NO774303L - Nye dehydrooligopeptider, fremgangsmaate til deres fremstilling samt deres anvendelse som legemiddel - Google Patents
Nye dehydrooligopeptider, fremgangsmaate til deres fremstilling samt deres anvendelse som legemiddelInfo
- Publication number
- NO774303L NO774303L NO774303A NO774303A NO774303L NO 774303 L NO774303 L NO 774303L NO 774303 A NO774303 A NO 774303A NO 774303 A NO774303 A NO 774303A NO 774303 L NO774303 L NO 774303L
- Authority
- NO
- Norway
- Prior art keywords
- group
- optionally substituted
- hydrogen atom
- tyrosine
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000003814 drug Substances 0.000 title description 4
- -1 cyclopentylidene- Chemical class 0.000 claims description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 206010028980 Neoplasm Diseases 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 239000000969 carrier Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 7
- 125000001769 aryl amino group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 claims description 5
- XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical class OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 claims description 5
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000005504 styryl group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentenylidene Natural products C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 230000000451 tissue damage Effects 0.000 claims 2
- 231100000827 tissue damage Toxicity 0.000 claims 2
- 241000282412 Homo Species 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000009089 cytolysis Effects 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 229960004441 tyrosine Drugs 0.000 description 67
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 235000004279 alanine Nutrition 0.000 description 23
- 229960003767 alanine Drugs 0.000 description 23
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000013543 active substance Substances 0.000 description 18
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 125000005843 halogen group Chemical group 0.000 description 12
- BWQBTJRPSDVWIR-UHFFFAOYSA-N 4-benzylidene-2-methyl-1,3-oxazol-5-one Chemical compound O=C1OC(C)=NC1=CC1=CC=CC=C1 BWQBTJRPSDVWIR-UHFFFAOYSA-N 0.000 description 11
- 239000003085 diluting agent Substances 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 11
- 235000011121 sodium hydroxide Nutrition 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 229940024606 amino acid Drugs 0.000 description 8
- 235000001014 amino acid Nutrition 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 150000001413 amino acids Chemical class 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 210000001519 tissue Anatomy 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- MWZPENIJLUWBSY-VIFPVBQESA-N methyl L-tyrosinate Chemical compound COC(=O)[C@@H](N)CC1=CC=C(O)C=C1 MWZPENIJLUWBSY-VIFPVBQESA-N 0.000 description 6
- 239000000825 pharmaceutical preparation Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- DIGHFXIWRPMGSA-NSHDSACASA-N tert-butyl (2s)-2-amino-3-(4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 DIGHFXIWRPMGSA-NSHDSACASA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- FNIJNQKPASQIFL-UHFFFAOYSA-N 2-methyl-4-(thiophen-2-ylmethylidene)-1,3-oxazol-5-one Chemical compound O=C1OC(C)=NC1=CC1=CC=CS1 FNIJNQKPASQIFL-UHFFFAOYSA-N 0.000 description 5
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- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 3
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Classifications
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- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- 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
- C07D307/38—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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- 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
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- 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
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- 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
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Landscapes
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762659114 DE2659114A1 (de) | 1976-12-28 | 1976-12-28 | Neue dehydrooligopeptide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE19772745584 DE2745584A1 (de) | 1977-10-11 | 1977-10-11 | Neue dehydrooligopeptide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO774303L true NO774303L (no) | 1978-06-29 |
Family
ID=25771313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO774303A NO774303L (no) | 1976-12-28 | 1977-12-14 | Nye dehydrooligopeptider, fremgangsmaate til deres fremstilling samt deres anvendelse som legemiddel |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4276288A (es) |
| JP (1) | JPS5382721A (es) |
| AT (1) | AT360185B (es) |
| AU (1) | AU509040B2 (es) |
| DK (1) | DK581577A (es) |
| ES (1) | ES465518A1 (es) |
| FI (1) | FI773922A (es) |
| FR (1) | FR2376128A1 (es) |
| GB (1) | GB1568137A (es) |
| NL (1) | NL7714440A (es) |
| NO (1) | NO774303L (es) |
| SE (1) | SE7714782L (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1141374A (en) * | 1978-07-03 | 1983-02-15 | Charles H. Stammer | Preparation of dehydropeptides |
| DE2904512A1 (de) * | 1979-02-07 | 1980-08-28 | Troponwerke Gmbh & Co Kg | Dehydropeptide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4906615A (en) * | 1980-12-18 | 1990-03-06 | Schering Corporation | Substituted dipeptides as inhibitors of enkephalinases |
| US4610816A (en) * | 1980-12-18 | 1986-09-09 | Schering Corporation | Substituted dipeptides as inhibitors of enkephalinases |
| US4465668A (en) * | 1981-02-27 | 1984-08-14 | Asahi Kasei Kogyo Kabushiki Kaisha | Method for improving intestinal absorption of cephalosporin derivatives |
| CS277405B6 (en) * | 1986-06-12 | 1993-03-17 | Vyzk Ustav Farm Biochem Sp | Peptides with 1-amino-1-cycloalkane carboxylic acid |
| US4970297A (en) * | 1987-03-13 | 1990-11-13 | Syntex (U.S.A.) Inc. | Transglutaminase inhibitors |
| US4996348A (en) * | 1987-07-29 | 1991-02-26 | Ciba-Geigy Corporation | N-alkenoyl enamides, their preparation and the use thereof |
-
1977
- 1977-12-14 NO NO774303A patent/NO774303L/no unknown
- 1977-12-21 GB GB53180/77A patent/GB1568137A/en not_active Expired
- 1977-12-22 AU AU31913/77A patent/AU509040B2/en not_active Expired
- 1977-12-23 FI FI773922A patent/FI773922A/fi not_active Application Discontinuation
- 1977-12-27 FR FR7739354A patent/FR2376128A1/fr active Granted
- 1977-12-27 DK DK581577A patent/DK581577A/da unknown
- 1977-12-27 SE SE7714782A patent/SE7714782L/xx unknown
- 1977-12-27 AT AT932677A patent/AT360185B/de not_active IP Right Cessation
- 1977-12-27 NL NL7714440A patent/NL7714440A/xx not_active Application Discontinuation
- 1977-12-28 JP JP15750877A patent/JPS5382721A/ja active Pending
- 1977-12-28 ES ES465518A patent/ES465518A1/es not_active Expired
-
1979
- 1979-10-09 US US06/082,451 patent/US4276288A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ATA932677A (de) | 1980-05-15 |
| NL7714440A (nl) | 1978-06-30 |
| SE7714782L (sv) | 1978-06-29 |
| GB1568137A (en) | 1980-05-29 |
| DK581577A (da) | 1978-06-29 |
| US4276288A (en) | 1981-06-30 |
| JPS5382721A (en) | 1978-07-21 |
| AU3191377A (en) | 1979-06-28 |
| AU509040B2 (en) | 1980-04-17 |
| FR2376128B1 (es) | 1980-06-13 |
| FR2376128A1 (fr) | 1978-07-28 |
| FI773922A (fi) | 1978-06-29 |
| AT360185B (de) | 1980-12-29 |
| ES465518A1 (es) | 1979-05-01 |
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