GB1346029A - - Google Patents

Info

Publication number
GB1346029A
GB1346029A GB15036/72*2A GB1503672A GB1346029A GB 1346029 A GB1346029 A GB 1346029A GB 1503672 A GB1503672 A GB 1503672A GB 1346029 A GB1346029 A GB 1346029A
Authority
GB
United Kingdom
Prior art keywords
compounds
formula
reacting
methoxybenzoyl
piperazine
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
GB15036/72*2A
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.)
Cassella Farbwerke Mainkur AG
Original Assignee
Cassella Farbwerke Mainkur AG
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
Application filed by Cassella Farbwerke Mainkur AG filed Critical Cassella Farbwerke Mainkur AG
Publication of GB1346029A publication Critical patent/GB1346029A/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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups

Abstract

1346029 Ketone derivatives CASSELLA FARBWERKE MAINKUR AG 30 March 1972 [2 April 1971] 15036/72 Heading C2C The invention comprises novel ketone derivatives of the formula and their pharmaceutically acceptable acid addition salts, wherein R 1 is CN, CONH 2 , COOH, COONa or COOK; R 2 is a radical of the formula or wherein X is C 1-4 alkylene, Y is -OCO- or -CONH-; R 3 and R 4 each are H or C 1-6 alkyl; and R 5 is H or OH, the nucleus I is optionally substituted by 1 to 3 alkoxy, alkyl or NO 2 radicals or halogen atoms; the nucleus II is optionally substituted by 1 to 3 alkoxy or alkyl radicals or halogen atoms; and the nucleus III is optionally substituted by 1 to 3 methoxy radicals and their preparation. The compounds are prepared by reacting compounds of the formula HR 2 with compounds of the formula or alternatively compounds in which Y is -OCO- may be obtained by esterifying the corresponding hydroxyalkylpiperazine derivatives, compounds in which R 1 is CN by the addition of hydrogen cyanide to compounds of the formula and compounds in which R 1 is COOH, COOK 1 or COONa by acid hydrolysis of the corresponding nitriles of the formula or by the diazotization of the corresponding carboxamides of the formula following by, if desired, conversion to the sodium or potassium salts. 3 - Benzoylacrylonitriles, in which the benzene ring is optionally substituted, are obtained by reacting KCN with the appropriate quaternary ammonium salts resulting from the reaction between trimethylamine and the corresponding 2-benzoylvinyl chlorides, obtained by treating the corresponding benzoyl chlorides with acetylene. 3 - (2,3,4 - Trimethoxybenzoyl)acrylic acid is obtained by diazotizing 3-(2,3,4-trimethoxybenzoyl)acrylamide, resulting from the hydrolysis of the corresponding acrylonitrile. 3<SP>1</SP>,4<SP>1</SP>,5<SP>1 </SP>- Trimethoxy - 2 - (1 - piperazine)- acetanilide is obtained by reacting piperazine with 2 - chloro - 3<SP>1</SP>,4<SP>1</SP>,5<SP>1</SP> - trimethoxyacetanilide resulting from the reaction between 3,4,5- trimethoxyaniline und chloroacetyl chloride. 1 - (2 - Hydroxyethyl) - 4 - [2 - (3 - methoxybenzoyl) - 1 - cyanoethyl]piperazine is prepared by 1 - (2 - hydroxyethyl)piperazine with 3- (3 - methoxybenzoyl)acrylonitrile, obtained by reacting KCN with 2-(3-methoxybenzoyl)vinyl chloride resulting from the reaction of thionyl chloride on 2-(3-methoxybenzoyl)vinyl alcohol sodium salt, which is made by reacting 3- methoxyacetophenone with ethyl formate and sodium methylate. Other methoxy substituted benzoylvinyl chlorides are obtained in a similar manner. Pharmaceutical compositions, suitable for oral, parenteral or rectal administration, contain the above novel compounds or acid addition salts thereof together with pharmaceutically acceptable diluents or carriers. The compounds exert dilatory action on the cerebral vessels.
GB15036/72*2A 1971-04-02 1972-03-30 Expired GB1346029A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19712116293 DE2116293A1 (en) 1971-04-02 1971-04-02 Ketone derivatives and processes for their preparation

Publications (1)

Publication Number Publication Date
GB1346029A true GB1346029A (en) 1974-02-06

Family

ID=5803749

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15036/72*2A Expired GB1346029A (en) 1971-04-02 1972-03-30

Country Status (10)

Country Link
US (1) US3846470A (en)
AR (3) AR192920A1 (en)
AT (3) AT315857B (en)
BE (1) BE781544A (en)
CS (3) CS159701B2 (en)
DD (1) DD96702A5 (en)
DE (1) DE2116293A1 (en)
FR (1) FR2132354B1 (en)
GB (1) GB1346029A (en)
NL (1) NL7203630A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4252804A (en) 1977-01-14 1981-02-24 Metabio-Joullie Therapeutically useful 3,4,5-trimethoxybenzene derivatives

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3980643A (en) * 1974-01-04 1976-09-14 Hokuriku Pharmaceutical Co., Ltd. Novel piperazine- and homopiperazine-monoalkanol esters and a process of production thereof
FR2481270A1 (en) * 1980-04-24 1981-10-30 Roussel Uclaf NOVEL SUBSTITUTED DERIVATIVES OF 4-PHENYL 4-OXO 2-HYDROXY BUTANOIC ACID, PROCESS FOR THEIR PREPARATION AND APPLICATIONS AS MEDICAMENTS
FR2481118A1 (en) * 1980-04-24 1981-10-30 Roussel Uclaf APPLICATION AS MEDICAMENTS OF DERIVATIVES SUBSTITUTED WITH PHENYL-4-OXO-2-BUTENOIC ACID
FR2489313A1 (en) * 1980-09-04 1982-03-05 Hoechst France PROCESS FOR THE PRODUCTION OF HYDROXYARYLGLYOXYLIC ACIDS AND THEIR ALKALI SALTS AND ITS APPLICATION TO THE MANUFACTURE OF SODIUM PARA-HYDROXYPHENYLGLYOXYLATE
FR2504127B1 (en) * 1981-04-17 1985-07-19 Roussel Uclaf NOVEL DERIVATIVES OF CARBOXYLIC ALIPHATIC PHENYL ACIDS, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATION AS MEDICAMENTS
FR2504004A1 (en) * 1981-04-17 1982-10-22 Roussel Uclaf APPLICATION AS MEDICAMENTS OF PHENYL ALIPHATIC CARBOXYLIC ACID DERIVATIVES
FR2515037A1 (en) * 1981-10-22 1983-04-29 Roussel Uclaf AS MEDICINES, CERTAIN MONO-SUBSTITUTED DERIVATIVES OF 4-PHENYL 4-OXO BUTEN-2-OIC ACID, AND THE COMPOSITIONS CONTAINING SAME
GB2108500B (en) * 1981-10-22 1985-05-15 Roussel Uclaf Aminobenzene medicaments
IT1210582B (en) * 1981-10-22 1989-09-14 Roussel Maestretti Spa 4-FENYL-4-OSSOBUTEN-2-OICO ACID DERIVATIVES EQUIPPED WITH PHARMACOLOGICAL PROPERTIES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
SE454355B (en) * 1983-01-24 1988-04-25 Roussel Uclaf ACRYLIC ACID DERIVATIVES CONTAINING A FURYL, PYRANYL, BENZOFURANYL, OXAZOLYL OR ISOXAZOLYL GROUP, PROCEDURES FOR PREPARING THEREOF, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEMSELVES
IT1169783B (en) * 1983-08-25 1987-06-03 Roussel Maestretti Spa DERIVATIVES OF 4-FENYL 4-BONE-BUTEN 2-OICO ACID, THEIR PREPARATION PROCEDURE AND THEIR APPLICATION AS MEDICINAL PRODUCTS
DE3521116A1 (en) * 1985-06-13 1986-12-18 Henkel KGaA, 4000 Düsseldorf SPECIAL BENZOYLALANINE AND THEIR USE AS CORROSION INHIBITORS FOR AQUEOUS SYSTEMS
DE69206299T2 (en) * 1991-03-29 1996-03-28 Tokuyama Corp Cyanoketone derivative and herbicide containing this as an active ingredient.
DE4443465A1 (en) * 1994-12-07 1996-06-13 Chemie Linz Deutschland Prepn. of (S,S)-(N-(1-ethoxycarbonyl-3-oxo-3-phenylpropyl)- alanine)-(phenylmethyl) ester

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE630296A (en) * 1962-03-31
DE1593837A1 (en) * 1967-06-29 1970-10-29 Degussa Process for the preparation of new aminoketones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4252804A (en) 1977-01-14 1981-02-24 Metabio-Joullie Therapeutically useful 3,4,5-trimethoxybenzene derivatives

Also Published As

Publication number Publication date
DD96702A5 (en) 1973-04-05
BE781544A (en) 1972-10-02
AT315857B (en) 1974-06-10
CS159701B2 (en) 1975-01-31
FR2132354A1 (en) 1972-11-17
US3846470A (en) 1974-11-05
NL7203630A (en) 1972-10-04
CS159703B2 (en) 1975-01-31
AT316522B (en) 1974-07-10
AR192920A1 (en) 1973-03-21
SU439983A3 (en) 1974-08-15
DE2116293A1 (en) 1972-10-19
CS159702B2 (en) 1975-01-31
FR2132354B1 (en) 1975-04-25
AR199200A1 (en) 1974-08-14
AT315185B (en) 1974-05-10
AR193462A1 (en) 1973-04-23

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees