CH642086A5 - Nitrosoharnstoff-verbindungen, verfahren zu deren herstellung sowie therapeutische zubereitung. - Google Patents
Nitrosoharnstoff-verbindungen, verfahren zu deren herstellung sowie therapeutische zubereitung. Download PDFInfo
- Publication number
- CH642086A5 CH642086A5 CH538379A CH538379A CH642086A5 CH 642086 A5 CH642086 A5 CH 642086A5 CH 538379 A CH538379 A CH 538379A CH 538379 A CH538379 A CH 538379A CH 642086 A5 CH642086 A5 CH 642086A5
- Authority
- CH
- Switzerland
- Prior art keywords
- chloroethyl
- glucopyranosyl
- urea
- group
- aldo
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 47
- 238000000034 method Methods 0.000 title claims description 11
- 230000001225 therapeutic effect Effects 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 heteromonocyclic radical Chemical class 0.000 claims description 152
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 claims description 87
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 37
- 239000002904 solvent Substances 0.000 claims description 24
- 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 16
- KFEUJDWYNGMDBV-LODBTCKLSA-N N-acetyllactosamine Chemical group O[C@@H]1[C@@H](NC(=O)C)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KFEUJDWYNGMDBV-LODBTCKLSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000003572 L-arabinopyranosyl group Chemical group [H]O[C@@]1([H])C([H])([H])OC([H])(*)[C@]([H])(O[H])[C@@]1([H])O[H] 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 125000000466 oxiranyl group Chemical group 0.000 claims description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 238000007034 nitrosation reaction Methods 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000000868 D-ribopyranosyl group Chemical group [H]O[C@]1([H])C([H])([H])OC([H])(*)[C@]([H])(O[H])[C@]1([H])O[H] 0.000 claims description 7
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
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- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- 125000003535 D-glucopyranosyl group Chemical group [H]OC([H])([H])[C@@]1([H])OC([H])(*)[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H] 0.000 claims description 5
- 125000000333 D-xylopyranosyl group Chemical group [H]O[C@]1([H])C([H])([H])OC([H])(*)[C@]([H])(O[H])[C@@]1([H])O[H] 0.000 claims description 5
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 claims description 5
- OSTGTTZJOCZWJG-UHFFFAOYSA-N nitrosourea Chemical class NC(=O)N=NO OSTGTTZJOCZWJG-UHFFFAOYSA-N 0.000 claims description 5
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 4
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 4
- 125000003804 aldohexopyranosyl group Chemical group [H]OC([H])([H])C1([H])OC([H])(*)C([H])(O[H])C([H])(O[H])C1([H])O[H] 0.000 claims description 4
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- 125000004076 pyridyl group Chemical group 0.000 claims description 4
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- 238000010898 silica gel chromatography Methods 0.000 description 12
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- ZOBLZIKVIHJGRN-JAJWTYFOSA-N 1-(2-chloroethyl)-1-nitroso-3-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]urea Chemical compound OC[C@H]1O[C@@H](NC(=O)N(CCCl)N=O)[C@H](O)[C@@H](O)[C@@H]1O ZOBLZIKVIHJGRN-JAJWTYFOSA-N 0.000 description 5
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- HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 1
- PREOONMJIVUPMI-UHFFFAOYSA-N 1,4-dioxan-2-ylmethanamine Chemical compound NCC1COCCO1 PREOONMJIVUPMI-UHFFFAOYSA-N 0.000 description 1
- ZOBLZIKVIHJGRN-KEWYIRBNSA-N 1-(2-chloroethyl)-1-nitroso-3-[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]urea Chemical compound OC[C@H]1OC(NC(=O)N(CCCl)N=O)[C@H](O)[C@@H](O)[C@@H]1O ZOBLZIKVIHJGRN-KEWYIRBNSA-N 0.000 description 1
- ZOBLZIKVIHJGRN-WZPXOXCRSA-N 1-(2-chloroethyl)-1-nitroso-3-[(3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]urea Chemical compound OC[C@H]1OC(NC(=O)N(CCCl)N=O)[C@@H](O)[C@@H](O)[C@@H]1O ZOBLZIKVIHJGRN-WZPXOXCRSA-N 0.000 description 1
- NWHBEOZVNMELBC-IZJGZUANSA-N 1-(2-chloroethyl)-1-nitroso-3-prop-2-enyl-3-[(3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]urea Chemical compound O[C@H]1COC(N(CC=C)C(=O)N(CCCl)N=O)[C@H](O)[C@H]1O NWHBEOZVNMELBC-IZJGZUANSA-N 0.000 description 1
- SQWPTILMZTWRJG-SCWFEDMQSA-N 1-(2-chloroethyl)-3-(cyclopropylmethyl)-1-nitroso-3-[(3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]urea Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)OC1N(C(=O)N(CCCl)N=O)CC1CC1 SQWPTILMZTWRJG-SCWFEDMQSA-N 0.000 description 1
- UAVSSEFHSYTYKJ-GKDVJIACSA-N 1-(2-chloroethyl)-3-(cyclopropylmethyl)-1-nitroso-3-[(3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]urea Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)COC1N(C(=O)N(CCCl)N=O)CC1CC1 UAVSSEFHSYTYKJ-GKDVJIACSA-N 0.000 description 1
- GSOHQPWFFILMQR-KBIHSYGRSA-N 1-(2-chloroethyl)-3-(furan-2-ylmethyl)-1-nitroso-3-[(3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]urea Chemical compound ClCCN(C(=O)N(C1[C@H](O)[C@H](O)[C@H](O)CO1)CC1=CC=CO1)N=O GSOHQPWFFILMQR-KBIHSYGRSA-N 0.000 description 1
- UHKBDYUSMUGOKE-YUBTXPFQSA-N 1-(2-chloroethyl)-3-[(3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-1-nitrosourea Chemical compound ClCCN(C(=O)NC1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](O2)CO)[C@H](O1)CO)N=O UHKBDYUSMUGOKE-YUBTXPFQSA-N 0.000 description 1
- DNFKPKMOWSYXLU-RRYROLNDSA-N 1-(2-chloroethyl)-3-cyclohexyl-1-nitroso-3-[(3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]urea Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)OC1N(C(=O)N(CCCl)N=O)C1CCCCC1 DNFKPKMOWSYXLU-RRYROLNDSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 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
- UKPLRVAKKXWITN-UHFFFAOYSA-N 2-cyclopentylethanamine Chemical compound NCCC1CCCC1 UKPLRVAKKXWITN-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- VTOXHSCNCPJKSA-YMWOCUMHSA-N 3-(2-chloroethyl)-1-(furan-2-ylmethyl)-1-[(3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]urea Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)OC1N(C(=O)NCCCl)CC1=CC=CO1 VTOXHSCNCPJKSA-YMWOCUMHSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- RMNFKEURYWIDHP-UHFFFAOYSA-N 4-(azidomethyl)-1,3-dioxolane Chemical compound [N-]=[N+]=NCC1COCO1 RMNFKEURYWIDHP-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 206010051779 Bone marrow toxicity Diseases 0.000 description 1
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 125000003318 D-arabinopyranosyl group Chemical group [H]O[C@]1([H])C([H])([H])OC([H])(*)[C@@]([H])(O[H])[C@]1([H])O[H] 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- 125000003125 D-talopyranosyl group Chemical group [H]OC([H])([H])[C@@]1([H])OC([H])(*)[C@@]([H])(O[H])[C@@]([H])(O[H])[C@@]1([H])O[H] 0.000 description 1
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 1
- 206010061968 Gastric neoplasm Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000006552 Lewis Lung Carcinoma Diseases 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 208000006268 Sarcoma 180 Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 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
- BGTOCAYOOXODIK-SOOFDHNKSA-N [(3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]urea Chemical compound C1([C@H](O)[C@H](O)[C@H](O)CO1)NC(=O)N BGTOCAYOOXODIK-SOOFDHNKSA-N 0.000 description 1
- BGTOCAYOOXODIK-IOVATXLUSA-N [(3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]urea Chemical compound NC(=O)NC1OC[C@@H](O)[C@H](O)[C@H]1O BGTOCAYOOXODIK-IOVATXLUSA-N 0.000 description 1
- BGTOCAYOOXODIK-HWQSCIPKSA-N [(3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]urea Chemical compound C1([C@H](O)[C@@H](O)[C@@H](O)CO1)NC(N)=O BGTOCAYOOXODIK-HWQSCIPKSA-N 0.000 description 1
- FKWQEFWENKGUGF-GASJEMHNSA-N [(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]urea Chemical compound NC(=O)NC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O FKWQEFWENKGUGF-GASJEMHNSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229960003116 amyl nitrite Drugs 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 231100000366 bone marrow toxicity Toxicity 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- 125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 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
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 229940117803 phenethylamine Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7826659 | 1978-06-10 | ||
| GB7902955 | 1979-01-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH642086A5 true CH642086A5 (de) | 1984-03-30 |
Family
ID=26267944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH538379A CH642086A5 (de) | 1978-06-10 | 1979-06-08 | Nitrosoharnstoff-verbindungen, verfahren zu deren herstellung sowie therapeutische zubereitung. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4241052A (OSRAM) |
| AT (1) | AT368516B (OSRAM) |
| CA (1) | CA1115696A (OSRAM) |
| CH (1) | CH642086A5 (OSRAM) |
| DE (1) | DE2921844C2 (OSRAM) |
| DK (1) | DK240779A (OSRAM) |
| ES (1) | ES481419A1 (OSRAM) |
| FR (1) | FR2440954A1 (OSRAM) |
| GB (1) | GB2023595B (OSRAM) |
| IT (1) | IT1192649B (OSRAM) |
| NL (1) | NL7904577A (OSRAM) |
| SE (1) | SE7904966L (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4314999A (en) * | 1978-07-31 | 1982-02-09 | Proter S.P.A. | N-Acyl derivatives of glucosamine having antitumor chemotherapeutic acitivity |
| JPS5940400B2 (ja) * | 1980-03-24 | 1984-09-29 | わかもと製薬株式会社 | 新規ｄ−アロ−ス誘導体及びこれを有効成分とする抗腫瘍剤 |
| JPS57165398A (en) * | 1981-04-02 | 1982-10-12 | Tanabe Seiyaku Co Ltd | Nitrosourea derivative and its preparation |
| US4902791A (en) * | 1983-08-30 | 1990-02-20 | Sanofi S.A. | Nitrosourea derivatives, process for their preparation and medicaments containing them |
| DE3346623A1 (de) * | 1983-12-14 | 1985-07-04 | Bayer Ag, 5090 Leverkusen | N-glycosylierte harnstoffe, carbamate und thiocarbamate, verfahren zu ihrer herstellung sowie ihre verwendung |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3577406A (en) * | 1968-05-23 | 1971-05-04 | Upjohn Co | Process for preparing the antibiotic streptozotocin |
| JPS5126876A (en) * | 1974-08-08 | 1976-03-05 | Suami T | Shinkina nitorosonyosojudotaino seizohoho |
| JPS5331664A (en) * | 1976-09-02 | 1978-03-25 | Suami T | Production of novel nitroso urea derivatives |
| JPS5395917A (en) * | 1977-02-03 | 1978-08-22 | Tokyo Tanabe Co | Process for preparing nitrosourea derivative of glucopyranose |
| US4182757A (en) * | 1977-07-29 | 1980-01-08 | Tanabe Seiyaku Co., Ltd. | Novel nitrosourea compounds and process for preparing the same |
-
1979
- 1979-05-14 US US06/038,638 patent/US4241052A/en not_active Expired - Lifetime
- 1979-05-29 DE DE2921844A patent/DE2921844C2/de not_active Expired
- 1979-06-07 FR FR7914636A patent/FR2440954A1/fr active Granted
- 1979-06-07 SE SE7904966A patent/SE7904966L/xx not_active Application Discontinuation
- 1979-06-08 DK DK240779A patent/DK240779A/da not_active Application Discontinuation
- 1979-06-08 CH CH538379A patent/CH642086A5/de not_active IP Right Cessation
- 1979-06-08 AT AT0411579A patent/AT368516B/de not_active IP Right Cessation
- 1979-06-08 CA CA329,296A patent/CA1115696A/en not_active Expired
- 1979-06-08 IT IT23412/79A patent/IT1192649B/it active
- 1979-06-08 ES ES481419A patent/ES481419A1/es not_active Expired
- 1979-06-11 GB GB7920247A patent/GB2023595B/en not_active Expired
- 1979-06-11 NL NL7904577A patent/NL7904577A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| SE7904966L (sv) | 1979-12-11 |
| ES481419A1 (es) | 1980-08-01 |
| DE2921844A1 (de) | 1979-12-20 |
| CA1115696A (en) | 1982-01-05 |
| FR2440954B1 (OSRAM) | 1982-07-02 |
| GB2023595A (en) | 1980-01-03 |
| FR2440954A1 (fr) | 1980-06-06 |
| GB2023595B (en) | 1983-03-16 |
| ATA411579A (de) | 1982-02-15 |
| AT368516B (de) | 1982-10-25 |
| NL7904577A (nl) | 1979-12-12 |
| US4241052A (en) | 1980-12-23 |
| IT1192649B (it) | 1988-04-27 |
| IT7923412A0 (it) | 1979-06-08 |
| DK240779A (da) | 1979-12-11 |
| DE2921844C2 (de) | 1984-11-22 |
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