SK12242000A3 - Triazolo[4,5-d]pyrimidíny, spôsoby ich prípravy a farmaceutický prostriedok, ktorý ich obsahuje - Google Patents

Triazolo[4,5-d]pyrimidíny, spôsoby ich prípravy a farmaceutický prostriedok, ktorý ich obsahuje Download PDF

Info

Publication number: SK12242000A3
Authority: SK; Slovakia
Prior art keywords: alkyl; pyrimidin; triazolo; amino; apci
Prior art date: 1998-02-17

Application number

SK1224-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Roger Brown

Garry Pairaudeau

Brian Springthorpe

Stephen Thom

Paul Willis

Original Assignee

Astrazeneca Uk Limited

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.)

1998-02-17

Filing date

1999-02-05

Publication date

2001-03-12

1998-02-17 Priority claimed from SE9800458A external-priority patent/SE9800458D0/xx

1998-10-26 Priority claimed from SE9803669A external-priority patent/SE9803669D0/xx

1999-02-05 Application filed by Astrazeneca Uk Limited filed Critical Astrazeneca Uk Limited

2001-03-12 Publication of SK12242000A3 publication Critical patent/SK12242000A3/sk

Links

150000003230 pyrimidines Chemical class 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 166
238000002360 preparation method Methods 0.000 claims abstract description 10
230000008569 process Effects 0.000 claims abstract description 8
150000001875 compounds Chemical class 0.000 claims description 207
-1 methylenedioxy Chemical group 0.000 claims description 143
229910052739 hydrogen Inorganic materials 0.000 claims description 68
125000004432 carbon atom Chemical group C* 0.000 claims description 44
125000000217 alkyl group Chemical group 0.000 claims description 43
125000005843 halogen group Chemical group 0.000 claims description 25
229910052736 halogen Inorganic materials 0.000 claims description 24
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 23
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 11
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 10
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
238000011282 treatment Methods 0.000 claims description 8
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000006239 protecting group Chemical group 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
239000012453 solvate Substances 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
208000010125 myocardial infarction Diseases 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
125000000524 functional group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
239000012458 free base Substances 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
125000006431 methyl cyclopropyl group Chemical group 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
210000004165 myocardium Anatomy 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
206010044008 tonsillitis Diseases 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 21
GIIGHSIIKVOWKZ-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidine Chemical class N1=CN=CC2=NNN=C21 GIIGHSIIKVOWKZ-UHFFFAOYSA-N 0.000 abstract description 4
239000003814 drug Substances 0.000 abstract description 4
239000000047 product Substances 0.000 description 112
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 109
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 102
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 description 69
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
239000000243 solution Substances 0.000 description 50
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
XRLDSWLMHUQECH-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1CCCC1 XRLDSWLMHUQECH-UHFFFAOYSA-N 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 13
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000000725 suspension Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
239000003480 eluent Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
229910004298 SiO 2 Inorganic materials 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
102100023038 WD and tetratricopeptide repeats protein 1 Human genes 0.000 description 9
239000002253 acid Substances 0.000 description 9
239000003146 anticoagulant agent Substances 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
150000001266 acyl halides Chemical class 0.000 description 6
230000002776 aggregation Effects 0.000 description 6
238000004220 aggregation Methods 0.000 description 6
239000002585 base Substances 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
239000003826 tablet Substances 0.000 description 6
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 5
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 5
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 5
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 5
239000005557 antagonist Substances 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
150000002431 hydrogen Chemical group 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
238000000746 purification Methods 0.000 description 5
230000001732 thrombotic effect Effects 0.000 description 5
230000002792 vascular Effects 0.000 description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
238000002835 absorbance Methods 0.000 description 4
125000006309 butyl amino group Chemical group 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
208000010110 spontaneous platelet aggregation Diseases 0.000 description 4
239000000126 substance Substances 0.000 description 4
125000000446 sulfanediyl group Chemical group *S* 0.000 description 4
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 3
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IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
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125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
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238000010511 deprotection reaction Methods 0.000 description 3
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230000010118 platelet activation Effects 0.000 description 3
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TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 3
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Classifications

- 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
- 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
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (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)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Diabetes (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

SK1224-2000A 1998-02-17 1999-02-05 Triazolo[4,5-d]pyrimidíny, spôsoby ich prípravy a farmaceutický prostriedok, ktorý ich obsahuje SK12242000A3 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
SE9800458A SE9800458D0 (sv)	1998-02-17	1998-02-17	Novel compounds
SE9803669A SE9803669D0 (sv)	1998-10-26	1998-10-26	Novel compounds
PCT/SE1999/000154 WO1999041254A1 (en)	1998-02-17	1999-02-05	NOVEL TRIAZOLO(4,5-d)PYRIMIDINE COMPOUNDS

Publications (1)

Publication Number	Publication Date
SK12242000A3 true SK12242000A3 (sk)	2001-03-12

Family

ID=26663214

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1224-2000A SK12242000A3 (sk)	1998-02-17	1999-02-05	Triazolo[4,5-d]pyrimidíny, spôsoby ich prípravy a farmaceutický prostriedok, ktorý ich obsahuje

Country Status (21)

Country	Link
US (1)	US6369064B1 (no)
EP (1)	EP1056749B1 (no)
JP (1)	JP2002503663A (no)
KR (1)	KR20010078696A (no)
CN (1)	CN1291193A (no)
AR (1)	AR015515A1 (no)
AT (1)	ATE232866T1 (no)
AU (1)	AU2650099A (no)
BR (1)	BR9907934A (no)
CA (1)	CA2316264A1 (no)
DE (1)	DE69905451T2 (no)
HU (1)	HUP0100328A3 (no)
ID (1)	ID27127A (no)
IL (1)	IL137812A0 (no)
MX (1)	MXPA00007634A (no)
NO (1)	NO20004089L (no)
NZ (1)	NZ505250A (no)
PL (1)	PL342430A1 (no)
SK (1)	SK12242000A3 (no)
TR (1)	TR200002380T2 (no)
WO (1)	WO1999041254A1 (no)

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SE9702773D0 (sv) *	1997-07-22	1997-07-22	Astra Pharma Prod	Novel compounds
SE9904129D0 (sv) *	1999-11-15	1999-11-15	Astra Pharma Prod	Novel compounds
GB0013488D0 (en)	2000-06-02	2000-07-26	Astrazeneca Ab	Chemical compound
AR028110A1 (es) *	2000-06-02	2003-04-23	Astrazeneca Ab	Nuevo proceso
US7086397B2 (en) *	2002-02-16	2006-08-08	Graham Lindley Spruiell	Patient usable emergency medical kit
GB0219746D0 (en) *	2002-08-23	2002-10-02	Inst Of Ex Botany Ascr	Azapurine derivatives
US7749981B2 (en) *	2003-10-21	2010-07-06	Inspire Pharmaceuticals, Inc.	Drug-eluting stents coated with non-nucleotide P2Y12 receptor antagonist compound
US7335648B2 (en) *	2003-10-21	2008-02-26	Inspire Pharmaceuticals, Inc.	Non-nucleotide composition and method for inhibiting platelet aggregation
US7504497B2 (en)	2003-10-21	2009-03-17	Inspire Pharmaceuticals, Inc.	Orally bioavailable compounds and methods for inhibiting platelet aggregation
WO2005040174A1 (en) *	2003-10-21	2005-05-06	Inspire Pharmaceuticals, Inc.	Tetrahydro-furo`3,4-d!dioxole compounds and compositions and method for inhibiting platelet aggregation
US7932376B2 (en)	2005-05-05	2011-04-26	Inspire Pharmaceuticals, Inc.	Pyrimidine-based non-nucleotide composition and method for inhibiting platelet aggregation
JPWO2007020935A1 (ja) *	2005-08-17	2009-02-26	小野薬品工業株式会社	Ｐ２ｙ１２受容体および／またはｐ２ｙ１４受容体ブロッカーを含有してなる疼痛治療剤
WO2008054795A2 (en)	2006-10-31	2008-05-08	Janssen Pharmaceutica, N.V.	Triazolopyrimidine derivatives as adp p2y12 receptor antagonists
MY156796A (en) *	2008-09-09	2016-03-31	Astrazeneca Ab	A process for preparing [1s- [1-alpha, 2-alpha, 3-beta (1s, 2r) 5-beta] ] -3- [7-[2-(3,4-difluorophenyl)-cyclopropylamino]-5-(propylthio)-3h-1,2,3-triazolo [4,5-d] pyrimidin-3-yl] -5-(2-hydroxyethoxy) cyclopentane-1, 2-diol and to it's intermediates.
WO2015027431A1 (en) *	2013-08-29	2015-03-05	Merck Sharp & Dohme Corp.	2,2-difluorodioxolo a2a receptor antagonists
WO2015162630A1 (en) *	2014-04-25	2015-10-29	Anlon Chemical Research Organization	Novel processes for preparing triazolo [4,5-d]- pyrimidines, including ticagrelor, vianew intermediates and new route of synthesis.
PT3433234T (pt)	2016-03-22	2021-12-22	Merck Sharp & Dohme	Moduladores alostéricos de recetores de acetilcolina nicotínica
CN111116592A (zh) *	2019-11-27	2020-05-08	杭州沧海帆医药科技有限公司	嘧啶并三氮唑类化合物及其医药用途
CN112876485A (zh) *	2021-01-25	2021-06-01	郭丽伟	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
US20250017936A1 (en) *	2021-11-22	2025-01-16	Purdue Research Foundation	Cell-potent bisubstrate inhibitors for nicotinamide n-methyltransferase (nnmt) and uses thereof

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US4742064A (en)	1985-09-10	1988-05-03	Regents Of The University Of Minnesota	Antiviral carbocyclic analogs of xylofuranosylpurines
GB8826205D0 (en)	1988-11-09	1988-12-14	Wellcome Found	Heterocyclic compounds
SK283206B6 (sk)	1995-07-11	2003-03-04	Astra Pharmaceuticals Ltd.	Inhibítory agregácie krvných doštičiek, spôsob ich prípravy, farmaceutická kompozícia s ich obsahom a ich použitie
AU5501598A (en) *	1996-12-20	1998-07-17	Astra Pharmaceuticals Limited	Triazolo{4,5-(d)}pyrimidinyl derivatives and their use as medicaments
SE9702772D0 (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

1999
- 1999-02-05 CA CA002316264A patent/CA2316264A1/en not_active Abandoned
- 1999-02-05 JP JP2000531447A patent/JP2002503663A/ja active Pending
- 1999-02-05 AT AT99906644T patent/ATE232866T1/de not_active IP Right Cessation
- 1999-02-05 US US09/269,330 patent/US6369064B1/en not_active Expired - Fee Related
- 1999-02-05 SK SK1224-2000A patent/SK12242000A3/sk unknown
- 1999-02-05 WO PCT/SE1999/000154 patent/WO1999041254A1/en not_active Ceased
- 1999-02-05 TR TR2000/02380T patent/TR200002380T2/xx unknown
- 1999-02-05 NZ NZ505250A patent/NZ505250A/xx unknown
- 1999-02-05 HU HU0100328A patent/HUP0100328A3/hu unknown
- 1999-02-05 KR KR1020007008936A patent/KR20010078696A/ko not_active Withdrawn
- 1999-02-05 MX MXPA00007634A patent/MXPA00007634A/es unknown
- 1999-02-05 PL PL99342430A patent/PL342430A1/xx not_active Application Discontinuation
- 1999-02-05 CN CN99802951A patent/CN1291193A/zh active Pending
- 1999-02-05 EP EP99906644A patent/EP1056749B1/en not_active Expired - Lifetime
- 1999-02-05 ID IDW20001348A patent/ID27127A/id unknown
- 1999-02-05 IL IL13781299A patent/IL137812A0/xx unknown
- 1999-02-05 DE DE69905451T patent/DE69905451T2/de not_active Expired - Fee Related
- 1999-02-05 AU AU26500/99A patent/AU2650099A/en not_active Abandoned
- 1999-02-05 BR BR9907934-8A patent/BR9907934A/pt not_active IP Right Cessation
- 1999-02-08 AR ARP990100529A patent/AR015515A1/es unknown
2000
- 2000-08-16 NO NO20004089A patent/NO20004089L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
NZ505250A (en)	2002-10-25
EP1056749B1 (en)	2003-02-19
US6369064B1 (en)	2002-04-09
JP2002503663A (ja)	2002-02-05
KR20010078696A (ko)	2001-08-21
NO20004089L (no)	2000-10-16
AR015515A1 (es)	2001-05-02
TR200002380T2 (tr)	2001-03-21
WO1999041254A1 (en)	1999-08-19
DE69905451T2 (de)	2003-11-20
HUP0100328A3 (en)	2003-04-28
ID27127A (id)	2001-03-01
EP1056749A1 (en)	2000-12-06
BR9907934A (pt)	2000-10-24
CN1291193A (zh)	2001-04-11
DE69905451D1 (de)	2003-03-27
MXPA00007634A (es)	2003-09-10
HUP0100328A2 (hu)	2001-09-28
IL137812A0 (en)	2001-10-31
AU2650099A (en)	1999-08-30
PL342430A1 (en)	2001-06-04
NO20004089D0 (no)	2000-08-16
ATE232866T1 (de)	2003-03-15
CA2316264A1 (en)	1999-08-19

Publication	Publication Date	Title
SK12242000A3 (sk)	2001-03-12	Triazolo[4,5-d]pyrimidíny, spôsoby ich prípravy a farmaceutický prostriedok, ktorý ich obsahuje
JP4125790B2 (ja)	2008-07-30	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
EP1386917B1 (en)	2011-06-22	Intermediates for the preparation of certain triazolopyrimidines as P2T antagonists
US6156756A (en)	2000-12-05	Triazolo [4,5-d]pyrimidine compounds, their use as medicaments, compositions containing them and processes for their preparation
SK188199A3 (en)	2000-10-09	Triazolo[4,5-d]pyrimidine compounds, process for their preparation, pharmaceutical compositions containing them and their use
SK188299A3 (en)	2000-08-14	Triazolo [4,5-d]pyrimidine compounds, preparation thereof, pharmaceutical compositions containing them and their use
EP1097153B1 (en)	2003-10-01	Novel triazolo[4,5-d]pyrimidine compounds
JP2003509426A (ja)	2003-03-11	新規化合物
CZ20002947A3 (cs)	2000-11-15	Nové triazolo(4,5-d)pyrimidiny, způsob jejich přípravy a farmaceutický prostředek, který je obsahuje
MXPA00000681A (en)	2001-05-07	Novel compounds
HK1061684B (en)	2012-02-10	Intermediates for the preparation of certain triazolopyrimidines as p2t antagonists
HK1061559A (en)	2004-09-24	Cyclopropane amines
CZ2000231A3 (cs)	2000-07-12	Nové sloučeniny
HK1156953A (en)	2012-06-22	Intermediates