Patent EP0276104A2 successfully refreshed from Google Patents.
Patent EP0034876A2 successfully refreshed from Google Patents.
EP0034876A2
Expired / Lapsed
EP
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Branched amides of L-aspartyl-D-amino acid dipeptides and compositions thereof
Assignee: Danisco Finland Oy
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Filing: 1981-01-08
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Granted: —
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Expires: 2001-01-08
Abstract
Abstract Amides of L-aspartyl-D-amino acid dipeptides of the formula and physiologically acceptable cationic and acid addition salts thereof wherein R a is methyl, ethyl, n-propyl or isopropyl and R is a branched aliphatic, alicyclic or heterocyclic member which is branched at the alpha carbon atom (the carbon atom bearing the amide nitrogen atom) and also branched again at one or both of the beta carbon atoms, are potent sweeteners which are free from undesirable flavour qualities and of high stability in conventional food processing. Sweetening compositions and sweetened edible compositions of such amides are also claimed
Inventors
- 👤 Thomas Mott Brennan
- 👤 Michael Ezell Hendrick
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-26 14:32
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/26; C07D307/30; C07D307/32; A; A23; A23L; A23L27/00; A23L27/30; A23L27/31; A23L27/32; C07C; C07C323/00; C07C323/23; C07C323/24; C07C323/25; C07C45/00; C07C45/004; C07C45/27; C07C45/29; C07C45/292; C07C45/61; C07C45/62; C07C45/63; C07C45/64; C07C45/67; C07C45/673; C07C45/68; C07C45/72; C07C45/74; C07C45/75; C07C49/00; C07C49/04; C07C49/16; C07C49/17; C07C49/173; C07C49/29; C07C49/293; C07C49/385; C07C49/39; C07C49/395; C07C49/403; C07C49/413; C07C49/523; C07C49/587; C07C49/647; C07D307/04; C07D307/18; C07D307/22; C07D331/00; C07D331/04; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/30; C07D333/32; C07D333/36; C07D335/00; C07D335/02; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06104; C07K5/06113; Y; Y10; Y10S; Y10S426/00; Y10S426/804; Y10S530/00; Y10S530/801
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
456 words
An L-aspartyl-D-amino acid dipeptide amide of the formula and the physiologically acceptable cationic and acid addition salts thereof, wherein R a is methyl, ethyl, n-propyl or isopropyl; and R is a branched member selected from the group consisting of fenchyl, diisopropylcarbinyl, d-methyl-t-butylcarbinyl, d-ethyl-t-butylcarbinyl, di-t-butylcarbinyl, 2-methylthio-2,4-dimethylpentan-3-yl, where at least one of R 3 , R 4 , R 5 ; R 6 is alkyl having from one to four carbon atoms and the remainder are hydrogen or alkyl having from one to four carbon atoms, X is O, S, SO, S0 2 , C=O or CHOH; m is zero, 1, 2, 3 or 4, n and p are each zero, 1, 2 or 3 where the sum of n + p is not greater than 3 and the sum of the carbon atoms in R 3 , R 4 , R 5 and R 6 is not greater than six, and when both of R 3 and R 4 or R 5 and R 6 are alkyl they are methyl or ethyl, where one of R 7 , R 8 , R 9 is alkyl having from one to four carbon atoms and the remainder are hydrogen or alkyl having from one to four carbon atoms and the sum of the carbon atoms in R 7 , R 8 and R 9 is not greater than six, where m and q are the same or different and each have the values previously defined for m, where each of R 12 and R 13 are methyl or ethyl, or R 12 is hydrogen and R 13 is alkyl having from one to four carbon atoms, Z is 0 or NH and t is 1 or 2, where w is 1, 2, 3 or 4, R 14 and R 16 are each alkyl having from one to four carbon atoms, R 15 is hydrogen, OH, or alkyl having from one to two carbon atoms, where the sum of the carbon atoms in R 14 , R 15 and R 16 is not greater than six and when both of R 14 and R 15 are alkyl they are methyl or ethyl, and where R 17 and R 19 are alkyl having from one to four carbon atoms, R 18 and R 20 are hydrogen or alkyl having from one to two carbon atoms, taken separately, A is OH and B is hydrogen, OH or methyl and when taken together A and B are where the sum of the carbon atoms in R 17 , R 18 , R 19 and R 20 is not greater than six and when both of R 17 and R 18 or R 19 and R 20 are alkyl they are methyl or ethyl.
Claim 2
Dependent Claim
456 words
An L-aspartyl-D-amino acid dipeptide amide of the formula and the physiologically acceptable cationic and acid addition salts thereof, wherein R a is methyl, ethyl, n-propyl or isopropyl; and R is a branched member selected from the group consisting of fenchyl, diisopropylcarbinyl, d-methyl-t-butylcarbinyl, d-ethyl-t-butylcarbinyl, di-t-butylcarbinyl, 2-methylthio-2,4-dimethylpentan-3-yl, where at least one of R 3 , R 4 , R 5 ; R 6 is alkyl having from one to four carbon atoms and the remainder are hydrogen or alkyl having from one to four carbon atoms, X is O, S, SO, S0 2 , C=O or CHOH; m is zero, 1, 2, 3 or 4, n and p are each zero, 1, 2 or 3 where the sum of n + p is not greater than 3 and the sum of the carbon atoms in R 3 , R 4 , R 5 and R 6 is not greater than six, and when both of R 3 and R 4 or R 5 and R 6 are alkyl they are methyl or ethyl, where one of R 7 , R 8 , R 9 is alkyl having from one to four carbon atoms and the remainder are hydrogen or alkyl having from one to four carbon atoms and the sum of the carbon atoms in R 7 , R 8 and R 9 is not greater than six, where m and q are the same or different and each have the values previously defined for m, where each of R 12 and R 13 are methyl or ethyl, or R 12 is hydrogen and R 13 is alkyl having from one to four carbon atoms, Z is 0 or NH and t is 1 or 2, where w is 1, 2, 3 or 4, R 14 and R 16 are each alkyl having from one to four carbon atoms, R 15 is hydrogen, OH, or alkyl having from one to two carbon atoms, where the sum of the carbon atoms in R 14 , R 15 and R 16 is not greater than six and when both of R 14 and R 15 are alkyl they are methyl or ethyl, and where R 17 and R 19 are alkyl having from one to four carbon atoms, R 18 and R 20 are hydrogen or alkyl having from one to two carbon atoms, taken separately, A is OH and B is hydrogen, OH or methyl and when taken together A and B are where the sum of the carbon atoms in R 17 , R 18 , R 19 and R 20 is not greater than six and when both of R 17 and R 18 or R 19 and R 20 are alkyl they are methyl or ethyl.
Claim 3
Dependent Claim
82 words
A compound according to claim 1 wherein R is a member selected from the group consisting of and where R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , A, B, X, Z, m, n, p, q, t and w are as previously defined.
Claim 4
Dependent Claim
13 words
A compound according to claim 1 wherein R is diisopropylcarbinyl, d-methyl-t-butylcarbinyl or di-t-butylcarbinyl.
Claim 5
Dependent Claim
46 words
A compound according to claim 2 wherein R is and R 17 , R 18 , R 19 and R 20 are each methyl, A is HO and B is hydrogen, OH or methyl or A and B taken together form and R a is methyl.
Claim 6
Dependent Claim
34 words
A compound according to claim 2 wherein R is and R 15 is OH , R 14 and R 16 are each methyl and w is 2 or 3, and R a is methyl.
Claim 7
Dependent Claim
14 words
The compound according to claim 2 wherein R is and R a is methyl.
Claim 8
Dependent Claim
21 words
A compound according to claim 2 wherein R is wherein R 7 , R 8 , R 9 are each methyl.
Claim 9
Dependent Claim
16 words
A compound according to claim 2 wherein R is and R a is methyl or ethyl.
Claim 10
Dependent Claim
143 words
A compound according to claim 2 wherein R is R a is methyl and when m is 2: R 3 -R 6 are each methyl, R 3 , R 4 , R 5 are each hydrogen and R is methyl, ethyl, isopropyl or t-butyl, or R 3 and R 5 are each hydrogen and - R 4 and R 6 are each methyl, and when m is 3: R 3 is hydrogen or methyl and R 4 , R 5 , R 6 are each methyl, R 3 , R 4 , R are each hydrogen and R 6 is isopropyl or t-butyl, R 3 and R 5 are each hydrogen, R 4 is methyl and R 6 is methyl, ethyl or isopropyl, or R 3 and R 4 are each hydrogen and R 5 and R 6 are each methyl or ethyl.
Claim 11
Dependent Claim
94 words
A compound according to claim 2 wherein R is R a is methyl or ethyl, and when n is 1 and p is zero: R 3 -R 6 are each methyl and X is 0, S or S0 2 , when n and p are each zero: R 3- R 6 are each methyl and X is S, SO 2 or C=O, when n and p are each 1: R 3 and R 5 are each hydrogen and R 4 and R 6 are each methyl and X is S or SO 2 .
Claim 12
Dependent Claim
35 words
A compound according to claim 1 wherein said compound is L-aspartyl-D-alanine N-(2,2,5,5,-tetramethylcyclopentyl)amide, L-aspartyl-D-alanine N-(2,2,4,4-tetramethyltetrahydro- thiophene-3-yl)amide L-aspartyl-D-alanine N-(t-butylcyclo p ropylcarbinyl) amide L-aspartyl-D-alanine N-(dicyclopropylcarbinyl) amide L-aspartyl-D-alanine N-(2,2,4,4-tetramethylthietan-3-yl) amide L-aspartyl-D-alanine N-(2,2,4,4-tetramethyl-1,1-dioxothietan -3-yl)amide, or L-aspartyl-D-2-aminobutyryl N-(2,2,4,4-tetramethyl-1, 1-dioxothietan -3-yl) amide.
Claim 13
Dependent Claim
27 words
A composition for sweetening edible materials which comprises a sweetening amount of a compound according to any one of claims 1 to 11 and a non-toxic carrier.
Claim 14
Dependent Claim
34 words
A composition for sweetening edible materials which comprises a sweetening amount of a mixture of a compound according to any one of claims 1 to 11 and saccharin or a physiologically acceptable salt thereof.
Claim 15
Dependent Claim
36 words
A sweetened edible composition which comprises an edible material and a sweetening amount of a compound as claimed in any one of claims 1 to 11, or a composition as claimed in claim 12 or 13.
Claim 16
Dependent Claim
16 words
A sweetened edible composition according to claim 14 wherein said edible material is a carbonated beverage.
Claim 17
Dependent Claim
79 words
A compound of the formula wherein m 1 is 1, 2 or 3 and when m 1 is 1: R 3 , R 4 , R 5 and R 6 are each methyl, when m 1 is 2: R 3 is methyl, ethyl or isopropyl and R 4 , R 5 and R 6 are each hydrogen, and when m 1 is 3: R 3 is t-butyl and R 4 , R 5 and R 6 are each hydrogen.
Claim 18
Dependent Claim
79 words
A compound of the formula wherein m 1 is 1, 2 or 3 and when m 1 is 1: R 3 , R 4 , R 5 and R 6 are each methyl, when m 1 is 2: R 3 is methyl, ethyl or isopropyl and R 4 , R 5 and R 6 are each hydrogen, and when m 1 is 3: R 3 is t-butyl and R 4 , R 5 and R 6 are each hydrogen.
Claim 19
Dependent Claim
44 words
A compound of the formula wherein when n 1 is zero and p 1 i a 1 , X1 or O, S or SO 2 ; and when n 1 and p 1 are each zero, X 1 is S, S0 2 or C=O.
Claim 20
Dependent Claim
44 words
A compound of the formula wherein when n 1 is zero and p 1 i a 1 , X1 or O, S or SO 2 ; and when n 1 and p 1 are each zero, X 1 is S, S0 2 or C=O.
Claim 21
Dependent Claim
255 words
A D-amino acid amide compound of the formula wherein R a is methyl, ethyl, isopropyl or n-propyl and R c is a member selected from the group consisting of fenchyl, diisopropylcarbinyl, d-methyl-t-butylcarbinyl, d-ethyl-t-butylcarbinyl, di-t-butylcarbinyl, cyclopropyl-t-butylcarbinyl, cyclopentyl-t-butylcarbinyl, dicyclopropylcarbinyl, where m 1 is 1, 2 or 3 and when m 1 is 1: R , R , R 50 and R 60 are each methyl, when m 1 is 2: R 30 is methyl, ethyl or isopropyl and R 40 , R 50 and R 60 are each hydrogen, or R 30 , and R 50 are each methyl and R 40 and R 60 are each hydrogen, and when m 1 is 3: (a) R 30 is isopropyl or t-butyl and R 40 , R 50 and R 60 are each hydrogen, (b) R30 is ethyl, R 50 is methyl and R 40 and R 60 are each hydrogen, or (c) R 30 and R 40 are each methyl and R 50 and R 60 are each hydrogen or methyl, and wherein when n 2 and p 2 are each zero; R 41 and R 61 are each methyl and X 2 is S, SO 2 , C=0 or CHOH, when n 2 is zero and p 2 is 1: R 41 and R 61 are each methyl and X 2 is O, S or SO 2 : and when n 2 is 1 and p 2 is 1: R 41 and R 61 are each hydrogen and X 2 is S or SO 2 .
Claim 22
Dependent Claim
255 words
A D-amino acid amide compound of the formula wherein R a is methyl, ethyl, isopropyl or n-propyl and R c is a member selected from the group consisting of fenchyl, diisopropylcarbinyl, d-methyl-t-butylcarbinyl, d-ethyl-t-butylcarbinyl, di-t-butylcarbinyl, cyclopropyl-t-butylcarbinyl, cyclopentyl-t-butylcarbinyl, dicyclopropylcarbinyl, where m 1 is 1, 2 or 3 and when m 1 is 1: R , R , R 50 and R 60 are each methyl, when m 1 is 2: R 30 is methyl, ethyl or isopropyl and R 40 , R 50 and R 60 are each hydrogen, or R 30 , and R 50 are each methyl and R 40 and R 60 are each hydrogen, and when m 1 is 3: (a) R 30 is isopropyl or t-butyl and R 40 , R 50 and R 60 are each hydrogen, (b) R30 is ethyl, R 50 is methyl and R 40 and R 60 are each hydrogen, or (c) R 30 and R 40 are each methyl and R 50 and R 60 are each hydrogen or methyl, and wherein when n 2 and p 2 are each zero; R 41 and R 61 are each methyl and X 2 is S, SO 2 , C=0 or CHOH, when n 2 is zero and p 2 is 1: R 41 and R 61 are each methyl and X 2 is O, S or SO 2 : and when n 2 is 1 and p 2 is 1: R 41 and R 61 are each hydrogen and X 2 is S or SO 2 .
References Cited (Backward Citations)
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