BG108347A - Нови производни на 5-тио-бета-d-ксилопиранозиди, метод за получаване, фармацевтични състави които ги съдържат и тяхното използване за терапия - Google Patents

Нови производни на 5-тио-бета-d-ксилопиранозиди, метод за получаване, фармацевтични състави които ги съдържат и тяхното използване за терапия Download PDF

Info

Publication number: BG108347A
Authority: BG; Bulgaria
Prior art keywords: group; formula; compound; alkyl group; substituents
Prior art date: 2001-05-11

Application number

BG108347A

Other languages

Bulgarian (bg)

English (en)

Inventor

Veronique Barberousse

Soth Samreth

Original Assignee

Laboratoires Fournier S.A.

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.)

2001-05-11

Filing date

2003-11-11

Publication date

2004-11-30

2003-11-11 Application filed by Laboratoires Fournier S.A. filed Critical Laboratoires Fournier S.A.

2004-11-30 Publication of BG108347A publication Critical patent/BG108347A/bg

Links

238000002360 preparation method Methods 0.000 title claims description 10
239000008194 pharmaceutical composition Substances 0.000 title claims description 8
230000001225 therapeutic effect Effects 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 70
150000003839 salts Chemical class 0.000 claims abstract description 18
125000001424 substituent group Chemical group 0.000 claims abstract description 15
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 13
150000004677 hydrates Chemical class 0.000 claims abstract description 9
239000012453 solvate Substances 0.000 claims abstract description 9
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
125000002757 morpholinyl group Chemical group 0.000 claims abstract description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
125000003386 piperidinyl group Chemical group 0.000 claims abstract description 5
125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 5
125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 claims abstract description 3
125000004193 piperazinyl group Chemical group 0.000 claims abstract description 3
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
239000003146 anticoagulant agent Substances 0.000 claims description 3
229940127217 antithrombotic drug Drugs 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
210000003462 vein Anatomy 0.000 claims description 2
229910014033 C-OH Inorganic materials 0.000 claims 1
229910014570 C—OH Inorganic materials 0.000 claims 1
230000003993 interaction Effects 0.000 claims 1
230000002265 prevention Effects 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
239000000243 solution Substances 0.000 description 30
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
-1 4-methyl-2-oxo-2H-1-benzopyran-7-yl Chemical group 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
239000002904 solvent Substances 0.000 description 13
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
208000007536 Thrombosis Diseases 0.000 description 8
239000000203 mixture Substances 0.000 description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
238000001990 intravenous administration Methods 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 5
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
239000003480 eluent Substances 0.000 description 5
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
108700003601 dimethylglycine Proteins 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
229940098779 methanesulfonic acid Drugs 0.000 description 4
239000002808 molecular sieve Substances 0.000 description 4
229940078490 n,n-dimethylglycine Drugs 0.000 description 4
210000002966 serum Anatomy 0.000 description 4
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
230000002785 anti-thrombosis Effects 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000012360 testing method Methods 0.000 description 3
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 2
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000002775 capsule Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
238000010253 intravenous injection Methods 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
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125000006239 protecting group Chemical group 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229930195734 saturated hydrocarbon Natural products 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
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125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
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OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 1
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108010014173 Factor X Proteins 0.000 description 1
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NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
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JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
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238000002474 experimental method Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
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230000002489 hematologic effect Effects 0.000 description 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 description 1
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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238000011017 operating method Methods 0.000 description 1
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239000000523 sample Substances 0.000 description 1
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210000002784 stomach Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000005303 weighing 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/075—Benzo[b]pyran-2-ones
- 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
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Hematology (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

BG108347A 2001-05-11 2003-11-11 Нови производни на 5-тио-бета-d-ксилопиранозиди, метод за получаване, фармацевтични състави които ги съдържат и тяхното използване за терапия BG108347A (bg)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR0106236A FR2824559B1 (fr)	2001-05-11	2001-05-11	Nouveaux derives 5-thio-beta-xylopyronasides, procede de preparation, compositions pharmaceutiques les contenant et leur utilisation en therapeutique

Publications (1)

Publication Number	Publication Date
BG108347A true BG108347A (bg)	2004-11-30

Family

ID=8863165

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG108347A BG108347A (bg)	2001-05-11	2003-11-11	Нови производни на 5-тио-бета-d-ксилопиранозиди, метод за получаване, фармацевтични състави които ги съдържат и тяхното използване за терапия

Country Status (23)

Country	Link
US (1)	US6927209B2 (cs)
EP (1)	EP1385858B1 (cs)
JP (1)	JP2004534036A (cs)
KR (1)	KR20030094351A (cs)
CN (1)	CN1518557A (cs)
AR (1)	AR035880A1 (cs)
AT (1)	ATE323097T1 (cs)
BG (1)	BG108347A (cs)
BR (1)	BR0209102A (cs)
CA (1)	CA2446763A1 (cs)
CZ (1)	CZ20033021A3 (cs)
DE (1)	DE60210595D1 (cs)
EE (1)	EE200300548A (cs)
FR (1)	FR2824559B1 (cs)
HU (1)	HUP0304065A2 (cs)
IL (1)	IL158587A0 (cs)
MX (1)	MXPA03010259A (cs)
NO (1)	NO20034985L (cs)
PL (1)	PL369632A1 (cs)
RU (1)	RU2003132704A (cs)
SK (1)	SK13762003A3 (cs)
WO (1)	WO2002092614A1 (cs)
ZA (1)	ZA200308317B (cs)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2860234B1 (fr) *	2003-09-25	2005-12-23	Fournier Lab Sa	Nouveaux derives 666 du thioxylose
WO2006110726A2 (en) *	2005-04-11	2006-10-19	Glaxo Group Limited	Dosage formulations and methods of treatment and prevention
FR2903698B1 (fr) *	2006-07-13	2009-01-30	Fournier S A Sa Lab	Nouveaux derives de 5-thioxylopyranose.
FR2906247B1 (fr) *	2006-09-27	2008-12-26	Fournier S A Sa Lab	Nouveaux derives de 5-thioxylopyranose
FR2906248B1 (fr) *	2006-09-27	2008-12-26	Fournier S A Sa Lab	Nouveaux derives de 5-thioxylopyranose
EP3200792A4 (en) *	2014-10-03	2018-05-09	The Institute for Cancer Research d/b/a The Research Institute of Fox Chase Cancer Center	Poly (adp-ribose) polymerase 1 inhibitors structurally unrelated to nad

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0421829B1 (fr)	1989-09-22	1994-11-09	Fournier Industrie Et Sante	Nouveaux benzopyranone-beta-D-thioxylosides, leur procédé de préparation et leur utilisation en thérapeutique

2001
- 2001-05-11 FR FR0106236A patent/FR2824559B1/fr not_active Expired - Fee Related
2002
- 2002-05-06 US US10/139,908 patent/US6927209B2/en not_active Expired - Fee Related
- 2002-05-07 JP JP2002589497A patent/JP2004534036A/ja not_active Withdrawn
- 2002-05-07 WO PCT/FR2002/001573 patent/WO2002092614A1/fr not_active Ceased
- 2002-05-07 HU HU0304065A patent/HUP0304065A2/hu unknown
- 2002-05-07 PL PL02369632A patent/PL369632A1/xx not_active Application Discontinuation
- 2002-05-07 KR KR10-2003-7013501A patent/KR20030094351A/ko not_active Withdrawn
- 2002-05-07 CZ CZ20033021A patent/CZ20033021A3/cs unknown
- 2002-05-07 EP EP02738222A patent/EP1385858B1/fr not_active Expired - Lifetime
- 2002-05-07 MX MXPA03010259A patent/MXPA03010259A/es not_active Application Discontinuation
- 2002-05-07 RU RU2003132704/04A patent/RU2003132704A/ru not_active Application Discontinuation
- 2002-05-07 SK SK1376-2003A patent/SK13762003A3/sk unknown
- 2002-05-07 IL IL15858702A patent/IL158587A0/xx unknown
- 2002-05-07 AT AT02738222T patent/ATE323097T1/de not_active IP Right Cessation
- 2002-05-07 DE DE60210595T patent/DE60210595D1/de not_active Expired - Fee Related
- 2002-05-07 CA CA002446763A patent/CA2446763A1/fr not_active Abandoned
- 2002-05-07 BR BR0209102-0A patent/BR0209102A/pt not_active IP Right Cessation
- 2002-05-07 CN CNA028097033A patent/CN1518557A/zh active Pending
- 2002-05-07 EE EEP200300548A patent/EE200300548A/xx unknown
- 2002-05-08 AR ARP020101682A patent/AR035880A1/es unknown
2003
- 2003-10-24 ZA ZA200308317A patent/ZA200308317B/en unknown
- 2003-11-10 NO NO20034985A patent/NO20034985L/no not_active Application Discontinuation
- 2003-11-11 BG BG108347A patent/BG108347A/bg unknown

Also Published As

Publication number	Publication date
RU2003132704A (ru)	2005-04-20
EE200300548A (et)	2004-02-16
EP1385858B1 (fr)	2006-04-12
SK13762003A3 (sk)	2004-04-06
KR20030094351A (ko)	2003-12-11
MXPA03010259A (es)	2004-03-10
PL369632A1 (en)	2005-05-02
CN1518557A (zh)	2004-08-04
WO2002092614A1 (fr)	2002-11-21
ATE323097T1 (de)	2006-04-15
BR0209102A (pt)	2004-07-13
HUP0304065A2 (hu)	2004-04-28
CZ20033021A3 (en)	2004-04-14
EP1385858A1 (fr)	2004-02-04
IL158587A0 (en)	2004-05-12
FR2824559B1 (fr)	2004-02-13
NO20034985D0 (no)	2003-11-10
CA2446763A1 (fr)	2002-11-21
JP2004534036A (ja)	2004-11-11
NO20034985L (no)	2003-11-10
FR2824559A1 (fr)	2002-11-15
DE60210595D1 (de)	2006-05-24
AR035880A1 (es)	2004-07-21
ZA200308317B (en)	2005-03-11
US6927209B2 (en)	2005-08-09
US20020198193A1 (en)	2002-12-26

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