FR2487343A1 - Nouveaux nitroso-carbamates, procede pour leur preparation et application a la synthese selective de n-nitrosourees - Google Patents
Nouveaux nitroso-carbamates, procede pour leur preparation et application a la synthese selective de n-nitrosourees Download PDFInfo
- Publication number
- FR2487343A1 FR2487343A1 FR8016453A FR8016453A FR2487343A1 FR 2487343 A1 FR2487343 A1 FR 2487343A1 FR 8016453 A FR8016453 A FR 8016453A FR 8016453 A FR8016453 A FR 8016453A FR 2487343 A1 FR2487343 A1 FR 2487343A1
- Authority
- FR
- France
- Prior art keywords
- radical
- formula
- compounds
- radicals
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 229960001052 streptozocin Drugs 0.000 title claims abstract description 12
- 229960001480 chlorozotocin Drugs 0.000 title claims abstract description 6
- 230000009935 nitrosation Effects 0.000 title claims description 4
- 238000007034 nitrosation reaction Methods 0.000 title claims description 4
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 title abstract description 11
- MKQWTWSXVILIKJ-LXGUWJNJSA-N Chlorozotocin Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](C=O)NC(=O)N(N=O)CCCl MKQWTWSXVILIKJ-LXGUWJNJSA-N 0.000 title abstract description 5
- 230000000247 oncostatic effect Effects 0.000 title abstract description 5
- DVBFAFMWCGVKDU-UHFFFAOYSA-N nitrosocarbamic acid Chemical compound OC(=O)NN=O DVBFAFMWCGVKDU-UHFFFAOYSA-N 0.000 title abstract 2
- OSTGTTZJOCZWJG-UHFFFAOYSA-N nitrosourea Chemical compound NC(=O)N=NO OSTGTTZJOCZWJG-UHFFFAOYSA-N 0.000 title description 5
- 239000000543 intermediate Substances 0.000 title description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 title 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title 1
- -1 cyanomethyl Chemical group 0.000 claims abstract description 52
- 229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 150000001412 amines Chemical class 0.000 claims abstract description 8
- 102100021906 Cyclin-O Human genes 0.000 claims abstract description 6
- 101000897441 Homo sapiens Cyclin-O Proteins 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000005544 phthalimido group Chemical group 0.000 claims abstract description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000005493 quinolyl group Chemical group 0.000 claims abstract description 3
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 3
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- 230000015572 biosynthetic process Effects 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 18
- 238000003786 synthesis reaction Methods 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000004157 Nitrosyl chloride Substances 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 claims description 4
- 235000019392 nitrosyl chloride Nutrition 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- YASNUXZKZNVXIS-CBNXCZCTSA-N [(3ar,6r,6ar)-4-[[2-chloroethyl(nitroso)carbamoyl]amino]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 4-nitrobenzoate Chemical compound C([C@@H]1[C@H]2OC(O[C@H]2C(NC(=O)N(CCCl)N=O)O1)(C)C)OC(=O)C1=CC=C([N+]([O-])=O)C=C1 YASNUXZKZNVXIS-CBNXCZCTSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 239000011669 selenium Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 1
- HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 150000003254 radicals Chemical class 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 11
- 238000004809 thin layer chromatography Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229960002317 succinimide Drugs 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 0 NC(*1)C(N)OC1N Chemical compound NC(*1)C(N)OC1N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- XNMDTRBCRPPMIY-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl)-methylcarbamic acid Chemical compound OC(=O)N(C)N1C(=O)CCC1=O XNMDTRBCRPPMIY-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- WJSDAFAYDXCQLE-UHFFFAOYSA-N (2,4,5-trichlorophenyl) n-(2-chloroethyl)-n-nitrosocarbamate Chemical compound ClCCN(N=O)C(=O)OC1=CC(Cl)=C(Cl)C=C1Cl WJSDAFAYDXCQLE-UHFFFAOYSA-N 0.000 description 2
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 description 2
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- QMJJEUBKQJZIGH-PFGBXZAXSA-N [(3r,4r,5r)-4,5-diacetyloxy-6-[[2-chloroethyl(nitroso)carbamoyl]amino]oxan-3-yl] acetate Chemical class CC(=O)O[C@@H]1COC(NC(=O)N(CCCl)N=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O QMJJEUBKQJZIGH-PFGBXZAXSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229960002442 glucosamine Drugs 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- CMULIYHPMNYIDD-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) n-(2-chloroethyl)carbamate Chemical compound ClCCNC(=O)OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CMULIYHPMNYIDD-UHFFFAOYSA-N 0.000 description 1
- WPRAEAZFPZVJRV-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) n-methyl-n-nitrosocarbamate Chemical compound O=NN(C)C(=O)OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl WPRAEAZFPZVJRV-UHFFFAOYSA-N 0.000 description 1
- FTCSFJOFZGYXFX-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl FTCSFJOFZGYXFX-UHFFFAOYSA-N 0.000 description 1
- OHDYMRIIHXGSEX-UHFFFAOYSA-N (2,4,5-trichlorophenyl) n-(2-chloroethyl)carbamate Chemical compound ClCCNC(=O)OC1=CC(Cl)=C(Cl)C=C1Cl OHDYMRIIHXGSEX-UHFFFAOYSA-N 0.000 description 1
- NFKDYWQXMAXPKK-UHFFFAOYSA-N (2,4,5-trichlorophenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC(Cl)=C(Cl)C=C1Cl NFKDYWQXMAXPKK-UHFFFAOYSA-N 0.000 description 1
- MZLZYXFTRYJBOP-UHFFFAOYSA-N (2-nitrophenyl) N-nitrosocarbamate Chemical class N(=O)NC(OC1=C(C=CC=C1)[N+](=O)[O-])=O MZLZYXFTRYJBOP-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
- ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 description 1
- WNKDMSWMBKGXNK-UHFFFAOYSA-N 2-chloroethyl(nitroso)carbamic acid Chemical compound OC(=O)N(N=O)CCCl WNKDMSWMBKGXNK-UHFFFAOYSA-N 0.000 description 1
- IGMMTYZWNUSEEU-UHFFFAOYSA-N 3-(2-chloroethyl)-1-cyclohexyl-1-nitrosourea Chemical compound ClCCNC(=O)N(N=O)C1CCCCC1 IGMMTYZWNUSEEU-UHFFFAOYSA-N 0.000 description 1
- KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- MXWFFHGKSSAIQL-UHFFFAOYSA-N cyclohexanamine;4-methylcyclohexan-1-amine Chemical compound NC1CCCCC1.CC1CCC(N)CC1 MXWFFHGKSSAIQL-UHFFFAOYSA-N 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 230000008034 disappearance Effects 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
- 238000004880 explosion Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- IZSWIFVPRPXNDN-UHFFFAOYSA-N methyl(nitroso)carbamic acid Chemical compound O=NN(C)C(O)=O IZSWIFVPRPXNDN-UHFFFAOYSA-N 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- LHKVDVFVJMYULK-UHFFFAOYSA-N nitrosylazide Chemical compound [N-]=[N+]=NN=O LHKVDVFVJMYULK-UHFFFAOYSA-N 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- FVLVBPDQNARYJU-UHFFFAOYSA-N semustine Chemical compound CC1CCC(NC(=O)N(CCCl)N=O)CC1 FVLVBPDQNARYJU-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/12—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8016453A FR2487343A1 (fr) | 1980-07-25 | 1980-07-25 | Nouveaux nitroso-carbamates, procede pour leur preparation et application a la synthese selective de n-nitrosourees |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8016453A FR2487343A1 (fr) | 1980-07-25 | 1980-07-25 | Nouveaux nitroso-carbamates, procede pour leur preparation et application a la synthese selective de n-nitrosourees |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2487343A1 true FR2487343A1 (fr) | 1982-01-29 |
| FR2487343B1 FR2487343B1 (enExample) | 1983-08-05 |
Family
ID=9244550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8016453A Granted FR2487343A1 (fr) | 1980-07-25 | 1980-07-25 | Nouveaux nitroso-carbamates, procede pour leur preparation et application a la synthese selective de n-nitrosourees |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2487343A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2614300A1 (fr) * | 1987-04-22 | 1988-10-28 | Sanofi Sa | Nouveau procede d'obtention de carbamates actives. |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000126A1 (de) * | 1977-06-15 | 1979-01-10 | Ciba-Geigy Ag | Glucofuranosid-6-yl-Nitrosoharnstoffderivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
-
1980
- 1980-07-25 FR FR8016453A patent/FR2487343A1/fr active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000126A1 (de) * | 1977-06-15 | 1979-01-10 | Ciba-Geigy Ag | Glucofuranosid-6-yl-Nitrosoharnstoffderivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
Non-Patent Citations (1)
| Title |
|---|
| CA1980 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2614300A1 (fr) * | 1987-04-22 | 1988-10-28 | Sanofi Sa | Nouveau procede d'obtention de carbamates actives. |
| EP0290313A1 (fr) * | 1987-04-22 | 1988-11-09 | Sanofi | Nouveau procédé d'obtention de nitrosocarbamates activés |
| US4883903A (en) * | 1987-04-22 | 1989-11-28 | Sanofi | Novel procedure for the preparation of activated nitrosocarbamates |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2487343B1 (enExample) | 1983-08-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0178980B1 (fr) | Dérivés de céphalosporines, procédé d'obtention et leur application à titre d'antibiotiques | |
| US6114569A (en) | Efficient synthesis of A 1,4-dihydro-2H-3,1-benzoxazin-2-one | |
| BE897952A (fr) | Procede de production d'imidazoles et intermediaires utilises a cet effet | |
| FR2487343A1 (fr) | Nouveaux nitroso-carbamates, procede pour leur preparation et application a la synthese selective de n-nitrosourees | |
| FR3021655A1 (fr) | Nouveaux composes de type 5-acylsulfanyl-histidine en tant que precurseurs des 5-sulfanylhistidines correspondantes et de leurs disulfures | |
| KR100399854B1 (ko) | 살절지동물성옥사디아진중간체 | |
| EP3110791B1 (fr) | Procede de preparation de derives d'acide 2,4-diamino-3-hydroxybutyrique | |
| EP0419348A1 (fr) | Nouveaux procédé de synthèse de dérivés d'oxazolopyridines | |
| BE660945A (enExample) | ||
| FR2597103A1 (fr) | Procede de preparation de derives d'oxazinobenzothiazine 6,6-dioxyde | |
| EP0955310B1 (fr) | Nouveaux dérivés de l'acide (3,4,7,8,9,10) -hexahydro-6,10-dioxo-6H-pyridazino /1,2-a/ /1,2/ diazépine-1-carboxylique, leur procédé de préparation et leur application à la préparation de médicaments | |
| EP0097550B1 (fr) | Procédé de préparation de dérivés de la cystamine à activité oncostatique | |
| FR2477142A1 (fr) | Nouveaux derives de la nitrosouree, leur procede de preparation et leur application en therapeutique | |
| EP0363263B1 (fr) | Procédé de préparation de dérives de l'acide propionique | |
| EP0155862A1 (fr) | Procédé de préparation de dérivés de l'acide carbamique | |
| EP0853612B1 (fr) | Derives d'alfa-hydrazinoacides et procede pour les fabriquer | |
| HU222843B1 (hu) | Nalfa-2-(4-nitro-fenil-szulfonil)-etoxi-karbonil-aminosavak és eljárások ilyen aminosavak előállítására | |
| EP0228356B1 (fr) | Nouveaux dérivés d'hydroxy-4 indole, leur procédé de préparation et leur utilisation | |
| EP0412014A1 (fr) | Dérivés benzothiaziniques, leur préparation et leurs applications comme médicaments ou comme intermédiaires de synthèse de médicaments | |
| KR930006198B1 (ko) | 신규 α-클로로케톤 유도체 및 그 제조법 | |
| KR960010101B1 (ko) | 4-오르소토릴티오세미카바지드의 제조방법 | |
| KR960007530B1 (ko) | 설포닐우레아 유도체의 제조방법 | |
| LU84564A1 (fr) | Nouveaux composes bicycliques et procede pour les preparer | |
| HU185953B (en) | Process for producing new 4.cabamoyloxy-oxaza-phosphorines | |
| FR2511677A1 (fr) | Procede de preparation d'esters des acides alcoxyvincaminiques et alcoxyapovincaminiques |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |