GB1383906A - Pyridazinones - Google Patents

Pyridazinones

Info

Publication number
GB1383906A
GB1383906A GB508271A GB508271A GB1383906A GB 1383906 A GB1383906 A GB 1383906A GB 508271 A GB508271 A GB 508271A GB 508271 A GB508271 A GB 508271A GB 1383906 A GB1383906 A GB 1383906A
Authority
GB
United Kingdom
Prior art keywords
group
compound
amino
alkyl
alkoxy
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
GB508271A
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.)
BDH Pharmaceuticals Ltd
Original Assignee
BDH Pharmaceuticals Ltd
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 BDH Pharmaceuticals Ltd filed Critical BDH Pharmaceuticals Ltd
Priority to GB508271A priority Critical patent/GB1383906A/en
Priority to IE138/72A priority patent/IE36062B1/en
Priority to IL38705A priority patent/IL38705A/en
Priority to ZA720784A priority patent/ZA72784B/en
Priority to AU38911/72A priority patent/AU465740B2/en
Priority to BE779390A priority patent/BE779390A/en
Priority to CA134,888A priority patent/CA987322A/en
Priority to DE19722207517 priority patent/DE2207517A1/en
Priority to ES399863A priority patent/ES399863A1/en
Priority to SE7202096A priority patent/SE405599B/en
Priority to NO520/72A priority patent/NO136045C/en
Priority to FR7205751A priority patent/FR2126247B1/fr
Priority to AT138072A priority patent/AT313289B/en
Priority to CH250172A priority patent/CH573921A5/xx
Priority to NL7202336A priority patent/NL7202336A/xx
Publication of GB1383906A publication Critical patent/GB1383906A/en
Priority to US05/522,538 priority patent/US3975388A/en
Priority to US05/680,843 priority patent/US4088762A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40Unsaturated compounds
    • C07C59/76Unsaturated compounds containing keto groups
    • C07C59/90Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups

Abstract

1383906 6-Phenyl-4,5-dihydro-3(2H)-pyridazinones BDH PHARMACEUTICALS Ltd 18 Feb 1972 [22 Feb 1971] 5082/71 Heading C2C Novel 6-phenyl-4,5-dihydro-3(2H)-pyridazinones of the general formula wherein X is a fluorine or chlorine atom or a straight or branched chain alkyl or alkoxy, hydroxymethyl, cycloalkyl, cycloalkoxy, aryloxy, hydroxyl, amino, non-heterocyclic substituted amino, piperidino, morpholino, pyrrolidino, 1,2,3,6 - tetrahydropyridino or 4-[3- azabicyclo(3,2,2)nonyl] group or a group of formula wherein R is a hydrogen atom or a C 1-5 alkyl, optionally substituted aryl, aralkyl, cinnamyl, ethoxycarbonyl or optionally substituted acyl group, and n is 1-5; except that when n is 1, X is not a C 1-3 alkyl, C 1-2 alkoxy or optionally acylated amino group or a 41-chlorine atom; when n is 2, the X substituents are not both methyl groups in the 2 and 5<SP>1</SP>, 3<SP>1</SP> and 4<SP>1</SP> or 2<SP>1</SP> and 4<SP>1</SP> positions or methoxy groups in the 2<SP>1</SP>- and 5<SP>1</SP>-positions or chlorine atoms in the 2<SP>1</SP>- and 4<SP>1</SP>- or 3<SP>1</SP>- and 4<SP>1</SP>-positions; and when n is 3, all three X substituents are not methoxy groups; are prepared (a) by reaction of a #- benzoyl-propionic acid of the general formula with hydrazine hydrate or (b) when X is an alkoxy group, by reaction of the corresponding compound in which X is a hydroxyl group with an alkyl halide in the presence of an acid binding agent. #-Benzoyl-propionic acids of the second general formula above are prepared (a) by hydrolysis of a corresponding alkyl ester (an ethoxycarbonyl group R may simultaneously be removed and, when X is a hydroxymethyl group, the starting material may be the corresponding chloromethyl derivative); (b) by reaction of a substituted benzene with succinic anhydride in the presence of aluminium chloride; (c) when X is an amino group, by reduction of the corresponding nitro compound; (d) when X is a chlorine atom, by diazotization of the corresponding amino compound, followed by treatment with an aqueous solution containing sodium chloride, hydrated copper sulphate, sodium metabisulphite and sodium hydroxide; (e) when X is an acetamido group, by acetylation of the corresponding amino compound, (f) when X is a hydroxyl group, by treatment of a succinic acid monophenyl ester with aluminium chloride, and (g) when X is an alkoxy group, by alkylation of the corresponding hydroxy compound. The #-benzoyl-propionic acid alkyl esters are prepared (a) when X is a basic group, by reaction of the corresponding compound in which X is a fluorine atom with XH; (b) when X is as alkoxy group, by alkylation of the corresponding hydroxy compound; (c) when X is a fluorine atom or hydroxy group, by esterification of the corresponding acid; and (d) when X is a chloromethyl group, by treatment of the corresponding compound in which X is a hydrogen atom with paraformaldehyde, anhydrous zinc chloride and hydrogen chloride. Pharmaceutical compositions having antihypertensive activity comprise, as active ingredient, a 6-phenyl-4,5-dihydro-3(2H)-pyridazinone of the first general formula above, in association with a pharmaceutically acceptable carrier or diluent.
GB508271A 1971-02-22 1971-02-22 Pyridazinones Expired GB1383906A (en)

Priority Applications (17)

Application Number Priority Date Filing Date Title
GB508271A GB1383906A (en) 1971-02-22 1971-02-22 Pyridazinones
IE138/72A IE36062B1 (en) 1971-02-22 1972-02-04 Pyridazinones
IL38705A IL38705A (en) 1971-02-22 1972-02-07 6-phenyl-4,5-dihydro-3(2h)-pyridazinone derivatives,their preparation and pharmaceutical compositions containing them
ZA720784A ZA72784B (en) 1971-02-22 1972-02-07 Pyridazinones
AU38911/72A AU465740B2 (en) 1971-02-22 1972-02-11 Pyridazinones
BE779390A BE779390A (en) 1971-02-22 1972-02-15 NEW PYRIDAZINONES AND THEIR PREPARATION
CA134,888A CA987322A (en) 1971-02-22 1972-02-15 Pyridazinones
DE19722207517 DE2207517A1 (en) 1971-02-22 1972-02-17 Pyridazinones, process for their preparation and medicinal preparations containing these compounds
ES399863A ES399863A1 (en) 1971-02-22 1972-02-17 Pyridazinones
SE7202096A SE405599B (en) 1971-02-22 1972-02-21 PROCEDURE FOR THE PREPARATION OF PYRIDAZINONS WITH THERAPEUTIC EFFECT
NO520/72A NO136045C (en) 1971-02-22 1972-02-21 ANALOGICAL PROCEDURE FOR THE PREPARATION OF THERAPEUTICALLY ACTIVE PYRIDAZINONES.
FR7205751A FR2126247B1 (en) 1971-02-22 1972-02-21
AT138072A AT313289B (en) 1971-02-22 1972-02-21 Process for the preparation of new pyridazinones
CH250172A CH573921A5 (en) 1971-02-22 1972-02-22
NL7202336A NL7202336A (en) 1971-02-22 1972-02-22
US05/522,538 US3975388A (en) 1971-02-22 1974-11-11 Pyridazinones
US05/680,843 US4088762A (en) 1971-02-22 1976-04-27 6-(P-PIPERAZINO)-PHENYL-4,5-DIHYDRO-3(2H)pyridazinones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB508271A GB1383906A (en) 1971-02-22 1971-02-22 Pyridazinones

Publications (1)

Publication Number Publication Date
GB1383906A true GB1383906A (en) 1974-02-12

Family

ID=9789426

Family Applications (1)

Application Number Title Priority Date Filing Date
GB508271A Expired GB1383906A (en) 1971-02-22 1971-02-22 Pyridazinones

Country Status (15)

Country Link
AT (1) AT313289B (en)
AU (1) AU465740B2 (en)
BE (1) BE779390A (en)
CA (1) CA987322A (en)
CH (1) CH573921A5 (en)
DE (1) DE2207517A1 (en)
ES (1) ES399863A1 (en)
FR (1) FR2126247B1 (en)
GB (1) GB1383906A (en)
IE (1) IE36062B1 (en)
IL (1) IL38705A (en)
NL (1) NL7202336A (en)
NO (1) NO136045C (en)
SE (1) SE405599B (en)
ZA (1) ZA72784B (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0071059A2 (en) * 1981-07-31 1983-02-09 A. Nattermann & Cie. GmbH 6-(5-(Omega-(1-imidazolyl)-alkyl)-thien-2-yl)-3-oxo-2,3,4,5-tetrahydropyridazines and their acid-addition salts, process for their preparation and pharmaceutical compounds containing them
EP0071060A2 (en) * 1981-07-31 1983-02-09 A. Nattermann & Cie. GmbH 6-(4-(Omega-(1-imidazolyl)-alkyl)-phenyl)-3-oxo-2,3,4,5-tetrahydro-pyridazines and their acid-addition salts, process for their preparation and pharmaceutical compounds containing them
EP0075436A1 (en) * 1981-09-17 1983-03-30 Warner-Lambert Company Substituted 4,5-dihydro-6-(substituted)-phenyl-3(2H)-pyridazinones and 6-(substituted)phenyl-3(2H)-pyridazinones
US4914093A (en) * 1984-10-12 1990-04-03 Sankyo Company Limited Pyridazinone derivatives, their preparation and use
US8633197B2 (en) 2007-06-08 2014-01-21 Janssen Pharmaceutica N.V. Piperidine/piperazine derivatives
US8835437B2 (en) 2007-06-08 2014-09-16 Janssen Pharmaceutica N.V. Piperidine/piperazine derivatives
US8946228B2 (en) 2007-06-08 2015-02-03 Janssen Pharmaceutica N.V. Piperidine/piperazine derivatives
US8981094B2 (en) 2007-06-08 2015-03-17 Janssen Pharmaceutica N.V. Piperidine/piperazine derivatives
US9107946B2 (en) 2008-06-05 2015-08-18 Janssen Pharmaceutica Nv Drug combinations comprising a DGAT inhibitor and a PPAR-agonist

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3975388A (en) * 1971-02-22 1976-08-17 Bdh Pharmaceuticals Limited Pyridazinones
US4011321A (en) * 1973-12-19 1977-03-08 Smith Kline & French Laboratories Limited Pharmaceutical compositions and methods of inhibiting β-adrenergic receptors
GB1488330A (en) * 1973-12-19 1977-10-12 Smith Kline French Lab Dihydropyridazinones
US4052395A (en) * 1975-09-11 1977-10-04 Sankyo Company Limited Agricultural fungicidal compositions containing 6-(substituted phenyl)-pyridazinones and said pyridazinones
DE2845456A1 (en) * 1978-10-19 1980-08-14 Merck Patent Gmbh 6-ARYLPYRIDAZIN-3-ONE AND METHOD FOR THE PRODUCTION THEREOF
DE2854475A1 (en) 1978-12-16 1980-07-03 Basf Ag NEW 3,4-DIAZA-BICYCLO ANGLE CLAMP ON 4.1.0 ANGLE CLAMP FOR HEPTING- (2) - ONE- (5), METHOD FOR THE PRODUCTION THEREOF AND THESE COMPOUNDS THERAPEUTIC AGENTS
ATE13294T1 (en) * 1981-03-04 1985-06-15 Ciba Geigy Ag PYRIDAZINONE, PROCESS FOR THEIR MANUFACTURE, PHARMACEUTICAL PREPARATIONS CONTAINING THESE COMPOUNDS AND THEIR USE.
EP0101156A3 (en) * 1982-06-24 1984-08-22 Smith Kline & French Laboratories Limited Process for preparing 6-(2-hydroxyphenyl)-3-pyridazinone
JPS6153270A (en) * 1984-08-17 1986-03-17 チバ・ガイギー・アクチエンゲゼルシヤフト Substituted pyridazinone, manufacture and medicine
GB8426804D0 (en) * 1984-10-23 1984-11-28 Ciba Geigy Ag Pyridazinones preparations
DE3804490A1 (en) * 1988-02-12 1989-08-24 Heumann Pharma Gmbh & Co SUBSTITUTED 6-PHENYLDIHYDRO-3 (2H) -PYRIDAZINONE, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS
DE3814057A1 (en) * 1988-04-26 1989-11-09 Heumann Pharma Gmbh & Co 6-OXO-PYRIDAZINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1670043C3 (en) * 1966-01-07 1975-05-22 Basf Ag, 6700 Ludwigshafen Process for the preparation of 3- (aminophenyl) pyridazone (6) derivatives

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0071059A2 (en) * 1981-07-31 1983-02-09 A. Nattermann & Cie. GmbH 6-(5-(Omega-(1-imidazolyl)-alkyl)-thien-2-yl)-3-oxo-2,3,4,5-tetrahydropyridazines and their acid-addition salts, process for their preparation and pharmaceutical compounds containing them
EP0071060A2 (en) * 1981-07-31 1983-02-09 A. Nattermann & Cie. GmbH 6-(4-(Omega-(1-imidazolyl)-alkyl)-phenyl)-3-oxo-2,3,4,5-tetrahydro-pyridazines and their acid-addition salts, process for their preparation and pharmaceutical compounds containing them
EP0071059A3 (en) * 1981-07-31 1984-03-21 A. Nattermann & Cie. Gmbh 6-(5-(omega-(1-imidazolyl)-alkyl)-thien-2-yl)-3-oxo-2,3,4,5-tetrahydropyridazines and their acid-addition salts, process for their preparation and pharmaceutical compounds containing them
EP0071060A3 (en) * 1981-07-31 1984-03-21 A. Nattermann & Cie. Gmbh 6-(4-(omega-(1-imidazolyl)-alkyl)-phenyl)-3-oxo-2,3,4,5-tetrahydro-pyridazines and their acid-addition salts, process for their preparation and pharmaceutical compounds containing them
EP0075436A1 (en) * 1981-09-17 1983-03-30 Warner-Lambert Company Substituted 4,5-dihydro-6-(substituted)-phenyl-3(2H)-pyridazinones and 6-(substituted)phenyl-3(2H)-pyridazinones
US4914093A (en) * 1984-10-12 1990-04-03 Sankyo Company Limited Pyridazinone derivatives, their preparation and use
US8946228B2 (en) 2007-06-08 2015-02-03 Janssen Pharmaceutica N.V. Piperidine/piperazine derivatives
US8835437B2 (en) 2007-06-08 2014-09-16 Janssen Pharmaceutica N.V. Piperidine/piperazine derivatives
US8633197B2 (en) 2007-06-08 2014-01-21 Janssen Pharmaceutica N.V. Piperidine/piperazine derivatives
US8981094B2 (en) 2007-06-08 2015-03-17 Janssen Pharmaceutica N.V. Piperidine/piperazine derivatives
US9120821B2 (en) 2007-06-08 2015-09-01 Janssen Pharmaceutica N.V. Piperidine/piperazine derivatives
US9227935B2 (en) 2007-06-08 2016-01-05 Janssen Pharmaceutical N.V. Piperidine/piperazine derivatives
US9499567B2 (en) 2007-06-08 2016-11-22 Janssen Pharmaceutica N.V. Piperidine/piperazine derivatives
US9688696B2 (en) 2007-06-08 2017-06-27 Janssen Pharmaceutica N.V. Piperidine/piperazine derivatives
US9107946B2 (en) 2008-06-05 2015-08-18 Janssen Pharmaceutica Nv Drug combinations comprising a DGAT inhibitor and a PPAR-agonist
US9724418B2 (en) 2008-06-05 2017-08-08 Janssen Pharmaceutica Nv Drug combinations comprising a DGAT inhibitor and a PPAR-agonist

Also Published As

Publication number Publication date
NO136045B (en) 1977-04-04
IL38705A0 (en) 1972-04-27
CH573921A5 (en) 1976-03-31
FR2126247A1 (en) 1972-10-06
CA987322A (en) 1976-04-13
NL7202336A (en) 1972-08-24
NO136045C (en) 1977-07-13
AU465740B2 (en) 1975-10-09
IE36062L (en) 1972-08-22
AT313289B (en) 1974-02-11
DE2207517A1 (en) 1972-12-14
ES399863A1 (en) 1975-06-16
AU3891172A (en) 1973-08-16
SE405599B (en) 1978-12-18
BE779390A (en) 1972-08-16
IL38705A (en) 1976-08-31
IE36062B1 (en) 1976-08-04
FR2126247B1 (en) 1975-08-01
ZA72784B (en) 1972-10-25

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee