Prodrugs of compounds that enhance antifungal activity and compositions of said prodrugs
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IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07D-207/16
C07D-211/60
C07C-259/06
C07C-271/60
C07C-275/16
C07C-309/15
C07D-239/557
C07D-241/08
C07D-263/22
C07D-205/04
C07D-273/08
C07D-211/34
C07D-211/44
C07D-211/58
C07D-211/62
A61K-031/223
A61K-031/40
A61K-031/661
A61K-031/495
A61K-031/5377
A61K-031/397
A61K-045/06
A61K-009/00
A61K-031/5375
C07D-309/12
C07D-295/185
C07D-295/192
C07D-295/205
C07F-009/09
출원번호
US-0597911
(2015-01-15)
등록번호
US-9636298
(2017-05-02)
발명자
/ 주소
Ajamian, Alain
Chantigny, Yves Andre
Vaisburg, Arkadii
Raeppel, Franck
Raeppel, Stephane
Deziel, Robert
출원인 / 주소
Ajamian, Alain
대리인 / 주소
McDonnell Boehnen Hulbert & Berghoff LLP
인용정보
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초록▼
The invention relates to prodrugs for use in the inhibition of histone deacetylase. The prodrugs of the present invention have good aqueous solubility and good aqueous stability. The prodrugs of the invention advantageously are metabolized to the active ingredient in plasma or in the blood stream of
The invention relates to prodrugs for use in the inhibition of histone deacetylase. The prodrugs of the present invention have good aqueous solubility and good aqueous stability. The prodrugs of the invention advantageously are metabolized to the active ingredient in plasma or in the blood stream of a warm-blooded animal. The invention also provides compositions and, and methods for making the prodrugs, and methods for using the prodrugs to treat fungal infections.
대표청구항▼
1. A compound that is a salt of N-(2-aminoacetoxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(6-aminohexanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(3-Aminopropanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(4-aminobutanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide, orN-(8-aminooctanoyloxy)-2-(4-
1. A compound that is a salt of N-(2-aminoacetoxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(6-aminohexanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(3-Aminopropanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(4-aminobutanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide, orN-(8-aminooctanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide. 2. A compound that is N-Hydroxy-N-(morpholinomethyl)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-hydroxy-N-((4-methylpiperazin-1-yl)methyl)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-hydroxy-N-(hydroxymethyl)-2-(4-(4-phenylbutyl)phenyl)acetamide,tert-butyl 8-oxo-8-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)octylcarbamate,Methyl (1-((2-(4-(4-phenylbutyl)phenyl)acetamidooxy)carbonyl)cyclopropyl)methylcarbamate,(S)-N,N′-(6-Oxo-6-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)hexane-1,5-diyl)bis(2-(2-(2-methoxyethoxy)ethoxy)acetamide),N-(Isopropylcarbamoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(Isopropylcarbamoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(ethylcarbamoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,(S)-N,N′-(6-Oxo-6-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)hexane-1,5-diyl)bis(2-(2-methoxyethoxy)acetamide),N-([ethoxycarbonylmethyl]carbamoyl)-N-([ethoxycarbonylmethyl]carbamoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,(S)-N,N′-(6-Oxo-6-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propylamino)hexane-1,5-diyl)diacetamide,(S)-N,N′-(3-oxo-3-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propylamino)propane-1,2-diyl)bis(3-methoxypropanamide,(S)-10-(2-acetoxyacetamido)-2,5,9,13-tetraoxo-1-(4-(4-phenylbutyl)phenyl)-4-oxa-3,8,12-triazatetradecan-14-yl acetate,N-1-(2-(2-(2-Methoxyethoxy)ethoxy)ethyl)-N-3-(2-(1-((2-(4-(4-phenylbutyl)phenyl)acetamidooxy)carbonylcyclopropyl)methyl)carbamoylethyl)urea,N-1-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-N-3-(2-(1-(4-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)carbonylpiperazine)carbamoyl)ethyl)urea,(S)-N,N′-(6-oxo-6-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propylamino)hexane-1,5-diyl)bis(3-methoxypropanamide),(S)-10-(2-acetoxyacetamido)-2,5,9,16-tetraoxo-1-(4-(4-phenylbutyl)phenyl)-4-oxa-3,8,15-triazaheptadecan-17-yl acetate),(S)-N,N′-(5-oxo-5-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propylamino)pentane-1,4-diyl)bis(3-methoxypropanamide)),(S)-dimethyl 6-oxo-6-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propylamino)hexane-1,5-diyldicarbamate),4-oxo-N,N-bis(12-oxo-2,5,8-trioxa-11-azatridecan-13-yl)-4-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)butanamide,(S)-10-(2-acetoxyacetamido)-2,5,9,15-tetraoxo-1-(4-(4-phenylbutyl)phenyl)-4-oxa-3,8,14-triazahexadecan-16-yl acetate),(S)-10-(2-acetoxyacetamido)-2,5,9,14-tetraoxo-1-(4-(4-phenylbutyl)phenyl)-4-oxa-3,8,13-triazapentadecan-15-yl acetate,(S)-N,N′-(4-oxo-4-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propylamino)butane-1,3-diyl)bis(3-methoxypropanamide),N,N′-((S)-6-Oxo-6-((S)-2-((2-(4-(4-phenylbutyl)phenyl)acetamidooxy)carbonyl)pyrrolidin-1-yl)hexane-1,5-diyl)bis(2-(2-(2- methoxyethoxy)ethoxy)acetamide),N,N′-((S)-6-oxo-6-((S)-2-((2-(4-(4-phenylbutyl)phenyl)acetamidooxy)carbonyl)pyrrolidin-1-yl)hexane-1,5-diyl)bis(2-(2- methoxyethoxy)acetamide),2-(2-(2-Methoxyethoxy)ethoxy)-N-(2-oxo-2-(4-oxo-4-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)butylamino)ethyl)-N-(10-oxo-2,5,8- trioxa-11-azatridecan-13-yl) acetamide, or2-(2-(2-methoxyethoxy)ethoxy)-N-(2-oxo-2-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propylamino)ethyl)-N-(10-oxo-2,5,8- trioxa-11-azatridecan-13-yl)acetamide. 3. A compound that is a pharmaceutically acceptable salt of the compound (S)-2,6-diamino-N-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propyl)hexanamide. 4. The compound according to claim 3 that is (S)-2,6-diamino-N-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propyl)hexanamide dihydrochloride. 5. A composition comprising the compound of claim 3 together with a pharmaceutically acceptable carrier, excipient, and/or diluent. 6. A composition comprising the compound of claim 4 together with a pharmaceutically acceptable carrier, excipient, and/or diluent. 7. A compound that is N-(3-cyclohexylpropanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(3-methoxypropanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(2-cyclopropylacetoxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-acetoxy-2-(4-(4-phenylbutyl)phenyl)acetamide,2-(4-(4-phenylbutyl)phenyl)-N-(propionyloxy)acetamide,2-(4-(4-Phenylbutyl)phenyl)-N-(2-propylpentanoyloxy)acetamide,N-(butyryloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(pentanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide(S)-2,6-diamino-N-((S)-1-oxo-1-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propan-2-yl)hexanamide,(S)-6-oxo-6-((S)-1-oxo-3-phenyl-1-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propan-2-ylamino)hexane-1,5-diamine,(S)-2-amino-N-(6-oxo-6-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)hexyl)-3-phenylpropanamide,(S)-2-amino-N-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propyl)propanamide,(2S,3S)-2-Amino-3-methyl-N-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propyl)pentanamide,(S)-2-amino-N-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propyl)-3-phenylpropanamide,(S)-2,6-diamino-N-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propyl)hexanamide,(S)-2-amino-N-(4-oxo-4-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)butyl)-3-phenylpropanamide,(S)-2-amino-3-(4-hydroxyphenyl)-N-(6-oxo-6-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)hexyl)propanamide,(S)-N,N′-(6-Oxo-6-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propylamino)hexane-1,5-diyl)bis(2-(2-(2- methoxyethoxy)ethoxy)acetamide),(S)-N,N′-(3-oxo-3-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propylamino)propane-1,2-diyl)bis(2-(2-(2- methoxyethoxy)ethoxy)acetamide),(S)-N,N′-(3-oxo-3-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propylamino)propane-1,2-diyl)bis(2-(2-methoxyethoxy)acetamide),(S)-N,N′-(4-oxo-4-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propylamino)butane-1,3-diyl)bis(2-(2-(2- methoxyethoxy)ethoxy)acetamide),N,N′-((S)-6-((S)-2-Methyl-3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propylamino)-6-oxohexane-1,5-diyl)bis(2-(2-(2-ethoxyethoxy)ethoxy)acetamide),(S)-N,N′-(5-oxo-5-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propylamino)pentane-1,4-diyl)bis(2-(2-methoxyethoxy)acetamide),(S)-N,N′-(5-oxo-5-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propylamino)pentane-1,4-diyl)bis(2-(2-(2- methoxyethoxy)ethoxy)acetamide),(S)-N,N′-(4-oxo-4-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propylamino)butane-1,3-diyl)bis(2,5,8,11,14-pentaoxahexadecan-16- amide),(S)-N,N′-(4-oxo-4-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propylamino)butane-1,3-diyl)bis(2,5,8,11,14,17-hexaoxanonadecan-19- amide),(S)-N,N′-(6-oxo-6-((1-((2-(4-(4-phenylbutyl)phenyl)acetamidooxy)carbonyl)cyclopropyl)methylamino)hexane-1,5-diyl)bis(2-(2- methoxyethoxy)acetamide),(S)-N,N′-(6-Oxo-6-(4-oxo-4-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)butylamino)hexane-1,5-diyl)bis(2-(2-(2- methoxyethoxy)ethoxy)acetamide),(S)-N,N′-(6-Oxo-6-(4-oxo-4-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)butylamino)hexane-1,5-diyl)bis(2-(2-(2- methoxyethoxy)ethoxy)acetamide),(S)-N,N′-(6-oxo-6-(4-oxo-4-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)butylamino)hexane-1,5-diyl)bis(2,5,8,11,14-pentaoxahexadecan-16- amide),(S)-N,N′-(6-oxo-6-((1-((2-(4-(4-phenylbutyl)phenyl)acetamidooxy)carbonyl)cyclopropyl)methylamino)hexane-1,5-diyl)bis(2-(2- methoxyethoxy)acetamide),(S)-N,N′-(6-oxo-6-(4-oxo-4-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)butylamino)hexane-1,5-diyl)bis(2,5,8,11-tetraoxatridecan-13-amide),(S)-N,N′-(6-oxo-6-(4-oxo-4-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)butylamino)hexane-1,5-diyl)bis(2,5,8,11,14,17-hexaoxanonadecan-19- amide),(S)-N,N′-(6-oxo-6-((1-((2-(4-(4-phenylbutyl)phenyl)acetamidooxy)carbonyl)cyclopropyl)methylamino)hexane-1,5-diyl)bis(2-(2-(2-methoxyethoxy)ethoxy)acetamide),(S)-N,N′-(6-(Methyl(4-oxo-4-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)butyl)amino)-6-oxohexane-1,5-diyl)bis(2-(2-(2- methoxyethoxy)ethoxy)acetamide),(S)-6,14-Dioxo-N-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propyl)-1,4-dioxa-7,13-diazacyclopentadecane-8-carboxamide,(S)-9,17-dioxo-N-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl) acetamidooxy)propyl)-1,4,7-trioxa-10,16-diazacyclo octadecane-11-carboxamide,2-(2-(2-Methoxyethoxy)ethoxy)-N-((1-((2-(4-(4-phenylbutyl)phenyl)acetamidooxy)carbonyl)cyclopropyl)methyl)acetamide,2-(2-(2-methoxyethoxy)ethoxy)-N-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propyl)acetamide,N-((1-((2-(4-(4-phenylbutyl)phenyl)acetamidooxy)carbonyl)cyclopropyl)methyl)-2,5,8,11,14-pentaoxahexadecan-16-amide,N-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propyl)-2,5,8,11,14-pentaoxahexadecan-16-amide,(S)-N-(2-Methyl-3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propyl)-2,5,8,11,14-pentaoxahexadecan-16-amide,(S)-N-(4-oxo-4-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)butan-2-yl)-2,5,8,11,14-pentaoxahexadecan-16-amide,N-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propyl)-2,5,8,11,14,17-hexaoxanonadecan-19-amide,N-((1-((2-(4-(4-phenylbutyl)phenyl)acetamidooxy)carbonyl)cyclopropyl)methyl)-2,5,8,11,14,17-hexaoxanonadecan-19-amide,N-(morpholine-4-carbonyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(2,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carbonyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,(S)-N-(2-(2-oxo-4-phenyloxazolidin-3-yl)acetoxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(4-2,5,8,11,14-pentaoxahexadecanepiperazine-1-carbonyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(4-2,5,8,11,14,17-hexaoxanonadecanepiperazine-1-carbonyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(1-2,5,8,11,14,17-Hexaoxanonadecanepiperidine-4-carbonyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(1-(2-(2-(2-Methoxyethoxy)ethoxy)acetyl)piperidine-4-carbonyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,(S)-N,N′-(6-(Methyl(4-oxo-4-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)butyl)amino)-6-oxohexane-1,5-diyl)bis(2-(2-(2- methoxyethoxy)ethoxy)acetamide),N-(2-(1-2,5,8,11-tetraoxatridecanepiperidin-4-yl)acetoxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(2-(1-(2-(2-(2-methoxyethoxy)ethoxy)acetyl)piperidin-4-yl)acetoxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(3-(1-2,5,8,11,14,17-Hexaoxanonadecanepiperidin-4-yl)propanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(2-(1-2,5,8,11,14,17-hexaoxanonadecanepiperidin-4-yloxy)acetoxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(4-(4-(2-(2-(2-Methoxyethoxy)ethoxy)acetyl)piperazin-1-yl)-4-oxobutanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(4-(1-2,5,8,11,14,17-Hexaoxanonadecanepiperidin-4-yl)butanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(4-(1-(2-(2-(2-methoxyethoxy)ethoxy)acetyl)azetidin-3-yl)butanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(3-(1-(2-(2-(2-methoxyethoxy)ethoxy)acetyl)piperidin-4-yl)propanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(3-(1-2,5,8,11,14-pentaoxahexadecanepiperidin-4-yl)propanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,4-oxo-4-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)butyl dihydrogen phosphate,2-(methyl((2-(4-(4-phenylbutyl)phenyl)acetamidooxy)carbonyl)amino)ethanesulfonic acid,ethyl 2-((2-(4-(4-phenylbutyl)phenyl)acetamidooxy)carbonylamino)acetate,2-(2-aminoethylamino)-N-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propyl)acetamide,2-(2-Aminoethylamino)-N-(4-oxo-4-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)butyl)acetamide,(S)-2-(4-(4-phenylbutyl)phenyl)-N-(pyrrolidine-2-carbonyloxy)acetamide,N-(4-Methylpiperazine-1-carbonyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(4-morpholinopiperidine-1-carbonyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,2-(4-(4-Phenylbutyl)phenyl)-N-(piperazine-1-carbonyloxy)acetamide,2-(4-(4-Phenylbutyl)phenyl)-N-(piperidine-4-carbonyloxy)acetamide,2-(4-(4-phenylbutyl)phenyl)-N-(2-(piperidin-4-yl)acetoxy)acetamide,2-(4-(4-Phenylbutyl)phenyl)-N-(3-(piperidin-4-yl)propanoyloxy) acetamide,2-(4-(4-phenylbutyl)phenyl)-N-(2-(piperidin-4-yloxy)acetoxy)acetamide,2-(4-(4-Phenylbutyl)phenyl)-N-(4-(piperidin-4-yl)butanoyloxy)acetamide,N-(4-oxo-4-(piperazin-1-yl)butanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(3-(2-oxopiperazin-1-yl)propanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide(S)-2,6-diamino-N-((S)-1-oxo-1-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propan-2-yl)hexanamide,(S)-6-oxo-6-((S)-1-oxo-3-phenyl-1-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propan-2-ylamino)hexane-1,5-diamine,N-(4-aminobenzoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,N-(6-aminohexanoyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide,2-amino-N-(4-((2-(4-(4-phenylbutyl)phenyl)acetamidooxy)carbonyl)phenyl)acetamide,(S)-2,6-diamino-N-(4-((2-(4-(4-phenylbutyl)phenyl)acetamidooxy)carbonyl)phenyl)hexanamide,(S)-2,6-Diamino-N-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propyl)hexanamide,(S)-2-amino-N-(4-oxo-4-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)butyl)-3-phenylpropanamide,(S)-2-amino-3-(4-hydroxyphenyl)-N-(6-oxo-6-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)hexyl)propanamide,N-((S)-1-((S)-2,6-Diaminohexanoyl)pyrrolidine-2-carbonyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide, or(S)-2-Amino-6-(2-(2-(2-methoxyethoxy)ethoxy)acetamido)-N-(3-oxo-3-(2-(4-(4-phenylbutyl)phenyl)acetamidooxy)propyl)hexanamide.
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