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US4434161A
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Sulfur and silicon-containing fatty acid amides
Assignee: Sandoz Inc
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Filing: 1982-09-29
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Granted: 1984-02-28
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Expires: 2002-09-29
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 17:28
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)
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 |