LT3115B - N-oxycarbonyl substituted 5'-deoxy-5-fluorcytidines - Google Patents

N-oxycarbonyl substituted 5'-deoxy-5-fluorcytidines Download PDF

Info

Publication number: LT3115B
Authority: LT; Lithuania
Prior art keywords: deoxy; fluoro; cytidine; carbonyl; radical
Prior art date: 1992-12-18

Application number

LTIP1627A

Other languages

English (en)

Lithuanian (lt)

Inventor

Motohiro Arasaki

Hideo Ishitsuka

Isami Kuruma

Masanori Miwa

Chikako Murasaki

Nobuo Shimma

Isao Umeda

Original Assignee

Hoffmann La Roche

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.)

1992-12-18

Filing date

1993-12-17

Publication date

1994-12-27

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=8210304&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=LT3115(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1993-12-17 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1994-07-15 Publication of LTIP1627A publication Critical patent/LTIP1627A/xx

1994-12-27 Publication of LT3115B publication Critical patent/LT3115B/lt

Links

YSNABXSEHNLERR-ZIYNGMLESA-N 5'-Deoxy-5-fluorocytidine Chemical class O[C@@H]1[C@H](O)[C@@H](C)O[C@H]1N1C(=O)N=C(N)C(F)=C1 YSNABXSEHNLERR-ZIYNGMLESA-N 0.000 title abstract description 7
-1 hydrocarbon radical Chemical class 0.000 claims abstract description 73
150000001875 compounds Chemical class 0.000 claims abstract description 52
206010028980 Neoplasm Diseases 0.000 claims abstract description 16
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 8
150000004677 hydrates Chemical class 0.000 claims abstract description 8
229930195733 hydrocarbon Natural products 0.000 claims abstract description 8
229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
239000012453 solvate Substances 0.000 claims abstract description 8
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 4
230000004962 physiological condition Effects 0.000 claims abstract description 4
125000006239 protecting group Chemical group 0.000 claims abstract 3
UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 claims description 20
UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 claims description 20
UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 claims description 20
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 9
238000000034 method Methods 0.000 claims description 7
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 5
239000002246 antineoplastic agent Substances 0.000 claims description 5
125000005933 neopentyloxycarbonyl group Chemical group 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 4
125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 4
230000001681 protective effect Effects 0.000 claims description 4
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
NQJDADBILIAZPU-JLTWGVLTSA-N 2-phenylethyl 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1H-pyrimidine-6-carboxylate Chemical compound C1=CC(N)(C(=O)OCCC=2C=CC=CC=2)NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NQJDADBILIAZPU-JLTWGVLTSA-N 0.000 claims description 2
WMJHGZFQHPCWQZ-GWBBYGMBSA-N [(2r,3r,4r,5r)-4-acetyloxy-5-[5-fluoro-2-oxo-4-(pentoxycarbonylamino)pyrimidin-1-yl]-2-methyloxolan-3-yl] acetate Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](C)O1 WMJHGZFQHPCWQZ-GWBBYGMBSA-N 0.000 claims description 2
KXINDFSMIQLNEG-GWBBYGMBSA-N [(2r,3r,4r,5r)-4-acetyloxy-5-[5-fluoro-4-(3-methylbutoxycarbonylamino)-2-oxopyrimidin-1-yl]-2-methyloxolan-3-yl] acetate Chemical compound C1=C(F)C(NC(=O)OCCC(C)C)=NC(=O)N1[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](C)O1 KXINDFSMIQLNEG-GWBBYGMBSA-N 0.000 claims description 2
URZZZRLMAFEEHO-ZAHKBLQYSA-N [(2r,3r,4r,5r)-4-benzoyloxy-5-[4-(butoxycarbonylamino)-5-fluoro-2-oxopyrimidin-1-yl]-2-methyloxolan-3-yl] benzoate Chemical compound C1=C(F)C(NC(=O)OCCCC)=NC(=O)N1[C@H]1[C@H](OC(=O)C=2C=CC=CC=2)[C@H](OC(=O)C=2C=CC=CC=2)[C@@H](C)O1 URZZZRLMAFEEHO-ZAHKBLQYSA-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
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
GUJMELSACJRCRS-INRGUWRVSA-N C1(CCCCC1)CCCOC(=O)C1(NC(N([C@H]2[C@H](O)[C@H](O)[C@@H](C)O2)C=C1F)=O)N Chemical compound C1(CCCCC1)CCCOC(=O)C1(NC(N([C@H]2[C@H](O)[C@H](O)[C@@H](C)O2)C=C1F)=O)N GUJMELSACJRCRS-INRGUWRVSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
PKXRGASHOJQDLD-APGPQJPKSA-N [(2r,3r,4r,5r)-4-acetyloxy-5-[4-(butoxycarbonylamino)-5-fluoro-2-oxopyrimidin-1-yl]-2-methyloxolan-3-yl] acetate Chemical compound C1=C(F)C(NC(=O)OCCCC)=NC(=O)N1[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](C)O1 PKXRGASHOJQDLD-APGPQJPKSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
239000013543 active substance Substances 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
FMPHIVCWEXSQON-PCLXQLDZSA-N cyclohexylmethyl 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxo-1H-pyrimidine-6-carboxylate Chemical compound C1(CCCCC1)COC(=O)C1(NC(N([C@H]2[C@H](O)[C@H](O)[C@@H](C)O2)C=C1F)=O)N FMPHIVCWEXSQON-PCLXQLDZSA-N 0.000 claims 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
OJLIMLARCDSSCZ-PNHWDRBUSA-N propyl n-[1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate Chemical compound C1=C(F)C(NC(=O)OCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 OJLIMLARCDSSCZ-PNHWDRBUSA-N 0.000 claims 1
150000003254 radicals Chemical class 0.000 abstract description 13
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
229910052799 carbon Inorganic materials 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 14
239000000203 mixture Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
241000282693 Cercopithecidae Species 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
241000282414 Homo sapiens Species 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
241000699670 Mus sp. Species 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
101710186969 Acylamidase Proteins 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
102000005922 amidase Human genes 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000010410 layer Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
ZWAOHEXOSAUJHY-ZIYNGMLESA-N doxifluridine Chemical compound O[C@@H]1[C@H](O)[C@@H](C)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ZWAOHEXOSAUJHY-ZIYNGMLESA-N 0.000 description 5
210000003608 fece Anatomy 0.000 description 5
XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 description 5
229960004413 flucytosine Drugs 0.000 description 5
229960002949 fluorouracil Drugs 0.000 description 5
210000004185 liver Anatomy 0.000 description 5
239000002243 precursor Substances 0.000 description 5
206010006895 Cachexia Diseases 0.000 description 4
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
239000002207 metabolite Substances 0.000 description 4
125000004742 propyloxycarbonyl group Chemical group 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
201000009030 Carcinoma Diseases 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
210000000577 adipose tissue Anatomy 0.000 description 3
230000001093 anti-cancer Effects 0.000 description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
125000004744 butyloxycarbonyl group Chemical group 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
208000029742 colonic neoplasm Diseases 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000008103 glucose Substances 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
239000000047 product Substances 0.000 description 3
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210000002966 serum Anatomy 0.000 description 3
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239000011734 sodium Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
125000003858 2-ethylbutoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])O*)C([H])([H])C([H])([H])[H] 0.000 description 2
STRZQWQNZQMHQR-UAKXSSHOSA-N 5-fluorocytidine Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 STRZQWQNZQMHQR-UAKXSSHOSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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241000282412 Homo Species 0.000 description 2
206010020751 Hypersensitivity Diseases 0.000 description 2
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 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
239000008118 PEG 6000 Substances 0.000 description 2
229920002584 Polyethylene Glycol 6000 Polymers 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
NWJBWNIUGNXJGO-RPULLILYSA-N [(2r,3r,4r,5r)-4-acetyloxy-5-(4-amino-5-fluoro-2-oxopyrimidin-1-yl)-2-methyloxolan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](C)O[C@H]1N1C(=O)N=C(N)C(F)=C1 NWJBWNIUGNXJGO-RPULLILYSA-N 0.000 description 2
GIEDPOVIGXKYGR-AXTGTSHSSA-N [(2r,3r,4r,5r)-4-acetyloxy-5-[5-fluoro-2-oxo-4-(propoxycarbonylamino)pyrimidin-1-yl]-2-methyloxolan-3-yl] acetate Chemical compound C1=C(F)C(NC(=O)OCCC)=NC(=O)N1[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](C)O1 GIEDPOVIGXKYGR-AXTGTSHSSA-N 0.000 description 2
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VFRJKOSAZBWSKR-JKGQPHCRSA-N butyl 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxo-1H-pyrimidine-6-carboxylate Chemical compound C1=C(F)C(C(=O)OCCCC)(N)NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 VFRJKOSAZBWSKR-JKGQPHCRSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- 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
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Medicinal Preparation (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

LTIP1627A 1992-12-18 1993-12-17 N-oxycarbonyl substituted 5'-deoxy-5-fluorcytidines LT3115B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP92121538		1992-12-18

Publications (2)

Publication Number	Publication Date
LTIP1627A LTIP1627A (en)	1994-07-15
LT3115B true LT3115B (en)	1994-12-27

Family

ID=8210304

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LTIP1627A LT3115B (en)	1992-12-18	1993-12-17	N-oxycarbonyl substituted 5'-deoxy-5-fluorcytidines

Country Status (40)

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US (1)	US5472949A (lv)
EP (1)	EP0602454B1 (lv)
JP (1)	JP2501297B2 (lv)
KR (1)	KR100347218B1 (lv)
CN (1)	CN1035617C (lv)
AT (1)	ATE137244T1 (lv)
AU (1)	AU671491B2 (lv)
BG (1)	BG61485B1 (lv)
BR (1)	BR9305089A (lv)
CA (1)	CA2103324C (lv)
CZ (1)	CZ284788B6 (lv)
DE (1)	DE69302360T2 (lv)
DK (1)	DK0602454T3 (lv)
EE (1)	EE03086B1 (lv)
ES (1)	ES2086856T3 (lv)
FI (1)	FI112365B (lv)
GE (1)	GEP20074251B (lv)
GR (1)	GR3020286T3 (lv)
HR (1)	HRP931430B1 (lv)
HU (2)	HU218291B (lv)
IL (1)	IL108000A0 (lv)
IS (1)	IS4108A (lv)
LT (1)	LT3115B (lv)
LV (1)	LV10625B (lv)
MY (1)	MY109282A (lv)
NO (1)	NO300066B1 (lv)
NZ (1)	NZ250414A (lv)
PH (1)	PH30168A (lv)
PL (1)	PL174100B1 (lv)
RO (1)	RO112619B1 (lv)
RU (2)	RU2458932C2 (lv)
SA (1)	SA93140409B1 (lv)
SI (1)	SI9300648B (lv)
SK (1)	SK281403B6 (lv)
SV (1)	SV1993000080A (lv)
TW (1)	TW372239B (lv)
UA (1)	UA39158C2 (lv)
UY (1)	UY23697A1 (lv)
YU (1)	YU49411B (lv)
ZA (1)	ZA939293B (lv)

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ES2384267T3 (es)	2005-07-21	2012-07-03	Nuvo Research Ag	Soluciones de clorito estabilizadas en combinación con fluoropirimidinas para el tratamiento del cáncer
RU2451524C2 (ru)	2005-11-04	2012-05-27	Вайет	Противоопухолевые комбинации с ингибиторами mtor, герцептином и/или hki-272
SI3184526T1 (sl)	2005-12-13	2019-03-29	Incyte Holdings Corporation	Derivati pirolo(2,3-D)pirimidina kot inhibitorji Janus kinaze
US20100160442A1 (en) *	2006-07-18	2010-06-24	Ossovskaya Valeria S	Formulations for cancer treatment
US20080085310A1 (en) *	2006-10-06	2008-04-10	Maria Oksana Bachynsky	Capecitabine rapidly disintegrating tablets
CN100425617C (zh) *	2006-10-31	2008-10-15	浙江海正药业股份有限公司	一种含氟嘧啶类化合物烷氧羰酰化的方法
ITMI20070435A1 (it)	2007-03-05	2008-09-06	Innovate Biotechnology Srl	2',3'-di-o-acil-5-fluoronucleosidi
KR20100015568A (ko) *	2007-04-20	2010-02-12	닥터 레디스 레보러터리즈 리미티드	카페시타빈의 제조 방법
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MX2009013402A (es)	2007-06-13	2010-02-24	Incyte Corp	Sales de inhibidor de janus cinasa (r)-3-(4-(7h-pirrolo[2,3-d]piri midin-4-il)-1h-pirazol-1-il)-3-ciclopentilpropanitrilo.
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WO2009042064A2 (en)	2007-09-21	2009-04-02	Nektar Therapeutics Al, Corporation	Oligomer-nucleoside phosphate conjugates
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- 1993-12-01 DE DE69302360T patent/DE69302360T2/de not_active Expired - Lifetime
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IS4108A (is)	1994-06-19
LTIP1627A (en)	1994-07-15
DE69302360T2 (de)	1996-10-31
EP0602454A1 (en)	1994-06-22
TW372239B (en)	1999-10-21
NO300066B1 (no)	1997-04-01
HRP931430A2 (en)	1998-06-30
UA39158C2 (uk)	2001-06-15
FI935616L (fi)	1994-06-19
RU2458932C2 (ru)	2012-08-20
SI9300648A (en)	1994-09-30
EE03086B1 (et)	1998-04-15
ATE137244T1 (de)	1996-05-15
RU2493162C1 (ru)	2013-09-20
NO934671L (no)	1994-06-20
CN1035617C (zh)	1997-08-13
AU5069093A (en)	1994-06-30
HUT65757A (en)	1994-07-28
RO112619B1 (ro)	1997-11-28
US5472949A (en)	1995-12-05
BG98304A (bg)	1994-01-03
EP0602454B1 (en)	1996-04-24
YU49411B (sh)	2006-01-16
BG61485B1 (bg)	1997-09-30
MY109282A (en)	1996-12-31
CN1094056A (zh)	1994-10-26
CZ284788B6 (cs)	1999-03-17
GR3020286T3 (en)	1996-09-30
ES2086856T3 (es)	1996-07-01
CZ273193A3 (en)	1994-07-13
ZA939293B (en)	1994-06-18
JPH06211891A (ja)	1994-08-02
DK0602454T3 (da)	1996-07-29
JP2501297B2 (ja)	1996-05-29
SI9300648B (sl)	2000-06-30
PL301541A1 (en)	1994-06-27
HU211965A9 (en)	1996-01-29
DE69302360D1 (de)	1996-05-30
CA2103324A1 (en)	1994-06-19
FI112365B (fi)	2003-11-28
AU671491B2 (en)	1996-08-29
CA2103324C (en)	1997-12-23
HU9303525D0 (en)	1994-04-28
SK144493A3 (en)	1994-10-05
BR9305089A (pt)	1994-07-05
GEP20074251B (en)	2007-12-10
HU218291B (en)	2000-07-28
LV10625A (lv)	1995-04-20
HK1005875A1 (en)	1999-01-29
UY23697A1 (es)	1994-06-08
IL108000A0 (en)	1994-04-12
YU77993A (sh)	1996-10-18
SA93140409B1 (ar)	2004-07-24
SK281403B6 (sk)	2001-03-12
FI935616A0 (fi)	1993-12-14
PH30168A (en)	1997-01-21
RU2135511C1 (ru)	1999-08-27
NZ250414A (en)	1995-12-21
HRP931430B1 (en)	1999-08-31
SV1993000080A (es)	1996-01-26
NO934671D0 (no)	1993-12-17
PL174100B1 (pl)	1998-06-30
LV10625B (en)	1996-04-20
KR100347218B1 (ko)	2003-01-24
KR940014428A (ko)	1994-07-18

Publication	Publication Date	Title
LT3115B (en)	1994-12-27	N-oxycarbonyl substituted 5'-deoxy-5-fluorcytidines
CN105085592B (zh)	2021-04-27	N-[(2`r)-2`-脱氧-2`-氟-2`-甲基-p-苯基-5`-尿苷酰基]-l-丙氨酸1-甲基乙基酯及其制备方法
TWI498117B (zh)	2015-09-01	核苷氨基磷酸酯
BRPI1100050A2 (pt)	2016-05-03	"sistema de controle de inclinação de lâmina,gerador de turbina eólica, e método de controle de inclinação de lâmina".
EP3252067B1 (en)	2019-05-29	Sugar moiety silyl ether derivative of 5-azacytidine
US9901641B2 (en)	2018-02-27	Silyl etherified derivatives of 5-azacytidines in carbohydrate moiety
KR101426101B1 (ko)	2014-08-13	3＇-에티닐시티딘 유도체
JP2002531573A (ja)	2002-09-24	グリセリルヌクレオチド、それらの製造法および使用
JP2004505899A (ja)	2004-02-26	５’−デオキシ−ｎ−（置換されたオキシカルボニル）−５−フルオロシトシン及びその誘導体、その製造方法、並びに、これを有効性分として含む抗癌剤組成物
WO2018230479A1 (ja)	2018-12-20	ヌクレオシド系抗がん剤又は抗ウィルス剤の５'位シリルエーテル誘導体
US8349834B2 (en)	2013-01-08	Dioxolane derivates for the treatment of cancer
HK1005875B (en)	1999-01-29	N-oxycarbonyl substituted 5'-deoxy-5-fluorocytidines
KR20040008410A (ko)	2004-01-31	신규5'-데옥시-ｎ-알킬옥시카르보닐-5-플루오로사이토신-5'-티오에스터 유도체, 그의 제조방법, 및 이를 유효성분으로포함하는 항암제
HK1130496B (en)	2012-11-02	3'-ethynylcytidine derivative
HK1169414B (en)	2016-07-29	N- [ (2 ' r) -2 ' -deoxy-2 ' -fluoro-2 ' -methyl-p-phenyl-5 ' -uridylyl] -l-alanine 1-methylethyl ester and process for its production
KR20030050504A (ko)	2003-06-25	신규5'-데옥시-ｎ-알킬옥시카르보닐-5-플루오로사이토신-5'-아미드 유도체, 그의 제조방법, 및 이를 유효성분으로포함하는 항암제

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