PT77349B - Process for the preparation of new n-nitroso compounds - Google Patents
Process for the preparation of new n-nitroso compounds Download PDFInfo
- Publication number
- PT77349B PT77349B PT77349A PT7734983A PT77349B PT 77349 B PT77349 B PT 77349B PT 77349 A PT77349 A PT 77349A PT 7734983 A PT7734983 A PT 7734983A PT 77349 B PT77349 B PT 77349B
- Authority
- PT
- Portugal
- Prior art keywords
- ethyl
- chloroethyl
- urea
- nitroso
- europa
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 39
- 230000008569 process Effects 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims description 11
- 150000004008 N-nitroso compounds Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 239000004202 carbamide Substances 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 29
- -1 diethylaminosulfonyl Chemical group 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 238000007034 nitrosation reaction Methods 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 239000004157 Nitrosyl chloride Substances 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
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- PRKAYYDFYSQRMQ-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-(2-hydroxyethylsulfamoyl)ethyl]-1-nitrosourea Chemical compound OCCNS(=O)(=O)CCNC(=O)N(N=O)CCCl PRKAYYDFYSQRMQ-UHFFFAOYSA-N 0.000 claims description 3
- NURVUPJHOGEIGJ-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-(dimethylsulfamoyl)ethyl]-3-methyl-1-nitrosourea Chemical compound CN(C)S(=O)(=O)CCN(C)C(=O)N(N=O)CCCl NURVUPJHOGEIGJ-UHFFFAOYSA-N 0.000 claims description 3
- IBIDCWMPCUHQCJ-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[3-(dimethylsulfamoyl)propyl]-1-nitrosourea Chemical compound CN(C)S(=O)(=O)CCCNC(=O)N(N=O)CCCl IBIDCWMPCUHQCJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 3
- UZGRTWBSSSBFBV-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-(dipropylsulfamoyl)ethyl]-1-nitrosourea Chemical compound CCCN(CCC)S(=O)(=O)CCNC(=O)N(CCCl)N=O UZGRTWBSSSBFBV-UHFFFAOYSA-N 0.000 claims description 2
- SATDQZURIZSSKI-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-(methylsulfamoyl)ethyl]-1-nitrosourea Chemical compound CNS(=O)(=O)CCNC(=O)N(N=O)CCCl SATDQZURIZSSKI-UHFFFAOYSA-N 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims 1
- VBYJDSHYVNCROJ-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-[ethyl(propyl)sulfamoyl]ethyl]-1-nitrosourea Chemical compound CCCN(CC)S(=O)(=O)CCNC(=O)N(N=O)CCCl VBYJDSHYVNCROJ-UHFFFAOYSA-N 0.000 claims 1
- PNNCWTXUWKENPE-UHFFFAOYSA-N [N].NC(N)=O Chemical compound [N].NC(N)=O PNNCWTXUWKENPE-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 229960004042 diazoxide Drugs 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 2
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 206010028980 Neoplasm Diseases 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 16
- 241001465754 Metazoa Species 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 201000011510 cancer Diseases 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- 230000004083 survival effect Effects 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000007774 longterm Effects 0.000 description 7
- RCLLNBVPCJDIPX-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-(dimethylsulfamoyl)ethyl]-1-nitrosourea Chemical compound CN(C)S(=O)(=O)CCNC(=O)N(N=O)CCCl RCLLNBVPCJDIPX-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000002512 chemotherapy Methods 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 231100001274 therapeutic index Toxicity 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000002246 antineoplastic agent Substances 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000002513 implantation Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WPXCIIMXSGOMHQ-UHFFFAOYSA-N 1-(2-chloroethyl)-1-nitroso-3-(2-sulfamoylethyl)urea Chemical compound NS(=O)(=O)CCNC(=O)N(N=O)CCCl WPXCIIMXSGOMHQ-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 230000009935 nitrosation Effects 0.000 description 3
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ARNQWXVAHAYACL-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-(2-methoxyethylsulfamoyl)ethyl]-1-nitrosourea Chemical compound COCCNS(=O)(=O)CCNC(=O)N(N=O)CCCl ARNQWXVAHAYACL-UHFFFAOYSA-N 0.000 description 2
- DXVCAMZHQNJBSQ-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[5-(dimethylsulfamoyl)pentyl]-1-nitrosourea Chemical compound CN(C)S(=O)(=O)CCCCCNC(=O)N(N=O)CCCl DXVCAMZHQNJBSQ-UHFFFAOYSA-N 0.000 description 2
- PIZGQSWCZNVPFH-UHFFFAOYSA-N 2-amino-n,n-dimethylethanesulfonamide;hydrochloride Chemical compound Cl.CN(C)S(=O)(=O)CCN PIZGQSWCZNVPFH-UHFFFAOYSA-N 0.000 description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 229960001480 chlorozotocin Drugs 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000003018 immunosuppressive agent Substances 0.000 description 2
- 229940125721 immunosuppressive agent Drugs 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000002826 nitrites Chemical class 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000011275 oncology therapy Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000011287 therapeutic dose Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- KZZILGDAMASFTG-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) n-(2-chloroethyl)-n-nitrosocarbamate Chemical compound ClCCN(N=O)C(=O)ON1C(=O)CCC1=O KZZILGDAMASFTG-UHFFFAOYSA-N 0.000 description 1
- DAJARBUJEJVGDQ-UHFFFAOYSA-N (4-nitrophenyl) n-(2-chloroethyl)-n-nitrosocarbamate Chemical compound [O-][N+](=O)C1=CC=C(OC(=O)N(CCCl)N=O)C=C1 DAJARBUJEJVGDQ-UHFFFAOYSA-N 0.000 description 1
- SYLKSJRDGLRPIU-UHFFFAOYSA-N 1,1-bis[2-(dimethylsulfamoyl)ethyl]-3-nitrosourea Chemical compound CN(C)S(=O)(=O)CCN(C(=O)NN=O)CCS(=O)(=O)N(C)C SYLKSJRDGLRPIU-UHFFFAOYSA-N 0.000 description 1
- CVMVXHUAVILQEG-UHFFFAOYSA-N 1-(2-chloroethyl)-1-nitroso-3-(2-piperidin-1-ylsulfonylethyl)urea Chemical compound ClCCN(N=O)C(=O)NCCS(=O)(=O)N1CCCCC1 CVMVXHUAVILQEG-UHFFFAOYSA-N 0.000 description 1
- CDKUMJRKCFEMQQ-UHFFFAOYSA-N 1-(2-chloroethyl)-1-nitroso-3-[2-(2-sulfamoylethylsulfamoyl)ethyl]urea Chemical compound NS(=O)(=O)CCNS(=O)(=O)CCNC(=O)N(N=O)CCCl CDKUMJRKCFEMQQ-UHFFFAOYSA-N 0.000 description 1
- KWTKHWMAWPEISV-UHFFFAOYSA-N 1-(2-chloroethyl)-3-(cyclopropylmethyl)-3-[2-(dimethylsulfamoyl)ethyl]-1-nitrosourea Chemical compound CN(C)S(=O)(=O)CCN(C(=O)N(CCCl)N=O)CC1CC1 KWTKHWMAWPEISV-UHFFFAOYSA-N 0.000 description 1
- YTIIROZXKZUCJX-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[1-(dimethylsulfamoyl)butan-2-yl]-1-nitrosourea Chemical compound CN(C)S(=O)(=O)CC(CC)NC(=O)N(CCCl)N=O YTIIROZXKZUCJX-UHFFFAOYSA-N 0.000 description 1
- IXSMZSRNCRZAJC-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-(cyclohexylsulfamoyl)ethyl]-1-nitrosourea Chemical compound ClCCN(N=O)C(=O)NCCS(=O)(=O)NC1CCCCC1 IXSMZSRNCRZAJC-UHFFFAOYSA-N 0.000 description 1
- ZQQVXYZFXFUCFI-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-(cyclopentylsulfamoyl)ethyl]-1-nitrosourea Chemical compound ClCCN(N=O)C(=O)NCCS(=O)(=O)NC1CCCC1 ZQQVXYZFXFUCFI-UHFFFAOYSA-N 0.000 description 1
- KRFQMDKBQFBUTL-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-(dimethylsulfamoyl)ethyl]-3-ethyl-1-nitrosourea Chemical compound CN(C)S(=O)(=O)CCN(CC)C(=O)N(CCCl)N=O KRFQMDKBQFBUTL-UHFFFAOYSA-N 0.000 description 1
- RUIGAHCLEIQCRC-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-(dimethylsulfamoyl)ethyl]urea Chemical compound CN(C)S(=O)(=O)CCNC(=O)NCCCl RUIGAHCLEIQCRC-UHFFFAOYSA-N 0.000 description 1
- ACLWRDBCKGMURO-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-(dimethylsulfamoyl)propyl]-1-nitrosourea Chemical compound CN(C)S(=O)(=O)C(C)CNC(=O)N(CCCl)N=O ACLWRDBCKGMURO-UHFFFAOYSA-N 0.000 description 1
- VIMFRMBQXYXLJW-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-(hexan-2-ylsulfamoyl)ethyl]-1-nitrosourea Chemical compound CCCCC(C)NS(=O)(=O)CCNC(=O)N(N=O)CCCl VIMFRMBQXYXLJW-UHFFFAOYSA-N 0.000 description 1
- ISRFYMURZYDPFN-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-[(1-hydroxy-2-methylpropan-2-yl)sulfamoyl]ethyl]-1-nitrosourea Chemical compound OCC(C)(C)NS(=O)(=O)CCNC(=O)N(N=O)CCCl ISRFYMURZYDPFN-UHFFFAOYSA-N 0.000 description 1
- NJSOEYVCGQIBSB-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-[(4-methylphenyl)methylsulfamoyl]ethyl]-1-nitrosourea Chemical compound CC1=CC=C(CNS(=O)(=O)CCNC(=O)N(CCCl)N=O)C=C1 NJSOEYVCGQIBSB-UHFFFAOYSA-N 0.000 description 1
- NZAPHSYUUVCOKD-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-[2-(methylsulfamoyl)ethylsulfamoyl]ethyl]-1-nitrosourea Chemical compound CNS(=O)(=O)CCNS(=O)(=O)CCNC(=O)N(N=O)CCCl NZAPHSYUUVCOKD-UHFFFAOYSA-N 0.000 description 1
- JIOFMEIIGMBFRU-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-[2-hydroxyethyl(methyl)sulfamoyl]ethyl]-1-nitrosourea Chemical compound OCCN(C)S(=O)(=O)CCNC(=O)N(CCCl)N=O JIOFMEIIGMBFRU-UHFFFAOYSA-N 0.000 description 1
- DJRNDZSSRVHPQO-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-[cyclohexyl(methyl)sulfamoyl]ethyl]-1-nitrosourea Chemical compound ClCCN(N=O)C(=O)NCCS(=O)(=O)N(C)C1CCCCC1 DJRNDZSSRVHPQO-UHFFFAOYSA-N 0.000 description 1
- MQRASTFDELIZFH-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-[ethyl(methyl)sulfamoyl]ethyl]-1-nitrosourea Chemical compound ClCCN(C(=O)NCCS(=O)(=O)N(C)CC)N=O MQRASTFDELIZFH-UHFFFAOYSA-N 0.000 description 1
- YNODPWNZUSTNGC-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-[methoxy(methyl)sulfamoyl]ethyl]-1-nitrosourea Chemical compound CON(C)S(=O)(=O)CCNC(=O)N(N=O)CCCl YNODPWNZUSTNGC-UHFFFAOYSA-N 0.000 description 1
- XRRCROCEBQBJHF-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[4-(dimethylsulfamoyl)butyl]-1-nitrosourea Chemical compound CN(C)S(=O)(=O)CCCCNC(=O)N(N=O)CCCl XRRCROCEBQBJHF-UHFFFAOYSA-N 0.000 description 1
- NMHWJHCZYFJCGV-UHFFFAOYSA-N 1-(2-chloroethyl)-3-cyclohexyl-3-[2-(dimethylsulfamoyl)ethyl]-1-nitrosourea Chemical compound CN(C)S(=O)(=O)CCN(C(=O)N(CCCl)N=O)C1CCCCC1 NMHWJHCZYFJCGV-UHFFFAOYSA-N 0.000 description 1
- CPRAQIDGBUBJKP-UHFFFAOYSA-N 2-[[2-chloroethyl(nitroso)carbamoyl]amino]-3-(dimethylsulfamoyl)-n,n-dimethylpropanamide Chemical compound CN(C)S(=O)(=O)CC(C(=O)N(C)C)NC(=O)N(CCCl)N=O CPRAQIDGBUBJKP-UHFFFAOYSA-N 0.000 description 1
- CTWPBQQPPONJLX-UHFFFAOYSA-N 2-[[2-chloroethyl(nitroso)carbamoyl]amino]-3-sulfamoylpropanamide Chemical compound NS(=O)(=O)CC(C(=O)N)NC(=O)N(CCCl)N=O CTWPBQQPPONJLX-UHFFFAOYSA-N 0.000 description 1
- DGUVEYAZTOUCEJ-UHFFFAOYSA-N 2-aminoethanesulfonamide;hydron;chloride Chemical compound Cl.NCCS(N)(=O)=O DGUVEYAZTOUCEJ-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- CFJAWSLTYSIGMC-UHFFFAOYSA-N 2-chloroethyl n-nitrosocarbamate Chemical compound ClCCOC(=O)NN=O CFJAWSLTYSIGMC-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- MRNIWHWHDCQRGQ-UHFFFAOYSA-N 3-[2-(butylsulfamoyl)ethyl]-1-(2-chloroethyl)-1-nitrosourea Chemical compound C(CCC)NS(=O)(=O)CCNC(N(N=O)CCCl)=O MRNIWHWHDCQRGQ-UHFFFAOYSA-N 0.000 description 1
- CPIZYYSABVGCPR-UHFFFAOYSA-N 3-[2-(dimethylsulfamoyl)ethyl]-1-methyl-1-nitrosourea Chemical compound CN(C)S(=O)(=O)CCNC(=O)N(C)N=O CPIZYYSABVGCPR-UHFFFAOYSA-N 0.000 description 1
- MBIYLMWPQOQCRC-UHFFFAOYSA-N 3-[2-[[2-chloroethyl(nitroso)carbamoyl]amino]ethylsulfonylamino]-n,n-dimethylpropanamide Chemical compound CN(C)C(=O)CCNS(=O)(=O)CCNC(=O)N(N=O)CCCl MBIYLMWPQOQCRC-UHFFFAOYSA-N 0.000 description 1
- JQGKGSFQAUHYTQ-UHFFFAOYSA-N 3-[2-[[2-chloroethyl(nitroso)carbamoyl]amino]ethylsulfonylamino]-n-methylpropanamide Chemical compound CNC(=O)CCNS(=O)(=O)CCNC(=O)N(N=O)CCCl JQGKGSFQAUHYTQ-UHFFFAOYSA-N 0.000 description 1
- JQROXQOSSGVQHV-UHFFFAOYSA-N 3-[2-[[2-chloroethyl(nitroso)carbamoyl]amino]ethylsulfonylamino]propanamide Chemical compound NC(=O)CCNS(=O)(=O)CCNC(=O)N(N=O)CCCl JQROXQOSSGVQHV-UHFFFAOYSA-N 0.000 description 1
- ZNZYXLUPHWDVDD-UHFFFAOYSA-N 3-[2-[benzyl(methyl)sulfamoyl]ethyl]-1-(2-chloroethyl)-1-nitrosourea Chemical compound ClCCN(N=O)C(=O)NCCS(=O)(=O)N(C)CC1=CC=CC=C1 ZNZYXLUPHWDVDD-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241001471112 Artocarpus tamaran Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000984642 Cura Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000011952 anionic catalyst Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 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
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229940013688 formic acid Drugs 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229960000443 hydrochloric acid Drugs 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- IDNHOWMYUQKKTI-UHFFFAOYSA-M lithium nitrite Chemical compound [Li+].[O-]N=O IDNHOWMYUQKKTI-UHFFFAOYSA-M 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 210000004324 lymphatic system Anatomy 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 229940127084 other anti-cancer agent Drugs 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- KAOQVXHBVNKNHA-UHFFFAOYSA-N propyl nitrite Chemical compound CCCON=O KAOQVXHBVNKNHA-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 238000011125 single therapy Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
-
- 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
- C07D295/22—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 with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
- C07C311/47—Y being a hetero atom
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Optical Head (AREA)
- Reverberation, Karaoke And Other Acoustics (AREA)
- Gyroscopes (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8205324A SE8205324L (sv) | 1982-09-17 | 1982-09-17 | Nya n-nitrosoforeningar, kompositioner innehallande sadana foreningar, framstellningsforfaranden och behandlingsmetoder |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT77349A PT77349A (en) | 1983-10-01 |
| PT77349B true PT77349B (en) | 1986-04-17 |
Family
ID=20347890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT77349A PT77349B (en) | 1982-09-17 | 1983-09-16 | Process for the preparation of new n-nitroso compounds |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4613695A (https=) |
| EP (1) | EP0106123B1 (https=) |
| JP (1) | JPS5973562A (https=) |
| KR (1) | KR910006763B1 (https=) |
| AT (1) | ATE17235T1 (https=) |
| AU (1) | AU559738B2 (https=) |
| CA (1) | CA1242200A (https=) |
| DE (1) | DE3361719D1 (https=) |
| DK (1) | DK423983A (https=) |
| ES (1) | ES525662A0 (https=) |
| FI (1) | FI76553C (https=) |
| GR (1) | GR79656B (https=) |
| HK (1) | HK35389A (https=) |
| HU (1) | HU194817B (https=) |
| IE (1) | IE55901B1 (https=) |
| IL (1) | IL69660A0 (https=) |
| NO (1) | NO159084C (https=) |
| NZ (1) | NZ205534A (https=) |
| PH (1) | PH21576A (https=) |
| PT (1) | PT77349B (https=) |
| SE (1) | SE8205324L (https=) |
| SG (1) | SG789G (https=) |
| ZA (1) | ZA836569B (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5001158A (en) * | 1984-04-11 | 1991-03-19 | Centre National De La Recherche Scientifique | Nitrosoureas compounds preparation thereof and utilization thereof in anticancerous |
| WO2001098268A2 (en) * | 2000-06-21 | 2001-12-27 | Bristol-Myers Squibb Pharma Company | Piperidine amides as modulators of chemokine receptor activity |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE50228B1 (en) * | 1979-10-03 | 1986-03-05 | Kefalas As | Nitrosourea derivatives,process for preparing them,and pharmaceutical compositions containing them |
-
1982
- 1982-09-17 SE SE8205324A patent/SE8205324L/xx not_active Application Discontinuation
-
1983
- 1983-08-26 IE IE2006/83A patent/IE55901B1/en not_active IP Right Cessation
- 1983-09-05 AU AU18707/83A patent/AU559738B2/en not_active Ceased
- 1983-09-05 IL IL69660A patent/IL69660A0/xx not_active IP Right Cessation
- 1983-09-05 ZA ZA836569A patent/ZA836569B/xx unknown
- 1983-09-06 US US06/529,718 patent/US4613695A/en not_active Expired - Fee Related
- 1983-09-08 KR KR1019830004238A patent/KR910006763B1/ko not_active Expired
- 1983-09-08 DE DE8383108853T patent/DE3361719D1/de not_active Expired
- 1983-09-08 AT AT83108853T patent/ATE17235T1/de not_active IP Right Cessation
- 1983-09-08 EP EP83108853A patent/EP0106123B1/en not_active Expired
- 1983-09-09 NZ NZ205534A patent/NZ205534A/en unknown
- 1983-09-13 FI FI833266A patent/FI76553C/fi not_active IP Right Cessation
- 1983-09-15 PH PH29543A patent/PH21576A/en unknown
- 1983-09-15 GR GR72451A patent/GR79656B/el unknown
- 1983-09-16 DK DK423983A patent/DK423983A/da not_active Application Discontinuation
- 1983-09-16 NO NO833354A patent/NO159084C/no unknown
- 1983-09-16 HU HU833220A patent/HU194817B/hu not_active IP Right Cessation
- 1983-09-16 ES ES525662A patent/ES525662A0/es active Granted
- 1983-09-16 CA CA000436928A patent/CA1242200A/en not_active Expired
- 1983-09-16 PT PT77349A patent/PT77349B/pt not_active IP Right Cessation
- 1983-09-16 JP JP58171054A patent/JPS5973562A/ja active Granted
-
1989
- 1989-01-05 SG SG7/89A patent/SG789G/en unknown
- 1989-04-27 HK HK353/89A patent/HK35389A/xx unknown
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| Date | Code | Title | Description |
|---|---|---|---|
| MM3A | Annulment or lapse |
Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 19941031 |