IE36016B1 - Nicotinic acid derivatives - Google Patents

Nicotinic acid derivatives

Info

Publication number
IE36016B1
IE36016B1 IE1468/71A IE146871A IE36016B1 IE 36016 B1 IE36016 B1 IE 36016B1 IE 1468/71 A IE1468/71 A IE 1468/71A IE 146871 A IE146871 A IE 146871A IE 36016 B1 IE36016 B1 IE 36016B1
Authority
IE
Ireland
Prior art keywords
hydroxy
nicotinic acid
acid
alkyl
give
Prior art date
Application number
IE1468/71A
Other versions
IE36016L (en
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of IE36016L publication Critical patent/IE36016L/en
Publication of IE36016B1 publication Critical patent/IE36016B1/en

Links

Classifications

    • 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
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1317239 2-Hydroxy-nicotinic acids F HOFFMANN-LA ROCHE & CO AG 23 Nov 1971 [23 Nov 1970 (2)] 54366/71 Heading C2C Novel 2-hydroxy-nicotinic acids of the general formula wherein R is a halogen atom in the 5- or 6- position, an amino group in the 4-position or a C 1-4 alkyl group in the 4- or 5-position, and base addition salts thereof are prepared (a) by base hydrolysis of a 2,6-dihalo-nicotinic acid at reflux temperature and acidification of the hydrolysis mixture to give a 6-halo-2-hydroxy-nicotinic acid, (b) by hydrogenation of 2-hydroxy-4- nitro-nicotinic acid-N-oxide to give 4-amino-2- hydroxy-nicotinic acid, (c) by reaction of 4- chloro-2-hydroxy-nicotinic acid with ammonia to give the product of (b), (d) by treatment of 4-chloro-2-hydroxy-nicotinic acid with a C 1-4 alkyl lithium or C 1-4 alkyl magnesium bromide to give a 2-hydroxy-4-C 1-4 alkyl-nicotinic acid, (e) by treatment of a 2-amino-4-C 1-4 alkylnicotinic acid with sodium nitrite and sulphuric acid to give a 2-hydroxy-4-C 1-4 alkyl-nicotinic acid, (f) by treatment of a 2-hydroxy-3-bromo- 5-C 1-4 alkyl-pyridine in an inert solvent with n-butyl lithium and carbon dioxide to give a 2 - hydroxy - 5 - C 1-4 alkyl - nicotinic acid, (g) by acid hydrolysis of a 2-hydroxy-3-cyano-5- C 1-4 alkyl-pyridine to give a 2-hydroxy-5-C 1-4 alkyl-nicotinic acid and (h) by treatment of 2- hydroxy-5-amino-nicotinic acid with sodium nitrite and hydrochloric acid/cuprous chloride or hydrobromic acid/cuprous bromide to give 5 - chloro- or bromo - 2 - hydroxy - nicotinic acid, followed optionally by salification of the product. 2 - Hydroxy - 3 - cyano - 5 - methyl - pyridine is prepared by reaction of 2-amino-3-bromo-5- 5-methyl-pyridine with cuprous cyanide and treatment of the resulting 2-amino-3-cyano-5- methyl-pyridine with sodium nitrite and sulphuric acid. 2 - Amino - 4 - methyl - nicotinic acid is prepared by reaction of 4-methylquinolinic acid with ammonia and reaction of the resulting 3 - carboxy - 4 - methyl - pyridine-2- carboxylic acid amide with aqueous sodium hydroxide and bromine, followed by sulphur dioxide. Pharmaceutical compositions having hypolipidemic activity comprise, as active ingredient, a 2-hydroxy-nicotinic acid of the above general formula or a pharmaceutically acceptable base addition salt thereof, in association with a compatible pharmaceutical carrier. [GB1317239A]
IE1468/71A 1970-11-23 1971-11-19 Nicotinic acid derivatives IE36016B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US9229670A 1970-11-23 1970-11-23
US9213770A 1970-11-23 1970-11-23

Publications (2)

Publication Number Publication Date
IE36016L IE36016L (en) 1972-05-23
IE36016B1 true IE36016B1 (en) 1976-07-21

Family

ID=26785310

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1468/71A IE36016B1 (en) 1970-11-23 1971-11-19 Nicotinic acid derivatives

Country Status (12)

Country Link
AR (1) AR192334A1 (en)
BE (1) BE775641A (en)
CH (1) CH558798A (en)
DE (1) DE2157334A1 (en)
ES (1) ES397243A1 (en)
FR (1) FR2115357B1 (en)
GB (1) GB1317239A (en)
HU (1) HU163713B (en)
IE (1) IE36016B1 (en)
IL (1) IL38089A (en)
NL (1) NL7115903A (en)
NO (1) NO133894C (en)

Also Published As

Publication number Publication date
NO133894C (en) 1976-07-14
IE36016L (en) 1972-05-23
ES397243A1 (en) 1975-04-16
DE2157334A1 (en) 1972-05-31
IL38089A (en) 1975-08-31
AU3556471A (en) 1973-05-17
AR192334A1 (en) 1973-02-14
IL38089A0 (en) 1972-01-27
BE775641A (en) 1972-05-23
FR2115357A1 (en) 1972-07-07
HU163713B (en) 1973-10-27
CH558798A (en) 1975-02-14
GB1317239A (en) 1973-05-16
NL7115903A (en) 1972-05-25
NO133894B (en) 1976-04-05
FR2115357B1 (en) 1974-10-18

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