Patent
Application of glutamine derivative in preparation of animal feed additive
| العنوان: | Application of glutamine derivative in preparation of animal feed additive |
|---|---|
| Patent Number: | 11964,929 |
| تاريخ النشر: | April 23, 2024 |
| Appl. No: | 17/311311 |
| Application Filed: | December 18, 2018 |
| مستخلص: | The present invention provides the use of a glutamine derivative in preparing animal feed additives, and particularly the use of a glutamine derivative having a structure of formula (I), a racemate thereof, a stereoisomer thereof, a geometric isomer thereof, a tautomer thereof, a solvate thereof, or a feed acceptable salt thereof. Animal breeding experiments revealed that, the provided compounds, including the glutamine derivative, the racemate thereof, the stereoisomer thereof, the geometric isomer thereof, the tautomer thereof, the solvate thereof, and the feed acceptable salt thereof, can be used as animal feed additives, exhibiting excellent effect in improving animal production performance such as growth and feed efficiency. [chemical expression included] |
| Inventors: | Peng, Xianfeng (Guangdong, CN) |
| Assignees: | WISORIG TECHNOLOGIES PTE. LIMITED (SG) |
| Claim: | 1. A method of improving animal production performance, wherein the method comprises administering an animal feed composition to an animal; and wherein the animal feed composition comprises a glutamine derivative having a structure of formula (I), a racemate thereof, a stereoisomer thereof, a geometric isomer thereof, a tautomer thereof, a solvate thereof, or a feed acceptable salt thereof; and an adjuvant suitable for feeds, [chemical expression included] wherein, Y is a C 1 -C 20 alkoxyl group or OH; X is a nitrogen-containing C 4 -C 10 cycloalkyl group, a NHC 1 -C 20 alkyl group, or a N(C 1 -C 20 alkyl group) 2 ; R 1 is R 1a C(═O), R 1b C(═O), R 1a S(═O) 2 , R 1b S(═O) 2 , or H; and R 2 is R 2a C(═O), R 2b C(═O), R 2a S(═O) 2 , or R 2b S(═O) 2 ; R 1b is a C 1 -C 20 alkyl group or a C 3 -C 7 cycloalkyl group, and R 2b is a C 3 -C 7 cycloalkyl group, wherein the C 3 -C 7 cycloalkyl group is optionally substituted with one, two, three, four, or five R 3 ; R 3 is —OH, —NH 2 , —CN, —SH, or —X 1 , wherein X 1 is selected from F, Cl, Br, or I; each of R 1a and R 2a is independently a C 6 -C 12 aryl group, a C 5 -C 12 heteroaryl group, a —(C 1 -C 4 alkylidene)-C 6 -C 12 heteroaryl group, or a —(C 1 -C 4 alkylidene)-C 5 -C 12 heteroaryl group, wherein the C 6 -C 12 aryl group, C 5 -C 12 heteroaryl group, —(C 1 -C 4 alkylidene)-C 6 -C 6 -C 12 aryl group or —(C 1 -C 4 alkylidene)-C 5 -C 12 heteroaryl group is optionally substituted with one, two, three, four, or five R 4 ; and R 4 is —OH, —NH 2 , —NO 2 , —CN, -SH, —X 2 , a —C 1 -C 5 alkoxy group, a —C 1 -C 5 alkyl group, or a —C 1 -C 5 alkyl group substituted with X 2 , wherein X 2 is selected from F, CI, Br, or I. |
| Claim: | 2. The method of claim 1 , wherein R 1 is R 1a C(═O) or H; R 2 is R 2a C(═O); each of R 1a and R 2a is independently a C 6 -C 12 aryl group, a C 5 -C 12 heteroaryl group, a —(C 1 -C 4 alkylidene)-C 6 -C 12 aryl group, or a —(C 1 -C 4 alkylidene)-C 5 -C 12 heteroaryl group, wherein the C 6 -C 12 aryl group, C 5 -C 12 heteroaryl group, —(C 1 -C 4 alkylidene)-C 6 -C 12 aryl group or —(C 1 -C 4 alkylidene)-C 5 -C 12 heteroaryl group is optionally substituted with one, two, three, four, or five R 4 ; R 4 —OH, —NH 2 , —NO 2 , —CN, —SH, —X 2 , a —C-C 5 alkoxy group, a —C 1 -C 5 alkyl group, or a —C 1 -C 5 alkyl group substituted with X 2 , wherein X 2 is selected from F, Cl, Br, or I. |
| Claim: | 3. The method of claim 1 , wherein R 1 is H; R 2 is R 2a C(═O); R 2a is a C 6 -C 12 aryl group or a —(C 1 -C 4 alkylidene)-C 6 -C 12 aryl group, wherein the C 6 -C 12 aryl group or —(C 1 -C 4 alkylidene)-C 6 -C 12 aryl group is optionally substituted with one, two, three, four, or five R 4 ; and R 4 —OH, —NH 2 , —NO 2 , —CN, —SH, —X 2 , —C 1 -C 5 alkoxy group, a —C 1 -C 5 alkyl group, or a —C 1 -C 5 alkyl group substituted with X 2 , wherein X 2 is selected from F, CI, Br, or I. |
| Claim: | 4. The method of claim 3 , wherein R 2a is a phenyl group or a —(C 1 -C 4 alkylidene)-phenyl group, wherein the phenyl group or —(C 1 -C 4 alkylidene)-phenyl group is optionally substituted with one, two, three, four, or five R 4 ; and R 4 is —OH, —NH 2 , —NO 2 , —CN, —SH, —X 2 , a —C 1 -C 5 alkoxy group, a —C 1 -C 5 alkyl group, or a —C 1 -C 5 alkyl group substituted with X 2 , wherein X 2 is selected from F, Cl, Br, or I. |
| Claim: | 5. The method of claim 1 , wherein R 1 is R 1b C(═O) or H; R 2 is R 2b C(═O); R 1b is C 1 -C 20 alkyl group or a C 3 -C 6 cycloalkyl group, R 2b is a C 3 -C 6 cycloalkyl group, wherein the C 1 -C 20 alkyl group or C 3 -C 6 cycloalkyl group is optionally substituted with one, two, three, four, or five R 3 ; and R 3 —OH, —NH 2 , —CN, —SH, or —X 1 , wherein X 1 is selected from F, Cl, Br, or I. |
| Claim: | 6. The method of claim 1 , wherein Y is a C 1 -C 20 alkoxyl group. |
| Claim: | 7. The method of claim 1 , wherein X is a nitrogen-containing C 4 -C 10 cycloalkyl group. |
| Claim: | 8. The method of claim 1 , wherein X is a NHC 1 -C 20 alkyl group. |
| Claim: | 9. The method of claim 8 , wherein X is a NHC 1 -C 10 alkyl group. |
| Claim: | 10. A feed composition, wherein the feed composition comprises at least one of the glutamine derivative having a structure of formula (I), the racemate thereof, the stereoisomer thereof, the geometric isomer thereof, the tautomer thereof, the solvate thereof, and the feed acceptable salt thereof; and an adjuvant suitable for feeds, [chemical expression included] wherein Y is a C 1 -C 20 alkoxyl group or OH; X is a nitrogen-containing C 4 -C 10 cycloalkyl group, a NHC 1 -C 20 alkyl group, or a N(C 1 -C 20 alkyl group) 2 ; R 1 is R 1a C (═O), R 1b C(═O), R 1a S(═O) 2 , R 1b S(═O) 2 , or H; and R 2 is R 2a C(═O), R 2b C(═O), R 2a S(═O) 2 , or R 2b S(═O) 2 ; R 1b is a C 1 -C 20 alkyl group or a C 3 -C 7 cycloalkyl group, and R 2b is a C 3 -C 7 cycloalkyl group, wherein the C 3 -C 7 cycloalkyl group is optionally substituted with one, two, three, four, or five R 3 ; R 3 is —OH, —NH 2 , —CN, —SH, or —X 1 , wherein X 1 is selected from F, CI, Br, or I; each of R 1a and R 2a is independently a C 6 -C 12 aryl group, a C 5 -C 12 heteroaryl group, a —(C 1 -C 4 alkylidene)-C 6 -C 12 aryl group, or a —(C 1 -C 4 alkylidene)-C 5 -C12 heteroaryl group, wherein the C 6 -C 12 aryl group, C 5 -C 12 heteroaryl group, —(C 1 -C 4 alkylidene)-C 6 -C 12 aryl group or —(C 1 -C 4 alkylidene)-C 5 -C 12 heteroaryl group is optionally substituted with one, two, three, four, or five R 4 ; and Ris —OH, —NH 2 , —NO 2 , —CN, —SH, —X 2 , a —C 1 -C 5 alkoxy group, a —C 1 -C 5 alkyl group, or a —C 1 -C 5 alkyl group substituted with X 2 , wherein X 2 is selected from F, Cl, Br, or I. |
| Claim: | 11. The feed composition according to claim 10 , wherein the feed composition further comprises an additional animal feed additive, wherein the additional animal feed additive is selected from at least one of nutritive feed additives, general feed additives, and medicinal feed additives. |
| Claim: | 12. The feed composition according to claim 10 , wherein the feed composition further comprises an animal feed raw material. |
| Claim: | 13. The feed composition of claim 10 for use in preparing an animal feed additive. |
| Claim: | 14. The feed composition according to claim 11 , wherein the feed composition further comprises an animal feed raw material. |
| Claim: | 15. The feed composition of claim 11 for use in preparing an animal feed additive. |
| Claim: | 16. The feed composition of claim 10 , wherein R 1 is R 1a (═O) or H; R 2 R 2a C(═O); each of R 1a and R 2a is independently a C 6 -C 12 aryl group, a C 5 -C 12 heteroaryl group, a —(C 1 -C 4 alkylidene)-C 6 -C 12 aryl group, or a —(C 1 -C 4 alkylidene)-C 5 -C 12 heteroaryl group, wherein the C 6 -C 12 aryl group, C 5 -C 12 heteroaryl group, —(C 1 -C 4 alkylidene)-C 6 -C 12 aryl group or —(C 1 -C 4 alkylidene)-C 5 -C 12 heteroaryl group is optionally substituted with one, two, three, four, or five R 4 ; R 4 is —OH, —NH 2 , —NO 2 , —CN, —SH, —X 2 , a —C 1 -C 5 alkoxy group, a —C 1 -C 5 alkyl group, or a —C 1 -C 5 alkyl group substituted with X 2 , wherein X 2 is selected from F, CI, Br, or I. |
| Claim: | 17. The feed composition of claim 10 , wherein R 1 is H; R 2 is R 2a C(═O); R 2a is a C 6 -C 12 aryl group or a —(C 1 -C 4 alkylidene)-C 6 -C 12 aryl group, wherein the C 6 -C 12 aryl group or —(C 1 -C 4 alkylidene)-C 6 -C 12 aryl group is optionally substituted with one, two, three, four, or five R 4 ; and R 4 —OH, —NH 2 , —NO 2 , —CN, —SH, —X 2 , a —C 1 -C 5 alkoxy group, a —C 1 -C 5 alkyl group, or a —C 1 -C 5 alkyl group substituted with X 2 , wherein X 2 is selected from F, CI, Br, or I. |
| Claim: | 18. The feed composition of claim 17 , wherein R 2a a phenyl group or a —(C 1 -C 4 alkylidene)-phenyl group, wherein the phenyl group or —(C 1 -C 4 alkylidene)-phenyl group is optionally substituted with one, two, three, four, or five R 4 ; and R 4 is —OH, —NH 2 , —NO 2 , —CN, —SH, —X 2 , a —C 1 -C 5 alkoxy group, a —C 1 -C 5 alkyl group, or a —C 1 -C 5 alkyl group substituted with X 2 , wherein X 2 is selected from F, Cl, Br, or I. |
| Claim: | 19. The feed composition of claim 10 for use in preparing an animal feed. |
| Claim: | 20. The feed composition of claim 11 for use in preparing an animal feed. |
| Patent References Cited: | 4791215 December 1988 Rovati et al. 20050100572 May 2005 Hatajima et al. 20060217321 September 2006 Ozeki 20170258122 September 2017 Elings et al. 101760499 June 2010 108041286 May 2018 |
| Other References: | International Search Report of PCTCN2018121709, dated Sep. 17, 2019. cited by applicant English Translation of International Search Report of PCTCN2018121709. cited by applicant Makovec, F., “New glutamic and aspartic derivatives with potent CCK-antagonistic activity,” European Journal of Medicinal Chemistry, vol. 21, p. 9-20, Dec. 31, 1986(Dec. 31, 1986). cited by applicant Ekborg-Ott, K. H., “Avoparcin, a new macrocyclic antibiotic chiral run buffer additive for capillary electrophoresis,” Electrophoresis , vol. 12, p. 2348-2457, Dec. 31, 1999 (Dec. 31, 1999). cited by applicant Tamura, K., “Dual G1 and G2/M phase inhibitor by SC-ααδ9, a combinatorially derived Cdc25 phosphatase inhibitor,” Oncogene, vol. 18, p. 6989-6996, Nov. 30, 1999 (Nov. 30, 1999). cited by applicant Conde, S., “Regioselective lipase-catalysed γ-monoamidation of D-glutamic acid diesters: effect of the N-protecting group,” Tetrahedron: Asymmetry, vol. 11, p. 2537-2545, Dec. 31, 2000 (Dec. 31, 2000). cited by applicant English Translation of CN108041286A. cited by applicant English Translation of CN101760499A. cited by applicant |
| Primary Examiner: | Li, Changqing |
| Attorney, Agent or Firm: | Kam Wah Law |
| رقم الانضمام: | edspgr.11964929 |
| قاعدة البيانات: | USPTO Patent Grants |
| الوصف غير متاح. |