GB1431063A - Amino derivatives of pyrido 2,3-d pyridazine carboxylic acids and esters - Google Patents

Amino derivatives of pyrido 2,3-d pyridazine carboxylic acids and esters

Info

Publication number
GB1431063A
GB1431063A GB2017373A GB2017373A GB1431063A GB 1431063 A GB1431063 A GB 1431063A GB 2017373 A GB2017373 A GB 2017373A GB 2017373 A GB2017373 A GB 2017373A GB 1431063 A GB1431063 A GB 1431063A
Authority
GB
United Kingdom
Prior art keywords
compound
alkyl
reaction
methylpyridine
butylamino
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
GB2017373A
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.)
ER Squibb and Sons LLC
Original Assignee
ER Squibb and Sons LLC
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 ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC
Publication of GB1431063A publication Critical patent/GB1431063A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3

Abstract

1431063 Amino derivatives of pyrido(2,3-D)- pyridazine carboxylic acid and esters E R SQUIBB & SONS Inc 27 April 1973 [12 May 1972] 20173/73 Heading C2C The invention comprises compounds of formula wherein R is H or C 1-7 alkyl, R 1 and R 2 each is H, C 1-7 alkyl, phenyl which may be substituted by one or two C 1-7 alkyl, -CF 3 , or -COOH, phenyl-C 1-7 alkylene, or the group -NR 1 R 2 is a pyrrolidino, piperidino, pyrazolyl, pyrimidinyl, pyrazinyl, dihydropyridazinyl or piperazinyl radical each of which may bear one hydroxy- (C 1-7 ) alkyl group, or one or two C 1-7 alkyl, and R 3 is H or C 1-7 alkyl; and physiologically acceptable acid addition salts thereof. These compounds may be obtained by reacting a compound of formula wherein R is C 1-7 alkyl, and R<SP>1</SP> and R<SP>2</SP> are as defined above, with hydrazine or hydrazine hydrate, and if desired alkylating the 5-hydroxy group of the product compound to obtain a compound in which R is a hydrogen atom and, if yet further desired forming an acid addition salt of the product. Example I describes the preparation of 4-butylamino-5-ethoxy-3-ethoxycarbonylpyrido[2,3-d]pyridazine in which the following intermediates are also prepared: (a) 3 - cyano - 5 - ethoxycarbonyl - 4 - hydroxy - 2- methylpyridine by the reaction of ethoxymethylene malonic acid diethyl ester and 3- aminocrotonic acid nitrile; (b) 4-chloro-3- cyano - 5 - ethoxycarbonyl - 2 - methylpyridine by the reaction of compound (a) with phosphorous oxychloride; (c) 4-butylamino-3-cyano-5-ethoxycarbonyl - 2 - methylpyridine by the reaction of compound (b) with n-butylamine; (d) 4-butylamino - 3 - cyano - 5 - ethoxycarbonylpyridine - 2- aldehyde by the reaction of compound (c) with methylpyridine in the presence of selenium dioxide; and (e) 4-butylamino-3-ethoxycarbonyl-5 hydroxygryrido[2,3-d]pyridazine prepared by the reaction of compound (d) with hydrazine hydrate and acetic acid.
GB2017373A 1972-05-12 1973-04-27 Amino derivatives of pyrido 2,3-d pyridazine carboxylic acids and esters Expired GB1431063A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US25277572A 1972-05-12 1972-05-12

Publications (1)

Publication Number Publication Date
GB1431063A true GB1431063A (en) 1976-04-07

Family

ID=22957497

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2017373A Expired GB1431063A (en) 1972-05-12 1973-04-27 Amino derivatives of pyrido 2,3-d pyridazine carboxylic acids and esters

Country Status (5)

Country Link
JP (1) JPS4948695A (en)
CA (1) CA1004223A (en)
DE (1) DE2322073A1 (en)
FR (1) FR2184763B1 (en)
GB (1) GB1431063A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004056825A1 (en) * 2002-12-23 2004-07-08 Syngenta Limited Pyridodiazines as plant fungicides

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9200689D0 (en) * 1992-01-14 1992-03-11 Rhone Poulenc Agriculture New compositions of matter
JP2578333Y2 (en) * 1992-09-04 1998-08-13 日産ディーゼル工業株式会社 Parking brake release device
US20090246198A1 (en) * 2008-03-31 2009-10-01 Takeda Pharmaceutical Company Limited Mapk/erk kinase inhibitors and methods of use thereof
EP2748166B1 (en) * 2011-08-23 2018-07-11 Asana BioSciences, LLC Pyrimido-pyridazinone compounds and use thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004056825A1 (en) * 2002-12-23 2004-07-08 Syngenta Limited Pyridodiazines as plant fungicides
US7410967B2 (en) 2002-12-23 2008-08-12 Syngenta Crop Protection, Inc. Pyridodiazines as plant fungicides

Also Published As

Publication number Publication date
FR2184763A1 (en) 1973-12-28
DE2322073A1 (en) 1973-11-22
CA1004223A (en) 1977-01-25
FR2184763B1 (en) 1976-04-09
JPS4948695A (en) 1974-05-11

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Legal Events

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