CS277405B6 - Peptides with 1-amino-1-cycloalkane carboxylic acid - Google Patents
Peptides with 1-amino-1-cycloalkane carboxylic acid Download PDFInfo
- Publication number
- CS277405B6 CS277405B6 CS864332A CS433286A CS277405B6 CS 277405 B6 CS277405 B6 CS 277405B6 CS 864332 A CS864332 A CS 864332A CS 433286 A CS433286 A CS 433286A CS 277405 B6 CS277405 B6 CS 277405B6
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- amino
- alanine
- residue
- ethyl ester
- cyclopentanecarboxylic acid
- Prior art date
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- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 33
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- 210000004556 brain Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 229940125532 enzyme inhibitor Drugs 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- WASOFSSPTCAPTC-UHFFFAOYSA-N ethyl 1-amino-2-(2-aminoacetyl)cyclopentane-1-carboxylate;hydrobromide Chemical compound Br.CCOC(=O)C1(N)CCCC1C(=O)CN WASOFSSPTCAPTC-UHFFFAOYSA-N 0.000 description 1
- KGFYDGSPGNELND-HRSFDNERSA-N ethyl 1-amino-2-[(2s)-2-[[(2s)-1-(2-aminoacetyl)pyrrolidine-2-carbonyl]amino]propanoyl]cyclopentane-1-carboxylate;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.CCOC(=O)C1(N)CCCC1C(=O)[C@H](C)NC(=O)[C@H]1N(C(=O)CN)CCC1 KGFYDGSPGNELND-HRSFDNERSA-N 0.000 description 1
- KQPZUHXMBHGLTA-FTIOSWPQSA-N ethyl 1-amino-2-[(2s)-2-[[(2s)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoyl]cyclohexane-1-carboxylate Chemical compound CCOC(=O)C1(N)CCCCC1C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1 KQPZUHXMBHGLTA-FTIOSWPQSA-N 0.000 description 1
- DPWIISOVPJXXLQ-KKEXSUDUSA-N ethyl 1-amino-2-[(2s)-2-[[(2s)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoyl]cyclopentane-1-carboxylate Chemical compound CCOC(=O)C1(N)CCCC1C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1 DPWIISOVPJXXLQ-KKEXSUDUSA-N 0.000 description 1
- INNOORNVLAWKJU-DOOHWEDMSA-N ethyl 1-amino-2-[2-[[(2s)-2-(phenylmethoxycarbonylamino)propanoyl]amino]acetyl]cyclopentane-1-carboxylate Chemical compound CCOC(=O)C1(N)CCCC1C(=O)CNC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1 INNOORNVLAWKJU-DOOHWEDMSA-N 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- IIECMOSBWZNVMW-ZFWWWQNUSA-N methyl (2s)-2-[[(2s)-1-[2-(phenylmethoxycarbonylamino)acetyl]pyrrolidine-2-carbonyl]amino]propanoate Chemical compound COC(=O)[C@H](C)NC(=O)[C@@H]1CCCN1C(=O)CNC(=O)OCC1=CC=CC=C1 IIECMOSBWZNVMW-ZFWWWQNUSA-N 0.000 description 1
- ZCFWQJLPKNJPMG-BONVTDFDSA-N methyl (2s)-2-[[(2s)-2-acetamido-3-(4-acetyloxyphenyl)propanoyl]amino]propanoate Chemical compound COC(=O)[C@H](C)NC(=O)[C@@H](NC(C)=O)CC1=CC=C(OC(C)=O)C=C1 ZCFWQJLPKNJPMG-BONVTDFDSA-N 0.000 description 1
- QVKTXSQKSHOWGE-IHFXXZKVSA-N methyl 1-amino-2-[(2s)-2-[[(2s)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoyl]cyclobutane-1-carboxylate Chemical compound COC(=O)C1(N)CCC1C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1 QVKTXSQKSHOWGE-IHFXXZKVSA-N 0.000 description 1
- SGXOPTPGZBLQAY-UHFFFAOYSA-N methyl 1-aminocyclobutane-1-carboxylate Chemical compound COC(=O)C1(N)CCC1 SGXOPTPGZBLQAY-UHFFFAOYSA-N 0.000 description 1
- VLNNACMZTDZCFH-UHFFFAOYSA-N methyl 1-aminocyclopentane-1-carboxylate Chemical compound COC(=O)C1(N)CCCC1 VLNNACMZTDZCFH-UHFFFAOYSA-N 0.000 description 1
- JDXWAHHAIDEOHK-GNZRSQJKSA-N methyl 2-[(2s)-2-acetamido-3-(4-acetyloxyphenyl)propanoyl]-1-aminocyclopentane-1-carboxylate Chemical compound COC(=O)C1(N)CCCC1C(=O)[C@@H](NC(C)=O)CC1=CC=C(OC(C)=O)C=C1 JDXWAHHAIDEOHK-GNZRSQJKSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000009054 pathological process Effects 0.000 description 1
- 230000035778 pathophysiological process Effects 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001050 pharmacotherapy Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 230000001810 trypsinlike Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06086—Dipeptides with the first amino acid being basic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS864332A CS277405B6 (en) | 1986-06-12 | 1986-06-12 | Peptides with 1-amino-1-cycloalkane carboxylic acid |
| CA000537992A CA1308515C (en) | 1986-06-12 | 1987-05-26 | Peptide derivatives and processes for their preparation |
| EP87305065A EP0249434B1 (de) | 1986-06-12 | 1987-06-09 | Peptidderivate und Verfahren zu deren Herstellung |
| AT8787305065T ATE105300T1 (de) | 1986-06-12 | 1987-06-09 | Peptidderivate und verfahren zu deren herstellung. |
| DE3789729T DE3789729T2 (de) | 1986-06-12 | 1987-06-09 | Peptidderivate und Verfahren zu deren Herstellung. |
| JP62144207A JPH082916B2 (ja) | 1986-06-12 | 1987-06-11 | ペプチド誘導体類及びそれらの製造方法 |
| US07/062,300 US4898930A (en) | 1986-06-12 | 1987-06-12 | Peptide derivatives and processes for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS864332A CS277405B6 (en) | 1986-06-12 | 1986-06-12 | Peptides with 1-amino-1-cycloalkane carboxylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS433286A3 CS433286A3 (en) | 1992-08-12 |
| CS277405B6 true CS277405B6 (en) | 1993-03-17 |
Family
ID=5385817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS864332A CS277405B6 (en) | 1986-06-12 | 1986-06-12 | Peptides with 1-amino-1-cycloalkane carboxylic acid |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4898930A (de) |
| EP (1) | EP0249434B1 (de) |
| JP (1) | JPH082916B2 (de) |
| AT (1) | ATE105300T1 (de) |
| CA (1) | CA1308515C (de) |
| CS (1) | CS277405B6 (de) |
| DE (1) | DE3789729T2 (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000005260A1 (en) * | 1998-07-20 | 2000-02-03 | Societe De Conseils De Recherches Et D'applications Scientifiques Sas | Peptide analogues of pacap |
| RU2142813C1 (ru) * | 1999-03-25 | 1999-12-20 | НИИ наркологии МЗРФ | Тетрапептид trp-nle-asp-phenh-ch(ch3)2, обладающий анксиолитической активностью |
| CN1164611C (zh) * | 2002-06-17 | 2004-09-01 | 厦门大学 | 丙-谷二肽合成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3704288A (en) * | 1970-04-16 | 1972-11-28 | Joseph A Skorcz | L-tyrosyl-1-aminocyclopentane-1-carbonyl-l-phenylalanine |
| NO774303L (no) * | 1976-12-28 | 1978-06-29 | Troponwerke Gmbh & Co Kg | Nye dehydrooligopeptider, fremgangsmaate til deres fremstilling samt deres anvendelse som legemiddel |
| US4278595A (en) * | 1979-12-10 | 1981-07-14 | Vega Laboratories, Inc. | Orally active MIF analogs with an effect on the central nervous system |
| US4690936A (en) * | 1980-03-05 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
| CS231227B1 (en) * | 1982-10-01 | 1984-10-15 | Evzen Kasafirek | 2,5-pierazindion derivatives |
| DE3300774A1 (de) * | 1983-01-12 | 1984-07-12 | Hoechst Ag, 6230 Frankfurt | Neue spirocyclische aminosaeuren, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung sowie neue spirocyclische aminosaeuren als zwischenprodukte und verfahren zu deren herstellung |
| DE3485587D1 (de) * | 1983-08-16 | 1992-04-23 | Univ Georgia Res Found | Herstellung von aminocyclopropancarbonsaeuren und von peptiden. |
| EP0212550A3 (de) * | 1985-08-14 | 1989-05-10 | G.D. Searle & Co. | Substituierte Dipeptidamide |
-
1986
- 1986-06-12 CS CS864332A patent/CS277405B6/cs not_active IP Right Cessation
-
1987
- 1987-05-26 CA CA000537992A patent/CA1308515C/en not_active Expired - Fee Related
- 1987-06-09 EP EP87305065A patent/EP0249434B1/de not_active Expired - Lifetime
- 1987-06-09 AT AT8787305065T patent/ATE105300T1/de not_active IP Right Cessation
- 1987-06-09 DE DE3789729T patent/DE3789729T2/de not_active Expired - Fee Related
- 1987-06-11 JP JP62144207A patent/JPH082916B2/ja not_active Expired - Lifetime
- 1987-06-12 US US07/062,300 patent/US4898930A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE3789729D1 (de) | 1994-06-09 |
| JPH082916B2 (ja) | 1996-01-17 |
| CA1308515C (en) | 1992-10-06 |
| ATE105300T1 (de) | 1994-05-15 |
| DE3789729T2 (de) | 1994-08-18 |
| EP0249434A2 (de) | 1987-12-16 |
| CS433286A3 (en) | 1992-08-12 |
| EP0249434A3 (en) | 1990-01-24 |
| US4898930A (en) | 1990-02-06 |
| JPS633000A (ja) | 1988-01-07 |
| EP0249434B1 (de) | 1994-05-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF00 | In force as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20000612 |