US4420475A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Silicon-bearing amides
Assignee: Sandoz Inc
•
Filing: 1980-12-11
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Granted: 1983-12-13
•
Expires: 2000-12-11
Abstract
Abstract Compounds of the formula I: <IMAGE> (I) wherein each of R1, R2 and R3 is, independently, (a) alkyl having from 1 to 22 carbon atoms; or (b) of the formula <IMAGE> in which m is 0, 1 or 2, and each 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; and R is of an aralkyl-, phenyl- tryptophanyl- or benzo-cycloalkyl-type, are obtained by hydrogenating corresponding alpha - beta ethylenically-unsaturated analogs (II), which in turn are obtained by hydrogenating corresponding alpha - beta acetylenically-unsaturated analogs. Compounds I and II are useful as anti-atheroslerotic agents.
Inventors
- 👤 II Robert E. Damon
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 17:29
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: 36
Claim 1
Independent Claim
377 words
A compound of the formula: ##STR33## wherein each of R 1 , R 2 and R 3 is, independently, alkyl having from 1 to 22 carbon atoms; or a radical of the formula ##STR34## 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; and R is a an aralkyl-type radical of the formula (a), (c) or (d) (a) ##STR35## 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 (ii) ##STR36## 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 (c) ##STR37## wherein R b is as defined above; R 4 is hydrogen; an equivalent of a cation which results in the formation of a salt which is pharmaceutically acceptable; alkyl having from 1 to 8 carbon atoms; or benzyl; R 5 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms or benzyl; or (d) ##STR38## wherein y and y' are as defined above; and j is a whole integer of from 1 to 4; providing that at least one of R 1 , R 2 and R 3 is of the formula ##STR39##
Claim 2
Dependent Claim
377 words
A compound of the formula: ##STR33## wherein each of R 1 , R 2 and R 3 is, independently, alkyl having from 1 to 22 carbon atoms; or a radical of the formula ##STR34## 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; and R is a an aralkyl-type radical of the formula (a), (c) or (d) (a) ##STR35## 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 (ii) ##STR36## 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 (c) ##STR37## wherein R b is as defined above; R 4 is hydrogen; an equivalent of a cation which results in the formation of a salt which is pharmaceutically acceptable; alkyl having from 1 to 8 carbon atoms; or benzyl; R 5 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms or benzyl; or (d) ##STR38## wherein y and y' are as defined above; and j is a whole integer of from 1 to 4; providing that at least one of R 1 , R 2 and R 3 is of the formula ##STR39##
Claim 3
Dependent Claim
463 words
A compound of the formula: ##STR40## wherein each of R 1 , R 2 and R 3 is, independently alkyl having from 1 to 22 carbon atoms; or a radical of the formula ##STR41## 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; and R is a radical of the formula (a), (b), (c) or (d) (a) ##STR42## 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 (ii) ##STR43## 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; (b) ##STR44## 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 : ##STR45## 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 (c) ##STR46## wherein R b is as defined above; R 4 is hydrogen; an equivalent of a cation which results in the formation of a salt which is pharmaceutically acceptable; alkyl having from 1 to 8 carbon atoms; or benzyl; R 5 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms or benzyl; or (d) ##STR47## wherein y and y' are as defined above; and j is a whole integer of from 1 to 4.
Claim 4
Dependent Claim
463 words
A compound of the formula: ##STR40## wherein each of R 1 , R 2 and R 3 is, independently alkyl having from 1 to 22 carbon atoms; or a radical of the formula ##STR41## 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; and R is a radical of the formula (a), (b), (c) or (d) (a) ##STR42## 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 (ii) ##STR43## 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; (b) ##STR44## 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 : ##STR45## 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 (c) ##STR46## wherein R b is as defined above; R 4 is hydrogen; an equivalent of a cation which results in the formation of a salt which is pharmaceutically acceptable; alkyl having from 1 to 8 carbon atoms; or benzyl; R 5 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms or benzyl; or (d) ##STR47## wherein y and y' are as defined above; and j is a whole integer of from 1 to 4.
Claim 5
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 6
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 2 to said mammal.
Claim 7
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 2 and a non-toxic pharmaceutically-acceptable carrier.
Claim 8
Dependent Claim
53 words
A process for the preparation of a compound of the formula: ##STR48## in which R, R 1 , R 2 and R 3 are as defined in claim 1, which comprises reducing a compound of the formula: ##STR49## in which R, R 1 , R 2 and R 3 are as defined above.
Claim 9
Dependent Claim
53 words
A process for the preparation of a compound of the formula ##STR50## in which R, R 1 , R 2 and R 3 are as defined in claim 1, which comprises reducing a compound of the formula ##STR51## in which R, R 1 , R 2 and R 3 are as defined above.
Claim 10
Dependent Claim
53 words
A process for the preparation of a compound of the formula: ##STR52## in which R, R 1 , R 2 and R 3 are as defined in claim 2, which comprises reducing a compound of the formula: ##STR53## in which R, R 1 , R 2 and R 3 are as defined above.
Claim 11
Dependent Claim
460 words
A compound of the formula: ##STR54## wherein each of R 1 , R 2 and R 3 is, independently alkyl having from 1 to 22 carbon atoms; or a radical of the formula ##STR55## 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; and R is a radical of the formula (a), (b), (c) or (d) (a) ##STR56## 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 (ii) ##STR57## 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; (b) ##STR58## 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 a radical of formaul R f : ##STR59## 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 (c) ##STR60## wherein R b is as defined above; R 4 is hydrogen; an equivalent of a cation which results in the formation of a salt which is pharmaceutically acceptable; alkyl having from 1 to 8 carbon atoms; or benzyl; R 5 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms or benzyl; or (d) ##STR61## wherein y and y' are as defined above; and j is a whole integer of from 1 to 4.
Claim 12
Dependent Claim
460 words
A compound of the formula: ##STR54## wherein each of R 1 , R 2 and R 3 is, independently alkyl having from 1 to 22 carbon atoms; or a radical of the formula ##STR55## 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; and R is a radical of the formula (a), (b), (c) or (d) (a) ##STR56## 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 (ii) ##STR57## 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; (b) ##STR58## 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 a radical of formaul R f : ##STR59## 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 (c) ##STR60## wherein R b is as defined above; R 4 is hydrogen; an equivalent of a cation which results in the formation of a salt which is pharmaceutically acceptable; alkyl having from 1 to 8 carbon atoms; or benzyl; R 5 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms or benzyl; or (d) ##STR61## wherein y and y' are as defined above; and j is a whole integer of from 1 to 4.
Claim 13
Dependent Claim
123 words
A process for the preparation of a compound of the formula: ##STR62## in which R, R 1 , R 2 and R 3 are as defined in claim 9, provided that when R is of type (c) then R 4 is alkyl or benzyl which comprises the steps of (a) reacting a dianion of the formula: ##STR63## in which R is as defined, and M is an equivalent of an active metal or a magnesium chloride or bromide with a tri substituted-halo silane of the formula ##STR64## in which R 1 , R 2 and R 3 are as defined, and Z is halo having an atomic weight of from about 19 to 127, to form an adduct; and (b) hydrolyzing said adduct.
Claim 14
Dependent Claim
15 words
A compound of claim 1, 2, or 9 in which R is of formula (a).
Claim 15
Dependent Claim
14 words
A compound of claim 2, or 9 in which R is of formula (b).
Claim 16
Dependent Claim
15 words
A compound of claim 1, 2, or 9 in which R is of formula (c).
Claim 17
Dependent Claim
15 words
A compound of claim 1, 2, or 9 in which R is of formula (d).
Claim 18
Dependent Claim
8 words
The compound of claim 1 which is 4-methyl-4-phenyl-4-sila-pentanoyl-(1'-phenyl-2'-p-tolyl)-ethylamide.
Claim 19
Dependent Claim
8 words
The compound of claim 1 which is 4,4-diphenyl-4-sila-pentanoyl-(1'-phenyl-2'-p-tolyl)ethylamide.
Claim 20
Dependent Claim
8 words
A compound of claim 1 which is 4,4-dimethyl-5-phenyl-4-sila-pentanoyl-(1'-phenyl-2'-p-tolyl)ethylamide.
Claim 21
Dependent Claim
8 words
The compound of claim 1 which is 4,4-diphenyl-4-sila-n-octanoyl-(1'-phenyl-2'-p-tolyl)ethylamide.
Claim 22
Dependent Claim
9 words
The compound of claim 1, which is 4-(o-methoxyphenyl)-4-methyl-4-sila-pentanoyl-(1'-benzyl-2'-phenyl) ethylamide.
Claim 23
Dependent Claim
23 words
A compound of claim 1, 2 or 9 in which two of R 1 , R 2 and R 3 are the same.
Claim 24
Dependent Claim
19 words
A compound of claim 1, 2 or 9 in which R 2 and R 3 are of type (b).
Claim 25
Dependent Claim
17 words
A compound of claim 1, 2 or 9 in which R 2 and R 3 are methyl.
Claim 26
Dependent Claim
14 words
A compound of claim 1, 2 or 9 in which R is 1-phenyl 2-(p-tolyl)ethyl.
Claim 27
Dependent Claim
8 words
The compound of claim 2 which is 4,4-dimethyl-4-sila-pent-2-enoyl-(1'-phenyl-2'-p-tolyl)-ethylamide.
Claim 28
Dependent Claim
8 words
A compound of claim 2 which is N-4,4-dimethyl-4-sila-pent-2-enoyl-benzylamide.
Claim 29
Dependent Claim
8 words
A compound of claim 2 which is 4,4-diphenyl-4-sila-n-oct-2-enoyl-(1'-phenyl-2'-p-tolyl)ethylamide.
Claim 30
Dependent Claim
8 words
The compound of claim 9 which is 4,4-diphenyl-4-sila-pent-2-ynoyl-(1'-phenyl-2'-tolyl)ethylamide.
Claim 31
Dependent Claim
8 words
The compound of claim 9 which is 4,4-dimethyl-4-sila-pent-2-ynoyl-(1'-phenyl-2'-tolyl)ethylamide.
Claim 32
Dependent Claim
23 words
A compound of claim 1, 2 or 9 provided that when R is of type (c), then R 4 is alkyl or benzyl.
Claim 33
Independent Claim
511 words
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 total cholesterol ester-reducing amount of a compound of the formula ##STR65## wherein each of R 1 , R 2 and R 3 is, independently, alkyl having from 1 to 22 carbon atoms; or a radical of the formula ##STR66## 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; and R is a radical of formula (a), (b), (c) or (d) (a) ##STR67## 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 (ii) ##STR68## 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; (b) ##STR69## 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 a radical of the structure R f : ##STR70## 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; (c) ##STR71## wherein R b is as defined above; R 4 is hydrogen; an equivalent of a cation which results in the formation of a salt which is pharmaceutically-acceptable; alkyl having from 1 to 8 carbon atoms or benzyl; and R 5 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms or benzyl; (d) ##STR72## wherein y and y' are as defined above; and j is a whole integer of from 1 to 4, with the proviso that at least one of R 1 , R 2 and R 3 is a radical of the formula ##STR73##
Claim 34
Independent Claim
511 words
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 total cholesterol ester-reducing amount of a compound of the formula ##STR65## wherein each of R 1 , R 2 and R 3 is, independently, alkyl having from 1 to 22 carbon atoms; or a radical of the formula ##STR66## 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; and R is a radical of formula (a), (b), (c) or (d) (a) ##STR67## 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 (ii) ##STR68## 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; (b) ##STR69## 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 a radical of the structure R f : ##STR70## 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; (c) ##STR71## wherein R b is as defined above; R 4 is hydrogen; an equivalent of a cation which results in the formation of a salt which is pharmaceutically-acceptable; alkyl having from 1 to 8 carbon atoms or benzyl; and R 5 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms or benzyl; (d) ##STR72## wherein y and y' are as defined above; and j is a whole integer of from 1 to 4, with the proviso that at least one of R 1 , R 2 and R 3 is a radical of the formula ##STR73##
Claim 35
Dependent Claim
25 words
A composition of claim 30 or 4, provided that when R of the compound is of type (c) then R 4 is alkyl or benzyl.
Claim 36
Dependent Claim
25 words
A method of claim 3 or 5 provided that when R of the compound is of type (c) then R 4 is alkyl or benzyl.
References Cited (Backward Citations)
US2610198A
Cited
US2607793A
Cited
US2973383A
Cited
US2919173A
Cited
US4088668A
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) | 1986-12-12 | 1987-06-13 | 1987-12-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-12-12 | 1991-06-13 | 1991-12-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-12-12 | 1995-06-13 | 1995-12-13 | $7700.00 | Window Closed / Lapsed |