NO831475L - Fremgangsmaate ved fremstilling av n-(n`-(2-klorethyl)-n`-nitroso-carbamoyl)-oligopeptidestere og -amider - Google Patents
Fremgangsmaate ved fremstilling av n-(n`-(2-klorethyl)-n`-nitroso-carbamoyl)-oligopeptidestere og -amiderInfo
- Publication number
- NO831475L NO831475L NO831475A NO831475A NO831475L NO 831475 L NO831475 L NO 831475L NO 831475 A NO831475 A NO 831475A NO 831475 A NO831475 A NO 831475A NO 831475 L NO831475 L NO 831475L
- Authority
- NO
- Norway
- Prior art keywords
- nitroso
- carbamoyl
- chloroethyl
- ppm
- methyl ester
- Prior art date
Links
- 150000001408 amides Chemical class 0.000 title claims abstract description 11
- -1 2-CHLORETHYL Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims 4
- 238000002360 preparation method Methods 0.000 title description 10
- 108010038807 Oligopeptides Proteins 0.000 claims abstract description 19
- 102000015636 Oligopeptides Human genes 0.000 claims abstract description 19
- 150000001413 amino acids Chemical class 0.000 claims abstract description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 150000004702 methyl esters Chemical class 0.000 claims abstract description 3
- 125000003368 amide group Chemical group 0.000 claims abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 51
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 14
- 229940024606 amino acid Drugs 0.000 claims description 11
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 6
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 3
- VQVHVJMFEBRIPO-UHFFFAOYSA-N 1-(2-chloroethyl)-3-diazo-1-nitrosourea Chemical compound ClCCN(N=O)C(=O)N=[N+]=[N-] VQVHVJMFEBRIPO-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 235000001014 amino acid Nutrition 0.000 abstract description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 19
- 238000001819 mass spectrum Methods 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 229960005190 phenylalanine Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 3
- CEMZBWPSKYISTN-YFKPBYRVSA-N methyl (2s)-2-amino-3-methylbutanoate Chemical compound COC(=O)[C@@H](N)C(C)C CEMZBWPSKYISTN-YFKPBYRVSA-N 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 2
- VPZXBVLAVMBEQI-VKHMYHEASA-N Glycyl-alanine Chemical compound OC(=O)[C@H](C)NC(=O)CN VPZXBVLAVMBEQI-VKHMYHEASA-N 0.000 description 2
- HSQGMTRYSIHDAC-BQBZGAKWSA-N Leu-Ala Chemical compound CC(C)C[C@H](N)C(=O)N[C@@H](C)C(O)=O HSQGMTRYSIHDAC-BQBZGAKWSA-N 0.000 description 2
- 108010079364 N-glycylalanine Proteins 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- VPZXBVLAVMBEQI-UHFFFAOYSA-N glycyl-DL-alpha-alanine Natural products OC(=O)C(C)NC(=O)CN VPZXBVLAVMBEQI-UHFFFAOYSA-N 0.000 description 2
- 108010071185 leucyl-alanine Proteins 0.000 description 2
- UIHPNZDZCOEZEN-YFKPBYRVSA-N methyl (2s)-2-amino-4-methylsulfanylbutanoate Chemical compound COC(=O)[C@@H](N)CCSC UIHPNZDZCOEZEN-YFKPBYRVSA-N 0.000 description 2
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- FVLVBPDQNARYJU-UHFFFAOYSA-N semustine Chemical compound CC1CCC(NC(=O)N(CCCl)N=O)CC1 FVLVBPDQNARYJU-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229960004295 valine Drugs 0.000 description 2
- VJXDBZDWOCSPNM-VIFPVBQESA-N (2s)-2-[(2-aminoacetyl)amino]-3-(4-hydroxyphenyl)propanamide Chemical compound NCC(=O)N[C@H](C(N)=O)CC1=CC=C(O)C=C1 VJXDBZDWOCSPNM-VIFPVBQESA-N 0.000 description 1
- RDIKFPRVLJLMER-BQBZGAKWSA-N Ala-Leu Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)[C@H](C)N RDIKFPRVLJLMER-BQBZGAKWSA-N 0.000 description 1
- 102100021906 Cyclin-O Human genes 0.000 description 1
- XBGGUPMXALFZOT-VIFPVBQESA-N Gly-Tyr Chemical compound NCC(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 XBGGUPMXALFZOT-VIFPVBQESA-N 0.000 description 1
- 101000897441 Homo sapiens Cyclin-O Proteins 0.000 description 1
- UCDHVOALNXENLC-KBPBESRZSA-N Leu-Gly-Tyr Chemical compound CC(C)C[C@H]([NH3+])C(=O)NCC(=O)N[C@H](C([O-])=O)CC1=CC=C(O)C=C1 UCDHVOALNXENLC-KBPBESRZSA-N 0.000 description 1
- GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- XBGGUPMXALFZOT-UHFFFAOYSA-N glycyl-L-tyrosine hemihydrate Natural products NCC(=O)NC(C(O)=O)CC1=CC=C(O)C=C1 XBGGUPMXALFZOT-UHFFFAOYSA-N 0.000 description 1
- 229940043257 glycylglycine Drugs 0.000 description 1
- 108010087823 glycyltyrosine Proteins 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960004452 methionine Drugs 0.000 description 1
- QVDXUKJJGUSGLS-LURJTMIESA-N methyl L-leucinate Chemical compound COC(=O)[C@@H](N)CC(C)C QVDXUKJJGUSGLS-LURJTMIESA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- OSTGTTZJOCZWJG-UHFFFAOYSA-N nitrosourea Chemical compound NC(=O)N=NO OSTGTTZJOCZWJG-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100001274 therapeutic index Toxicity 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
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or 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
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3134923A DE3134923C1 (de) | 1981-09-03 | 1981-09-03 | N-[N'-(2-Chloraethyl)-N'-nitroso-carbamoyl]-oligopeptidester und -amide und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO831475L true NO831475L (no) | 1983-04-26 |
Family
ID=6140795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO831475A NO831475L (no) | 1981-09-03 | 1983-04-26 | Fremgangsmaate ved fremstilling av n-(n`-(2-klorethyl)-n`-nitroso-carbamoyl)-oligopeptidestere og -amider |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0074103B1 (ja) |
| JP (1) | JPS58501769A (ja) |
| AT (1) | ATE17735T1 (ja) |
| AU (1) | AU8900982A (ja) |
| BR (1) | BR8207845A (ja) |
| DD (1) | DD209192A5 (ja) |
| DE (2) | DE3134923C1 (ja) |
| DK (1) | DK77583A (ja) |
| FI (1) | FI830768L (ja) |
| GR (1) | GR76534B (ja) |
| HU (1) | HU190643B (ja) |
| IL (1) | IL66689A (ja) |
| MC (1) | MC1526A1 (ja) |
| NO (1) | NO831475L (ja) |
| WO (1) | WO1983000860A1 (ja) |
| YU (1) | YU195982A (ja) |
| ZA (1) | ZA826481B (ja) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2987263A (en) * | 1959-02-16 | 1961-06-06 | William R Senn | Apparatus for granulating phosphate rock fertilizer or the like |
| FR2540491A1 (fr) * | 1983-02-08 | 1984-08-10 | Centre Nat Rech Scient | Nouvelles nitrosourees, leur procede de preparation et leur application therapeutique |
| JPS6288472A (ja) * | 1985-10-14 | 1987-04-22 | Sharp Corp | フアクシミリの読取記録装置 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5113722A (en) * | 1974-07-23 | 1976-02-03 | Suami T | Shinkina nitoroshinyosojudotaino seizoho |
-
1981
- 1981-09-03 DE DE3134923A patent/DE3134923C1/de not_active Expired
-
1982
- 1982-08-30 GR GR69161A patent/GR76534B/el unknown
- 1982-08-31 YU YU01959/82A patent/YU195982A/xx unknown
- 1982-09-01 IL IL66689A patent/IL66689A/xx unknown
- 1982-09-03 WO PCT/EP1982/000191 patent/WO1983000860A1/en active Application Filing
- 1982-09-03 AU AU89009/82A patent/AU8900982A/en not_active Abandoned
- 1982-09-03 EP EP82108166A patent/EP0074103B1/de not_active Expired
- 1982-09-03 DD DD82243011A patent/DD209192A5/de unknown
- 1982-09-03 AT AT82108166T patent/ATE17735T1/de not_active IP Right Cessation
- 1982-09-03 BR BR8207845A patent/BR8207845A/pt unknown
- 1982-09-03 MC MC82EP8200191D patent/MC1526A1/xx unknown
- 1982-09-03 JP JP57502693A patent/JPS58501769A/ja active Pending
- 1982-09-03 DE DE8282108166T patent/DE3268831D1/de not_active Expired
- 1982-09-03 HU HU823208A patent/HU190643B/hu unknown
- 1982-09-03 ZA ZA826481A patent/ZA826481B/xx unknown
-
1983
- 1983-02-22 DK DK77583A patent/DK77583A/da not_active Application Discontinuation
- 1983-03-08 FI FI830768A patent/FI830768L/fi not_active Application Discontinuation
- 1983-04-26 NO NO831475A patent/NO831475L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU195982A (en) | 1985-08-31 |
| WO1983000860A1 (en) | 1983-03-17 |
| DK77583D0 (da) | 1983-02-22 |
| EP0074103B1 (de) | 1986-01-29 |
| ZA826481B (en) | 1983-07-27 |
| EP0074103A1 (de) | 1983-03-16 |
| DE3268831D1 (en) | 1986-03-13 |
| FI830768A0 (fi) | 1983-03-08 |
| JPS58501769A (ja) | 1983-10-20 |
| DD209192A5 (de) | 1984-04-25 |
| AU8900982A (en) | 1983-03-28 |
| HU190643B (en) | 1986-09-29 |
| DE3134923C1 (de) | 1983-06-09 |
| FI830768L (fi) | 1983-03-08 |
| DK77583A (da) | 1983-03-17 |
| MC1526A1 (fr) | 1984-04-13 |
| BR8207845A (pt) | 1983-08-30 |
| GR76534B (ja) | 1984-08-10 |
| ATE17735T1 (de) | 1986-02-15 |
| IL66689A (en) | 1986-02-28 |
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