CZ297200B6 - Nové inhibitory agregace krevních desticek - Google Patents
Nové inhibitory agregace krevních desticek Download PDFInfo
- Publication number
- CZ297200B6 CZ297200B6 CZ0002598A CZ2598A CZ297200B6 CZ 297200 B6 CZ297200 B6 CZ 297200B6 CZ 0002598 A CZ0002598 A CZ 0002598A CZ 2598 A CZ2598 A CZ 2598A CZ 297200 B6 CZ297200 B6 CZ 297200B6
- Authority
- CZ
- Czechia
- Prior art keywords
- formula
- triazolo
- compound
- pyrimidin
- alkyl
- Prior art date
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- 208000010110 spontaneous platelet aggregation Diseases 0.000 title claims abstract description 14
- 239000003112 inhibitor Substances 0.000 title 1
- -1 5-tetrazolyl Chemical group 0.000 claims abstract description 229
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 75
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 claims abstract description 58
- 238000011282 treatment Methods 0.000 claims abstract description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 9
- 239000003814 drug Substances 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 206010002388 Angina unstable Diseases 0.000 claims abstract description 8
- 208000007814 Unstable Angina Diseases 0.000 claims abstract description 8
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims abstract description 8
- 208000010125 myocardial infarction Diseases 0.000 claims abstract description 8
- 238000007887 coronary angioplasty Methods 0.000 claims abstract description 7
- 208000035475 disorder Diseases 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 162
- 238000000034 method Methods 0.000 claims description 118
- 125000006309 butyl amino group Chemical group 0.000 claims description 72
- 239000002253 acid Substances 0.000 claims description 69
- 229960005261 aspartic acid Drugs 0.000 claims description 61
- 125000006239 protecting group Chemical group 0.000 claims description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 45
- 239000002904 solvent Substances 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 239000012442 inert solvent Substances 0.000 claims description 32
- 239000002585 base Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 23
- 230000008569 process Effects 0.000 claims description 22
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 20
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 19
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 15
- 239000011734 sodium Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 230000007062 hydrolysis Effects 0.000 claims description 14
- 238000006460 hydrolysis reaction Methods 0.000 claims description 14
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 12
- 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 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- 159000000000 sodium salts Chemical class 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000004494 ethyl ester group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 230000009467 reduction Effects 0.000 claims description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
- 239000011707 mineral Substances 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- 239000012434 nucleophilic reagent Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000004911 3,3-dimethylbutylamino group Chemical group CC(CCN*)(C)C 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 238000006772 olefination reaction Methods 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 5
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- 229910052727 yttrium Inorganic materials 0.000 claims description 5
- STUQITWXBMZUGY-UHFFFAOYSA-N 6-hydroxy-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound OC1=CC(O)=NC(S)=N1 STUQITWXBMZUGY-UHFFFAOYSA-N 0.000 claims description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 238000006193 diazotization reaction Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- IQGYCVKWCYGVBK-UHFFFAOYSA-N 5,6-diamino-1h-pyrimidine-2,4-dithione Chemical compound NC=1NC(=S)NC(=S)C=1N IQGYCVKWCYGVBK-UHFFFAOYSA-N 0.000 claims description 3
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001540 azides Chemical class 0.000 claims description 3
- 238000010511 deprotection reaction Methods 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 229960002897 heparin Drugs 0.000 claims description 3
- 229920000669 heparin Polymers 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- 150000002826 nitrites Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- XTCGLTVNRHPGDH-UHFFFAOYSA-N 5,6-dihydroxy-3-azabicyclo[2.2.1]heptan-2-one Chemical compound C1C2C(O)C(O)C1C(=O)N2 XTCGLTVNRHPGDH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 238000006396 nitration reaction Methods 0.000 claims description 2
- 150000002905 orthoesters Chemical class 0.000 claims description 2
- 238000010647 peptide synthesis reaction Methods 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 2
- 239000000047 product Substances 0.000 description 106
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- 239000000243 solution Substances 0.000 description 76
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 53
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- 229910004298 SiO 2 Inorganic materials 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- 238000004587 chromatography analysis Methods 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 17
- 238000002955 isolation Methods 0.000 description 17
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 15
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 13
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
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- 238000003756 stirring Methods 0.000 description 8
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- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 7
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
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- 239000005557 antagonist Substances 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
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- WTVSOESDARPVQO-UHFFFAOYSA-N triazolo[4,5-d]pyrimidin-7-one Chemical compound O=C1N=CN=C2N=NN=C12 WTVSOESDARPVQO-UHFFFAOYSA-N 0.000 description 1
- VKDYDXILKHBYHT-UHFFFAOYSA-O tributylazanium;azide Chemical compound [N-]=[N+]=[N-].CCCC[NH+](CCCC)CCCC VKDYDXILKHBYHT-UHFFFAOYSA-O 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
-
- 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
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9514074.5A GB9514074D0 (en) | 1995-07-11 | 1995-07-11 | Compounds |
| GBGB9520311.3A GB9520311D0 (en) | 1995-10-05 | 1995-10-05 | Compounds |
| GBGB9522837.5A GB9522837D0 (en) | 1995-11-08 | 1995-11-08 | Compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ2598A3 CZ2598A3 (cs) | 1998-08-12 |
| CZ297200B6 true CZ297200B6 (cs) | 2006-09-13 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ0002598A CZ297200B6 (cs) | 1995-07-11 | 1996-07-04 | Nové inhibitory agregace krevních desticek |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US5747496A (enExample) |
| EP (1) | EP0840740B1 (enExample) |
| JP (1) | JP4084415B2 (enExample) |
| KR (1) | KR100444123B1 (enExample) |
| CN (1) | CN1069321C (enExample) |
| AR (1) | AR003453A1 (enExample) |
| AT (1) | ATE217010T1 (enExample) |
| AU (1) | AU699034B2 (enExample) |
| BR (1) | BR9609467A (enExample) |
| CA (1) | CA2226758A1 (enExample) |
| CZ (1) | CZ297200B6 (enExample) |
| DE (1) | DE69621021T2 (enExample) |
| EE (1) | EE03616B1 (enExample) |
| HU (1) | HU221880B1 (enExample) |
| IL (1) | IL122814A (enExample) |
| IS (1) | IS1790B (enExample) |
| MY (1) | MY116542A (enExample) |
| NO (1) | NO310624B1 (enExample) |
| NZ (1) | NZ312258A (enExample) |
| PL (1) | PL182680B1 (enExample) |
| SA (1) | SA96170272B1 (enExample) |
| SK (1) | SK283206B6 (enExample) |
| TR (1) | TR199800019T1 (enExample) |
| TW (1) | TW427996B (enExample) |
| WO (1) | WO1997003084A1 (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4125790B2 (ja) * | 1996-12-20 | 2008-07-30 | アストラゼネカ・アクチエボラーグ | トリアゾロ［４，５−ｄ］ピリミジニル誘導体および医薬としてのその使用 |
| SE9702772D0 (sv) * | 1997-07-22 | 1997-07-22 | Astra Pharma Prod | Novel compounds |
| SE9702773D0 (sv) * | 1997-07-22 | 1997-07-22 | Astra Pharma Prod | Novel compounds |
| SE9702774D0 (sv) * | 1997-07-22 | 1997-07-22 | Astra Pharma Prod | Novel compounds |
| TW530058B (en) * | 1997-07-22 | 2003-05-01 | Astra Pharma Prod | Triazolo [4,5-d]pyrimidine compounos and their use and process for preparation |
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| CN112915063B (zh) * | 2021-01-25 | 2022-12-20 | 刘红枚 | 一种用于治疗子宫平滑肌高频率强直性收缩相关疾病的化合物 |
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- 1996-07-04 CN CN96196720A patent/CN1069321C/zh not_active Expired - Fee Related
- 1996-07-04 AT AT96923160T patent/ATE217010T1/de not_active IP Right Cessation
- 1996-07-04 BR BR9609467A patent/BR9609467A/pt active Search and Examination
- 1996-07-04 US US08/737,005 patent/US5747496A/en not_active Expired - Fee Related
- 1996-07-04 HU HU9802448A patent/HU221880B1/hu active IP Right Grant
- 1996-07-04 KR KR10-1998-0700187A patent/KR100444123B1/ko not_active Expired - Fee Related
- 1996-07-04 WO PCT/SE1996/000911 patent/WO1997003084A1/en not_active Ceased
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- 1996-07-04 DE DE69621021T patent/DE69621021T2/de not_active Expired - Fee Related
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- 1996-07-04 CA CA002226758A patent/CA2226758A1/en not_active Abandoned
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- 1996-07-11 AR ARP960103538A patent/AR003453A1/es active IP Right Grant
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| EP0215759A1 (en) * | 1985-09-10 | 1987-03-25 | The Regents Of The University Of Minnesota | Antiviral carbocyclic analogs of xylofuranosylpurines |
| DE4004558A1 (de) * | 1989-02-27 | 1990-09-27 | Sanyo Kokusaku Pulp Co | 2',3'-didesoxypurinnucleoside und verfahren zu ihrer herstellung |
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| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
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