Patent US4411925A successfully refreshed from Google Patents.
US4411925A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Branched amides of L-aspartyl-d-amino acid dipeptides
Assignee: Danisco Finland Oy
•
Filing: 1980-11-05
•
Granted: 1983-10-25
•
Expires: 2000-11-05
Abstract
Abstract Amides of L-aspartyl-D-amino acid dipeptides of the formula <IMAGE> (I) and physiologically acceptable cationic and acid addition salts thereof wherein Ra is methyl, ethyl, n-propyl or isopropyl; 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, <IMAGE> <IMAGE> <IMAGE> <IMAGE> <IMAGE> said amides are potent sweeteners having advantages over the prior art, edible compositions containing them, methods for their use in edible compositions and novel amine and amide intermediates useful in their production.
Inventors
- 👤 Thomas M. Brennan
- 👤 Michael E. Hendrick
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 12:16
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: 95
Claim 1
Independent Claim
462 words
An L-aspartyl-D-amino acid dipeptide amide of the formula ##STR412## 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, ##STR413## 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, SO 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, ##STR414## 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, ##STR415## where m and q are the same or different and each have the values previously defined for m, ##STR416## 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, ##STR417## 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 ##STR418## 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 ##STR419## 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
462 words
An L-aspartyl-D-amino acid dipeptide amide of the formula ##STR412## 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, ##STR413## 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, SO 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, ##STR414## 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, ##STR415## where m and q are the same or different and each have the values previously defined for m, ##STR416## 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, ##STR417## 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 ##STR418## 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 ##STR419## 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 ##STR420## 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
10 words
A compound according to claim 2 wherein R is ##STR421##
Claim 5
Dependent Claim
13 words
A compound according to claim 1 wherein R is diisopropylcarbinyl, d-methyl-t-butylcarbinyl or di-t-butylcarbinyl.
Claim 6
Dependent Claim
10 words
A compound according to claim 2 wherein R is ##STR422##
Claim 7
Dependent Claim
16 words
A compound according to claim 5 wherein A is OH and B is hydrogen or methyl.
Claim 8
Dependent Claim
25 words
A compound according to claim 6 wherein R 17 , R 18 , R 19 and R 20 are each methyl and B is hydrogen.
Claim 9
Dependent Claim
11 words
The compound according to claim 7 wherein R a is methyl.
Claim 10
Dependent Claim
13 words
The compound according to claim 5 wherein A and B are each OH.
Claim 11
Dependent Claim
21 words
A compound according to claim 9 wherein R 17 , R 18 , R 19 and R 20 are each methyl.
Claim 12
Dependent Claim
11 words
The compound according to claim 10 wherein R a is methyl.
Claim 13
Dependent Claim
14 words
A compound according to claim 5 wherein A and B taken together form ##STR423##
Claim 14
Dependent Claim
21 words
A compound according to claim 12 wherein R 17 , R 18 , R 19 and R 20 are each methyl.
Claim 15
Dependent Claim
11 words
A compound according to claim 13 wherein R a is methyl.
Claim 16
Dependent Claim
10 words
A compound according to claim 12 wherein R is ##STR424##
Claim 17
Dependent Claim
11 words
A compound according to claim 15 wherein R 15 is OH.
Claim 18
Dependent Claim
21 words
A compound according to claim 16 wherein w is 2 or 3 and R 14 and R 16 are each methyl.
Claim 19
Dependent Claim
15 words
The compound according to claim 17 wherein R a is methyl and w is 3.
Claim 20
Dependent Claim
10 words
A compound according to claim 2 wherein R is ##STR425##
Claim 21
Dependent Claim
15 words
A compound according to claim 19 wherein R 12 and R 13 are each methyl.
Claim 22
Dependent Claim
18 words
The compound according to claim 20 wherein R a is methyl, t is 1 and Z is O.
Claim 23
Dependent Claim
10 words
A compound according to claim 4 wherein R is diisopropylcarbinyl.
Claim 24
Dependent Claim
11 words
The compound according to claim 22 wherein R a is methyl.
Claim 25
Dependent Claim
10 words
A compound according to claim 4 wherein R is d-methyl-t-butylcarbinyl.
Claim 26
Dependent Claim
11 words
The compound according to claim 24 wherein R a is methyl.
Claim 27
Dependent Claim
10 words
A compound according to claim 4 wherein R is di-t-butylcarbinyl.
Claim 28
Dependent Claim
11 words
The compound according to claim 26 wherein R a is methyl.
Claim 29
Dependent Claim
10 words
A compound according to claim 3 wherein R is ##STR426##
Claim 30
Dependent Claim
10 words
A compound according to claim 28 wherein R is ##STR427##
Claim 31
Dependent Claim
18 words
A compound according to claim 29 wherein R 7 , R 8 and R 9 are each methyl.
Claim 32
Dependent Claim
11 words
The compound according to claim 30 wherein R a is methyl.
Claim 33
Dependent Claim
10 words
A compound according to claim 3 wherein R is ##STR428##
Claim 34
Dependent Claim
10 words
A compound according to claim 32 wherein R is ##STR429##
Claim 35
Dependent Claim
11 words
The compound according to claim 33 wherein R a is ethyl.
Claim 36
Dependent Claim
11 words
The compound according to claim 33 wherein R a is methyl.
Claim 37
Dependent Claim
10 words
A compound according to claim 3 wherein R is ##STR430##
Claim 38
Dependent Claim
10 words
A compound according to claim 36 wherein m is 2.
Claim 39
Dependent Claim
22 words
A compound according to claim 37 wherein R 3 , R 4 , R 5 , and R 6 are each methyl.
Claim 40
Dependent Claim
11 words
The compound according to claim 38 wherein R a is methyl.
Claim 41
Dependent Claim
30 words
A compound according to claim 37 wherein R 3 , R 4 and R 5 are each hydrogen and R 6 is alkyl having from one to four carbon atoms.
Claim 42
Dependent Claim
15 words
A compound according to claim 40 wherein R 6 is methyl, ethyl, isopropyl or t-butyl.
Claim 43
Dependent Claim
16 words
The compound according to claim 41 wherein R a is methyl and R 6 is isopropyl.
Claim 44
Dependent Claim
28 words
The compound according to claim 37 wherein R a is methyl, R 3 and R 5 are each hydrogen and R 4 and R 6 are each methyl.
Claim 45
Dependent Claim
10 words
A compound according to claim 36 wherein m is 3.
Claim 46
Dependent Claim
21 words
A compound according to claim 44 wherein R 3 , R 4 , R 5 and R 6 are each methyl.
Claim 47
Dependent Claim
11 words
The compound according to claim 45 wherein R a is methyl.
Claim 48
Dependent Claim
30 words
A compound according to claim 44 wherein R 3 , R 4 and R 5 are each hydrogen and R 6 is alkyl having from one to four carbon atoms.
Claim 49
Dependent Claim
13 words
A compound according to claim 47 wherein R 6 is isopropyl or t-butyl.
Claim 50
Dependent Claim
11 words
A compound according to claim 48 wherein R a is methyl.
Claim 51
Dependent Claim
31 words
A compound according to claim 44 wherein R 3 and R 5 are each hydrogen and R 4 and R 6 are each alkyl having from one to four carbon atoms.
Claim 52
Dependent Claim
15 words
A compound according to claim 50 wherein R 4 and R 6 are each methyl.
Claim 53
Dependent Claim
11 words
The compound according to claim 51 wherein R a is methyl.
Claim 54
Dependent Claim
16 words
A compound according to claim 50 wherein R 4 is methyl and R 6 is isopropyl.
Claim 55
Dependent Claim
11 words
The compound according to claim 53 wherein R a is methyl.
Claim 56
Dependent Claim
30 words
A compound according to claim 44 wherein R 3 is hydrogen and R 4 , R 5 and R 6 are each alkyl having from one to four carbon atoms.
Claim 57
Dependent Claim
18 words
A compound according to claim 55 wherein R 4 , R 5 and R 6 are each methyl.
Claim 58
Dependent Claim
11 words
The compound according to claim 56 wherein R a is methyl.
Claim 59
Dependent Claim
25 words
A compound according to claim 44 wherein R 3 and R 4 are each hydrogen and R 5 R 6 are each methyl or ethyl.
Claim 60
Dependent Claim
20 words
The compound according to claim 58 wherein R a is methyl and R 5 and R 6 are each methyl.
Claim 61
Dependent Claim
10 words
A compound according to claim 3 wherein R is ##STR431##
Claim 62
Dependent Claim
17 words
A compound according to claim 60 wherein X is O, n is 1 and p is zero.
Claim 63
Dependent Claim
21 words
A compound according to claim 61 wherein R 3 , R 4 , R 5 and R 6 are each methyl.
Claim 64
Dependent Claim
11 words
The compound according to claim 62 wherein R a is methyl.
Claim 65
Dependent Claim
21 words
A compound according to claim 60 wherein X is S or SO 2 , n is 1 and p is zero.
Claim 66
Dependent Claim
21 words
A compound according to claim 64 wherein R 3 , R 4 , R 5 and R 6 are each methyl.
Claim 67
Dependent Claim
15 words
The compound according to claim 65 wherein R a is methyl and X is S.
Claim 68
Dependent Claim
21 words
A compound according to claim 60 wherein X is S or SO 2 , and n and p are each zero.
Claim 69
Dependent Claim
21 words
A compound according to claim 67 wherein R 3 , R 4 , R 5 and R 6 are each methyl.
Claim 70
Dependent Claim
13 words
A compound according to claim 68 wherein R a is methyl or ethyl.
Claim 71
Dependent Claim
15 words
The compound according to claim 69 wherein R a is methyl and X is S.
Claim 72
Dependent Claim
17 words
The compound according to claim 69 wherein R a is methyl and X is SO 2 .
Claim 73
Dependent Claim
20 words
A compound according to claim 60 wherein X is S or SO 2 and n and p are each 1.
Claim 74
Dependent Claim
31 words
The compound according to claim 72 wherein R a is methyl, X is S, R 3 and R 5 are each hydrogen and R 4 and R 6 are each methyl.
Claim 75
Dependent Claim
17 words
A compound according to claim 60 wherein X is C═O and n and p are each zero.
Claim 76
Dependent Claim
26 words
The compound according to claim 74 wherein R a is methyl and R 3 , R 4 , R 5 and R 6 are each methyl.
Claim 77
Dependent Claim
16 words
A compound of claim 60 wherein X is CHOH and n and p are each zero.
Claim 78
Dependent Claim
26 words
The compound according to claim 76 wherein R a is methyl and R 3 , R 4 , R 5 and R 6 are each methyl.
Claim 79
Dependent Claim
22 words
A composition for sweetening edible materials which comprises a sweetening amount of a compound according to claim 1 and a non-toxic carrier.
Claim 80
Dependent Claim
12 words
A composition according to claim 78 wherein said compound is L-aspartyl-D-alanine N-(dicyclopropylcarbinyl)amide.
Claim 81
Dependent Claim
12 words
A composition according to claim 78 wherein said compound is L-aspartyl-D-alanine N-(2,2,4,4-tetramethylthietan-3-yl)amide.
Claim 82
Dependent Claim
12 words
A composition according to claim 78 wherein said compound is L-aspartyl-D-alanine N-(2,2,4,4-tetramethyl-1,1-dioxothietan-3-yl)amide.
Claim 83
Dependent Claim
29 words
A composition for sweetening edible materials which comprises a sweetening amount of a mixture of a compound according to claim 1 and saccharin or a physiologically acceptable salt thereof.
Claim 84
Dependent Claim
17 words
A composition according to claim 82 wherein said compound is L-aspartyl-D-alanine N-(dicyclopropylcarbinyl)amide, L-aspartyl-D-alanine N-(2,2,4,4-tetramethylthietan-3-yl)amide or L-aspartyl-D-alanine N-(2,2,4,4-tetramethyl-1,1-dioxothietan-3-yl)amide.
Claim 85
Dependent Claim
12 words
A composition according to claim 83 wherein said compound is L-aspartyl-D-alanine N-(dicyclopropylcarbinyl)amide.
Claim 86
Dependent Claim
22 words
A composition according to claim 84 wherein said compound and said saccharin are in a weight ratio of from 1:1 to 1:9.
Claim 87
Dependent Claim
20 words
A sweetened edible composition which comprises an edible material and a sweetening amount of a compound according to claim 1.
Claim 88
Dependent Claim
20 words
A sweetened edible composition which comprises an edible material and a sweetening amount of a compound according to claim 3.
Claim 89
Dependent Claim
16 words
A sweetened edible composition according to claim 86 wherein said edible material is a carbonated beverage.
Claim 90
Dependent Claim
16 words
A sweetened edible composition according to claim 87 wherein said edible material is a carbonated beverage.
Claim 91
Dependent Claim
19 words
A sweetened edible composition according to claim 89 wherein said compound is L-aspartyl-D-alanine N-(dicyclopropylcarbinyl)amide, L-aspartyl-D-alanine N-(2,2,4,4-tetramethylthietan-3-yl)amide or L-aspartyl-D-alanine N-(2,2,4,4-tetramethyl-1,1-dioxothietan-3-yl)amide.
Claim 92
Dependent Claim
20 words
A method for sweetening edible materials which comprises adding thereto a sweetening amount of a compound according to claim 1.
Claim 93
Dependent Claim
12 words
A method according to claim 91 wherein said compound is L-aspartyl-D-alanine N-(dicyclopropylcarbinyl)amide.
Claim 94
Dependent Claim
12 words
A method according to claim 91 wherein said compound is L-aspartyl-D-alanine N-(2,2,4,4-tetramethylthietan-3-yl)amide.
Claim 95
Dependent Claim
12 words
A method according to claim 91 wherein said compound is L-aspartyl-D-alanine N-(2,2,4,4-tetramethyl-1,1-dioxothietan-3yl)amide.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-10-24 | 1987-04-25 | 1987-10-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-10-24 | 1991-04-25 | 1991-10-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-10-24 | 1995-04-25 | 1995-10-25 | $7700.00 | Window Closed / Lapsed |