Claims
- 1. A compound of the formula: ##STR20## wherein A is an unsaturated fatty acid hydrocarbon chain of 7 to 23 carbon atoms in which each unsaturated ethylene moiety of the formula:
- --CH.dbd.CH--
- is replaced by a cyclopropanyl group of the formula ##STR21## said A having 1 to 4 such cyclopropanyl groups; and R is: (a) an aralkyl radical of the structure ##STR22## 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) ##STR23## 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) ##STR24## 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 ##STR25## 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 : ##STR26## 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) a benzocycloalkyl nucleus of the structure: ##STR27## wherein R.sup.1 and R.sup.2 are as defined above; and j is a whole integer of from 1 to 4.
- 2. A compound of claim 1 in which R is a type (a).
- 3. A compound of claim 1 in which R is of type (b).
- 4. A compound of claim 1 in which R is of type (c).
- 5. A compound of claim 2 in which g is 0.
- 6. A compound of claim 2 in which g is 1.
- 7. A compound of claim 2 in which R.sup.3 is of type (iii).
- 8. A compound of claim 3 in which R.sup.0 is a radical of the structure ##STR28## in which B, f and Q are as defined.
- 9. A compound of claim 1 wherein A is a cyclopropanyl-bearing hydrocarbon radical of the formula: ##STR29## wherein n is a whole integer of from 1 to 15; m is 1 or 2; and p is a whole integer of from 1 to 13, provided that when m is 1, then n+p is from 3 to 19, and when m is 2 then n+p is from 2 to 16.
- 10. A compound of claim 10 in which the hydrogen atoms of each propanyl group are in the cis configuration.
- 11. A compound of claim 9 in which m is 1.
- 12. A compound of claim 11 in which the total of n+p is an odd number.
- 13. A compound of claim 9 in which m is 2.
- 14. A compound of claim 13 in which the total of n+p is an even number.
- 15. A compound of claim 13 in which n is 4 and p is 6.
- 16. The compound of claim 15 which is (d (+) )-N-(.alpha.-methylbenzyl)-cis,cis-2-[2-pentylcyclopropyl)-methyl]cyclopropanoctanamide.
- 17. A compound of claim 11 in which n is 7 and p is 6.
- 18. The compound of claim 17 which is N-(.alpha.-methylbenzyl)-(cis)-2-octyl-cyclopropanoctanamide.
- 19. The compound of claim 17 which is N-[.alpha.-(p-methylbenzyl)-p-methyl-phenylethyl]-cis-2-octyl-cyclopropanoctanamide.
- 20. A compound of claim 17 which is N-[1-(benzyl)-2-(phenyl)ethyl]-cis-2-octyl-cyclopropanoctanamide.
- 21. The compound of claim 17 which is (d (+))-N-(.alpha.-methylbenzyl)-cis-2-octyl-cyclopropanoctanamide.
- 22. A pharmaceutical composition suitable for reducing the cholesterol ester content of an arterial wall of a mammal comprising a cholesterol ester-reducing effective amount of a compound of the formula: ##STR30## wherein A is an unsaturated fatty acid hydrocarbon chain of 7 to 23 carbon atoms in which each unsaturated ethylene moiety of the formula:
- --CH.dbd.CH--
- is replaced by a cyclopropanyl group of the formula ##STR31## said A having 1 to 4 such cyclopropanyl groups; and R is:
- (a) an aralkyl radical of the structure ##STR32## 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) ##STR33## 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) ##STR34## 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 ##STR35## 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 : ##STR36## 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) a benzocycloalkyl nucleus of the structure: ##STR37## wherein R.sup.1 and R.sup.2 are as defined above; and j is a whole integer of from 1 to 4;
- and a non-toxic pharmaceutically-acceptable carrier.
- 23. A composition of claim 22 in solid form.
- 24. A composition of claim 22, in which the compound is present in an amount of from about 25 to 2,500 milligrams.
- 25. A composition of claim 24 in which the compound is N-(.alpha.-methylbenzyl)-cis-2-octyl-cyclopropanoctanamide.
- 26. A composition of claim 24 in which the compound is N-[.alpha.-(p-methylbenzyl)-p-methyl-phenylethyl]-cis-2-octylcyclopropanoctanamide.
- 27. A composition of claim 24 in which the compound is N-[1-(benzyl)-2-(phenyl)ethyl]-cis-2-octyl-cyclopropanoctanamide.
- 28. A composition of claim 22 in which A of the compound is a cyclopropanyl-bearing hydrocarbon radical of the formula: ##STR38## wherein n is a whole integer of from 1 to 15; m is 1 or 2; and p is a whole integer of from 1 to 13, provided that when m is 1, then n+p is from 3 to 19, and when m is 2 then n+p is from 2 to 16.
- 29. 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 of the formula: ##STR39## wherein A is an unsaturated fatty acid hydrocarbon chain of 7 to 23 carbon atoms in which each unsaturated ethylene moiety of the formula:
- --CH.dbd.CH--
- is replaced by a cyclopropanyl group of the formula ##STR40## said A having 1 to 4 such cyclopropanyl groups; and R is:
- (a) an aralkyl radical of the structure ##STR41## 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) ##STR42## 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, an 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) ##STR43## 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 ##STR44## 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 : ##STR45## 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) a benzocycloalkyl nucleus of the structure: ##STR46## wherein R.sup.1 and R.sup.2 are as defined above; and j is a whole integer of from 1 to 4.
- 30. A method of claim 29 in which the compound is N-(.alpha.-methylbenzyl)-cis-2-octyl-cyclopropanoctanamide.
- 31. A method of claim 29 in which the compound is N-[.alpha.-(p-methylbenzyl)-p-methyl-phenylethyl]-cis-2-octylcyclopropanoctanamide.
- 32. A method of claim 29 in which the compound is N-[1-(benzyl)-2-(phenyl)ethyl]-cis-2-octyl-cyclopropanoctanamide.
- 33. A method of claim 29 in which A of the compound is a cyclopropanyl-bearing hydrocarbon radical of the formula: ##STR47## wherein n is a whole integer of from 1 to 15; m is 1 or 2; and p is a whole integer of from 1 to 13, provided that when m is 1, then n+p is from 3 to 19, and when m is 2 then n+p is from 2 to 16.
Priority Claims (1)
Number |
Date |
Country |
Kind |
2856856 |
Dec 1978 |
DEX |
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Parent Case Info
This is a continuation-in-part of copending application Ser. No. 872,836 filed Jan. 27, 1978, now abandoned.
US Referenced Citations (4)
Non-Patent Literature Citations (1)
Entry |
Fieser & Fieser, Advanced Organic Chem. (1961) p. 549. |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
872836 |
Jan 1978 |
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