IL122814A - 1-[5, 7-DISUBSTITUTED- 1, 2, 3-TRIAZOLO [4, 5-d] PYRIMIDIN-3-YL] RIBOHEPTOFURANURONIC ACID AND ANALOGS THEREOF, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM - Google Patents

1-[5, 7-DISUBSTITUTED- 1, 2, 3-TRIAZOLO [4, 5-d] PYRIMIDIN-3-YL] RIBOHEPTOFURANURONIC ACID AND ANALOGS THEREOF, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Info

Publication number: IL122814A
Authority: IL; Israel
Prior art keywords: formula; compound; product; giving; protecting
Prior art date: 1995-07-11

Application number

IL12281496A

Other languages

English (en)

Other versions

IL122814A0 (en

Original Assignee

Astrazeneca Ab

Astra Pharma Prod

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.)

1995-07-11

Filing date

1996-07-04

Publication date

2001-04-30

1995-07-11 Priority claimed from GBGB9514074.5A external-priority patent/GB9514074D0/en

1995-10-05 Priority claimed from GBGB9520311.3A external-priority patent/GB9520311D0/en

1995-11-08 Priority claimed from GBGB9522837.5A external-priority patent/GB9522837D0/en

1996-07-04 Application filed by Astrazeneca Ab, Astra Pharma Prod filed Critical Astrazeneca Ab

1998-08-16 Publication of IL122814A0 publication Critical patent/IL122814A0/xx

2001-04-30 Publication of IL122814A publication Critical patent/IL122814A/en

Links

239000002253 acid Substances 0.000 title claims description 52
238000002360 preparation method Methods 0.000 title claims description 5
239000008194 pharmaceutical composition Substances 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 206
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125000000217 alkyl group Chemical group 0.000 claims abstract description 22
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208000010110 spontaneous platelet aggregation Diseases 0.000 claims abstract description 5
239000000651 prodrug Substances 0.000 claims abstract description 4
229940002612 prodrug Drugs 0.000 claims abstract description 4
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238000000034 method Methods 0.000 claims description 93
239000002904 solvent Substances 0.000 claims description 42
238000006243 chemical reaction Methods 0.000 claims description 36
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238000011282 treatment Methods 0.000 claims description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
125000006239 protecting group Chemical group 0.000 claims description 23
239000012442 inert solvent Substances 0.000 claims description 21
239000002585 base Substances 0.000 claims description 13
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239000001257 hydrogen Substances 0.000 claims description 13
230000007062 hydrolysis Effects 0.000 claims description 12
238000006460 hydrolysis reaction Methods 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
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
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YEDTWOLJNQYBPU-UHFFFAOYSA-N [Na].[Na].[Na] Chemical compound [Na].[Na].[Na] YEDTWOLJNQYBPU-UHFFFAOYSA-N 0.000 claims 1
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-1 5-tetrazolyl Chemical group 0.000 abstract description 7
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238000004587 chromatography analysis Methods 0.000 description 25
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
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239000007787 solid Substances 0.000 description 12
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238000010992 reflux Methods 0.000 description 11
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239000000725 suspension Substances 0.000 description 9
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
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229910052723 transition metal Inorganic materials 0.000 description 8
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238000011321 prophylaxis Methods 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
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238000002835 absorbance Methods 0.000 description 4
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
239000012346 acetyl chloride Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
206010038687 Respiratory distress Diseases 0.000 description 1
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QHIATDVFSBQTJE-UHFFFAOYSA-L [OH-].[Li+].O.[OH-].[Na+] Chemical compound [OH-].[Li+].O.[OH-].[Na+] QHIATDVFSBQTJE-UHFFFAOYSA-L 0.000 description 1
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Substances CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
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229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
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239000004411 aluminium Substances 0.000 description 1
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XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
239000012964 benzotriazole Substances 0.000 description 1
238000012925 biological evaluation Methods 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
239000012267 brine Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
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GPOGKMPXBDGPJH-UHFFFAOYSA-N butan-2-yl acetate hydrochloride Chemical compound Cl.CCC(C)OC(C)=O GPOGKMPXBDGPJH-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
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238000000502 dialysis Methods 0.000 description 1
RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
229910000071 diazene Inorganic materials 0.000 description 1
JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
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KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 description 1
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230000002489 hematologic effect Effects 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
WQPDUTSPKFMPDP-OUMQNGNKSA-N hirudin Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(OS(O)(=O)=O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]1NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@H](C(NCC(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N2)=O)CSSC1)C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)[C@@H](C)O)CSSC1)C(C)C)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 WQPDUTSPKFMPDP-OUMQNGNKSA-N 0.000 description 1
229940006607 hirudin Drugs 0.000 description 1
229940106780 human fibrinogen Drugs 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000010410 layer Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
USSBDBZGEDUBHE-UHFFFAOYSA-L magnesium;2-oxidooxycarbonylbenzoate Chemical compound [Mg+2].[O-]OC(=O)C1=CC=CC=C1C([O-])=O USSBDBZGEDUBHE-UHFFFAOYSA-L 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
239000002777 nucleoside Substances 0.000 description 1
125000003835 nucleoside group Chemical group 0.000 description 1
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239000000843 powder Substances 0.000 description 1
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
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108090000623 proteins and genes Proteins 0.000 description 1
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125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
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238000011084 recovery Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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241000894007 species Species 0.000 description 1
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239000012730 sustained-release form Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 description 1
QGVNJRROSLYGKF-UHFFFAOYSA-N thiobarbital Chemical compound CCC1(CC)C(=O)NC(=S)NC1=O QGVNJRROSLYGKF-UHFFFAOYSA-N 0.000 description 1
239000003868 thrombin inhibitor Substances 0.000 description 1
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230000003582 thrombocytopenic effect Effects 0.000 description 1
208000014754 thrombocytosis disease Diseases 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000009736 wetting Methods 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
- C07H19/16—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)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Biotechnology (AREA)
Heart & Thoracic Surgery (AREA)
Genetics & Genomics (AREA)
Cardiology (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Diabetes (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Hematology (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)

IL12281496A 1995-07-11 1996-07-04 1-[5, 7-DISUBSTITUTED- 1, 2, 3-TRIAZOLO [4, 5-d] PYRIMIDIN-3-YL] RIBOHEPTOFURANURONIC ACID AND ANALOGS THEREOF, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM IL122814A (en)

Applications Claiming Priority (4)

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
PCT/SE1996/000911 WO1997003084A1 (en)	1995-07-11	1996-07-04	New inhibitors of platelet aggregation

Publications (2)

Publication Number	Publication Date
IL122814A0 IL122814A0 (en)	1998-08-16
IL122814A true IL122814A (en)	2001-04-30

Family

ID=27267806

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12281496A IL122814A (en)	1995-07-11	1996-07-04	1-[5, 7-DISUBSTITUTED- 1, 2, 3-TRIAZOLO [4, 5-d] PYRIMIDIN-3-YL] RIBOHEPTOFURANURONIC ACID AND ANALOGS THEREOF, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Country Status (25)

Country	Link
US (1)	US5747496A (2)
EP (1)	EP0840740B1 (2)
JP (1)	JP4084415B2 (2)
KR (1)	KR100444123B1 (2)
CN (1)	CN1069321C (2)
AR (1)	AR003453A1 (2)
AT (1)	ATE217010T1 (2)
AU (1)	AU699034B2 (2)
BR (1)	BR9609467A (2)
CA (1)	CA2226758A1 (2)
CZ (1)	CZ297200B6 (2)
DE (1)	DE69621021T2 (2)
EE (1)	EE03616B1 (2)
HU (1)	HU221880B1 (2)
IL (1)	IL122814A (2)
IS (1)	IS1790B (2)
MY (1)	MY116542A (2)
NO (1)	NO310624B1 (2)
NZ (1)	NZ312258A (2)
PL (1)	PL182680B1 (2)
SA (1)	SA96170272B1 (2)
SK (1)	SK283206B6 (2)
TR (1)	TR199800019T1 (2)
TW (1)	TW427996B (2)
WO (1)	WO1997003084A1 (2)

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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
AR017014A1 (es) *	1997-07-22	2001-08-22	Astrazeneca Ab	Compuestos de triazolo [4,5-d]pirimidina, composiciones farmaceuticas, uso de los mismos para preparar medicamentos y procesos para la preparacionde dichos compuestos
SE9702772D0 (sv) *	1997-07-22	1997-07-22	Astra Pharma Prod	Novel compounds
MXPA00007634A (es) *	1998-02-17	2003-09-10	Astrazeneca Uk Ltd	Nuevos compuestos de triazol (4,5-d) pirimidina.
SE9802574D0 (sv) *	1998-07-17	1998-07-17	Astra Pharma Prod	Novel compounds
TWI229674B (en)	1998-12-04	2005-03-21	Astra Pharma Prod	Novel triazolo[4,5-d]pyrimidine compounds, pharmaceutical composition containing the same, their process for preparation and uses
SE9904128D0 (sv) *	1999-11-15	1999-11-15	Astra Pharma Prod	Novel compounds
SE9904129D0 (sv) *	1999-11-15	1999-11-15	Astra Pharma Prod	Novel compounds
SE9904377D0 (sv) *	1999-12-01	1999-12-01	Astra Pharma Prod	Pharmaceutical combinations
GB0013407D0 (en) *	2000-06-02	2000-07-26	Astrazeneca Ab	Forms of a chemical compound
GB0013488D0 (en)	2000-06-02	2000-07-26	Astrazeneca Ab	Chemical compound
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EP1615931A1 (en) *	2003-04-09	2006-01-18	Biogen Idec MA Inc.	Triazolopyrazines and methods of making and using the same
WO2004092171A2 (en) *	2003-04-09	2004-10-28	Biogen Idec Ma Inc.	Triazolo[1,5-a]pyrimidines and pyrazolo[1,5-a]pyrimidines useful as a2a adenosin e receptor antagonists
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DE602004027409D1 (de) *	2003-10-21	2010-07-08	Inspire Pharmaceuticals Inc	Tetrahydrofuroä3,4-düdioxolverbindungen und zusammensetzungen und verfahren zur inhibierung der trombozytenaggregation
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1996
- 1996-07-04 WO PCT/SE1996/000911 patent/WO1997003084A1/en not_active Ceased
- 1996-07-04 CA CA002226758A patent/CA2226758A1/en not_active Abandoned
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- 1996-07-04 TW TW085108062A patent/TW427996B/zh not_active IP Right Cessation
- 1996-07-04 TR TR1998/00019T patent/TR199800019T1/xx unknown
- 1996-07-04 DE DE69621021T patent/DE69621021T2/de not_active Expired - Fee Related
- 1996-07-04 JP JP50574897A patent/JP4084415B2/ja not_active Expired - Fee Related
- 1996-07-04 CZ CZ0002598A patent/CZ297200B6/cs not_active IP Right Cessation
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- 1996-07-04 EP EP96923160A patent/EP0840740B1/en not_active Expired - Lifetime
- 1996-07-04 KR KR10-1998-0700187A patent/KR100444123B1/ko not_active Expired - Fee Related
- 1996-07-04 SK SK23-98A patent/SK283206B6/sk unknown
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- 1996-07-04 HU HU9802448A patent/HU221880B1/hu active IP Right Grant
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HUP9802448A2 (hu)	1999-05-28
JPH11508914A (ja)	1999-08-03
AU6375196A (en)	1997-02-10
CN1069321C (zh)	2001-08-08
AR003453A1 (es)	1998-08-05
NZ312258A (en)	1999-08-30
SK2398A3 (en)	1999-01-11
HUP9802448A3 (en)	2000-03-28
SK283206B6 (sk)	2003-03-04
CZ297200B6 (cs)	2006-09-13
EE9800026A (et)	1998-08-17
JP4084415B2 (ja)	2008-04-30
MY116542A (en)	2004-02-28
EP0840740A1 (en)	1998-05-13
KR100444123B1 (ko)	2004-10-14
CN1195353A (zh)	1998-10-07
AU699034B2 (en)	1998-11-19
PL182680B1 (pl)	2002-02-28
CA2226758A1 (en)	1997-01-30
DE69621021T2 (de)	2002-10-31
CZ2598A3 (cs)	1998-08-12
ATE217010T1 (de)	2002-05-15
SA96170272B1 (ar)	2006-06-04
HU221880B1 (hu)	2003-02-28
IS4647A (is)	1998-01-08
NO310624B1 (no)	2001-07-30
EP0840740B1 (en)	2002-05-02
NO980080L (no)	1998-03-06
KR19990028885A (ko)	1999-04-15
BR9609467A (pt)	1999-03-02
EE03616B1 (et)	2002-02-15
IS1790B (is)	2001-11-28
TW427996B (en)	2001-04-01
NO980080D0 (no)	1998-01-08
MX9800308A (es)	1998-09-30
US5747496A (en)	1998-05-05
WO1997003084A1 (en)	1997-01-30
IL122814A0 (en)	1998-08-16
TR199800019T1 (xx)	1998-05-21
PL324396A1 (en)	1998-05-25
DE69621021D1 (de)	2002-06-06

Legal Events

Date	Code	Title
2001-10-31	FF	Patent granted
2001-11-25	KB	Patent renewed
2002-08-14	KB	Patent renewed
2006-09-05	KB	Patent renewed
2011-02-28	MM9K	Patent not in force due to non-payment of renewal fees

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