Use Of Aminodithiol As A Reducing Agent For Hair Perming

• US 20080138309A1
• Filed: 01/19/2006
• Published: 06/12/2008
• Est. Priority Date: 01/20/2005
• Status: Abandoned Application

• Current Assignee: L'Oreal SA
• Original Assignee: L'Oreal SA
• Inventors: Malle, Gerald, Blaise, Christian
• Application Number:
  US11/795,608
• Publication Number:
  US 20080138309A1
• Time in Patent Office: Days
• US Class Current: 424/70.51
• CPC Class Codes: A61K 8/447 containing sulfur
• CPC Class Codes: A61K 8/46 containing sulfur A61K8/44 takes precedence
• CPC Class Codes: A61Q 5/04 Preparations for permanent waving or straightening the hair
• CPC Class Codes: C07C 323/41 Y being a hydrogen or an acyclic carbon atom
• CPC Class Codes: C07C 323/52 the carbon skeleton being acyclic and saturated
• CPC Class Codes: C07C 323/58 with amino groups bound to the carbon skeleton
• CPC Class Codes: C07C 323/59 with acylated amino groups bound to the carbon skeleton
• CPC Class Codes: C07C 323/60 with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
• CPC Class Codes: C07K 5/02 containing at least one abnormal peptide link

Abstract

The present invention relates to the use of aminodithiols as reducing agents for hair perming. It further relates to a hair perming method using these aminodithiols.

Claims

1. Use of at least one aminodithiol of general formula (I), in a reducing composition for the hair, as reducing agent for the first step of an operation for the perming of keratin fibres, especially hair:

2. Use according to claim 1, characterized in that the compound of formula (I) is selected from:

2,2′

-oxybis[N-(2-mercaptoethyl)acetamide]

N,N′

-(1,2-dioxo-1,2-ethanediyl)bis(L-cysteine dimethyl ester)

N,N′

-(1,3-dioxo-1,3-propanediyl)bis(L-cysteine dimethyl ester)

N,N′

-(1,4-dioxo-1,4-butanediyl)bis(L-cysteine dimethyl ester)

N,N′

-(1,2-dioxo-1,2-ethanediyl)-bis-L-cysteine

N,N′

-(1,4-dioxo-1,4-butanediyl)-bis-L-cysteine

N,N′

-(1,5-dioxo-1,5-pentanediyl)bis(L-cysteine dimethyl ester)

N,N′

-(1,6-dioxo-1,6-hexanediyl)bis(L-cysteine dimethyl ester)

N,N′

-(1,7-dioxo-1,7-heptanediyl)bis(L-cysteine dimethyl ester)

N,N′

-(1,8-dioxo-1,8-octanediyl)bis(L-cysteine dimethyl ester)

N,N′

-(1,2-ethanediyl)bis(L-cysteine dibutyl ester)

N,N′

-(1,2-ethanediyl)bis(L-cysteine dimethyl ester)

N,N′

-(1,2-ethanediyl)bis(L-cysteine dipropyl ester)

N,N′

-(1,2-ethanediyl)-bis-L-cysteine

N,N′

-(1,2-ethanediyl)bis(L-cysteine diethyl ester)

N,N′

-(1,2-ethanediyl)bis(DL-cysteine diethyl ester)

N,N′

-(1,2-ethanediyl)-bis-L-homocysteine

N,N′

-(1,3-propanediyl)-bis-L-cysteine

N,N′

-(1,3-propanediyl)-bis-L-homocysteine

N,N′

-1,3-(2-hydroxypropanediyl)-bis-L-cysteine

N,N′

-1,3-(2-hydroxypropanediyl)-bis-L-homocysteine

N,N′

-carbonyl-bis(L-cysteine)

N-[2-[[(1R)-1-carboxy-2-mercaptoethyl]amino]ethyl]-L-cysteine 1-ethyl ester

N-[2-[(2-mercaptoethyl)amino]ethyl]-L-cysteine 1-ethyl ester

N-[2-[(2-mercaptoethyl)amino]ethyl]-L-cysteine

N-(2-mercaptoethyl)-2-[(2-mercaptoethyl)amino]-acetamide

N-[(2-mercaptoethyl)glycyl]-L-cysteine

N-[(2-mercaptoethyl)glycyl]-L-cysteine ethyl ester

N-(1-carboxy-2-mercaptoethyl)-3-[(1-carboxy-2-mercaptoethyl)amino]aspartic acid

2,2′

-(ethylenediimino)diethanethiol dihydrochloride

3,7-diaza-1,9-nonanedithiol

3,6-diaza-1,8-octanedithiol

N,N′

-bis(2-mercaptoethyl)ethanediamide

N,N′

-bis(2-mercaptoethyl)butanediamide

N,N′

-bis(2-mercaptoethyl)hexanediamide

1,4-bis[(2-mercaptoethyl)amino]-2,3-butanediol

N,N′

-bis(mercaptoethyl)urea

1,2-ethanediylbis[(2-mercaptoethyl)carbamic] acid

2-[(1-carboxy-2-mercaptoethylaminooxalyl)amino]-3-mercaptopropionic acid

methyl 3-mercapto-2-[(2-mercapto-1-methoxycarbonylethylaminooxalyl)amino]propionate

ethyl 3-mercapto-2-[(2-mercapto-1-ethoxycarbonylethylaminooxalyl)amino]propionate

N,N′

-bis[2-(methylamino)-2-oxo-1-(mercaptomethyl)ethyl]ethanediamide

N,N′

-bis[2-(ethylamino)-2-oxo-1-(mercaptomethyl)ethyl]ethanediamide

N,N′

-bis[2-(dimethylamino)-2-oxo-1-(mercaptomethyl)ethyl]ethanediamide

N,N′

-bis[2-[(2-hydroxypropyl)amino]-2-oxo-1-(mercaptomethyl)ethyl]ethanediamide

N,N′

-bis[2-[(2-hydroxyethyl)amino]-2-oxo-1-(mercaptomethyl)ethyl]ethanediamide

N,N′

-bis[2-{[2-(dimethylamino)ethyl]amino}-2-oxo-1-(mercaptomethyl)ethyl]ethanediamide

N,N′

-bis[2-{[3-(dimethylamino)propyl]amino}-2-oxo-1-(mercaptomethyl)ethyl]ethanediamide

2-({3-[(1-carboxy-2-mercaptoethyl)amino]-3-oxopropanoxyl}amino)-3-mercaptopropionic acid

methyl 2-[3-{[2-methoxy-2-oxo-1-(mercaptomethyl)ethyl]amino}-(3-oxopropanoxyl)amino]-3-mercaptopropanoate

ethyl 2-[3-{[2-ethoxy-2-oxo-1-(mercaptomethyl)ethyl]-amino}-(3-oxopropanoxyl)amino]-3-mercaptopropanoate

N,N′

-bis[2-(methylamino)-2-oxo-1-(mercaptomethyl)ethyl]malonamide

N,N′

-bis[2-(ethylamino)-2-oxo-1-(mercaptomethyl)ethyl]malonamide

N,N′

-bis[2-(2-hydroxypropylamino)-2-oxo-1-(mercaptomethyl)ethyl]malonamide

N,N′

-bis[2-(2-hydroxyethylamino)-2-oxo-1-(mercaptomethyl)ethyl]malonamide

N,N′

-bis[2-(dimethylamino)-2-oxo-1-(mercaptomethyl)ethyl]malonamide

N,N′

-bis[2-{[2-(dimethylamino)ethyl]amino}-2-oxo-1-(mercaptomethyl)ethyl]malonamide

N,N′

-bis[2-{[3-(dimethylamino)propyl]amino}-2-oxo-1-(mercaptomethyl)ethyl]malonamide

2-({[(1-carboxy-2-mercaptoethyl)amino]acetyl}amino)-3-mercaptopropionic acid

methyl 2-[({[2-methoxy-2-oxo-1-(mercaptomethyl)ethyl]amino}acetyl)amino]-3-mercaptopropanoate

ethyl 2-[({[2-ethoxy-2-oxo-1-(mercaptomethyl)ethyl]amino}acetyl)amino]-3-mercaptopropanoate

N-methyl-2-[({[2-methylamino-2-oxo-1-(mercaptomethyl)ethyl]amino}acetyl)amino]-3-mercaptomethylpropanamide

N-methyl-2-[({[2-hydroxypropylamino-2-oxo-1-(mercaptomethyl)ethyl]amino}acetyl)amino]-3-mercaptomethylpropanamide

N-methyl-2-[({[2-hydroxyethylamino-2-oxo-1-(mercaptomethyl)ethyl]amino}acetyl)amino]-3-mercaptomethylpropanamide

2-({[2-dimethylamino-2-oxo-1-(mercaptomethyl)ethyl]amino}acetyl)amino-N,N-dimethyl-3-mercaptopropanamide

2-({[2-diethylamino-2-oxo-1-(mercaptomethyl)ethyl]amino}acetyl)amino-N,N-dimethyl-3-mercaptopropanamide

N-[2-(dimethylamino)ethyl]-2-methyl-6,9-dioxo-7,12-bis(mercaptomethyl)-2,5,8,11-tetraazamidecan-13-amide

N-[3-(dimethylamino)propyl]-2-methyl-6,9-dioxo-7,12-bis(mercaptomethyl)-2,5,8,11-tetraazamidecan-13-amide

N,N′

-1,2-ethanediylbis(3-mercaptopropanamide)

N,N′

-1,3-propanediylbis(3-mercaptopropanamide)

N,N′

-1,3-(2-hydroxypropanediyl)bis(3-mercaptopropanamide)

N,N′

-1,4-butanediylbis(3-mercaptopropanamide)

N,N′

-1,5-pentanediylbis(3-mercaptopropanamide)

N,N′

-1,6-hexanediylbis(3-mercaptopropanamide)

N,N′

-1,2-ethanediylbis(4-mercaptobutanamide)

N,N′

-1,3-propanediylbis(4-mercaptobutanamide)

N,N′

-1,3-(2-hydroxypropanediyl)bis(4-mercaptobutanamide)

N,N′

-1,4-butanediylbis(4-mercaptobutanamide)

N-[2-(2-carboxy-3-mercaptopropionylamino)ethyl]-2-mercaptomethylmalonamic acid

methyl N-[2-(2-methoxycarbonyl-3-mercaptopropionylamino)ethyl]-2-mercaptomethylmalonamate

ethyl N-[2-(2-ethoxycarbonyl-3-mercaptopropionylamino)ethyl]-2-mercaptomethylmalonamate

2-[2-(2-carbamoyl-3-mercaptopropionylamino)ethylcarbamoyl]-3-mercaptopropionamide

3-mercapto-N-[2-(3-mercapto-2-methylcarbamoylpropionylamino)ethyl]-2-methylcarbamoylpropionamide

3-mercapto-N-[2-(3-mercapto-2-ethylcarbamoylpropionylamino)ethyl]-2-ethylcarbamoylpropionamide

2-dimethylcarbamoyl-N-[2-(2-dimethylcarbamoyl-3-mercaptopropionylamino)ethyl]-3-mercaptopropionamide

N-[3-(2-carboxy-3-mercaptopropionylamino)propyl]-2-mercaptomethylmalonamic acid

methyl N-[3-(2-methoxycarbonyl-3-mercaptopropionylamino)propyl]-2-mercaptomethylmalonamate

ethyl N-[3-(2-ethoxycarbonyl-3-mercaptopropionylamino)propyl]-2-mercaptomethylmalonamate

2-[3-(2-carbamoyl-3-mercaptopropionylamino)propylcarbamoyl]-3-mercaptopropionamide

3-mercapto-N-[3-(3-mercapto-2-methylcarbamoylpropionylamino)propyl]-2-methylcarbamoylpropionamide

3-mercapto-N-[3-(3-mercapto-2-ethylcarbamoylpropionylamino)propyl]-2-ethylcarbamoylpropionamide

2-dimethylcarbamoyl-N-[3-(2-dimethylcarbamoyl-3-mercaptopropionylamino)propyl]-3-mercaptopropionamide

N-[3-(2-carboxy-3-mercaptopropionylamino)-2-hydroxypropyl]-2-mercaptomethylmalonamic acid

methyl N-[3-(2-methoxycarbonyl-3-mercaptopropionylamino)-2-hydroxypropyl]-2-mercaptomethylmalonamate

ethyl N-[3-(2-ethoxycarbonyl-3-mercaptopropionylamino)-2-hydroxypropyl]-2-mercaptomethylmalonamate

2-[3-(2-carbamoyl-3-mercaptopropionylamino)-2-hydroxypropylcarbamoyl]-3-mercaptopropionamide

3-mercapto-N-[3-(3-mercapto-2-methylcarbamoylpropionylamino)-2-hydroxypropyl]-2-methylcarbamoylpropionamide

3-mercapto-N-[3-(3-mercapto-2-ethylcarbamoylpropionylamino)-2-hydroxypropyl]-2-ethylcarbamoylpropionamide

2-dimethylcarbamoyl-N-[3-(2-dimethylcarbamoyl-3-mercaptopropionylamino)-2-hydroxypropyl]-3-mercaptopropionamide.

3. Use according to claim 1, characterized in that the compound of formula (I) is selected from:

2,2′

-oxybis[N-(2-mercaptoethyl)acetamide]

N,N′

-(1,2-dioxo-1,2-ethanediyl)bis(L-cysteine dimethyl ester)

N,N′

-(1,4-dioxo-1,4-butanediyl)bis(L-cysteine dimethyl ester)

N,N′

-(1,4-dioxo-1,4-butanediyl)-bis-L-cysteine

N,N′

-(1,2-ethanediyl)-bis-L-cysteine

N,N′

-(1,2-ethanediyl)-bis-L-homocysteine

N,N′

-(1,3-propanediyl)-bis-L-cysteine

N,N′

-(1,3-propanediyl)-bis-L-homocysteine

N,N′

-1,3-(2-hydroxypropanediyl)-bis-L-cysteine

N,N′

-1,3-(2-hydroxypropanediyl)-bis-L-homocysteine

N,N′

-carbonylbis(L-cysteine)

N-[2-[[(1R)-1-carboxy-2-mercaptoethyl]amino]ethyl]-L-cysteine 1-ethyl ester

N-[2-[(2-mercaptoethyl)amino]ethyl]-L-cysteine 1-ethyl ester

N-[2-[(2-mercaptoethyl)amino]ethyl]-L-cysteine

N-(2-mercaptoethyl)-2-[(2-mercaptoethyl)amino]-acetamide

N-[(2-mercaptoethyl)glycyl]-L-cysteine

N-(1-carboxy-2-mercaptoethyl)-3-[(1-carboxy-2-mercaptoethyl)amino]aspartic acid

2,2′

-(ethylenediimino)diethanethiol dihydrochloride

3,6-diaza-1,8-octanedithiol

N,N′

-bis(2-mercaptoethyl)ethanediamide

N,N′

-bis(2-mercaptoethyl)butanediamide

N,N′

-bis(2-mercaptoethyl)hexanediamide

1,4-bis[(2-mercaptoethyl)amino]-2,3-butanediol

N,N′

-bis(mercaptoethyl)urea

1,2-ethanediylbis[(2-mercaptoethyl)carbamic] acid

N,N′

-1,2-ethanediylbis(3-mercaptopropanamide)

N,N′

-1,3-propanediylbis(3-mercaptopropanamide)

N,N′

-1,3-(2-hydroxypropanediyl)bis(3-mercaptopropanamide)

N,N′

-1,4-butanediylbis(3-mercaptopropanamide)

N,N′

-1,5-pentanediylbis(3-mercaptopropanamide)

N,N′

-1,2-ethanediylbis(4-mercaptobutanamide)

N,N′

-1,3-propanediylbis(4-mercaptobutanamide)

N,N′

-1,3-(2-hydroxypropanediyl)bis(4-mercaptobutanamide)

N,N′

-1,4-butanediylbis(4-mercaptobutanamide)

N-[2-(2-carboxy-3-mercaptopropionylamino)ethyl]-2-mercaptomethylmalonamic acid

methyl N-[2-(2-methoxycarbonyl-3-mercaptopropionylamino)ethyl]-2-mercaptomethylmalonamate

ethyl N-[2-(2-ethoxycarbonyl-3-mercaptopropionylamino)ethyl]-2-mercaptomethylmalonamate

2-[2-(2-carbamoyl-3-mercaptopropionylamino)ethylcarbamoyl]-3-mercaptopropionamide

3-mercapto-N-[2-(3-mercapto-2-methylcarbamoylpropionylamino)ethyl]-2-methylcarbamoylpropionamide

3-mercapto-N-[2-(3-mercapto-2-ethylcarbamoylpropionylamino)ethyl]-2-ethylcarbamoylpropionamide

2-dimethylcarbamoyl-N-[2-(2-dimethylcarbamoyl-3-mercaptopropionylamino)ethyl]-3-mercaptopropionamide

N-[3-(2-carboxy-3-mercaptopropionylamino)propyl]-2-mercaptomethylmalonamic acid

methyl N-[3-(2-methoxycarbonyl-3-mercaptopropionylamino)propyl]-2-mercaptomethylmalonamate

ethyl N-[3-(2-ethoxycarbonyl-3-mercaptopropionylamino)propyl]-2-mercaptomethylmalonamate

2-[3-(2-carbamoyl-3-mercaptopropionylamino)propylcarbamoyl]-3-mercaptopropionamide

3-mercapto-N-[3-(3-mercapto-2-methylcarbamoylpropionylamino)propyl]-2-methylcarbamoylpropionamide

3-mercapto-N-[3-(3-mercapto-2-ethylcarbamoylpropionylamino)propyl]-2-ethylcarbamoylpropionamide

2-dimethylcarbamoyl-N-[3-(2-dimethylcarbamoyl-3-mercaptopropionylamino)propyl]-3-mercaptopropionamide

N-[3-(2-carboxy-3-mercaptopropionylamino)-2-hydroxypropyl]-2-mercaptomethylmalonamic acid

methyl N-[3-(2-methoxycarbonyl-3-mercaptopropionylamino)-2-hydroxypropyl]-2-mercaptomethylmalonamate

ethyl N-[3-(2-ethoxycarbonyl-3-mercaptopropionylamino)-2-hydroxypropyl]-2-mercaptomethylmalonamate

2-[3-(2-carbamoyl-3-mercaptopropionylamino)-2-hydroxypropylcarbamoyl]-3-mercaptopropionamide

3-mercapto-N-[3-(3-mercapto-2-methylcarbamoylpropionylamino)-2-hydroxypropyl]-2-methylcarbamoylpropionamide

3-mercapto-N-[3-(3-mercapto-2-ethylcarbamoylpropionylamino)-2-hydroxypropyl]-2-ethylcarbamoylpropionamide

2-dimethylcarbamoyl-N-[3-(2-dimethylcarbamoyl-3-mercaptopropionylamino)-2-hydroxypropyl]-3-mercaptopropionamide.

4. Use according to claim 1, characterized in that the reducing agent of general formula (I) is advantageously present, in a cosmetically acceptable medium, at a concentration of between 0.05 and 35% by weight, preferably of between 1 and 25% by weight, based on the total weight of the reducing composition.

5. Use according to claims 1 to 4, characterized in that the pH of the reducing composition for the hair is between 4 and 11, more particularly between 6 and 10.

6. Use according to any one of the preceding claims, characterized in that the reducing composition for the hair also contains a surfactant of non-ionic, anionic, cationic or amphoteric type.

7. Use according to claim 6, characterized in that the surfactant is present at a maximum concentration of 30% by weight, preferably of between 0.5 and 10% by weight, based on the total weight of the reducing composition.

8. Use according to claim 4, characterized in that the cosmetically acceptable medium is water or an aqueous-alcoholic solution in which the alcohol is C₁-C₈, such as ethanol, isopropanol or butanol.

9. Hair perming method comprising the application of a reducing composition comprising, as reducing agent, a compound of formula (I):

10. Method according to claim 9, characterized in that the hair perming consists, in a first step, in reducing the disulphide bonds of the keratin by applying the reducing composition for about 5 to 60 min and then, in a second step, in re-forming said bonds by applying an oxidizing composition or optionally by allowing the atmospheric oxygen to take effect.

11. Method according to claim 9 or 10, characterized in that, after application of the reducing composition, the hair is subjected to a heat treatment by heating to a temperature of between 30 and 60°

C.

12. Method according to claim 9, characterized in that the hair shaping consists of a hair uncurling or straightening method in which the reducing composition is applied to the hair, after which the hair is subjected to mechanical shaping in order to fix it in its new shape.

13. Hair perming kit comprising, in a first compartment, a composition according to the invention comprising a compound of formula (I) as reducing composition, and, in a second compartment, an oxidizing composition,

14. Aminodithiols of general formula (II) below:

15. Aminodithiol of formula (II) according to claim 14, selected from:

2-[(1-carboxy-2-mercaptoethylaminooxalyl)amino]-3-mercaptopropionic acid

N,N′

-bis[2-(methylamino)-2-oxo-1-(mercaptomethyl)ethyl]ethanediamide

N,N′

-bis[2-(ethylamino)-2-oxo-1-(mercaptomethyl)ethyl]ethanediamide

N,N′

-bis[2-(dimethylamino)-2-oxo-1-(mercaptomethyl)ethyl]ethanediamide

N,N′

-bis[2-[2-hydroxypropylamino]-2-oxo-1-(mercaptomethyl)ethyl]ethanediamide

N,N′

-bis[2-[2-hydroxyethylamino]-2-oxo-1-(mercaptomethyl)ethyl]ethanediamide

N,N′

-bis[2-{[2-(dimethylamino)ethyl]amino}-2-oxo-1-(mercaptomethyl)ethyl]ethanediamide

N,N′

-bis[2-{[3-(dimethylamino)propyl]amino}-2-oxo-1-(mercaptomethyl)ethyl]ethanediamide

2-({3-[(1-carboxy-2-mercaptoethyl)amino]-3-oxopropanoxyl}amino)-3-mercaptopropionic acid

N,N′

-bis[2-(methylamino)-2-oxo-1-(mercaptomethyl)ethyl]malonamide

N,N′

-bis[2-(ethylamino)-2-oxo-1-(mercaptomethyl)ethyl]malonamide

N,N′

-bis[2-(2-hydroxypropylamino)-2-oxo-1-(mercaptomethyl)ethyl]malonamide

N,N′

-bis[2-(2-hydroxyethylamino)-2-oxo-1-(mercaptomethyl)ethyl]malonamide

N,N′

-bis[2-(dimethylamino)-2-oxo-1-(mercaptomethyl)ethyl]malonamide

N,N′

-bis[2-{[2-(dimethylamino)ethyl]amino}-2-oxo-1-(mercaptomethyl)ethyl]malonamide

N,N′

-bis[2-{[3-(dimethylamino)propyl]amino}-2-oxo-1-(mercaptomethyl)ethyl]malonamide

2-({[(1-carboxy-2-mercaptoethyl)amino]acetyl}amino)-3-mercaptopropionic acid

N-methyl-2-[({[2-methylamino-2-oxo-1-(mercaptomethyl)ethyl]amino}acetyl)amino]-3-mercaptomethylpropanamide

N-methyl-2-[({[2-hydroxypropylamino-2-oxo-1-(mercaptomethyl)ethyl]amino}acetyl)amino]-3-mercaptomethylpropanamide

N-methyl-2-[({[2-hydroxyethylamino-2-oxo-1-(mercaptomethyl)ethyl]amino}acetyl)amino]-3-mercaptomethylpropanamide

2-({[2-dimethylamino-2-oxo-1-(mercaptomethyl)ethyl]amino}acetyl)amino-N,N-dimethyl-3-mercaptopropanamide

2-({[2-diethylamino-2-oxo-1-(mercaptomethyl)ethyl]amino}acetyl)amino-N,N-dimethyl-3-mercaptopropanamide

N-[2-(dimethylamino)ethyl]-2-methyl-6,9-dioxo-7,12-bis(mercaptomethyl)-2,5,8,11-tetraazamidecan-13-amide

N-[3-(dimethylamino)propyl]-2-methyl-6,9-dioxo-7,12-bis(mercaptomethyl)-2,5,8,11-tetraazamidecan-13-amide

N,N′

-(1,3-propanediyl)-bis-L-homocysteine

N,N′

-1,3-(2-hydroxypropanediyl)-bis-L-cysteine

N,N′

-1,3-(2-hydroxypropanediyl)-bis-L-homocysteine

N,N′

-1,5-pentanediylbis(3-mercaptopropionamide)

N,N′

-1,3-propanediylbis(4-mercaptobutanamide)

N,N′

-1,3-(2-hydroxypropanediyl)bis(3-mercaptopropionamide)

N,N′

-1,3-(2-hydroxypropanediyl)bis(4-mercaptobutanamide)

N,N′

-1,4-butanediylbis(4-mercaptobutanamide)

N-[2-(2-carboxy-3-mercaptopropionylamino)ethyl]-2-mercaptomethylmalonamic acid

2-[2-(2-carbamoyl-3-mercaptopropionylamino)ethylcarbamoyl]-3-mercaptopropionamide

3-mercapto-N-[2-(3-mercapto-2-methylcarbamoylpropionylamino)ethyl]-2-methylcarbamoylpropionamide

3-mercapto-N-[2-(3-mercapto-2-ethylcarbamoylpropionylamino)ethyl]-2-ethylcarbamoylpropionamide

2-dimethylcarbamoyl-N-[2-(2-dimethylcarbamoyl-3-mercaptopropionylamino)ethyl]-3-mercaptopropionamide

N-[3-(2-carboxy-3-mercaptopropionylamino)propyl]-2-mercaptomethylmalonamic acid

2-[3-(2-carbamoyl-3-mercaptopropionylamino)propylcarbamoyl]-3-mercaptopropionamide

3-mercapto-N-[3-(3-mercapto-2-methylcarbamoylpropionylamino)propyl]-2-methylcarbamoylpropionamide

3-mercapto-N-[3-(3-mercapto-2-ethylcarbamoylpropionylamino)propyl]-2-ethylcarbamoylpropionamide

2-dimethylcarbamoyl-N-[3-(2-dimethylcarbamoyl-3-mercaptopropionylamino)propyl]-3-mercaptopropionamide

N-[3-(2-carboxy-3-mercaptopropionylamino)-2-hydroxypropyl]-2-mercaptomethylmalonamic acid

2-[3-(2-carbamoyl-3-mercaptopropionylamino)-2-hydroxypropylcarbamoyl]-3-mercaptopropionamide

3-mercapto-N-[3-(3-mercapto-2-methylcarbamoylpropionylamino)-2-hydroxypropyl]-2-methylcarbamoylpropionamide

3-mercapto-N-[3-(3-mercapto-2-ethylcarbamoylpropionylamino)-2-hydroxypropyl]-2-ethylcarbamoylpropionamide

2-dimethylcarbamoyl-N-[3-(2-dimethylcarbamoyl-3-mercaptopropionylamino)-2-hydroxypropyl]-3-mercaptopropionamide.