-12 1966-07-26 Upjohn Co 1-chloro-3, 4-dihydro 2-naphthaldehyde oxime and ethers thereof
US3937841A (en) 1967-04-05 1976-02-10 U.S. Philips Corporation Treatment of depression
CH512184A (en) 1969-08-06 1971-09-15 Ciba Geigy Ag Cyclohexone or cyclohexenone-n-alkyl - carbomoyloximes for the control of ticks
CA943138A (en) 1969-11-10 1974-03-05 Don R. Baker Certain oxime compositions and their use in controlling fungi
US3928446A (en) 1974-04-11 1975-12-23 Hoffmann La Roche Preparation of 3-oxo-19-nor-{66 {hu 4{b -steroids from 10-{8 3-substituted-alkyl{9 -desasteroids

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2134904A (en) * 1983-02-08 1984-08-22 Egyt Gyogyszervegyeszeti Gyar Basic oxime ethers
EP0168245A2 (en) * 1984-07-10 1986-01-15 Egis Gyogyszergyar Basic oxime ethers, pharmaceutical compositions possessing antianginal activityand the use of basic oxime ethers for manufactoring medicaments for the treatment of angina
EP0168245A3 (en) * 1984-07-10 1987-04-29 Egis Gyogyszergyar Pharmaceutical compositions of antianginal activity
EP0619298A2 (en) * 1993-04-09 1994-10-12 Egis Gyogyszergyar Rt. (Phenylmethylene)-2-(alkyl)-1- omega-(amino)-alkoxyimino -cycloalkane derivatives, a process for preparing them as well as medicaments containing them and the use of them
EP0619298A3 (en) * 1993-04-09 1996-03-06 Egyt Gyogyszervegyeszeti Gyar (Phenylmethylene)-2-(alkyl)-1- omega-(amino)-alkoxyimino -cycloalkane derivatives, a process for preparing them as well as medicaments containing them and the use of them.

Also Published As

Publication number Publication date
DE2609017C3 (en) 1981-05-27
CA1071201A (en) 1980-02-05
SE7600969L (en) 1977-07-30
SE410733B (en) 1979-10-29
FI760218A (en) 1977-07-30
DK149043C (en) 1986-05-26
DE2609017B2 (en) 1980-10-09
FR2339397A1 (en) 1977-08-26
CH626058A5 (en) 1981-10-30
ATA813776A (en) 1977-07-15
DK149043B (en) 1985-12-30
FR2339397B1 (en) 1979-10-05
DK32576A (en) 1977-07-28
DD125547A5 (en) 1977-05-04
FI65615B (en) 1984-02-29
FI65615C (en) 1984-06-11
BE838213A (en) 1976-05-28
DE2609017A1 (en) 1977-09-08
NL180585C (en) 1987-03-16
JPS5715746B2 (en) 1982-04-01
NL7600945A (en) 1977-08-02
JPS5295643A (en) 1977-08-11
AT342019B (en) 1978-03-10
NL180585B (en) 1986-10-16

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19940127