US4108987A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Cyclic hexapeptides
Assignee: Merck and Co Inc
•
Filing: 1977-09-12
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Granted: 1978-08-22
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Expires: 1997-09-12
Abstract
Abstract Synthetic novel cyclic hexapeptides having the structure: Cyclo[(N-alkylamino acid)-X-(N-alkylamino acid)'-X-(N-alkylamino acid)"-X] wherein (N-alkylamino acid), (N-alkylamino acid)' and (N-alkylamino acid)" have the structure: ##STR1## wherein R 1 is a lower alkyl group having 1 to 3 carbon atoms and R 2 is hydrogen and methyl or R 1 and R 2 are --CH 2 --N, n being an integer 2 or 3, and form a 4- or 5- membered ring; and X is D- or L-Ala, D- or L-Phe, D- or L-Leu, D- or L-p-halophenylalanyl or D- or L-p-nitrophenylalanyl, with the proviso that when R 1 is methyl and R 2 is hydrogen, X is not D-Ala are prepared. Oral administration of these cyclic peptides improves the digestive efficiency of certain herbivorous animals.
Inventors
- 👤 Daniel F. Veber
- 👤 Stephen F. Brady
- 👤 Sandor L. Varga
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 02:39
CPC Classifications
C; C07; C07K; C07K7/00; C07K7/64; A; A23; A23K; A23K20/00; A23K20/10; A23K20/142; A23K20/147; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/27
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
105 words
The peptides having the structure: cyclo[(N-alkylamino acid)-X-(N-alkylamino acid)'-X-(N-alkylamino acid)"-X] wherein (N-alkylamino acid), (N-alkylamino acid)' and (N-alkylamino acid)" have the structure: ##STR6## wherein R 1 is a lower alkyl group having 1 to 3 carbon atoms and R 2 is hydrogen and methyl or R 1 and R 2 are --CH 2 -- n , n being an integer 2 or 3, and form a 4- or 5-membered ring; and X is D- or L-Ala, D- or L-Phe, D- or L-Leu, D- or L-p-halophenylalanyl or D- or L-p-nitrophenylalanyl, with the proviso that when R 1 is methyl and R 2 is hydrogen, X is not D-Ala.
Claim 2
Dependent Claim
105 words
The peptides having the structure: cyclo[(N-alkylamino acid)-X-(N-alkylamino acid)'-X-(N-alkylamino acid)"-X] wherein (N-alkylamino acid), (N-alkylamino acid)' and (N-alkylamino acid)" have the structure: ##STR6## wherein R 1 is a lower alkyl group having 1 to 3 carbon atoms and R 2 is hydrogen and methyl or R 1 and R 2 are --CH 2 -- n , n being an integer 2 or 3, and form a 4- or 5-membered ring; and X is D- or L-Ala, D- or L-Phe, D- or L-Leu, D- or L-p-halophenylalanyl or D- or L-p-nitrophenylalanyl, with the proviso that when R 1 is methyl and R 2 is hydrogen, X is not D-Ala.
Claim 3
Dependent Claim
79 words
The peptides according to claim 1 wherein (N-alkylamino acid), (N-alkylamino acid)' and (N-alkylamino acid)" are selected from the group consisting of Sar, D- or L-Pro and X is D- or L-Ala or D- or L-Phe and wherein when Pro is D, X is L-Ala or L-Phe or L-p-chlorophenylalanyl or L-p-nitrophenylalanyl; and when Pro is L, X is D-Ala or D-Phe or D-p-chlorophenylalanyl or D-p-nitrophenylalanyl; and wherein when N-alkylamino acid is Sar, X is not D-Ala or D- or L-Phe.
Claim 4
Dependent Claim
32 words
The peptides according to claim 2 having the structure: cyclo(D-Pro-Ala) 3 , cyclo(D-Pro-Phe) 3 , cyclo(Pro-D-Phe) 3 , cyclo(Sar-Ala) 3 , cyclo(Pro-D-Ala) 3 , cyclo(Sar-D-Phe) (Pro-D-Phe) 2 , and cyclo(p-chlorophenylalanyl-D-Pro) 3 .
Claim 5
Dependent Claim
10 words
The peptide according to claim 3 having the structure: ##STR7##
Claim 6
Dependent Claim
10 words
The peptide according to claim 3 having the structure: ##STR8##
Claim 7
Dependent Claim
10 words
The peptide according to claim 3 having the structure: ##STR9##
Claim 8
Dependent Claim
132 words
A composition useful for increasing the efficiency of feed utilization by ruminant animals having a developed rumen function comprising an inert carrier and a VFA-increasing amount of the peptide having the structure: cyclo[(N-alkylamino acid)-X-(N-alkylamino acid)'-X-(N-alkylamino acid)"-X] wherein (N-alkylamino acid), (N-alkylamino acid)' and (N-alkylamino acid)" have the structure: ##STR10## wherein R 1 is a lower alkyl group having 1 to 3 carbon atoms and R 2 is hydrogen and methyl or R 1 and R 2 are --CH 2 -- n , n being an integer 2 or 3, and form a 4- or 5-membered ring; and X is D- or L-Ala, D- or L-Phe, D- or L-Leu, D- or L-p-halophenylalanyl or D- or L-p-nitrophenylalanyl, with the proviso that when R 1 is methyl and R 2 is hydrogen, X is not D-Ala.
Claim 9
Dependent Claim
132 words
A composition useful for increasing the efficiency of feed utilization by ruminant animals having a developed rumen function comprising an inert carrier and a VFA-increasing amount of the peptide having the structure: cyclo[(N-alkylamino acid)-X-(N-alkylamino acid)'-X-(N-alkylamino acid)"-X] wherein (N-alkylamino acid), (N-alkylamino acid)' and (N-alkylamino acid)" have the structure: ##STR10## wherein R 1 is a lower alkyl group having 1 to 3 carbon atoms and R 2 is hydrogen and methyl or R 1 and R 2 are --CH 2 -- n , n being an integer 2 or 3, and form a 4- or 5-membered ring; and X is D- or L-Ala, D- or L-Phe, D- or L-Leu, D- or L-p-halophenylalanyl or D- or L-p-nitrophenylalanyl, with the proviso that when R 1 is methyl and R 2 is hydrogen, X is not D-Ala.
Claim 10
Dependent Claim
21 words
A composition according to claim 7 wherein said compound comprises from about 0.00005 to about 0.5% by weight of said composition.
Claim 11
Dependent Claim
21 words
A composition according to claim 7 wherein said compound comprises from about 0.00025 to about 0.1% by weight of said composition.
Claim 12
Dependent Claim
139 words
A concentrated premix composition for addition to the feed of a ruminant, useful for the increased utilization of feed, which comprises from about 0.1 to about 50% by weight of the peptide having the structure: cyclo[(N-alkylamino acid)-X-(N-alkylamino acid)'-X-(N-alkylamino acid)"-X] wherein (N-alkylamino acid), (N-alkylamino acid)' and (N-alkylamino acid)" have the structure: ##STR11## wherein R 1 is a lower alkyl group having 1 to 3 carbon atoms and R 2 is hydrogen and methyl or R 1 and R 2 are --CH 2 -- n , n being an integer 2 or 3, and form a 4- or 5-membered ring; and X is D- or L-Ala, D- or L-Phe, D- or L-Leu, D- or L-p-halophenylalanyl or D- or L-p-nitrophenylalanyl, with the proviso that when R 1 is methyl and R 2 is hydrogen, X is not D-Ala and an inert carrier.
Claim 13
Dependent Claim
139 words
A concentrated premix composition for addition to the feed of a ruminant, useful for the increased utilization of feed, which comprises from about 0.1 to about 50% by weight of the peptide having the structure: cyclo[(N-alkylamino acid)-X-(N-alkylamino acid)'-X-(N-alkylamino acid)"-X] wherein (N-alkylamino acid), (N-alkylamino acid)' and (N-alkylamino acid)" have the structure: ##STR11## wherein R 1 is a lower alkyl group having 1 to 3 carbon atoms and R 2 is hydrogen and methyl or R 1 and R 2 are --CH 2 -- n , n being an integer 2 or 3, and form a 4- or 5-membered ring; and X is D- or L-Ala, D- or L-Phe, D- or L-Leu, D- or L-p-halophenylalanyl or D- or L-p-nitrophenylalanyl, with the proviso that when R 1 is methyl and R 2 is hydrogen, X is not D-Ala and an inert carrier.
Claim 14
Dependent Claim
20 words
The concentrated premix composition of claim 10 which comprises from about 2 to about 25% by weight of said peptide.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-08-21 | 1982-02-20 | 1982-08-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-08-21 | 1986-02-20 | 1986-08-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-08-21 | 1990-02-20 | 1990-08-22 | $7700.00 | Window Closed / Lapsed |