SK284199B6 - Triazolo[4,5-d]pyrimidínové zlúčeniny, spôsob ich prípravy, farmaceutické kompozície s ich obsahom a ich použitie - Google Patents

Triazolo[4,5-d]pyrimidínové zlúčeniny, spôsob ich prípravy, farmaceutické kompozície s ich obsahom a ich použitie Download PDF

Info

Publication number: SK284199B6
Authority: SK; Slovakia
Prior art keywords: triazolo; pyrimidin; amino; propylthio; cyclopentane
Prior art date: 1997-07-22

Application number

SK1881-99A

Other languages

English (en)

Slovak (sk)

Other versions

SK188199A3 (en

Inventor

Simon Guile

Anthony Ingall

Brian Springthorpe

Paul Willis

Original Assignee

Astra Pharmaceuticals Ltd.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-07-22

Filing date

1998-07-15

Publication date

2004-10-05

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26663042&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK284199(B6) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1997-07-22 Priority claimed from SE9702775A external-priority patent/SE9702775D0/xx

1997-07-22 Priority claimed from SE9702773A external-priority patent/SE9702773D0/xx

1998-07-15 Application filed by Astra Pharmaceuticals Ltd. filed Critical Astra Pharmaceuticals Ltd.

2000-10-09 Publication of SK188199A3 publication Critical patent/SK188199A3/sk

2004-10-05 Publication of SK284199B6 publication Critical patent/SK284199B6/sk

Links

150000001875 compounds Chemical class 0.000 title claims description 299
238000000034 method Methods 0.000 claims abstract description 278
230000008569 process Effects 0.000 claims abstract description 9
238000002360 preparation method Methods 0.000 claims abstract description 8
-1 triazolo [4,5-d] pyrimidine compound Chemical class 0.000 claims description 604
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 353
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 246
125000001847 2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 claims description 111
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 92
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 72
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
VCVOSERVUCJNPR-UHFFFAOYSA-N cyclopentane-1,2-diol Chemical compound OC1CCCC1O VCVOSERVUCJNPR-UHFFFAOYSA-N 0.000 claims description 49
229910052739 hydrogen Inorganic materials 0.000 claims description 48
MVHTVXFDPMHZNE-UHFFFAOYSA-N cyclopentane-1,2,3-triol Chemical compound OC1CCC(O)C1O MVHTVXFDPMHZNE-UHFFFAOYSA-N 0.000 claims description 43
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 40
239000001257 hydrogen Substances 0.000 claims description 35
125000005843 halogen group Chemical group 0.000 claims description 31
125000006309 butyl amino group Chemical group 0.000 claims description 28
229910052736 halogen Inorganic materials 0.000 claims description 26
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
150000002431 hydrogen Chemical group 0.000 claims description 22
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 13
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
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125000006239 protecting group Chemical group 0.000 claims description 10
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230000001732 thrombotic effect Effects 0.000 claims description 9
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125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
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CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 8
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 7
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
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206010010904 Convulsion Diseases 0.000 claims description 6
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125000000524 functional group Chemical group 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
208000010125 myocardial infarction Diseases 0.000 claims description 6
239000012453 solvate Substances 0.000 claims description 6
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125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
239000004305 biphenyl Substances 0.000 claims description 5
125000006317 cyclopropyl amino group Chemical group 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 4
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 4
ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical compound OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 0.000 claims description 4
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HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 4
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
JEXQWCBPEWHFKC-UHFFFAOYSA-N 2-cyclopentylethanol Chemical compound OCCC1CCCC1 JEXQWCBPEWHFKC-UHFFFAOYSA-N 0.000 claims description 3
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206010002383 Angina Pectoris Diseases 0.000 claims description 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
208000018262 Peripheral vascular disease Diseases 0.000 claims description 3
SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims description 3
125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
230000000302 ischemic effect Effects 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
230000001052 transient effect Effects 0.000 claims description 3
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 2
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
208000035475 disorder Diseases 0.000 claims description 2
230000000640 hydroxylating effect Effects 0.000 claims description 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
230000002265 prevention Effects 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims description 2
WYTAAQUZGZIURL-UHFFFAOYSA-N 5-(hydroxymethyl)-1-(2H-pyrimidin-1-yl)cyclopentane-1,2-diol Chemical compound N=1CN(C=CC1)C1(C(CCC1CO)O)O WYTAAQUZGZIURL-UHFFFAOYSA-N 0.000 claims 3
125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
229910052757 nitrogen Inorganic materials 0.000 claims 2
125000003944 tolyl group Chemical group 0.000 claims 2
MGDNEWHBNWTXCL-UHFFFAOYSA-N 1-(2-hydroxyethyl)cyclopentane-1,2-diol Chemical compound OCCC1(O)CCCC1O MGDNEWHBNWTXCL-UHFFFAOYSA-N 0.000 claims 1
HZZLQJDXXAKQKP-UHFFFAOYSA-N 4-[7-[[2-[3-(dimethylamino)phenyl]cyclopropyl]amino]-5-propylsulfanyltriazolo[4,5-d]pyrimidin-3-yl]cyclopentane-1,2,3-triol Chemical compound C=12N=NN(C3C(C(O)C(O)C3)O)C2=NC(SCCC)=NC=1NC1CC1C1=CC=CC(N(C)C)=C1 HZZLQJDXXAKQKP-UHFFFAOYSA-N 0.000 claims 1
LLBKVVXGHZUMHM-UHFFFAOYSA-N C1CC(C(C1CCO)(N2CN=CC=C2)O)O Chemical compound C1CC(C(C1CCO)(N2CN=CC=C2)O)O LLBKVVXGHZUMHM-UHFFFAOYSA-N 0.000 claims 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 75
239000003814 drug Substances 0.000 abstract description 5
GIIGHSIIKVOWKZ-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidine Chemical class N1=CN=CC2=NNN=C21 GIIGHSIIKVOWKZ-UHFFFAOYSA-N 0.000 abstract description 2
239000000047 product Substances 0.000 description 301
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239000011541 reaction mixture Substances 0.000 description 53
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238000004128 high performance liquid chromatography Methods 0.000 description 22
239000000725 suspension Substances 0.000 description 20
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229940043376 ammonium acetate Drugs 0.000 description 16
235000019257 ammonium acetate Nutrition 0.000 description 16
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125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
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Classifications

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- C07—ORGANIC CHEMISTRY
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- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/04—Drugs for disorders of the respiratory system for throat disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- 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
- 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
- A61P9/10—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
- 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
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Pulmonology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Hematology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Otolaryngology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

SK1881-99A 1997-07-22 1998-07-15 Triazolo[4,5-d]pyrimidínové zlúčeniny, spôsob ich prípravy, farmaceutické kompozície s ich obsahom a ich použitie SK284199B6 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
SE9702775A SE9702775D0 (sv)	1997-07-22	1997-07-22	Novel compounds
SE9702773A SE9702773D0 (sv)	1997-07-22	1997-07-22	Novel compounds
PCT/SE1998/001393 WO1999005143A1 (en)	1997-07-22	1998-07-15	Novel compounds

Publications (2)

Publication Number	Publication Date
SK188199A3 SK188199A3 (en)	2000-10-09
SK284199B6 true SK284199B6 (sk)	2004-10-05

Family

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Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1881-99A SK284199B6 (sk)	1997-07-22	1998-07-15	Triazolo[4,5-d]pyrimidínové zlúčeniny, spôsob ich prípravy, farmaceutické kompozície s ich obsahom a ich použitie

Country Status (30)

Country	Link
EP (1)	EP0996621B1 (cs)
JP (1)	JP4187406B2 (cs)
KR (2)	KR20050084540A (cs)
CN (1)	CN1154650C (cs)
AR (2)	AR017014A1 (cs)
AT (1)	ATE251161T1 (cs)
AU (1)	AU745381B2 (cs)
BR (1)	BR9810802B1 (cs)
CA (1)	CA2296665C (cs)
CZ (1)	CZ302629B6 (cs)
DE (1)	DE69818668T2 (cs)
DK (1)	DK0996621T3 (cs)
EE (1)	EE04193B1 (cs)
EG (1)	EG24412A (cs)
ES (1)	ES2207846T3 (cs)
HU (1)	HU230074B1 (cs)
IL (2)	IL133959A0 (cs)
IS (1)	IS2236B (cs)
MY (1)	MY123196A (cs)
NO (1)	NO315854B1 (cs)
NZ (1)	NZ502381A (cs)
PL (1)	PL200325B1 (cs)
PT (1)	PT996621E (cs)
RU (1)	RU2225407C2 (cs)
SA (1)	SA98190487B1 (cs)
SK (1)	SK284199B6 (cs)
TR (1)	TR200000197T2 (cs)
TW (1)	TW530058B (cs)
UA (1)	UA66801C2 (cs)
WO (1)	WO1999005143A1 (cs)

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1998
- 1998-07-10 AR ARP980103366A patent/AR017014A1/es active IP Right Grant
- 1998-07-10 TW TW087111177A patent/TW530058B/zh not_active IP Right Cessation
- 1998-07-15 DK DK98934107T patent/DK0996621T3/da active
- 1998-07-15 KR KR1020057013833A patent/KR20050084540A/ko not_active Ceased
- 1998-07-15 UA UA2000020981A patent/UA66801C2/uk unknown
- 1998-07-15 EP EP98934107A patent/EP0996621B1/en not_active Expired - Lifetime
- 1998-07-15 ES ES98934107T patent/ES2207846T3/es not_active Expired - Lifetime
- 1998-07-15 CA CA002296665A patent/CA2296665C/en not_active Expired - Lifetime
- 1998-07-15 EE EEP200000044A patent/EE04193B1/xx active Protection Beyond IP Right Term
- 1998-07-15 RU RU2000104113/04A patent/RU2225407C2/ru active Protection Beyond IP Right Term
- 1998-07-15 HU HU0004333A patent/HU230074B1/hu unknown
- 1998-07-15 NZ NZ502381A patent/NZ502381A/en not_active IP Right Cessation
- 1998-07-15 SK SK1881-99A patent/SK284199B6/sk not_active IP Right Cessation
- 1998-07-15 JP JP2000504139A patent/JP4187406B2/ja not_active Expired - Lifetime
- 1998-07-15 AU AU83706/98A patent/AU745381B2/en not_active Expired
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- 1998-07-15 BR BRPI9810802-6A patent/BR9810802B1/pt not_active IP Right Cessation
- 1998-07-15 AT AT98934107T patent/ATE251161T1/de active
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- 1998-07-15 KR KR1020007000652A patent/KR100535837B1/ko not_active Expired - Lifetime
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- 1998-07-15 CZ CZ20000233A patent/CZ302629B6/cs not_active IP Right Cessation
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- 1998-07-15 IL IL13395998A patent/IL133959A0/xx active IP Right Grant
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- 1998-07-15 PL PL338516A patent/PL200325B1/pl unknown
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- 1998-07-22 EG EG86498A patent/EG24412A/xx active
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2000
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Publication number	Publication date
NO20000312D0 (no)	2000-01-21
ATE251161T1 (de)	2003-10-15
NO20000312L (no)	2000-03-21
NO315854B1 (no)	2003-11-03
DE69818668D1 (de)	2003-11-06
CA2296665C (en)	2008-06-10
AU745381B2 (en)	2002-03-21
NZ502381A (en)	2001-12-21
CZ302629B6 (cs)	2011-08-10
RU2225407C2 (ru)	2004-03-10
CN1154650C (zh)	2004-06-23
IS2236B (is)	2007-05-15
JP2001510842A (ja)	2001-08-07
PT996621E (pt)	2004-02-27
PL200325B1 (pl)	2008-12-31
HK1026421A1 (en)	2000-12-15
EG24412A (en)	2009-05-25
EP0996621A1 (en)	2000-05-03
IL133959A0 (en)	2001-04-30
DK0996621T3 (da)	2004-02-02
CZ2000233A3 (cs)	2000-07-12
TR200000197T2 (tr)	2000-06-21
HUP0004333A3 (en)	2001-11-28
IL133959A (en)	2007-10-31
EP0996621B1 (en)	2003-10-01
HU230074B1 (hu)	2015-06-29
PL338516A1 (en)	2000-11-06
IS5354A (is)	2000-01-20
UA66801C2 (uk)	2004-06-15
JP4187406B2 (ja)	2008-11-26
EE04193B1 (et)	2003-12-15
SA98190487B1 (ar)	2006-08-20
CN1270590A (zh)	2000-10-18
TW530058B (en)	2003-05-01
AU8370698A (en)	1999-02-16
AR017014A1 (es)	2001-08-22
KR20050084540A (ko)	2005-08-26
WO1999005143A1 (en)	1999-02-04
MY123196A (en)	2006-05-31
HUP0004333A2 (hu)	2001-04-28
CA2296665A1 (en)	1999-02-04
DE69818668T2 (de)	2004-08-12
SK188199A3 (en)	2000-10-09
KR100535837B1 (ko)	2006-01-12
ES2207846T3 (es)	2004-06-01
KR20010022083A (ko)	2001-03-15
AR077553A2 (es)	2011-09-07
BR9810802A (pt)	2000-09-12
EE200000044A (et)	2000-10-16
BR9810802B1 (pt)	2010-10-19

Legal Events

Date	Code	Title	Description
2018-09-03	MK4A	Patent expired	Expiry date: 20180715

Publication	Publication Date	Title
SK284199B6 (sk)	2004-10-05	Triazolo[4,5-d]pyrimidínové zlúčeniny, spôsob ich prípravy, farmaceutické kompozície s ich obsahom a ich použitie
US6251910B1 (en)	2001-06-26	1,2,3-triazolo[4,5-d]pyrimidines as P2T receptor antagonists
US7250419B2 (en)	2007-07-31	Trisubstituted triazolopyrimidines for use in platelet aggregation inhibition
US6156756A (en)	2000-12-05	Triazolo [4,5-d]pyrimidine compounds, their use as medicaments, compositions containing them and processes for their preparation
DE69905451T2 (de)	2003-11-20	Neue triazolo(4,5d) pyrimidinverbindungen
MXPA00000685A (en)	2001-05-07	Novel compounds
HK1026421B (en)	2004-05-28	Triazolo(4,5-d) pyrimidine derivatives as anti-thrombotic agents
CZ2000231A3 (cs)	2000-07-12	Nové sloučeniny
HK1156953A (en)	2012-06-22	Intermediates