SK12442001A3 - Cyklické fosforamidáty, spôsob ich prípravy a farmaceutické kompozície, ktoré ich obsahujú - Google Patents
Cyklické fosforamidáty, spôsob ich prípravy a farmaceutické kompozície, ktoré ich obsahujú Download PDFInfo
- Publication number
- SK12442001A3 SK12442001A3 SK1244-2001A SK12442001A SK12442001A3 SK 12442001 A3 SK12442001 A3 SK 12442001A3 SK 12442001 A SK12442001 A SK 12442001A SK 12442001 A3 SK12442001 A3 SK 12442001A3
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- Slovakia
- Prior art keywords
- group
- aryl
- alkyl
- atoms
- substituted
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- 238000000034 method Methods 0.000 title claims abstract description 136
- -1 Cyclic phosphoramidates Chemical class 0.000 title claims description 92
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 229940002612 prodrug Drugs 0.000 claims abstract description 245
- 239000000651 prodrug Substances 0.000 claims abstract description 245
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 214
- 239000003814 drug Substances 0.000 claims abstract description 179
- 229940079593 drug Drugs 0.000 claims abstract description 175
- 210000004185 liver Anatomy 0.000 claims abstract description 109
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 claims abstract description 13
- 230000002708 enhancing effect Effects 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 398
- 229910052721 tungsten Inorganic materials 0.000 claims description 295
- 125000003118 aryl group Chemical group 0.000 claims description 286
- 125000001072 heteroaryl group Chemical group 0.000 claims description 226
- 125000004429 atom Chemical group 0.000 claims description 209
- 229910052739 hydrogen Inorganic materials 0.000 claims description 201
- 239000001257 hydrogen Substances 0.000 claims description 197
- 150000001875 compounds Chemical class 0.000 claims description 177
- 125000005842 heteroatom Chemical group 0.000 claims description 140
- 229910052799 carbon Inorganic materials 0.000 claims description 119
- 229910052698 phosphorus Inorganic materials 0.000 claims description 116
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 115
- 125000002723 alicyclic group Chemical group 0.000 claims description 112
- 125000003107 substituted aryl group Chemical group 0.000 claims description 112
- 229910052720 vanadium Inorganic materials 0.000 claims description 109
- 150000001350 alkyl halides Chemical group 0.000 claims description 107
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 106
- 125000004432 carbon atom Chemical group C* 0.000 claims description 88
- 150000002431 hydrogen Chemical class 0.000 claims description 85
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 79
- 125000004423 acyloxy group Chemical group 0.000 claims description 72
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 72
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 70
- 125000002252 acyl group Chemical group 0.000 claims description 69
- 150000001721 carbon Chemical group 0.000 claims description 66
- 230000000694 effects Effects 0.000 claims description 63
- 125000004437 phosphorous atom Chemical group 0.000 claims description 59
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 57
- 239000011574 phosphorus Substances 0.000 claims description 57
- 210000004027 cell Anatomy 0.000 claims description 48
- 239000003112 inhibitor Substances 0.000 claims description 48
- 102000004190 Enzymes Human genes 0.000 claims description 47
- 108090000790 Enzymes Proteins 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 39
- 229910052717 sulfur Inorganic materials 0.000 claims description 38
- 239000013543 active substance Substances 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 35
- 125000006413 ring segment Chemical group 0.000 claims description 35
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 claims description 34
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 claims description 34
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 34
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 33
- 230000001965 increasing effect Effects 0.000 claims description 32
- 101150053185 P450 gene Proteins 0.000 claims description 31
- OIRDTQYFTABQOQ-UHTZMRCNSA-N Vidarabine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O OIRDTQYFTABQOQ-UHTZMRCNSA-N 0.000 claims description 31
- 229910019142 PO4 Inorganic materials 0.000 claims description 30
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- 238000011282 treatment Methods 0.000 claims description 29
- 241001465754 Metazoa Species 0.000 claims description 28
- 206010028980 Neoplasm Diseases 0.000 claims description 27
- 125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 25
- 125000004434 sulfur atom Chemical group 0.000 claims description 25
- OIRDTQYFTABQOQ-UHFFFAOYSA-N ara-adenosine Natural products Nc1ncnc2n(cnc12)C1OC(CO)C(O)C1O OIRDTQYFTABQOQ-UHFFFAOYSA-N 0.000 claims description 24
- 101150035354 araA gene Proteins 0.000 claims description 24
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 23
- ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 claims description 23
- 125000005750 substituted cyclic group Chemical group 0.000 claims description 23
- 231100000419 toxicity Toxicity 0.000 claims description 23
- 230000001988 toxicity Effects 0.000 claims description 23
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- 201000011510 cancer Diseases 0.000 claims description 19
- 239000010452 phosphate Substances 0.000 claims description 19
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical class ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims description 17
- 150000004712 monophosphates Chemical class 0.000 claims description 17
- 101100002068 Bacillus subtilis (strain 168) araR gene Proteins 0.000 claims description 16
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- 235000000346 sugar Nutrition 0.000 claims description 16
- JNTOCHDNEULJHD-UHFFFAOYSA-N Penciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(CCC(CO)CO)C=N2 JNTOCHDNEULJHD-UHFFFAOYSA-N 0.000 claims description 15
- 108091000080 Phosphotransferase Proteins 0.000 claims description 14
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 14
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 230000003285 pharmacodynamic effect Effects 0.000 claims description 14
- 102000020233 phosphotransferase Human genes 0.000 claims description 14
- 108090000623 proteins and genes Proteins 0.000 claims description 14
- 231100001274 therapeutic index Toxicity 0.000 claims description 14
- 239000002246 antineoplastic agent Substances 0.000 claims description 13
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 208000006454 hepatitis Diseases 0.000 claims description 13
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- 230000001976 improved effect Effects 0.000 claims description 13
- 229960000329 ribavirin Drugs 0.000 claims description 13
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 13
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 12
- 206010012601 diabetes mellitus Diseases 0.000 claims description 12
- IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000001226 triphosphate Substances 0.000 claims description 12
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 claims description 12
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 claims description 11
- RLAHNGKRJJEIJL-RFZPGFLSSA-N [(2r,4r)-4-(2,6-diaminopurin-9-yl)-1,3-dioxolan-2-yl]methanol Chemical compound C12=NC(N)=NC(N)=C2N=CN1[C@H]1CO[C@@H](CO)O1 RLAHNGKRJJEIJL-RFZPGFLSSA-N 0.000 claims description 11
- FRPXSOOHWNMLPH-LURJTMIESA-N [(2s)-1-(6-aminopurin-9-yl)-3-hydroxypropan-2-yl]oxymethylphosphonic acid Chemical compound NC1=NC=NC2=C1N=CN2C[C@@H](CO)OCP(O)(O)=O FRPXSOOHWNMLPH-LURJTMIESA-N 0.000 claims description 11
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- HBUBKKRHXORPQB-FJFJXFQQSA-N (2R,3S,4S,5R)-2-(6-amino-2-fluoro-9-purinyl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O HBUBKKRHXORPQB-FJFJXFQQSA-N 0.000 claims description 10
- XHXFQGAZAVKMFF-UHFFFAOYSA-N 2-(2,6-diaminopurin-9-yl)ethoxymethylphosphonic acid Chemical compound NC1=NC(N)=C2N=CN(CCOCP(O)(O)=O)C2=N1 XHXFQGAZAVKMFF-UHFFFAOYSA-N 0.000 claims description 10
- BYEIJZFKOAXBBV-ATZCPNFKSA-N N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine Chemical compound CC(C)[C@H](C(O)=O)NC(=O)[C@H](CS)NC(=O)CCC[C@H](N)C(O)=O BYEIJZFKOAXBBV-ATZCPNFKSA-N 0.000 claims description 10
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- 229910052736 halogen Inorganic materials 0.000 claims description 10
- QOVUZUCXPAZXDZ-RXMQYKEDSA-N 2-amino-9-[(3r)-3,4-dihydroxybutyl]-3h-purin-6-one Chemical compound O=C1NC(N)=NC2=C1N=CN2CC[C@@H](O)CO QOVUZUCXPAZXDZ-RXMQYKEDSA-N 0.000 claims description 9
- VWFCHDSQECPREK-LURJTMIESA-N Cidofovir Chemical compound NC=1C=CN(C[C@@H](CO)OCP(O)(O)=O)C(=O)N=1 VWFCHDSQECPREK-LURJTMIESA-N 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 210000003734 kidney Anatomy 0.000 claims description 9
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 9
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- BCSLVBZWCFTDPK-UDJQAZALSA-N 2-amino-9-[(2r,3r,4s)-3,4-bis(hydroxymethyl)oxetan-2-yl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](CO)[C@H]1CO BCSLVBZWCFTDPK-UDJQAZALSA-N 0.000 claims description 8
- SWFJAJRDLUUIOA-IBCQBUCCSA-N 5-ethyl-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(CC)=CN1[C@H]1[C@@H](F)[C@H](O)[C@@H](CO)O1 SWFJAJRDLUUIOA-IBCQBUCCSA-N 0.000 claims description 8
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- PYJIWOQTJHPDAK-PRJMDXOYSA-N [(1s,2r,3s)-3-(6-aminopurin-9-yl)-2-(hydroxymethyl)cyclobutyl]methanol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1C[C@H](CO)[C@H]1CO PYJIWOQTJHPDAK-PRJMDXOYSA-N 0.000 claims description 8
- BFZJTDBFUROXJA-UHFFFAOYSA-N [1-(6-aminopurin-9-yl)-3-fluoropropan-2-yl]oxymethylphosphonic acid Chemical compound NC1=NC=NC2=C1N=CN2CC(CF)OCP(O)(O)=O BFZJTDBFUROXJA-UHFFFAOYSA-N 0.000 claims description 8
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- IPVFGAYTKQKGBM-BYPJNBLXSA-N 1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione Chemical compound F[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 IPVFGAYTKQKGBM-BYPJNBLXSA-N 0.000 claims description 7
- GIMSJJHKKXRFGV-BYPJNBLXSA-N 4-amino-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one Chemical compound C1=C(I)C(N)=NC(=O)N1[C@H]1[C@@H](F)[C@H](O)[C@@H](CO)O1 GIMSJJHKKXRFGV-BYPJNBLXSA-N 0.000 claims description 7
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- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65842—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring
- C07F9/65846—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring the phosphorus atom being part of a six-membered ring which may be condensed with another ring system
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- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65848—Cyclic amide derivatives of acids of phosphorus, in which two nitrogen atoms belong to the ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Tropical Medicine & Parasitology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Communicable Diseases (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Virology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12301399P | 1999-03-05 | 1999-03-05 | |
US15312799P | 1999-09-08 | 1999-09-08 | |
PCT/US2000/005672 WO2000052015A2 (en) | 1999-03-05 | 2000-03-03 | Novel phosphorus-containing prodrugs |
Publications (1)
Publication Number | Publication Date |
---|---|
SK12442001A3 true SK12442001A3 (sk) | 2002-06-04 |
Family
ID=26821130
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK1244-2001A SK12442001A3 (sk) | 1999-03-05 | 2000-03-03 | Cyklické fosforamidáty, spôsob ich prípravy a farmaceutické kompozície, ktoré ich obsahujú |
Country Status (19)
Country | Link |
---|---|
EP (2) | EP1165570B9 (ja) |
JP (1) | JP5063837B2 (ja) |
CN (1) | CN1321999C (ja) |
AT (1) | ATE337324T1 (ja) |
AU (1) | AU775332B2 (ja) |
CA (1) | CA2362805A1 (ja) |
CY (1) | CY1105799T1 (ja) |
CZ (1) | CZ20013180A3 (ja) |
DE (1) | DE60030263T2 (ja) |
DK (1) | DK1165570T3 (ja) |
ES (1) | ES2272268T3 (ja) |
HK (1) | HK1043796B (ja) |
HU (1) | HUP0200260A3 (ja) |
IL (2) | IL145052A0 (ja) |
MX (1) | MXPA01008937A (ja) |
NZ (1) | NZ513728A (ja) |
PT (1) | PT1165570E (ja) |
SK (1) | SK12442001A3 (ja) |
WO (1) | WO2000052015A2 (ja) |
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US7193081B2 (en) | 2002-05-13 | 2007-03-20 | Metabasis Therapeutics, Inc. | Process for preparation of cyclic prodrugs of PMEA and PMPA |
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BR112019025659A2 (pt) | 2017-06-05 | 2020-08-25 | Viking Therapeutics, Inc. | composições para o tratamento de fibrose |
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JPH09241284A (ja) * | 1996-03-08 | 1997-09-16 | Koji Yamashita | 新規なオキシアザホスホリン誘導体 |
GB9618634D0 (en) * | 1996-09-06 | 1996-10-16 | Univ Southampton | Anti cancer drugs |
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JP2001515482A (ja) * | 1997-03-07 | 2001-09-18 | メタバシス・セラピューティクス・インコーポレイテッド | フルクトース−1,6−ビスホスファターゼの新規なベンズイミダゾールインヒビター |
AU6691798A (en) | 1997-03-07 | 1998-09-22 | Metabasis Therapeutics, Inc. | Novel indole and azaindole inhibitors of fructose-1,6-bisphosphatase |
ATE246197T1 (de) * | 1998-09-09 | 2003-08-15 | Metabasis Therapeutics Inc | Neue heteroaromatische fructose 1,6- bisphosphatase inhibitoren |
-
2000
- 2000-03-03 MX MXPA01008937A patent/MXPA01008937A/es active IP Right Grant
- 2000-03-03 CZ CZ20013180A patent/CZ20013180A3/cs unknown
- 2000-03-03 DE DE60030263T patent/DE60030263T2/de not_active Expired - Lifetime
- 2000-03-03 IL IL14505200A patent/IL145052A0/xx active IP Right Grant
- 2000-03-03 HU HU0200260A patent/HUP0200260A3/hu unknown
- 2000-03-03 NZ NZ513728A patent/NZ513728A/en not_active IP Right Cessation
- 2000-03-03 ES ES00917729T patent/ES2272268T3/es not_active Expired - Lifetime
- 2000-03-03 DK DK00917729T patent/DK1165570T3/da active
- 2000-03-03 AU AU38658/00A patent/AU775332B2/en not_active Expired
- 2000-03-03 PT PT00917729T patent/PT1165570E/pt unknown
- 2000-03-03 AT AT00917729T patent/ATE337324T1/de not_active IP Right Cessation
- 2000-03-03 WO PCT/US2000/005672 patent/WO2000052015A2/en active IP Right Grant
- 2000-03-03 SK SK1244-2001A patent/SK12442001A3/sk unknown
- 2000-03-03 CN CNB00807173XA patent/CN1321999C/zh not_active Expired - Lifetime
- 2000-03-03 EP EP00917729A patent/EP1165570B9/en not_active Expired - Lifetime
- 2000-03-03 EP EP06119343A patent/EP1724276A1/en not_active Withdrawn
- 2000-03-03 JP JP2000602240A patent/JP5063837B2/ja not_active Expired - Lifetime
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2001
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-
2002
- 2002-07-02 HK HK02104972.2A patent/HK1043796B/zh not_active IP Right Cessation
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Also Published As
Publication number | Publication date |
---|---|
HK1043796A1 (en) | 2002-09-27 |
ATE337324T1 (de) | 2006-09-15 |
DE60030263D1 (de) | 2006-10-05 |
PT1165570E (pt) | 2007-01-31 |
EP1165570A2 (en) | 2002-01-02 |
JP5063837B2 (ja) | 2012-10-31 |
CN1353719A (zh) | 2002-06-12 |
CA2362805A1 (en) | 2000-09-08 |
HUP0200260A3 (en) | 2002-11-28 |
DE60030263T2 (de) | 2007-08-30 |
MXPA01008937A (es) | 2004-04-05 |
EP1724276A1 (en) | 2006-11-22 |
CN1321999C (zh) | 2007-06-20 |
ES2272268T3 (es) | 2007-05-01 |
EP1165570B1 (en) | 2006-08-23 |
HUP0200260A2 (en) | 2002-06-29 |
CY1105799T1 (el) | 2011-02-02 |
WO2000052015A2 (en) | 2000-09-08 |
CZ20013180A3 (cs) | 2002-02-13 |
AU775332B2 (en) | 2004-07-29 |
NZ513728A (en) | 2001-09-28 |
IL145052A (en) | 2007-07-24 |
IL145052A0 (en) | 2002-06-30 |
JP2002538161A (ja) | 2002-11-12 |
HK1043796B (zh) | 2007-02-23 |
EP1165570B9 (en) | 2007-02-21 |
AU3865800A (en) | 2000-09-21 |
DK1165570T3 (da) | 2006-12-18 |
WO2000052015A3 (en) | 2001-02-15 |
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