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US4297349A Expired / Lapsed US ⏱️ 0.0 years remaining

Silicon-bearing carboxylic acids and amides

Assignee: Sandoz Inc
•
Filing: 1980-04-15
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Granted: 1981-10-27
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Expires: 2000-04-15
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Abstract

Abstract The final products are compounds of the formula <IMAGE> wherein (a) each of R1, R2 and R3 alkyl having from 1 to 22 carbon atoms; or (b) one or more is a phenyl or alkylphenyl type, n is from 3 to 20; and R is of an aralkyl-, phenyl-tryptophanyl- or benzocycloalkyl-type, eg D,L-5,5-dimethyl-5-sila-pentadecanoyl-1'-phenyl-2'-p-tolyl-ethylamide, are useful as antiatherosclerotic agents, and are prepared from corresponding carboxylic acids (or their derivatives).

Inventors

  • 👤 Sandor Barcza

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 23:17
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/081; C07F7/0812; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/10; C07D209/18; C07D209/20; C07F3/00; C07F3/02

Claims Analysis

Total Claims: 23
Claim 1
Independent Claim 532 words
A compound of the formula: ##STR27## wherein n is a whole integer of from 3 to 20, each of R 1 , R 2 and R 3 is, independently, either (a) alkyl having from 1 to 22 carbon atoms; or (b) a radical of the formula ##STR28## in which m is 0, 1 or 2, and each of R' and R" is, independently, 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 127; provided that the sum of n and the number of carbon atoms in any one of R 1 , R 2 or R 3 is not greater than 34 when any of R 1 , R 2 or R 3 is of type (a); and R is of type (a) an aralkyl-type radical of the structure: ##STR29## 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 ##STR30## 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 ##STR31## 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, ie. 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 : ##STR32## 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: ##STR33## wherein R b is as defined above; R 4 is alkyl having from 1 to 8 carbon atoms or benzyl (unsubstituted); and R 5 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms or benzyl (unsubstituted); or R is (d) a benzocycloalkyl radical of the structure: ##STR34## wherein y and y' are as defined above; and j is a whole integer of from 1 to 4.
Claim 2
Dependent Claim 532 words
A compound of the formula: ##STR27## wherein n is a whole integer of from 3 to 20, each of R 1 , R 2 and R 3 is, independently, either (a) alkyl having from 1 to 22 carbon atoms; or (b) a radical of the formula ##STR28## in which m is 0, 1 or 2, and each of R' and R" is, independently, 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 127; provided that the sum of n and the number of carbon atoms in any one of R 1 , R 2 or R 3 is not greater than 34 when any of R 1 , R 2 or R 3 is of type (a); and R is of type (a) an aralkyl-type radical of the structure: ##STR29## 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 ##STR30## 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 ##STR31## 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, ie. 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 : ##STR32## 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: ##STR33## wherein R b is as defined above; R 4 is alkyl having from 1 to 8 carbon atoms or benzyl (unsubstituted); and R 5 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms or benzyl (unsubstituted); or R is (d) a benzocycloalkyl radical of the structure: ##STR34## wherein y and y' are as defined above; and j is a whole integer of from 1 to 4.
Claim 3
Dependent Claim 21 words
A compound of claim 1, in which each of R 1 , R 2 and R 3 is of type (a).
Claim 4
Dependent Claim 22 words
A compound of claim 1, in which any of R 1 , R 2 , and R 3 is of type (b).
Claim 5
Dependent Claim 12 words
A compound of claim 1 in which R is of type (a).
Claim 6
Dependent Claim 12 words
A compound of claim 1 in which R is of type (b).
Claim 7
Dependent Claim 12 words
A compound of claim 1 in which R is of type (c).
Claim 8
Dependent Claim 12 words
A compound of claim 1 in which R is of type (d).
Claim 9
Dependent Claim 15 words
A compound of claim 1 in which R 1 and R 2 are both methyl.
Claim 10
Dependent Claim 8 words
The compound of claim 1 which is D,L-5,5-dimethyl-5-sila-pentadecanoyl-1'-phenyl-2'-tolyl-ethylamide.
Claim 11
Dependent Claim 8 words
The compound of claim 1 which is 6,6-dimethyl-6-sila-n-hexadecanoyl-1'-benzyl-2'-phenyl-ethylamide.
Claim 12
Dependent Claim 8 words
The compound of claim 1 which is D,L-6,6-dimethyl-6-sila-n-hexadecanoyl-1'-phenyl-2'-p-tolyl-ethylamide.
Claim 13
Dependent Claim 9 words
The compound of claim 1 which is 5,5-dimethyl-5-sila-n-pentadecanoyl-1'-benzyl-2'-phenyl ethylamide.
Claim 14
Dependent Claim 36 words
A method of reducing the cholesterol ester content of an arterial wall, in a mammal in need of such treatment, comprising administering a total cholesterol ester-reducing amount of a compound of claim 1 to said mammal.
Claim 15
Dependent Claim 34 words
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 claim 1 and a non-toxic pharmaceutically-acceptable carrier.
Claim 16
Dependent Claim 23 words
A method of claim 13 in which the compound is present in an amount of from about 10 milligrams to about 5,000 milligrams.
Claim 17
Dependent Claim 23 words
A method of claim 13 in which the compound is present in an amount of from about 10 milligrams to about 2,000 milligrams.
Claim 18
Dependent Claim 11 words
A method of claim 13 in which the compound is D,L-5,5-dimethyl-5-sila-n-pentadecanoyl-1'-phenyl-2'-p-tolyl-ethylyamide.
Claim 19
Dependent Claim 23 words
A composition of claim 9 in which the compound is present in an amount of from about 2.5 milligrams to about 2,500 milligrams.
Claim 20
Dependent Claim 9 words
A composition of claim 14 in a solid form.
Claim 21
Dependent Claim 11 words
A composition of claim 14 in which the carrier is solid.
Claim 22
Dependent Claim 11 words
A composition of claim 14 in which the carrier is liquid.
Claim 23
Dependent Claim 11 words
A composition of claim 14 in which the compound is D,L-5,5-dimethyl-5-sila-n-pentadecanoyl-1'-phenyl-2'-p-tolyl-ethylamide.

References Cited (Backward Citations)

US2610199A Cited
US2629727A Cited
US2894967A Cited
US2973383A Cited
US3068152A Cited
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US3529007A Cited
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GB2012261A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-10-26 1985-04-27 1985-10-27 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-10-26 1989-04-27 1989-10-27 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-10-26 1993-04-27 1993-10-27 $7700.00 Window Closed / Lapsed

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