GB1383906A - Pyridazinones - Google Patents
PyridazinonesInfo
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated 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.
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)
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)
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)
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 |
-
1971
- 1971-02-22 GB GB508271A patent/GB1383906A/en not_active Expired
-
1972
- 1972-02-04 IE IE138/72A patent/IE36062B1/en unknown
- 1972-02-07 ZA ZA720784A patent/ZA72784B/en unknown
- 1972-02-07 IL IL38705A patent/IL38705A/en unknown
- 1972-02-11 AU AU38911/72A patent/AU465740B2/en not_active Expired
- 1972-02-15 CA CA134,888A patent/CA987322A/en not_active Expired
- 1972-02-15 BE BE779390A patent/BE779390A/en unknown
- 1972-02-17 ES ES399863A patent/ES399863A1/en not_active Expired
- 1972-02-17 DE DE19722207517 patent/DE2207517A1/en active Pending
- 1972-02-21 FR FR7205751A patent/FR2126247B1/fr not_active Expired
- 1972-02-21 AT AT138072A patent/AT313289B/en not_active IP Right Cessation
- 1972-02-21 SE SE7202096A patent/SE405599B/en unknown
- 1972-02-21 NO NO520/72A patent/NO136045C/en unknown
- 1972-02-22 CH CH250172A patent/CH573921A5/xx not_active IP Right Cessation
- 1972-02-22 NL NL7202336A patent/NL7202336A/xx not_active Application Discontinuation
Cited By (16)
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 |