GB1351522A - 4,7-dihydro-4-oxo-1h-pyrazolo 3,4-b-pyridine-5-carboxylic acids and esters thereof - Google Patents

4,7-dihydro-4-oxo-1h-pyrazolo 3,4-b-pyridine-5-carboxylic acids and esters thereof

Info

Publication number
GB1351522A
GB1351522A GB1376771A GB1376771A GB1351522A GB 1351522 A GB1351522 A GB 1351522A GB 1376771 A GB1376771 A GB 1376771A GB 1376771 A GB1376771 A GB 1376771A GB 1351522 A GB1351522 A GB 1351522A
Authority
GB
United Kingdom
Prior art keywords
ethyl
pyrazolo
pyridine
alkyl
methyl
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
GB1376771A
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 GB1351522A publication Critical patent/GB1351522A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/38—Nitrogen atoms
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1351522 4,7-Dihydro-4-oxo-1H-pyrazolo- [3,4-b] pyridine-5-carboxylic acids and esters thereof E R SQUIBB & SONS Inc 7 May 1971 [28 May 1970] 13767/71 Heading C2C Novel compounds of the formula wherein R 1 is C 1-7 alkyl, phenyl or phenyl-C 1-7 alkylene; R 2 and R 3 each is hydrogen or C 1-7 alkyl and R 4 is C 1-7 alkyl may be prepared by alkylating a compound II in salt form, in an inert organic solvent, adding water to the salt of the enol form of compound I to produce an esterified compound I and optionally hydrolysing the ester group. The intermediate ethyl 1-ethyl-4-hydroxy-3- methyl - 1H - pyrazolo - [3,4 - d]pyridine - 5- carboxylate may be prepared by cyclizing diethyl {[(1 - ethyl - 3 - methyl - 5 - pyrazolyl)amino]- methylene}malonate which is in turn prepared by condensing 1-ethyl-3-methyl-5-amino pyrazole with ethoxymethylene malonic acid diethyl ester. Pharmaceutical compositions of the compounds I show hypoglycemic and anti-inflammatory activity when administered orally, parenterally or topically with the usual excipients.
GB1376771A 1970-05-28 1971-05-07 4,7-dihydro-4-oxo-1h-pyrazolo 3,4-b-pyridine-5-carboxylic acids and esters thereof Expired GB1351522A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US4165270A 1970-05-28 1970-05-28

Publications (1)

Publication Number Publication Date
GB1351522A true GB1351522A (en) 1974-05-01

Family

ID=21917637

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1376771A Expired GB1351522A (en) 1970-05-28 1971-05-07 4,7-dihydro-4-oxo-1h-pyrazolo 3,4-b-pyridine-5-carboxylic acids and esters thereof

Country Status (6)

Country Link
CA (1) CA944352A (en)
CH (1) CH528528A (en)
DE (1) DE2125631A1 (en)
FR (1) FR2100699B1 (en)
GB (1) GB1351522A (en)
HU (1) HU162493B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4622326A (en) * 1985-12-23 1986-11-11 Hoechst-Roussel Pharmaceuticals Inc. 6H-isoxazolo(5,4-d)pyrazolo(3,4-b)pyridines, and their use as antihypertensive and analgesic agents

Also Published As

Publication number Publication date
CH528528A (en) 1972-09-30
FR2100699A1 (en) 1972-03-24
DE2125631A1 (en) 1971-12-09
HU162493B (en) 1973-02-28
FR2100699B1 (en) 1974-11-15
CA944352A (en) 1974-03-26

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees