US4774255A
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US
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Pyroglutamic acid esters, their synthesis and use in topical products
Assignee: CPPD Inc C/O CT Corp SYSTEM 208 LASALLE STREET CHICAGO ILLINOIS A CORP OF
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Filing: 1985-08-09
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Granted: 1988-09-27
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Expires: 2005-08-09
Abstract
Abstract Esters of pyroglutamic acid having the structure: <IMAGE> (1) where R' and R'' are the same or different and are each represented by H or the grouping CH3[(CH2)w(CHCH3)x(CHOH)y(CH=CH)z]- where n is an integer of from 1 to 3 w is zero, or an integer of from 1 to 21 x is zero, or an integer of from 1 to 4 y is zero, or an integer of from 1 to 2 z is zero, or an integer of from 1 to 4 provided that the total number of carbon atoms in each of said grouping will not exceed 22; and provided also that when the subgrouping (CH=CH) is present, then the total number of carbon atoms in said grouping will be from 16 to 22. Synthesis, and uses of the said esters in topical compositions are also provided.
Inventors
- 👤 John G. Black
- 👤 Ian R. Scott
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 15:49
CPC Classifications
A; A61; A61Q; A61Q19/00; A61Q19/007; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/49; A61K8/4906; A61K8/4913; A61P; A61P17/00; A61P3/00; C; C07; C07D; C07D207/00; C07D207/02; C07D207/18; C07D207/22; C07D207/24; C07D207/26; C07D207/273; C07D207/277; C07D207/28
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
29 words
Ester of pyroglutamic acid chosen from: 2-[pyroglutamoyloxy]-propionic acid methyl-2-[pyroglutamoyloxy]-acetate ethyl-2-[pyroglutamoyloxy]-n-propionate ethyl-2-[pyroglutamoyloxy]-n-butyrate ethyl-2-[pyroglutamoyloxy]-n-valerate ethyl-2-[pyroglutamoyloxy]-n-caproate ethyl-2-[pyroglutamoyloxy]-n-heptylate ethyl-2-[pyroglutamoyloxy]-n-caprylate ethyl-2-[pyroglutamoyloxy]-n-pelargonate ethyl-2-[pyroglutamoyloxy]-3-hydroxybutyrate iso-propyl-2-[pyroglutamoyloxy]-n-propionate iso-propyl-2-[pyroglutamoyloxy]-n-caprylate n-propyl-2-[pyroglutamoyloxy]-n-propionate n-propyl-2-[pyroglutamoyloxy]-n-caprylate stearyl-2-[pyroglutamoyloxy]-n-propionate 12-hydroxystearyl-2-[pyroglutamoyloxy]-n-propionate stearyl-2-[pyroglutamoyloxy]stearate palmityl-2-[pyroglutamoyloxy]-n-propionate linoleyl-2-[pyroglutamoyloxy]-n-propionate linoleyl-2-[pyroglutamoyloxy]-n-caprylate lauryl-2-[pyroglutamoyloxy]-n-caprylate stearyl-2-[pyroglutamoyloxy]-n-caprylate.
Claim 2
Dependent Claim
29 words
Ester of pyroglutamic acid chosen from: 2-[pyroglutamoyloxy]-propionic acid methyl-2-[pyroglutamoyloxy]-acetate ethyl-2-[pyroglutamoyloxy]-n-propionate ethyl-2-[pyroglutamoyloxy]-n-butyrate ethyl-2-[pyroglutamoyloxy]-n-valerate ethyl-2-[pyroglutamoyloxy]-n-caproate ethyl-2-[pyroglutamoyloxy]-n-heptylate ethyl-2-[pyroglutamoyloxy]-n-caprylate ethyl-2-[pyroglutamoyloxy]-n-pelargonate ethyl-2-[pyroglutamoyloxy]-3-hydroxybutyrate iso-propyl-2-[pyroglutamoyloxy]-n-propionate iso-propyl-2-[pyroglutamoyloxy]-n-caprylate n-propyl-2-[pyroglutamoyloxy]-n-propionate n-propyl-2-[pyroglutamoyloxy]-n-caprylate stearyl-2-[pyroglutamoyloxy]-n-propionate 12-hydroxystearyl-2-[pyroglutamoyloxy]-n-propionate stearyl-2-[pyroglutamoyloxy]stearate palmityl-2-[pyroglutamoyloxy]-n-propionate linoleyl-2-[pyroglutamoyloxy]-n-propionate linoleyl-2-[pyroglutamoyloxy]-n-caprylate lauryl-2-[pyroglutamoyloxy]-n-caprylate stearyl-2-[pyroglutamoyloxy]-n-caprylate.
Claim 3
Dependent Claim
11 words
The ester of claim 1 wherein the ester is ethyl-2-pyroglutamoyloxy propionate.
Claim 4
Dependent Claim
12 words
The ester of claim 1 wherein the ester is ethyl 2-pyroglutamoyloxy n-butyrate.
Claim 5
Dependent Claim
11 words
The ester of claim 1 wherein the ester is ethyl-2-pyroglutamyl n-valerate.
Claim 6
Dependent Claim
11 words
The ester of claim 1 wherein the ester is iso-propyl-2-pyroglutamoyloxy propionate.
Claim 7
Dependent Claim
11 words
The ester of claim 1 wherein the ester is n-propyl-2-pyroglutamoyloxy propionate.
Claim 8
Dependent Claim
17 words
An ester of pyroglutamic acid selected from: glyceryl mono(2-pyroglutamoyloxy propionate), glyceryl di(2-pyroglutamoyloxy propionate), or glyceryl mono(2-pyroglutamoyloxy n-caprylate).
Claim 9
Dependent Claim
17 words
An ester of pyroglutamic acid selected from: glyceryl mono(2-pyroglutamoyloxy propionate), glyceryl di(2-pyroglutamoyloxy propionate), or glyceryl mono(2-pyroglutamoyloxy n-caprylate).
Claim 10
Dependent Claim
159 words
A composition for topical treatment of human skin which comprises an effective amount of from 0.01 to 79% by weight of an ester of pyroglutamic acid having the structure: ##STR7## where R' and R" are the same or different and are each represented by H or the grouping: CH.sub.3 [(CH.sub.2).sub.w (CHCH.sub.3).sub.x (CHOH).sub.y (CH═CH).sub.z ]-- where n is an integer of from 1 to 3; w is zero, or an integer of from 1 to 21; x is zero, or an integer of from 1 to 4; y is zero, or an integer of from 1 to 2; z is zero, or an integer of from 1 to 4 provided that the total number of carbon atoms in each of said grouping will not exceed 22; and provided also that when the subgrouping (CH═CH) is present, then the total number of carbon atoms in said grouping will be from 16 to 22, together with a physiologically and cosmetically acceptable diluent.
Claim 11
Dependent Claim
159 words
A composition for topical treatment of human skin which comprises an effective amount of from 0.01 to 79% by weight of an ester of pyroglutamic acid having the structure: ##STR7## where R' and R" are the same or different and are each represented by H or the grouping: CH.sub.3 [(CH.sub.2).sub.w (CHCH.sub.3).sub.x (CHOH).sub.y (CH═CH).sub.z ]-- where n is an integer of from 1 to 3; w is zero, or an integer of from 1 to 21; x is zero, or an integer of from 1 to 4; y is zero, or an integer of from 1 to 2; z is zero, or an integer of from 1 to 4 provided that the total number of carbon atoms in each of said grouping will not exceed 22; and provided also that when the subgrouping (CH═CH) is present, then the total number of carbon atoms in said grouping will be from 16 to 22, together with a physiologically and cosmetically acceptable diluent.
Claim 12
Dependent Claim
11 words
The composition of claim 8, which further comprises a sunscreen agent.
Claim 13
Dependent Claim
13 words
The composition of claim 8, which is a solution, dispersion, gel or cream.
Claim 14
Dependent Claim
51 words
The composition of claim 8, wherein the grouping: CH.sub.3 [(CH.sub.2).sub.w (CHCH.sub.3).sub.x (CHOH).sub.y (CH═CH).sub.z ]-- is chosen from methyl ethyl n-propyl iso-propyl n-butyl iso-butyl n-valeryl iso-valeryl caproyl n-heptyl caprylyl capryl lauryl myristyl palmityl stearyl arachidyl behenyl 2-hydroxy ethyl 2-hydroxy-n-propyl 3-hydroxy-n-propyl 2-hydroxy-n-butyl 3-hydroxy butyl 4-hydroxy butyl 2,3-dihydroxy-n-propyl 2,3-dihydroxy-n-butyl 12-hydroxystearyl linoleyl linolenyl, and arachidonyl.
Claim 15
Dependent Claim
19 words
The composition of claim 8 wherein the ester is: glyceryl mono(2-pyroglutamoyloxy propionate) glyceryl di(2-pyroglutamoyloxy propionate), or glyceryl mono(2-pyroglutamoyloxy n-caprylate).
Claim 16
Dependent Claim
11 words
The composition of claim 8 wherein the ester is ethyl-2-pyroglutamoyloxy propionate.
Claim 17
Dependent Claim
12 words
The composition of claim 8 wherein the ester is ethyl 2-pyroglutamoyloxy n-butyrate.
Claim 18
Dependent Claim
11 words
The composition of claim 8 wherein the ester is ethyl-2-pyroglutamoyloxy n-valerate.
Claim 19
Dependent Claim
11 words
The composition of claim 8 wherein the ester is iso-propyl-2-pyroglutamoyloxy propionate.
Claim 20
Dependent Claim
11 words
The composition of claim 8 wherein the ester is n-propyl-2-pyroglutamoyloxy propionate.
References Cited (Backward Citations)
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Cited
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-09-27 | 1992-03-28 | 1992-09-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-09-27 | 1996-03-28 | 1996-09-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-09-27 | 2000-03-28 | 2000-09-27 | $7700.00 | Window Closed / Lapsed |