NL7906191A - Nieuwe nitrosoureumderivaten en de bereidingswijze daarvan. - Google Patents

Nieuwe nitrosoureumderivaten en de bereidingswijze daarvan. Download PDF

Info

Publication number: NL7906191A
Authority: NL; Netherlands
Prior art keywords: chloroethyl; methoxy; urea; nitroso; compound according
Prior art date: 1978-08-25

Application number

NL7906191A

Other languages

English (en)

Dutch (nl)

Original Assignee

Tanabe Seiyaku Co

Priority date (The priority date 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 date listed.)

1978-08-25

Filing date

1979-08-14

Publication date

1980-02-27

1978-08-25 Priority claimed from GB7834564A external-priority patent/GB2028795A/en

1979-08-14 Application filed by Tanabe Seiyaku Co filed Critical Tanabe Seiyaku Co

1980-02-27 Publication of NL7906191A publication Critical patent/NL7906191A/nl

Links

238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 57
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 55
-1 2-hydroxyethoxy Chemical group 0.000 claims description 54
WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 claims description 50
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 47
239000004202 carbamide Substances 0.000 claims description 30
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 11
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 8
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 claims description 6
230000000259 anti-tumor effect Effects 0.000 claims description 6
239000012442 inert solvent Substances 0.000 claims description 6
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
230000000694 effects Effects 0.000 claims description 5
125000004807 2-methylethylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])([H])[*:1] 0.000 claims description 4
125000003436 D-mannopyranosyl 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 4
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 4
125000002947 alkylene group Chemical group 0.000 claims description 4
230000000719 anti-leukaemic effect Effects 0.000 claims description 4
HIWPGCMGAMJNRG-UHFFFAOYSA-N beta-sophorose Chemical group OC1C(O)C(CO)OC(O)C1OC1C(O)C(O)C(O)C(CO)O1 HIWPGCMGAMJNRG-UHFFFAOYSA-N 0.000 claims description 4
LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 claims description 4
238000007034 nitrosation reaction Methods 0.000 claims description 4
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 3
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 3
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 3
125000003728 aldopentopyranosyl group Chemical group [H]OC1([H])C([H])([H])OC([H])(*)C([H])([#1,#8])C1([H])O[H] 0.000 claims description 3
230000009935 nitrosation Effects 0.000 claims description 3
MJQWUOKBJIPRTA-NFLHVTIKSA-N 1-(2-chloroethyl)-3-(3-methoxypropyl)-1-nitroso-3-[(3s,4r,5r)-3,4,5-trihydroxyoxan-2-yl]urea Chemical compound COCCCN(C(=O)N(CCCl)N=O)C1OC[C@@H](O)[C@@H](O)[C@@H]1O MJQWUOKBJIPRTA-NFLHVTIKSA-N 0.000 claims description 2
239000002552 dosage form Substances 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000004806 1-methylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
239000005977 Ethylene Substances 0.000 claims 2
239000003814 drug Substances 0.000 claims 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
IKOCQLFDKDJOCV-PETCMJGMSA-N 1-(2-chloroethyl)-3-(1-methoxypropan-2-yl)-1-nitroso-3-[(3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]urea Chemical compound ClCCN(N=O)C(=O)N(C(C)COC)C1OC[C@H](O)[C@H](O)[C@H]1O IKOCQLFDKDJOCV-PETCMJGMSA-N 0.000 claims 1
KNPHNSBJKMRUBX-PETCMJGMSA-N 1-(2-chloroethyl)-3-(2-methoxypropyl)-1-nitroso-3-[(3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]urea Chemical compound ClCCN(N=O)C(=O)N(CC(C)OC)C1OC[C@H](O)[C@H](O)[C@H]1O KNPHNSBJKMRUBX-PETCMJGMSA-N 0.000 claims 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 126
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 24
239000000843 powder Substances 0.000 description 23
241000699670 Mus sp. Species 0.000 description 22
239000000047 product Substances 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 19
239000000243 solution Substances 0.000 description 17
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
238000000354 decomposition reaction Methods 0.000 description 12
239000000155 melt Substances 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
229960002160 maltose Drugs 0.000 description 11
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
231100000331 toxic Toxicity 0.000 description 10
230000002588 toxic effect Effects 0.000 description 10
GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 9
DKXNBNKWCZZMJT-UHFFFAOYSA-N O4-alpha-D-Mannopyranosyl-D-mannose Natural products O=CC(O)C(O)C(C(O)CO)OC1OC(CO)C(O)C(O)C1O DKXNBNKWCZZMJT-UHFFFAOYSA-N 0.000 description 9
GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 9
WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 8
206010003445 Ascites Diseases 0.000 description 8
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 8
230000005764 inhibitory process Effects 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 5
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 5
208000007093 Leukemia L1210 Diseases 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
HYGYSIDIKIGPJA-UHFFFAOYSA-N chloroform;ethyl acetate;methanol Chemical compound OC.ClC(Cl)Cl.CCOC(C)=O HYGYSIDIKIGPJA-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
235000019253 formic acid Nutrition 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
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 4
FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 4
SRBFZHDQGSBBOR-SOOFDHNKSA-N D-ribopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@@H]1O SRBFZHDQGSBBOR-SOOFDHNKSA-N 0.000 description 4
206010028980 Neoplasm Diseases 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
PYMYPHUHKUWMLA-LMVFSUKVSA-N aldehydo-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
230000012010 growth Effects 0.000 description 4
OSTGTTZJOCZWJG-UHFFFAOYSA-N nitrosourea Chemical class NC(=O)N=NO OSTGTTZJOCZWJG-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 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
230000004083 survival effect Effects 0.000 description 4
231100001274 therapeutic index Toxicity 0.000 description 4
210000004881 tumor cell Anatomy 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
201000009030 Carcinoma Diseases 0.000 description 3
208000003468 Ehrlich Tumor Carcinoma Diseases 0.000 description 3
GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000006482 condensation reaction Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
208000032839 leukemia Diseases 0.000 description 3
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150000003672 ureas Chemical class 0.000 description 3
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BPGIOCZAQDIBPI-UHFFFAOYSA-N 2-ethoxyethanamine Chemical compound CCOCCN BPGIOCZAQDIBPI-UHFFFAOYSA-N 0.000 description 2
101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 2
102100021906 Cyclin-O Human genes 0.000 description 2
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241001465754 Metazoa Species 0.000 description 2
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229910052783 alkali metal Inorganic materials 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
229940040526 anhydrous sodium acetate Drugs 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
206010073071 hepatocellular carcinoma Diseases 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
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230000003449 preventive effect Effects 0.000 description 2
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229910052708 sodium Inorganic materials 0.000 description 2
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239000007858 starting material Substances 0.000 description 2
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
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AOAUBUNFKBFOSH-OZRWLHRGSA-N 1-(2-chloroethyl)-3-(3-methoxypropyl)-1-nitroso-3-[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]urea Chemical compound COCCCN(C(=O)N(CCCl)N=O)C1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O AOAUBUNFKBFOSH-OZRWLHRGSA-N 0.000 description 1
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BEPBUBQTPQJKFM-PBVVMKELSA-N 1-(2-chloroethyl)-3-[(3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-(2-methoxyethyl)-1-nitrosourea Chemical compound ClCCN(N=O)C(=O)N(CCOC)C1O[C@H](CO)[C@@H](O)[C@H]1O BEPBUBQTPQJKFM-PBVVMKELSA-N 0.000 description 1
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HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 1
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DGJMFCAWGKNEAZ-UHFFFAOYSA-N 2-(methoxymethoxy)ethanamine Chemical compound COCOCCN DGJMFCAWGKNEAZ-UHFFFAOYSA-N 0.000 description 1
BSULWPSUVMOMAN-UHFFFAOYSA-N 2-azidoethanol Chemical compound OCCN=[N+]=[N-] BSULWPSUVMOMAN-UHFFFAOYSA-N 0.000 description 1
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PFRILIFJPBOYQU-PIITVSDKSA-N 3-(2-chloroethyl)-1-(1-methoxypropan-2-yl)-1-[(3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]urea Chemical compound ClCCNC(=O)N(C(C)COC)C1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O PFRILIFJPBOYQU-PIITVSDKSA-N 0.000 description 1
ZWHRINOHSILDHT-PETCMJGMSA-N 3-(2-chloroethyl)-1-(1-methoxypropan-2-yl)-1-[(3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]urea Chemical compound ClCCNC(=O)N(C(C)COC)C1OC[C@H](O)[C@H](O)[C@H]1O ZWHRINOHSILDHT-PETCMJGMSA-N 0.000 description 1
MYQYQHCVMIGKGV-BCSIVCRRSA-N 3-(2-chloroethyl)-1-(2,2-diethoxyethyl)-1-[(3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]urea Chemical compound CCOC(OCC)CN(C(=O)NCCCl)C1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O MYQYQHCVMIGKGV-BCSIVCRRSA-N 0.000 description 1
IPJSWHNWLFONKL-WSSOQDAQSA-N 3-(2-chloroethyl)-1-(2-methoxyethyl)-1-[(3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]urea Chemical compound ClCCNC(=O)N(CCOC)C1OC[C@@H](O)[C@H](O)[C@H]1O IPJSWHNWLFONKL-WSSOQDAQSA-N 0.000 description 1
IPJSWHNWLFONKL-IZJGZUANSA-N 3-(2-chloroethyl)-1-(2-methoxyethyl)-1-[(3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]urea Chemical compound ClCCNC(=O)N(CCOC)C1OC[C@H](O)[C@H](O)[C@H]1O IPJSWHNWLFONKL-IZJGZUANSA-N 0.000 description 1
ZTRUQRAJKUWWHK-PETCMJGMSA-N 3-(2-chloroethyl)-1-(2-methoxypropyl)-1-[(3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]urea Chemical compound ClCCNC(=O)N(CC(C)OC)C1OC[C@H](O)[C@H](O)[C@H]1O ZTRUQRAJKUWWHK-PETCMJGMSA-N 0.000 description 1
QIWAEWXUCVZJNR-GKDVJIACSA-N 3-(2-chloroethyl)-1-(3-methoxypropyl)-1-[(3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]urea Chemical compound COCCCN(C(=O)NCCCl)C1OC[C@H](O)[C@H](O)[C@H]1O QIWAEWXUCVZJNR-GKDVJIACSA-N 0.000 description 1
MFBFVIUPIAPNGF-OZRWLHRGSA-N 3-(2-chloroethyl)-1-(3-methoxypropyl)-1-[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]urea Chemical compound COCCCN(C(=O)NCCCl)C1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O MFBFVIUPIAPNGF-OZRWLHRGSA-N 0.000 description 1
JCHFDCQEDQQUGA-QHPFDFDXSA-N 3-(2-chloroethyl)-1-[(3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-(2-ethoxyethyl)urea Chemical compound CCOCCN(C(=O)NCCCl)C1O[C@H](CO)[C@@H](O)[C@H]1O JCHFDCQEDQQUGA-QHPFDFDXSA-N 0.000 description 1
HILNRNQWKMPKDG-PBVVMKELSA-N 3-(2-chloroethyl)-1-[(3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-(2-methoxyethyl)urea Chemical compound ClCCNC(=O)N(CCOC)C1O[C@H](CO)[C@@H](O)[C@H]1O HILNRNQWKMPKDG-PBVVMKELSA-N 0.000 description 1
HTTNJQAFJLVWCN-UHFFFAOYSA-N 3-azidopropane-1,2-diol Chemical compound OCC(O)CN=[N+]=[N-] HTTNJQAFJLVWCN-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
JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 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
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
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
SRBFZHDQGSBBOR-OWMBCFKOSA-N L-ribopyranose Chemical compound O[C@H]1COC(O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-OWMBCFKOSA-N 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
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000005718 Stomach Neoplasms Diseases 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-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
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
239000002253 acid Substances 0.000 description 1
150000008043 acidic salts Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
229960003116 amyl nitrite Drugs 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 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
238000009835 boiling Methods 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
229940061627 chloromethyl methyl ether Drugs 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000010908 decantation Methods 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
239000000839 emulsion Substances 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
206010017758 gastric cancer Diseases 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
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
208000003747 lymphoid leukemia Diseases 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000002772 monosaccharides Chemical class 0.000 description 1
IUVIGVRSTLVOQI-UHFFFAOYSA-N n-methoxypropan-1-amine Chemical compound CCCNOC IUVIGVRSTLVOQI-UHFFFAOYSA-N 0.000 description 1
CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
TVPPZASKIXGUJQ-UHFFFAOYSA-N n-propyl azide Chemical compound CCCN=[N+]=[N-] TVPPZASKIXGUJQ-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
150000002832 nitroso derivatives Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 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
239000002244 precipitate Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000003132 pyranosyl group Chemical group 0.000 description 1
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate 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
201000011549 stomach cancer Diseases 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 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

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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NL7906191A 1978-08-25 1979-08-14 Nieuwe nitrosoureumderivaten en de bereidingswijze daarvan. NL7906191A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB7834564		1978-08-25
GB7834564A GB2028795A (en)	1978-08-25	1978-08-25	Novel nitrosourea compounds and process for preparing the same
GB7902957		1979-01-27
GB7902957		1979-01-27

Publications (1)

Publication Number	Publication Date
NL7906191A true NL7906191A (nl)	1980-02-27

Family

ID=26268660

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7906191A NL7906191A (nl)	1978-08-25	1979-08-14	Nieuwe nitrosoureumderivaten en de bereidingswijze daarvan.

Country Status (10)

Country	Link
US (1)	US4241053A (de)
AT (1)	AT368517B (de)
CA (1)	CA1121347A (de)
CH (1)	CH640867A5 (de)
DE (1)	DE2933663C2 (de)
ES (1)	ES483636A1 (de)
FR (1)	FR2434174A1 (de)
GB (1)	GB2031875B (de)
IT (1)	IT1193213B (de)
NL (1)	NL7906191A (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57165398A (en) *	1981-04-02	1982-10-12	Tanabe Seiyaku Co Ltd	Nitrosourea derivative and its preparation
US4386026A (en) *	1981-04-20	1983-05-31	Merck & Co., Inc.	Cell-specific glycopeptide ligands
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)

* Cited by examiner, † Cited by third party
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
- 1979-08-14 US US06/066,421 patent/US4241053A/en not_active Expired - Lifetime
- 1979-08-14 NL NL7906191A patent/NL7906191A/nl not_active Application Discontinuation
- 1979-08-20 DE DE2933663A patent/DE2933663C2/de not_active Expired
- 1979-08-21 IT IT25246/79A patent/IT1193213B/it active
- 1979-08-23 CA CA000334307A patent/CA1121347A/en not_active Expired
- 1979-08-23 FR FR7921268A patent/FR2434174A1/fr active Granted
- 1979-08-24 CH CH773279A patent/CH640867A5/de not_active IP Right Cessation
- 1979-08-24 AT AT0568979A patent/AT368517B/de not_active IP Right Cessation
- 1979-08-24 ES ES483636A patent/ES483636A1/es not_active Expired
- 1979-08-24 GB GB7929525A patent/GB2031875B/en not_active Expired

Also Published As

Publication number	Publication date
ES483636A1 (es)	1980-09-01
IT1193213B (it)	1988-06-15
ATA568979A (de)	1982-02-15
GB2031875A (en)	1980-04-30
FR2434174A1 (fr)	1980-03-21
IT7925246A0 (it)	1979-08-21
CA1121347A (en)	1982-04-06
DE2933663A1 (de)	1980-03-13
US4241053A (en)	1980-12-23
CH640867A5 (de)	1984-01-31
FR2434174B1 (de)	1982-07-02
AT368517B (de)	1982-10-25
GB2031875B (en)	1983-01-12
DE2933663C2 (de)	1986-02-27

Legal Events

Date	Code	Title
1981-11-02	BA	A request for search or an international-type search has been filed
1982-04-01	BB	A search report has been drawn up
1983-04-05	BC	A request for examination has been filed
1983-12-01	BV	The patent application has lapsed
1985-01-01	A85	Still pending on 85-01-01
1988-04-05	BV	The patent application has lapsed

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