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US4434161A Expired / Lapsed US ⏱️ 0.0 years remaining

Sulfur and silicon-containing fatty acid amides

Assignee: Sandoz Inc
•
Filing: 1982-09-29
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Granted: 1984-02-28
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Expires: 2002-09-29
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Abstract

Abstract Sulfur and silicon-containing amides, e.g. N-5-sila-3-thia-5,5-dimethyl-pentadecanoyl-1-phenyl-2-(4-methylphenyl) -ethylamine, are useful as anti-atherosclerotic agents. The amides are obtainable by acylation of a primary amine (the substituents on the amine being of the aralkyl phenyl, tryptophanyl, benzocycloalkyl-type) with a corresponding sulfur and silicon-containing carboxylic acid (or active form thereof).

Inventors

  • 👤 Sandor Barcza

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 10:23
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/081; C07F7/0812

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 619 words
A compound of the formula: ##STR17## wherein each of R 1 , R 2 and R 3 is, independently, alkyl having from 1 to 22 carbon atoms, alkenyl having from 2 to 22 carbon atoms, cycloalkyl having from 3 to 20 ring carbon atoms, aryl having from 6 to 14 aromatic ring carbon atoms, or aralkyl having from 6 to 14 aromatic ring carbon atoms and from 1 to 4 carbon atoms in the alkylene portion thereof; or R 2 and R 3 may be joined to form together with the silicon atom a saturated sila-hydrocarbyl ring having from 4 to 20 ring members, provided that the total number of carbon atoms in R 1 +R 2 +R 3 , other than aromatic ring carbon atoms or substituents thereon, is not more than 35, each of R 4 and R 5 is, independently, an alkylene chain having from 1 to 6 carbon atoms, or a cycloalkylene radical having from 3 to 6 ring carbon atoms; said cycloalkyl and cycloalkylene radicals may bear from 1 to 4 lower alkyl groups having from 1 to 6 carbon atoms; said aryl radicals, or portions thereof, may bear 1 or 2 halo substituents, each having an atomic weight of from about 19 to 80, or from 1 to 3 lower alkyl or alkoxy radicals each having from 1 to 6 carbon atoms; and R is of type (a) an aralkyl-type radical of the structure ##STR18## wherein g is 0, 1 or 2; R a is a hydrogen atom, halo having an atomic weight of from about 19 to 127, alkoxy having from 1 to 4 carbon atoms, or alkyl having from 1 to 4 carbon atoms, or trifluoromethyl; R b 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 c is subtype (i) a hydrogen atom; subtype (ii) a radical of the structure ##STR19## in which p is 0, 1 or 2, and y is a hydrogen atom, halo having an atomic weight of from about 19 to 127, alkoxy having from 1 to 4 carbon atoms, or alkyl having from 1 to 4 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 subtype (iii) alkyl having from 1 to 8 carbon atoms; or R is of type (b) a phenyl-type radical of the structure ##STR20## in which R b is as defined above, and R o is a hydrogen atom, halo having an atomic weight of from about 19 to 127, alkoxy having from 1 to 4 carbon atoms, or alkyl having from 1 to 4 carbon atoms; or R o is a radical of the structure R f : ##STR21## in which D is --CH 2 -- or --O--; f is 0 or 1; and W 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 of type (c) an indolyl radical of the structure: ##STR22## wherein R b is as defined above; R 6 is alkyl having from 1 to 8 carbon atoms or benzyl; and R 7 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms or benzyl; or R is (d) a benzocycloalkyl nucleus of the structure: ##STR23## wherein y and y' are as defined above; and j is a whole integer of from 1 to 4.
Claim 2
Dependent Claim 619 words
A compound of the formula: ##STR17## wherein each of R 1 , R 2 and R 3 is, independently, alkyl having from 1 to 22 carbon atoms, alkenyl having from 2 to 22 carbon atoms, cycloalkyl having from 3 to 20 ring carbon atoms, aryl having from 6 to 14 aromatic ring carbon atoms, or aralkyl having from 6 to 14 aromatic ring carbon atoms and from 1 to 4 carbon atoms in the alkylene portion thereof; or R 2 and R 3 may be joined to form together with the silicon atom a saturated sila-hydrocarbyl ring having from 4 to 20 ring members, provided that the total number of carbon atoms in R 1 +R 2 +R 3 , other than aromatic ring carbon atoms or substituents thereon, is not more than 35, each of R 4 and R 5 is, independently, an alkylene chain having from 1 to 6 carbon atoms, or a cycloalkylene radical having from 3 to 6 ring carbon atoms; said cycloalkyl and cycloalkylene radicals may bear from 1 to 4 lower alkyl groups having from 1 to 6 carbon atoms; said aryl radicals, or portions thereof, may bear 1 or 2 halo substituents, each having an atomic weight of from about 19 to 80, or from 1 to 3 lower alkyl or alkoxy radicals each having from 1 to 6 carbon atoms; and R is of type (a) an aralkyl-type radical of the structure ##STR18## wherein g is 0, 1 or 2; R a is a hydrogen atom, halo having an atomic weight of from about 19 to 127, alkoxy having from 1 to 4 carbon atoms, or alkyl having from 1 to 4 carbon atoms, or trifluoromethyl; R b 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 c is subtype (i) a hydrogen atom; subtype (ii) a radical of the structure ##STR19## in which p is 0, 1 or 2, and y is a hydrogen atom, halo having an atomic weight of from about 19 to 127, alkoxy having from 1 to 4 carbon atoms, or alkyl having from 1 to 4 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 subtype (iii) alkyl having from 1 to 8 carbon atoms; or R is of type (b) a phenyl-type radical of the structure ##STR20## in which R b is as defined above, and R o is a hydrogen atom, halo having an atomic weight of from about 19 to 127, alkoxy having from 1 to 4 carbon atoms, or alkyl having from 1 to 4 carbon atoms; or R o is a radical of the structure R f : ##STR21## in which D is --CH 2 -- or --O--; f is 0 or 1; and W 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 of type (c) an indolyl radical of the structure: ##STR22## wherein R b is as defined above; R 6 is alkyl having from 1 to 8 carbon atoms or benzyl; and R 7 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms or benzyl; or R is (d) a benzocycloalkyl nucleus of the structure: ##STR23## wherein y and y' are as defined above; and j is a whole integer of from 1 to 4.
Claim 3
Dependent Claim 12 words
A compound of claim 1 in which R is of type (a)
Claim 4
Dependent Claim 12 words
A compound of claim 1 in which R is of type (b)
Claim 5
Dependent Claim 12 words
A compound of claim 1 in which R is of type (c)
Claim 6
Dependent Claim 12 words
A compound of claim 1 in which R is of type (d)
Claim 7
Dependent Claim 22 words
A compound of claim 1 in which R 2 and R 3 are lower alkyl having from 1 to 4 carbon atoms.
Claim 8
Dependent Claim 15 words
A compound of claim 6 in which R 2 and R 3 are the same.
Claim 9
Dependent Claim 14 words
A compound of claim 7 in which R 2 and R 3 are methyl.
Claim 10
Dependent Claim 16 words
A compound of claim 1 in which each of R 4 and R 5 is methylene.
Claim 11
Dependent Claim 8 words
The compound of claim 1 which is N-5-sila-3-thia-5,5-dimethyl-pentadecanoyl-1-phenyl-2-(4-methylphenyl)-ethylamine.
Claim 12
Dependent Claim 36 words
A method of inhibiting the accumulation of cholesterol ester in an arterial wall of a mammal in need of such treatment, comprising administering a cholesterol ester-inhibiting amount of a compound of claim 1 to said mammal.
Claim 13
Dependent Claim 33 words
A pharmaceutical composition suitable for inhibiting the accumulation of cholesterol ester in arterial wall of a mammal comprising a cholesterol ester-inhibiting-effective amount of a compound of claim 1 and a non-toxic pharmaceutically-acceptable carrier.
Claim 14
Dependent Claim 8 words
A composition of claim 12 in solid form.
Claim 15
Dependent Claim 21 words
A composition of claim 12, in which the compound is present in an amount of from about 250 to 7,500 milligrams.
Claim 16
Dependent Claim 21 words
A method of claim 11 in which the daily dose of the compound is from about 500 mg to 15,000 mg.

References Cited (Backward Citations)

US3660454A Cited
US3812164A Cited
US4328216A Cited
US4297349A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-02-27 1987-08-29 1988-02-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-02-27 1991-08-29 1992-02-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-02-27 1995-08-29 1996-02-28 $7700.00 Window Closed / Lapsed

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