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US 4,229,463 AGranted
Unsaturated fatty acid hydrazides
AssigneeSandoz Ltd.
InventorFaizulla G. Kathawala
Life of this patent
Estimating the term…
Abstract
Mono- or poly-unsaturated fatty acid hydrazides, e.g. cis,-9-octadecenoic acid, 2-(o-methylphenyl)-hydrazide are useful as pharmaceutical agents and are obtainable by reacting a derivative, e.g. mixed anhydride, of a long chain unsaturated carboxylic acid with an appropriate hydrazine compound.
Claims29
A compound which is a hydrazide of the formula:
- ##STR15## wherein A is the residue of an unsaturated fatty acid minus the carboxylic function and has from 7 to 23 carbon atoms and has from 1 to 4 ethylenically unsaturated positions;
- and
- R is:
- (a) an aralkyl radical of the structure ##STR16## wherein g is 0 or 1;
- wherein
- R.sup.1 is a hydrogen atom, halo having an atomic weight of from about 19 to 80, alkoxy having from 1 to 3 carbon atoms;
- or alkyl having from 1 to 3 carbon atoms;
- R.sup.2 is a hydrogen atom, alkyl having from 1 to 3 carbon atoms, alkoxy having from 1 to 3 carbon atoms, or halo having an atomic weight of from about 19 to 36;
- and
- R.sup.3 is a benzyl radical of the formula (iii) ##STR17## wherein y is a hydrogen atom, halo having an atomic weight of from about 19 to 80, alkoxy having from 1 to 3 carbon atoms, or alkyl having from 1 to 3 carbon atoms;
- and
- y' is a hydrogen atom, alkoxy having from 1 to 3 carbon atoms, alkyl having from 1 to 3 carbon atoms, or halo having an atomic weight of from about 19 to 36;
- or R is:
- (b) a phenyl radical of the structure ##STR18## wherein R.sup.2 is as defined above, and
- R.sup.0 is a hydrogen atom, halo having an atomic weight of from about 19 to 80, alkyl having from 1 to 3 carbon atoms;
- alkoxy having from 1 to 3 carbon atoms;
- or a radical of the structure R.sup.f :
- ##STR19## in which B is --CH.sub.2 -- or --O--;
- f is 0 or 1;
- and
- Q is a hydrogen atom, halo having an atomic weight of from about 19 to 80, alkoxy having from 1 to 3 carbon atoms, or alkyl having from 1 to 3 carbon atoms;
- or R is:
- (c) an indolyl radical of the structure:
- ##STR20## wherein R.sup.1 is as defined above, and
- R.sup.5 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms or benzyl (unsubstituted);
- or R is (d) a benzocycloalkyl nucleus of the structure:
- ##STR21## wherein R.sup.1 and R.sup.2 are as defined above;
- and
- j is a whole integer of from 1 to 4;
- or a non-toxic pharmaceutically acceptable acid addition salt thereof.
27 more elements
A method of reducing the cholesterol ester content of an arterial wall in a mammal in need of such treatment, comprising administering to said mammal a cholesterol ester-reducing amount of a compound which is a hydrazide of the formula:
- ##STR23## wherein A is the residue of an unsaturated fatty acid minus the carboxylic function and has from 7 to 23 carbon atoms and has from 1 to 4 ethylenically unsaturated positions;
- and
- R is:
- (a) an aralkyl radical of the structure ##STR24## wherein g is 0 or 1;
- wherein
- R.sup.1 is a hydrogen atom, halo having an atomic weight of from about 19 to 80, alkoxy having from 1 to 3 carbon atoms;
- or alkyl having from 1 to 3 carbon atoms;
- R.sup.2 is a hydrogen atom, alkyl having from 1 to 3 carbon atoms, alkoxy having from 1 to 3 carbon atoms, or halo having an atomic weight of from about 19 to 36;
- and
- R.sup.3 is (i) a hydrogen atom, a phenyl radical of the structure ii):
- ##STR25## wherein y is a hydrogen atom, halo having an atomic weight of from about 19 to 80, alkoxy having from 1 to 3 carbon atoms, or alkyl having from 1 to 3 carbon atoms;
- and
- y' is a hydrogen atom, alkoxy having from 1 to 3 carbon atoms, alkyl having from 1 to 3 carbon atoms, or halo having an atomic weight of from about 19 to 36;
- or
- a benzyl radical of the formula (iii) ##STR26## wherein y and y' are as defined above;
- or iv) alkyl having from 1 to 8 carbon atoms;
- or R is:
- (b) a phenyl radical of the structure ##STR27## wherein R.sup.2 is as defined above, and
- R.sup.0 is a hydrogen atom, halo having an atomic weight of from about 19 to 80, alkyl having from 1 to 3 carbon atoms;
- alkoxy having from 1 to 3 carbon atoms;
- or a radical of the structure R.sup.f :
- ##STR28## in which B is --CH.sub.2 -- or --O--;
- f is 0 or 1;
- and
- Q is a hydrogen atom, halo having an atomic weight of from about 19 to 80, alkoxy having from 1 to 3 carbon atoms, or alkyl having from 1 to 3 carbon atoms;
- or R is:
- (c) an indolyl radical of the structure:
- ##STR29## wherein R.sup.1 is as defined above, and
- R.sup.5 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms or benzyl (unsubstituted);
- or
- R is (d) a benzocycloalkyl nucleus of the structure:
- ##STR30## wherein R.sup.1 and R.sup.2 are as defined above;
- and
- j is a whole integer of from 1 to 4;
- or a non-toxic pharmaceutically acceptable acid addition salt thereof.
32 more elements
Dependencies are inferred from the claim text.