ES2438144T3 - Preparación de compuestos de tioarabinofuranosilo - Google Patents
Preparación de compuestos de tioarabinofuranosilo Download PDFInfo
- Publication number
- ES2438144T3 ES2438144T3 ES10170453.4T ES10170453T ES2438144T3 ES 2438144 T3 ES2438144 T3 ES 2438144T3 ES 10170453 T ES10170453 T ES 10170453T ES 2438144 T3 ES2438144 T3 ES 2438144T3
- Authority
- ES
- Spain
- Prior art keywords
- thio
- arabinofuranosyl
- compound
- cytosine
- reacting
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title description 6
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims abstract description 46
- 229940104302 cytosine Drugs 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 14
- -1 4-thio-β-D-arabinofuranosyl Chemical group 0.000 claims abstract description 10
- IKLAQYSWAUFKAH-FTFTVQOISA-N [(3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)thiolan-2-yl] acetate Chemical compound CC(=O)OC1S[C@H](CO)[C@@H](O)[C@@H]1O IKLAQYSWAUFKAH-FTFTVQOISA-N 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 4
- 150000004252 dithioacetals Chemical class 0.000 claims abstract 3
- 125000000328 arabinofuranosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims abstract 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- NALRCAPFICWVAQ-AMVSKUEXSA-N (2s,3s,4s)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol Chemical compound COC1O[C@@H](CO)[C@@H](O)[C@@H]1O NALRCAPFICWVAQ-AMVSKUEXSA-N 0.000 claims description 3
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 3
- JBWYRBLDOOOJEU-UHFFFAOYSA-N 1-[chloro-(4-methoxyphenyl)-phenylmethyl]-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1C(Cl)(C=1C=CC(OC)=CC=1)C1=CC=CC=C1 JBWYRBLDOOOJEU-UHFFFAOYSA-N 0.000 claims description 2
- PYMYPHUHKUWMLA-WISUUJSJSA-N aldehydo-L-xylose Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WISUUJSJSA-N 0.000 claims description 2
- 229930195726 aldehydo-L-xylose Natural products 0.000 claims description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 2
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 claims description 2
- 229960004413 flucytosine Drugs 0.000 claims description 2
- XVAQPCSGOYVDDU-LIVPZPDMSA-N (2r,3s,4r)-5,5-bis(benzylsulfanyl)-1,3,4-tris(phenylmethoxy)pentan-2-ol Chemical compound C([C@@H](O)[C@H](OCC=1C=CC=CC=1)[C@@H](OCC=1C=CC=CC=1)C(SCC=1C=CC=CC=1)SCC=1C=CC=CC=1)OCC1=CC=CC=C1 XVAQPCSGOYVDDU-LIVPZPDMSA-N 0.000 claims 1
- UHDGCWIWMRVCDJ-STUHELBRSA-N 4-amino-1-[(3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1C1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-STUHELBRSA-N 0.000 claims 1
- QDVOFRWTPUEFTR-MNCSTQPFSA-N 4-amino-1-[(2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)thiolan-2-yl]-5-fluoropyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)S1 QDVOFRWTPUEFTR-MNCSTQPFSA-N 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PYYNNAZSZNYELP-WRENHGGMSA-N [(3s,4s,5r)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)thiolan-2-yl] acetate Chemical compound C([C@H]1SC([C@H]([C@@H]1OCC=1C=CC=CC=1)OCC=1C=CC=CC=1)OC(=O)C)OCC1=CC=CC=C1 PYYNNAZSZNYELP-WRENHGGMSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- HWRDLVHHHOIMJE-JOYOFOISSA-N (3s,4s,5r)-2-benzylsulfanyl-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)thiolane Chemical compound C([C@@H]1[C@H]([C@H](OCC=2C=CC=CC=2)C(SCC=2C=CC=CC=2)S1)OCC=1C=CC=CC=1)OCC1=CC=CC=C1 HWRDLVHHHOIMJE-JOYOFOISSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 238000005341 cation exchange Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 2
- LJIOTBMDLVHTBO-CUYJMHBOSA-N (2s)-2-amino-n-[(1r,2r)-1-cyano-2-[4-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]phenyl]cyclopropyl]butanamide Chemical compound CC[C@H](N)C(=O)N[C@]1(C#N)C[C@@H]1C1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)N2CCN(C)CC2)C=C1 LJIOTBMDLVHTBO-CUYJMHBOSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- HMFHBZSHGGEWLO-HWQSCIPKSA-N L-arabinofuranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@H]1O HMFHBZSHGGEWLO-HWQSCIPKSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 238000011394 anticancer treatment Methods 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000005450 thionucleoside Substances 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9386998P | 1998-07-23 | 1998-07-23 | |
| US93869P | 1998-07-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2438144T3 true ES2438144T3 (es) | 2014-01-16 |
Family
ID=22241386
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10170453.4T Expired - Lifetime ES2438144T3 (es) | 1998-07-23 | 1999-07-23 | Preparación de compuestos de tioarabinofuranosilo |
| ES10179999T Expired - Lifetime ES2402799T3 (es) | 1998-07-23 | 1999-07-23 | Prepreparación de compuestos de tioarabinofuranosilo y utilización de los mismos |
| ES99935854T Expired - Lifetime ES2376862T3 (es) | 1998-07-23 | 1999-07-23 | Utilización de compuestos de tioarabinofuranosilo |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10179999T Expired - Lifetime ES2402799T3 (es) | 1998-07-23 | 1999-07-23 | Prepreparación de compuestos de tioarabinofuranosilo y utilización de los mismos |
| ES99935854T Expired - Lifetime ES2376862T3 (es) | 1998-07-23 | 1999-07-23 | Utilización de compuestos de tioarabinofuranosilo |
Country Status (9)
| Country | Link |
|---|---|
| US (5) | US6576621B1 (OSRAM) |
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| AT (1) | ATE531376T1 (OSRAM) |
| AU (1) | AU747012B2 (OSRAM) |
| CA (1) | CA2338415C (OSRAM) |
| ES (3) | ES2438144T3 (OSRAM) |
| NZ (1) | NZ509405A (OSRAM) |
| WO (1) | WO2000004866A2 (OSRAM) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1100512B1 (en) * | 1998-07-23 | 2011-11-02 | Southern Research Institute | Use of thioarabinofuranosyl compounds |
| US20060127990A1 (en) * | 2002-08-22 | 2006-06-15 | Geneticlab Co., Ltd | 4'-thionucleotide |
| US7524831B2 (en) | 2005-03-02 | 2009-04-28 | Schering Corporation | Treatments for Flaviviridae virus infection |
| JP5417184B2 (ja) * | 2007-03-23 | 2014-02-12 | サザン リサーチ インスティテュート | 関節炎を治療及び予防する方法 |
| AR064165A1 (es) | 2007-12-06 | 2009-03-18 | Richmond Sa Com Ind Y Financie | Un procedimiento para la preparacion de capecitabina e intermediarios utilizables en dicho procedimiento |
| JP5622725B2 (ja) * | 2008-06-25 | 2014-11-12 | エンド ファーマスーティカルズ ソリューションズ インコーポレイテッド．Ｅｎｄｏ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｓｏｌｕｔｉｏｎｓｉｎｃ． | エキセナチド及び他のポリペプチド類の持続的送達 |
| US20110218170A1 (en) * | 2010-03-02 | 2011-09-08 | Southern Research Institute | Use of 2'-deoxy-4'-thiocytidine and its analogues as dna hypomethylating anticancer agents |
| TWI637963B (zh) | 2012-03-28 | 2018-10-11 | 富士軟片股份有限公司 | １－（２－脫氧－２－氟－４－硫－β－Ｄ－阿拉伯呋喃糖基）胞嘧啶之鹽 |
| WO2015125781A1 (ja) | 2014-02-18 | 2015-08-27 | 富士フイルム株式会社 | チオラン骨格型糖化合物の製造方法およびチオラン骨格型糖化合物 |
| JP6351107B2 (ja) * | 2014-02-18 | 2018-07-04 | 富士フイルム株式会社 | チオラン骨格型糖化合物の製造方法およびチオラン骨格型糖化合物 |
| JP6245527B2 (ja) * | 2014-03-24 | 2017-12-13 | 富士フイルム株式会社 | チオラン環もしくはチアン環骨格を有する化合物の製造方法 |
| TWI678373B (zh) | 2014-10-31 | 2019-12-01 | 日商富士軟片股份有限公司 | 硫代核苷衍生物或其鹽及醫藥組合物 |
| CN108368147A (zh) * | 2015-05-27 | 2018-08-03 | 南方研究院 | 用于治疗癌症的核苷酸 |
| WO2017091836A1 (en) * | 2015-11-25 | 2017-06-01 | University Of South Carolina | Enhancement of cytarabine activity by inhibiting cdk8/19 |
| JP7008025B2 (ja) | 2016-08-31 | 2022-01-25 | 富士フイルム株式会社 | 抗腫瘍剤、抗腫瘍効果増強剤及び抗腫瘍用キット |
| AU2018404329B2 (en) | 2018-01-29 | 2021-09-09 | Fujifilm Corporation | Antitumor agent for biliary tract cancer and method for treating biliary tract cancer |
| KR102810546B1 (ko) * | 2018-04-19 | 2025-05-20 | 써던 리서취 인스티튜트 | 암의 치료를 위한 4'-티오-뉴클레오타이드 및 -뉴클레오사이드 전구약물 |
| AU2020287343A1 (en) * | 2019-06-05 | 2021-12-09 | Southern Research Institute | Thiarabine- and thiarabine prodrug-based treatments |
| EP4138843A4 (en) | 2020-04-23 | 2024-07-10 | Southern Research Institute | COMPOSITION FOR THE TREATMENT OF BLOOD CANCER USING 4'-THIO-5-AZA-2'-DEOXYCYTIDINE AND USES THEREOF |
Family Cites Families (10)
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| DE69034209T2 (de) * | 1989-09-15 | 2006-08-10 | Southern Research Institute, Birmingham | 2'-deoxy-4'-thioribonucleoside als antivirale und antikrebsmittel |
| IE74701B1 (en) * | 1989-10-04 | 1997-07-30 | Univ Birmingham | Further antiviral pyrimidine nucleosides |
| EP0461225B1 (en) * | 1989-12-08 | 1998-03-18 | City Of Hope | Circumvention of human tumor drug resistance |
| JPH09249690A (ja) | 1995-07-14 | 1997-09-22 | Yamasa Shoyu Co Ltd | ４’−チオアラビノプリンヌクレオシド |
| JPH0925289A (ja) | 1995-07-14 | 1997-01-28 | Yamasa Shoyu Co Ltd | ４’−チオアラビノピリミジンヌクレオシドの製造方法 |
| JP2943690B2 (ja) | 1996-04-17 | 1999-08-30 | 日本電気株式会社 | セル衝突検出装置 |
| EP0980424A2 (en) | 1997-05-09 | 2000-02-23 | Ribozyme Pharmaceuticals, Inc. | Enzymatic nucleic acids: synthesis, selection and use |
| US6548657B1 (en) * | 1997-06-09 | 2003-04-15 | Ribozyme Pharmaceuticals, Inc. | Method for screening nucleic acid catalysts |
| WO1999043690A1 (en) | 1998-02-25 | 1999-09-02 | Rational Drug Design Laboratories | L-4'-arabinofuranonucleoside compound and medicine composition comprising the same |
| EP1100512B1 (en) * | 1998-07-23 | 2011-11-02 | Southern Research Institute | Use of thioarabinofuranosyl compounds |
-
1999
- 1999-07-23 EP EP99935854A patent/EP1100512B1/en not_active Expired - Lifetime
- 1999-07-23 NZ NZ509405A patent/NZ509405A/en not_active IP Right Cessation
- 1999-07-23 AT AT99935854T patent/ATE531376T1/de active
- 1999-07-23 AU AU51239/99A patent/AU747012B2/en not_active Expired
- 1999-07-23 ES ES10170453.4T patent/ES2438144T3/es not_active Expired - Lifetime
- 1999-07-23 ES ES10179999T patent/ES2402799T3/es not_active Expired - Lifetime
- 1999-07-23 EP EP10170453.4A patent/EP2335706B1/en not_active Expired - Lifetime
- 1999-07-23 EP EP10179999A patent/EP2332551B1/en not_active Expired - Lifetime
- 1999-07-23 CA CA002338415A patent/CA2338415C/en not_active Expired - Lifetime
- 1999-07-23 WO PCT/US1999/016630 patent/WO2000004866A2/en not_active Ceased
- 1999-07-23 JP JP2000560859A patent/JP4719356B2/ja not_active Expired - Fee Related
- 1999-07-23 ES ES99935854T patent/ES2376862T3/es not_active Expired - Lifetime
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2000
- 2000-01-28 US US09/493,247 patent/US6576621B1/en not_active Expired - Lifetime
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2003
- 2003-04-07 US US10/407,135 patent/US6870052B2/en not_active Expired - Lifetime
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2004
- 2004-09-13 US US10/938,542 patent/US7138385B2/en not_active Expired - Lifetime
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2006
- 2006-08-24 US US11/509,030 patent/US7691820B2/en not_active Expired - Fee Related
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2010
- 2010-02-23 US US12/710,537 patent/US8178510B2/en not_active Expired - Fee Related
- 2010-04-27 JP JP2010102499A patent/JP2010202655A/ja active Pending
- 2010-10-29 JP JP2010243705A patent/JP5357857B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2338415A1 (en) | 2000-02-03 |
| EP2335706B1 (en) | 2013-10-23 |
| JP4719356B2 (ja) | 2011-07-06 |
| CA2338415C (en) | 2006-10-10 |
| US6576621B1 (en) | 2003-06-10 |
| EP1100512B1 (en) | 2011-11-02 |
| ATE531376T1 (de) | 2011-11-15 |
| WO2000004866A3 (en) | 2000-04-20 |
| JP2011032281A (ja) | 2011-02-17 |
| US20100216797A1 (en) | 2010-08-26 |
| EP2335706A1 (en) | 2011-06-22 |
| US8178510B2 (en) | 2012-05-15 |
| US7691820B2 (en) | 2010-04-06 |
| JP2002521318A (ja) | 2002-07-16 |
| EP2332551A1 (en) | 2011-06-15 |
| ES2376862T3 (es) | 2012-03-20 |
| US20050038025A1 (en) | 2005-02-17 |
| US6870052B2 (en) | 2005-03-22 |
| AU5123999A (en) | 2000-02-14 |
| EP1100512A2 (en) | 2001-05-23 |
| US7138385B2 (en) | 2006-11-21 |
| US20060287320A1 (en) | 2006-12-21 |
| JP5357857B2 (ja) | 2013-12-04 |
| EP2332551B1 (en) | 2013-01-09 |
| ES2402799T3 (es) | 2013-05-09 |
| JP2010202655A (ja) | 2010-09-16 |
| AU747012B2 (en) | 2002-05-09 |
| NZ509405A (en) | 2004-10-29 |
| WO2000004866A2 (en) | 2000-02-03 |
| EP1100512A4 (en) | 2001-10-10 |
| US20030203872A1 (en) | 2003-10-30 |
| WO2000004866A9 (en) | 2000-08-10 |
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