SK283879B6 - Deriváty gemcitabínu, spôsob ich prípravy, ich použitie a farmaceutický prostriedok s ich obsahom - Google Patents

Deriváty gemcitabínu, spôsob ich prípravy, ich použitie a farmaceutický prostriedok s ich obsahom Download PDF

Info

Publication number: SK283879B6
Authority: SK; Slovakia
Prior art keywords: gemcitabine; ester; elaidic acid; amide; derivatives
Prior art date: 1997-01-24

Application number

SK1029-99A

Other languages

English (en)

Slovak (sk)

Other versions

SK102999A3 (en

Inventor

Finn Myhren

Bernt Borretzen

Are Dalen

Marit Liland Sandvold

Original Assignee

Conpharma As

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.)

1997-01-24

Filing date

1998-01-23

Publication date

2004-04-06

1997-01-24 Priority claimed from GB9701427A external-priority patent/GB2321454A/en

1998-01-23 Application filed by Conpharma As filed Critical Conpharma As

2000-05-16 Publication of SK102999A3 publication Critical patent/SK102999A3/sk

2004-04-06 Publication of SK283879B6 publication Critical patent/SK283879B6/sk

Links

SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical class O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 title claims abstract description 78
150000001408 amides Chemical class 0.000 claims abstract description 16
-1 trans-eicosenoyl Chemical group 0.000 claims abstract description 13
125000002252 acyl group Chemical group 0.000 claims abstract description 12
229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
239000002246 antineoplastic agent Substances 0.000 claims abstract description 3
125000004016 elaidoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])/C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract 2
125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract 2
229960005277 gemcitabine Drugs 0.000 claims description 63
150000001875 compounds Chemical class 0.000 claims description 17
238000000034 method Methods 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
235000014113 dietary fatty acids Nutrition 0.000 claims description 4
239000000194 fatty acid Substances 0.000 claims description 4
229930195729 fatty acid Natural products 0.000 claims description 4
150000004665 fatty acids Chemical class 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
238000006467 substitution reaction Methods 0.000 claims description 4
230000000259 anti-tumor effect Effects 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
230000008569 process Effects 0.000 claims description 2
229940041181 antineoplastic drug Drugs 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
230000001093 anti-cancer Effects 0.000 abstract 1
239000003443 antiviral agent Substances 0.000 abstract 1
230000004083 survival effect Effects 0.000 description 20
FATBGEAMYMYZAF-MDZDMXLPSA-N Elaidamide Chemical compound CCCCCCCC\C=C\CCCCCCCC(N)=O FATBGEAMYMYZAF-MDZDMXLPSA-N 0.000 description 15
210000004027 cell Anatomy 0.000 description 12
241000699670 Mus sp. Species 0.000 description 11
230000000694 effects Effects 0.000 description 11
230000001988 toxicity Effects 0.000 description 11
231100000419 toxicity Toxicity 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
230000007774 longterm Effects 0.000 description 10
206010028980 Neoplasm Diseases 0.000 description 7
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
239000003112 inhibitor Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
239000002777 nucleoside Substances 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
201000011510 cancer Diseases 0.000 description 5
150000003833 nucleoside derivatives Chemical class 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
108010033174 Deoxycytidine kinase Proteins 0.000 description 4
102100029588 Deoxycytidine kinase Human genes 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
230000001472 cytotoxic effect Effects 0.000 description 4
ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
DYCJFJRCWPVDHY-LSCFUAHRSA-N NBMPR Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(SCC=3C=CC(=CC=3)[N+]([O-])=O)=C2N=C1 DYCJFJRCWPVDHY-LSCFUAHRSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
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238000001727 in vivo Methods 0.000 description 3
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
230000036457 multidrug resistance Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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238000004809 thin layer chromatography Methods 0.000 description 3
BITHHVVYSMSWAG-KTKRTIGZSA-N (11Z)-icos-11-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 description 2
MLQBTMWHIOYKKC-MDZDMXLPSA-N (e)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C\CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-MDZDMXLPSA-N 0.000 description 2
CKTSBUTUHBMZGZ-SHYZEUOFSA-N 2'‐deoxycytidine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 CKTSBUTUHBMZGZ-SHYZEUOFSA-N 0.000 description 2
FPAQLJHSZVFKES-UHFFFAOYSA-N 5-Eicosenoic acid Natural products CCCCCCCCCCCCCCC=CCCCC(O)=O FPAQLJHSZVFKES-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CKTSBUTUHBMZGZ-UHFFFAOYSA-N Deoxycytidine Natural products O=C1N=C(N)C=CN1C1OC(CO)C(O)C1 CKTSBUTUHBMZGZ-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
YMOXEIOKAJSRQX-QPPQHZFASA-N Gemcitabine triphosphate Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1 YMOXEIOKAJSRQX-QPPQHZFASA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
238000002512 chemotherapy Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
230000001085 cytostatic effect Effects 0.000 description 2
230000003013 cytotoxicity Effects 0.000 description 2
231100000135 cytotoxicity Toxicity 0.000 description 2
IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003480 eluent Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
230000009036 growth inhibition Effects 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
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230000003211 malignant effect Effects 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
229940090007 persantine Drugs 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
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239000000126 substance Substances 0.000 description 2
238000001356 surgical procedure Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
238000012360 testing method Methods 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
210000004881 tumor cell Anatomy 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
208000003174 Brain Neoplasms Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004322 Butylated hydroxytoluene Substances 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
206010059866 Drug resistance Diseases 0.000 description 1
208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
206010061535 Ovarian neoplasm Diseases 0.000 description 1
241000283984 Rodentia Species 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
239000012317 TBTU Substances 0.000 description 1
102100034838 Thymidine kinase, cytosolic Human genes 0.000 description 1
CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000008512 biological response Effects 0.000 description 1
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
230000037396 body weight Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
229940095259 butylated hydroxytoluene Drugs 0.000 description 1
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229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
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230000004700 cellular uptake Effects 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
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238000002648 combination therapy Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
230000002950 deficient Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000013461 design Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000013583 drug formulation Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
229960005144 gemcitabine hydrochloride Drugs 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
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125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000000367 immunologic factor Substances 0.000 description 1
238000002513 implantation Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000000415 inactivating effect Effects 0.000 description 1
239000003978 infusion fluid Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
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210000000936 intestine Anatomy 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
150000004668 long chain fatty acids Chemical class 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
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239000000463 material Substances 0.000 description 1
201000001441 melanoma Diseases 0.000 description 1
239000003607 modifier Substances 0.000 description 1
235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
KUHRIIPUCPOQMQ-UHFFFAOYSA-N n,n-diethyl-3-(ethyliminomethylideneamino)propan-1-amine Chemical compound CCN=C=NCCCN(CC)CC KUHRIIPUCPOQMQ-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000003835 nucleoside group Chemical class 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
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239000001301 oxygen Substances 0.000 description 1
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230000026731 phosphorylation Effects 0.000 description 1
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230000036470 plasma concentration Effects 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
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GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1

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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- 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

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Virology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Physical Or Chemical Processes And Apparatus (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK1029-99A 1997-01-24 1998-01-23 Deriváty gemcitabínu, spôsob ich prípravy, ich použitie a farmaceutický prostriedok s ich obsahom SK283879B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB9701427A GB2321454A (en)	1997-01-24	1997-01-24	Gemcitabine esters and amides
PCT/NO1998/000020 WO1998032762A1 (fr)	1997-01-24	1998-01-23	Derives de gemcitabine

Publications (2)

Publication Number	Publication Date
SK102999A3 SK102999A3 (en)	2000-05-16
SK283879B6 true SK283879B6 (sk)	2004-04-06

Family

ID=26310850

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1029-99A SK283879B6 (sk)	1997-01-24	1998-01-23	Deriváty gemcitabínu, spôsob ich prípravy, ich použitie a farmaceutický prostriedok s ich obsahom

Country Status (15)

Country	Link
US (1)	US6384019B1 (fr)
EP (1)	EP0986570B9 (fr)
JP (1)	JP4352115B2 (fr)
KR (1)	KR100483256B1 (fr)
AT (1)	ATE236188T1 (fr)
AU (1)	AU720451B2 (fr)
CA (1)	CA2278056C (fr)
DE (1)	DE69812934T2 (fr)
DK (1)	DK0986570T3 (fr)
HU (1)	HU224918B1 (fr)
NZ (1)	NZ336676A (fr)
PL (1)	PL186888B1 (fr)
SK (1)	SK283879B6 (fr)
UA (1)	UA67736C2 (fr)
WO (1)	WO1998032762A1 (fr)

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1998
- 1998-01-23 CA CA002278056A patent/CA2278056C/fr not_active Expired - Lifetime
- 1998-01-23 AT AT98901592T patent/ATE236188T1/de active
- 1998-01-23 PL PL98334856A patent/PL186888B1/pl unknown
- 1998-01-23 HU HU0000721A patent/HU224918B1/hu not_active IP Right Cessation
- 1998-01-23 WO PCT/NO1998/000020 patent/WO1998032762A1/fr not_active Ceased
- 1998-01-23 DE DE69812934T patent/DE69812934T2/de not_active Expired - Lifetime
- 1998-01-23 US US09/355,112 patent/US6384019B1/en not_active Expired - Lifetime
- 1998-01-23 JP JP53186298A patent/JP4352115B2/ja not_active Expired - Lifetime
- 1998-01-23 EP EP98901592A patent/EP0986570B9/fr not_active Expired - Lifetime
- 1998-01-23 DK DK98901592T patent/DK0986570T3/da active
- 1998-01-23 NZ NZ336676A patent/NZ336676A/xx not_active IP Right Cessation
- 1998-01-23 KR KR10-1999-7006584A patent/KR100483256B1/ko not_active Expired - Fee Related
- 1998-01-23 UA UA99084763A patent/UA67736C2/uk unknown
- 1998-01-23 SK SK1029-99A patent/SK283879B6/sk not_active IP Right Cessation
- 1998-01-23 AU AU57827/98A patent/AU720451B2/en not_active Expired

Also Published As

Publication number	Publication date
PL186888B1 (pl)	2004-03-31
HUP0000721A2 (hu)	2001-05-28
NZ336676A (en)	2000-01-28
JP4352115B2 (ja)	2009-10-28
HU224918B1 (en)	2006-04-28
PL334856A1 (en)	2000-03-27
CA2278056A1 (fr)	1998-07-30
SK102999A3 (en)	2000-05-16
ATE236188T1 (de)	2003-04-15
JP2001509160A (ja)	2001-07-10
DK0986570T3 (da)	2003-07-28
KR100483256B1 (ko)	2005-04-15
CA2278056C (fr)	2006-12-12
HUP0000721A3 (en)	2002-12-28
US20020042391A1 (en)	2002-04-11
KR20000070351A (ko)	2000-11-25
WO1998032762A1 (fr)	1998-07-30
US6384019B1 (en)	2002-05-07
EP0986570A1 (fr)	2000-03-22
DE69812934D1 (de)	2003-05-08
DE69812934T2 (de)	2004-01-29
AU5782798A (en)	1998-08-18
UA67736C2 (uk)	2004-07-15
EP0986570B9 (fr)	2004-01-02
EP0986570B1 (fr)	2003-04-02
AU720451B2 (en)	2000-06-01

Legal Events

Date	Code	Title	Description
2015-10-02	MM4A	Patent lapsed due to non-payment of maintenance fees	Effective date: 20150123

Publication	Publication Date	Title
SK283879B6 (sk)	2004-04-06	Deriváty gemcitabínu, spôsob ich prípravy, ich použitie a farmaceutický prostriedok s ich obsahom
JP5087052B2 (ja)	2012-11-28	改良された治療剤
CA2140653A1 (fr)	1994-03-03	Inhibiteurs de la proteine kinase et composes connexes combines avec le taxol
RU2194711C2 (ru)	2002-12-20	Производные гемцитабина
EP1460082A1 (fr)	2004-09-22	Dérivés phospholipidiques de clofarabine
MXPA99006790A (en)	2000-01-21	Gemcitabine derivatives
NO318934B1 (no)	2005-05-30	Gemcitabinderivater