IE57892B1 - Glutamic and aspartic acid derivatives - Google Patents
Glutamic and aspartic acid derivativesInfo
- Publication number
- IE57892B1 IE57892B1 IE1502/85A IE150285A IE57892B1 IE 57892 B1 IE57892 B1 IE 57892B1 IE 1502/85 A IE1502/85 A IE 1502/85A IE 150285 A IE150285 A IE 150285A IE 57892 B1 IE57892 B1 IE 57892B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- formula
- compound according
- pharmaceutically
- img
- Prior art date
Links
- 150000001509 aspartic acid derivatives Chemical class 0.000 title 1
- 150000002306 glutamic acid derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 6
- 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 6
- WHUUTDBJXJRKMK-UHFFFAOYSA-N glutamic acid Chemical class OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims abstract description 5
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims abstract description 4
- -1 morpholino, piperidino Chemical group 0.000 claims abstract description 4
- 229920001184 polypeptide Polymers 0.000 claims abstract description 4
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 3
- 208000022531 anorexia Diseases 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 206010061428 decreased appetite Diseases 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 5
- 239000000730 antalgic agent Substances 0.000 claims description 5
- 229940035676 analgesics Drugs 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 235000013922 glutamic acid Nutrition 0.000 claims description 3
- 239000004220 glutamic acid Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- 238000003436 Schotten-Baumann reaction Methods 0.000 claims description 2
- 150000001263 acyl chlorides Chemical class 0.000 claims description 2
- 230000002421 anti-septic effect Effects 0.000 claims description 2
- 239000002948 appetite stimulant Substances 0.000 claims description 2
- 235000003704 aspartic acid Nutrition 0.000 claims description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000731 choleretic agent Substances 0.000 claims description 2
- 230000001989 choleretic effect Effects 0.000 claims description 2
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 claims description 2
- 210000002569 neuron Anatomy 0.000 claims description 2
- 230000001575 pathological effect Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 230000000975 bioactive effect Effects 0.000 abstract description 3
- 230000003042 antagnostic effect Effects 0.000 abstract description 2
- 210000002249 digestive system Anatomy 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 230000036407 pain Effects 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 8
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 101800001982 Cholecystokinin Proteins 0.000 description 4
- 102100025841 Cholecystokinin Human genes 0.000 description 4
- 229940107137 cholecystokinin Drugs 0.000 description 4
- 229960005181 morphine Drugs 0.000 description 4
- 229940127240 opiate Drugs 0.000 description 4
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- 229960002989 glutamic acid Drugs 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 108010092674 Enkephalins Proteins 0.000 description 2
- URLZCHNOLZSCCA-VABKMULXSA-N Leu-enkephalin Chemical class C([C@@H](C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=CC=C1 URLZCHNOLZSCCA-VABKMULXSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- PNCQTRSFSYUTDV-VIFPVBQESA-N (2s)-2-[(3,4-dichlorobenzoyl)amino]pentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)C1=CC=C(Cl)C(Cl)=C1 PNCQTRSFSYUTDV-VIFPVBQESA-N 0.000 description 1
- GWKOSRIHVSBBIA-REOHCLBHSA-N (3s)-3-aminooxolane-2,5-dione Chemical class N[C@H]1CC(=O)OC1=O GWKOSRIHVSBBIA-REOHCLBHSA-N 0.000 description 1
- LHUMPWOBZPBWRA-VIFPVBQESA-N 3,4-dichloro-n-[(3s)-2,6-dioxooxan-3-yl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)N[C@@H]1C(=O)OC(=O)CC1 LHUMPWOBZPBWRA-VIFPVBQESA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- BYBJDDZACMHGTC-UHFFFAOYSA-N 5-(dibutylamino)-4-[(3,4-dichlorobenzoyl)amino]-5-oxopentanoic acid Chemical compound CCCCN(CCCC)C(=O)C(CCC(O)=O)NC(=O)C1=CC=C(Cl)C(Cl)=C1 BYBJDDZACMHGTC-UHFFFAOYSA-N 0.000 description 1
- 208000031872 Body Remains Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- GGISZLOBBISXOZ-UHFFFAOYSA-N acetic acid;chloroform Chemical compound CC(O)=O.ClC(Cl)Cl GGISZLOBBISXOZ-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 229940029995 appetite stimulants Drugs 0.000 description 1
- 229960005261 aspartic acid Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000010234 biliary secretion Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- OJLGASCOGOIOJR-UHFFFAOYSA-N soyasaponin gammag Natural products CC1=C(O)C(=O)CC(OC2CC(C)(C)CC3C4=CCC5C6(C)CCC(OC7OC(C(O)C(O)C7OC8OC(CO)C(O)C(O)C8O)C(=O)O)C(C)(CO)C6CCC5(C)C4(C)CCC23C)O1 OJLGASCOGOIOJR-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/66—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT67644/84A IT1178982B (it) | 1984-06-25 | 1984-06-25 | Derivati del acido gludamico aventi attivita antagonista su polipep tidi bioattivi e procedimento per la loro preparazione |
| IT68070/84A IT1196751B (it) | 1984-10-26 | 1984-10-26 | Alogeno e ciano derivati dell'acido glutammico ed aspartico ad attivita antagonista su polipeptidi bioattivi e procedimento per la loro preparazione |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE851502L IE851502L (en) | 1985-12-22 |
| IE57892B1 true IE57892B1 (en) | 1993-05-05 |
Family
ID=26329809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1502/85A IE57892B1 (en) | 1984-06-25 | 1985-06-17 | Glutamic and aspartic acid derivatives |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4791215A (enExample) |
| AT (1) | AT390949B (enExample) |
| AU (1) | AU566601B2 (enExample) |
| BE (1) | BE902726A (enExample) |
| CA (1) | CA1325633C (enExample) |
| CH (1) | CH674203A5 (enExample) |
| DE (1) | DE3522506A1 (enExample) |
| DK (1) | DK285685A (enExample) |
| ES (1) | ES8604859A1 (enExample) |
| FR (1) | FR2566397B1 (enExample) |
| GB (1) | GB2160869B (enExample) |
| IE (1) | IE57892B1 (enExample) |
| NL (1) | NL8501829A (enExample) |
| NZ (1) | NZ212436A (enExample) |
| SE (1) | SE503111C2 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1215169B (it) * | 1985-12-17 | 1990-01-31 | Rotta Research Lab | Derivati alchil ossigenati degli acidi glutammico ed aspartico ad attivita antagonista su polipeptidi bioattivi e procedimento per la loro preparazione |
| IT1196849B (it) * | 1986-02-16 | 1988-11-25 | Rotta Research Lab | Nuovi derivati degli acidi 5 pentilammino 5 oxo pentaoico e 4 pentilammino 4 oxo butanoico ad attivita antagonista della colecistochinina e procedimento per la loro preparazione |
| US4880938A (en) * | 1986-06-16 | 1989-11-14 | Merck & Co., Inc. | Amino acid analogs |
| US5089638A (en) * | 1986-06-16 | 1992-02-18 | Merck & Co., Inc. | Amino acid analogs as CCK-antagonists |
| IT1217123B (it) * | 1987-02-05 | 1990-03-14 | Rotta Research Lab | Derivati otticamente attivi dell acido 5 pentilammino 5 oxo pentanoico r ad attivita antagonista della colecistochinina e procedimento per la loro preparazione |
| US4971978A (en) * | 1987-09-21 | 1990-11-20 | Nadzan Alex M | Derivatives of D-glutamic acid and D-aspartic acid |
| WO1990003399A1 (en) * | 1988-09-30 | 1990-04-05 | Australian Commercial Research & Development Limited | Amino acid transport proteins, amino acid analogues, assay apparatus, uses thereof for treatment and diagnosis of cancer |
| FR2643371B1 (fr) * | 1989-02-17 | 1993-11-05 | Roussel Uclaf | Nouveaux derives de l'acide 2-amino pentanedioique, leur procede de preparation et leur application comme medicaments |
| DE69017302T3 (de) * | 1989-08-04 | 1999-08-05 | Merck Sharp & Dohme Ltd., Hoddesdon, Hertfordshire | Zentrale Cholecystokinin-Antagonisten zur Behandlung von psychiatrischen Krankheiten. |
| IE912285A1 (en) * | 1990-07-12 | 1992-01-15 | Black James Foundation | Amino acid derivatives |
| IT1241029B (it) * | 1990-12-11 | 1993-12-27 | Rotta Research Lab | Derivati amidici biciclici e policiclici degli acidi glutammico, aspartico e 2-ammino adipico ad attivita' antigastrinica e procedimento per la loro preparazione |
| US5217957A (en) * | 1991-08-20 | 1993-06-08 | Warner-Lambert Company | Cholecystokinin antagonists useful for treating depression |
| US5153191A (en) * | 1991-08-20 | 1992-10-06 | Warner-Lambert Company | Cholecystokinin antagonists useful for treating depression |
| EP0617621A4 (en) * | 1991-12-20 | 1995-04-05 | Merck Sharp & Dohme | CENTRAL CHOLECYSTOKININE ANTAGONISTS WITH PHARMACEUTICAL EFFECTIVENESS. |
| US5716958A (en) * | 1994-10-27 | 1998-02-10 | Tobishi Pharmaceutical Co., Ltd. | Amino acid derivative having anti-CCK activity |
| GB9721746D0 (en) * | 1997-10-15 | 1997-12-10 | Panos Therapeutics Limited | Compositions |
| EP2491980A2 (en) * | 2003-11-27 | 2012-08-29 | Shiseido Company Limited | Parakeratosis inhibitor and skin preparation for external use |
| CN108912007B (zh) * | 2018-06-20 | 2021-02-26 | 中国农业科学院兰州畜牧与兽药研究所 | 一种右氯谷胺的制备方法 |
| WO2020093188A1 (zh) * | 2018-11-05 | 2020-05-14 | 黄华成 | 天门冬氨酸脂肪酰基衍生物在制备动物饲料添加剂中的应用 |
| EP3888471A4 (en) * | 2018-12-18 | 2021-12-22 | Peng, Xianfeng | USE OF A GLUTAMINE DERIVATIVE IN THE MANUFACTURE OF ANIMAL FEED ADDITIVE |
| CN113272273B (zh) * | 2019-08-15 | 2023-09-15 | 弗门尼舍有限公司 | 味道改良化合物及其用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2828327A (en) * | 1953-12-17 | 1958-03-25 | Monsanto Chemicals | Esters of n-aroylaspartic acids |
| US3551419A (en) * | 1964-07-31 | 1970-12-29 | Rotta Research Lab | Amino acid amides and process for their production |
| JPS5111608B2 (enExample) * | 1972-06-07 | 1976-04-13 |
-
1985
- 1985-06-17 IE IE1502/85A patent/IE57892B1/en not_active IP Right Cessation
- 1985-06-17 NZ NZ212436A patent/NZ212436A/xx unknown
- 1985-06-18 US US06/746,065 patent/US4791215A/en not_active Expired - Lifetime
- 1985-06-18 CA CA000484341A patent/CA1325633C/en not_active Expired - Fee Related
- 1985-06-19 GB GB08515555A patent/GB2160869B/en not_active Expired
- 1985-06-20 FR FR8509383A patent/FR2566397B1/fr not_active Expired
- 1985-06-20 CH CH2617/85A patent/CH674203A5/it not_active IP Right Cessation
- 1985-06-20 SE SE8503097A patent/SE503111C2/sv not_active IP Right Cessation
- 1985-06-21 BE BE0/215244A patent/BE902726A/fr not_active IP Right Cessation
- 1985-06-22 ES ES544462A patent/ES8604859A1/es not_active Expired
- 1985-06-24 DK DK285685A patent/DK285685A/da not_active Application Discontinuation
- 1985-06-24 AU AU44109/85A patent/AU566601B2/en not_active Ceased
- 1985-06-24 AT AT0186985A patent/AT390949B/de not_active IP Right Cessation
- 1985-06-24 DE DE19853522506 patent/DE3522506A1/de active Granted
- 1985-06-25 NL NL8501829A patent/NL8501829A/nl not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2566397B1 (fr) | 1988-08-05 |
| GB2160869B (en) | 1988-03-16 |
| AU566601B2 (en) | 1987-10-22 |
| AU4410985A (en) | 1986-01-02 |
| DE3522506C2 (enExample) | 1988-03-10 |
| IE851502L (en) | 1985-12-22 |
| SE8503097L (sv) | 1985-12-26 |
| DE3522506A1 (de) | 1986-01-02 |
| DK285685A (da) | 1985-12-26 |
| AT390949B (de) | 1990-07-25 |
| GB8515555D0 (en) | 1985-07-24 |
| NZ212436A (en) | 1989-04-26 |
| DK285685D0 (da) | 1985-06-24 |
| ES544462A0 (es) | 1986-03-16 |
| CH674203A5 (enExample) | 1990-05-15 |
| BE902726A (fr) | 1985-10-16 |
| NL8501829A (nl) | 1986-01-16 |
| CA1325633C (en) | 1993-12-28 |
| ES8604859A1 (es) | 1986-03-16 |
| US4791215A (en) | 1988-12-13 |
| ATA186985A (de) | 1990-01-15 |
| SE503111C2 (sv) | 1996-03-25 |
| FR2566397A1 (fr) | 1985-12-27 |
| SE8503097D0 (sv) | 1985-06-20 |
| GB2160869A (en) | 1986-01-02 |
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