CA1325633C - Derivatives of glutamic acid and aspartic acid having antagonistic activities towards bioactive polypeptides and method for their preparation - Google Patents
Derivatives of glutamic acid and aspartic acid having antagonistic activities towards bioactive polypeptides and method for their preparationInfo
- Publication number
- CA1325633C CA1325633C CA000484341A CA484341A CA1325633C CA 1325633 C CA1325633 C CA 1325633C CA 000484341 A CA000484341 A CA 000484341A CA 484341 A CA484341 A CA 484341A CA 1325633 C CA1325633 C CA 1325633C
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- Canada
- Prior art keywords
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- compounds
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- Prior art date
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- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 10
- 102000004196 processed proteins & peptides Human genes 0.000 title claims abstract description 10
- 230000000975 bioactive effect Effects 0.000 title claims abstract description 9
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 title claims abstract description 7
- 229920001184 polypeptide Polymers 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 15
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical class OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 235000003704 aspartic acid Nutrition 0.000 title claims description 3
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 title claims description 3
- 230000003042 antagnostic effect Effects 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- 238000011282 treatment Methods 0.000 claims abstract description 36
- WHUUTDBJXJRKMK-UHFFFAOYSA-N glutamic acid Chemical class OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 3
- 230000000694 effects Effects 0.000 claims description 30
- 241001465754 Metazoa Species 0.000 claims description 26
- 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 claims description 24
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
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- RJEUERNNQHNSKG-CCKFTAQKSA-N (2s)-2-amino-n-[(2r)-1-[[2-[[(2s)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-1-oxopropan-2-yl]-3-(4-hydroxyphenyl)propanamide Chemical compound C([C@H](N)C(=O)N[C@H](C)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)C1=CC=C(O)C=C1 RJEUERNNQHNSKG-CCKFTAQKSA-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
- RGPBQGGBWIMGMA-BJMVGYQFSA-N 5-[(e)-[5-(4-bromophenyl)-6-hydroxy-3,6-dihydro-1,3,4-oxadiazin-2-ylidene]methyl]-1h-pyrimidine-2,4-dione Chemical compound OC1O\C(=C\C=2C(NC(=O)NC=2)=O)NN=C1C1=CC=C(Br)C=C1 RGPBQGGBWIMGMA-BJMVGYQFSA-N 0.000 description 1
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- 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
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- YDGWVHHYXBMDAD-UHFFFAOYSA-N ethyl formate;propan-2-one Chemical compound CC(C)=O.CCOC=O YDGWVHHYXBMDAD-UHFFFAOYSA-N 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229960005195 morphine hydrochloride Drugs 0.000 description 1
- XELXKCKNPPSFNN-BJWPBXOKSA-N morphine hydrochloride trihydrate Chemical compound O.O.O.Cl.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O XELXKCKNPPSFNN-BJWPBXOKSA-N 0.000 description 1
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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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT67644-A/84 | 1984-06-25 | ||
| 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-A/84 | 1984-10-26 | ||
| 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA1325633C true CA1325633C (en) | 1993-12-28 |
Family
ID=26329809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000484341A Expired - Fee Related CA1325633C (en) | 1984-06-25 | 1985-06-18 | Derivatives of glutamic acid and aspartic acid having antagonistic activities towards bioactive polypeptides and method for their preparation |
Country Status (15)
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 |
| 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 |
| IT1196849B (it) * | 1986-12-16 | 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 |
| 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 |
| WO1993012791A1 (en) * | 1991-12-20 | 1993-07-08 | Merck Sharp & Dohme Limited | Central cholecystokinin antagonists having pharmaceutical activity |
| 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 |
| KR101165288B1 (ko) * | 2003-11-27 | 2012-07-19 | 가부시키가이샤 시세이도 | 부전각화 억제제 |
| 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 |
| WO2020124351A1 (zh) * | 2018-12-18 | 2020-06-25 | 黄华成 | 一种谷氨酰胺衍生物在制备动物饲料添加剂中的应用 |
| US20220304352A1 (en) * | 2019-08-15 | 2022-09-29 | Firmenich Sa | Taste-modifying compounds and uses thereof |
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 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-06-07 | 1976-04-13 |
-
1985
- 1985-06-17 NZ NZ212436A patent/NZ212436A/xx unknown
- 1985-06-17 IE IE1502/85A patent/IE57892B1/en not_active IP Right Cessation
- 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 AT AT0186985A patent/AT390949B/de not_active IP Right Cessation
- 1985-06-24 DE DE19853522506 patent/DE3522506A1/de active Granted
- 1985-06-24 DK DK285685A patent/DK285685A/da not_active Application Discontinuation
- 1985-06-24 AU AU44109/85A patent/AU566601B2/en not_active Ceased
- 1985-06-25 NL NL8501829A patent/NL8501829A/nl not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU566601B2 (en) | 1987-10-22 |
| DK285685D0 (da) | 1985-06-24 |
| SE8503097L (sv) | 1985-12-26 |
| AT390949B (de) | 1990-07-25 |
| DE3522506A1 (de) | 1986-01-02 |
| IE851502L (en) | 1985-12-22 |
| US4791215A (en) | 1988-12-13 |
| NZ212436A (en) | 1989-04-26 |
| AU4410985A (en) | 1986-01-02 |
| GB2160869A (en) | 1986-01-02 |
| CH674203A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-05-15 |
| NL8501829A (nl) | 1986-01-16 |
| FR2566397B1 (fr) | 1988-08-05 |
| BE902726A (fr) | 1985-10-16 |
| IE57892B1 (en) | 1993-05-05 |
| ATA186985A (de) | 1990-01-15 |
| SE503111C2 (sv) | 1996-03-25 |
| SE8503097D0 (sv) | 1985-06-20 |
| DE3522506C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-03-10 |
| ES544462A0 (es) | 1986-03-16 |
| FR2566397A1 (fr) | 1985-12-27 |
| DK285685A (da) | 1985-12-26 |
| GB2160869B (en) | 1988-03-16 |
| GB8515555D0 (en) | 1985-07-24 |
| ES8604859A1 (es) | 1986-03-16 |
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