SK1342001A3 - Triazolopyridine, method and intermediates for the preparation thereof and pharmaceutical composition based thereon - Google Patents

Triazolopyridine, method and intermediates for the preparation thereof and pharmaceutical composition based thereon Download PDF

Info

Publication number: SK1342001A3
Authority: SK; Slovakia
Prior art keywords: carbon atoms; alkyl; hydrogen; acid; amino
Prior art date: 1998-07-27

Application number

SK134-2001A

Other languages

English (en)

Slovak (sk)

Inventor

William J Hoekstra

Edward C Lawson

Bruce E Maryanoff

Original Assignee

Ortho Mcneil Pharm Inc

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.)

1998-07-27

Filing date

1999-07-21

Publication date

2002-04-04

1999-07-21 Application filed by Ortho Mcneil Pharm Inc filed Critical Ortho Mcneil Pharm Inc

2002-04-04 Publication of SK1342001A3 publication Critical patent/SK1342001A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 32
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 13
238000002360 preparation method Methods 0.000 title claims description 16
OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 title claims description 16
239000000543 intermediate Substances 0.000 title abstract description 29
150000001875 compounds Chemical class 0.000 claims abstract description 120
102100025306 Integrin alpha-IIb Human genes 0.000 claims abstract description 22
101710149643 Integrin alpha-IIb Proteins 0.000 claims abstract description 22
230000001404 mediated effect Effects 0.000 claims abstract description 15
230000008569 process Effects 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 106
125000000217 alkyl group Chemical group 0.000 claims description 76
229910052739 hydrogen Inorganic materials 0.000 claims description 74
239000001257 hydrogen Substances 0.000 claims description 72
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 56
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 47
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 47
239000002253 acid Substances 0.000 claims description 43
150000002431 hydrogen Chemical class 0.000 claims description 36
-1 3-quinolinyl Chemical group 0.000 claims description 35
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 30
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
125000003118 aryl group Chemical group 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 14
239000003937 drug carrier Substances 0.000 claims description 13
125000002252 acyl group Chemical group 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000003710 aryl alkyl group Chemical group 0.000 claims description 11
125000001072 heteroaryl group Chemical group 0.000 claims description 11
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 6
XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 claims description 5
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 5
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 5
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 5
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
230000005764 inhibitory process Effects 0.000 claims description 4
230000001732 thrombotic effect Effects 0.000 claims description 4
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
AYSYSOQSKKDJJY-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]pyridine Chemical compound C1=CC=CN2C=NN=C21 AYSYSOQSKKDJJY-UHFFFAOYSA-N 0.000 claims description 2
150000001491 aromatic compounds Chemical class 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
208000007536 Thrombosis Diseases 0.000 abstract description 16
150000008523 triazolopyridines Chemical class 0.000 abstract description 9
239000005557 antagonist Substances 0.000 abstract description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 74
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
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239000007787 solid Substances 0.000 description 26
235000002639 sodium chloride Nutrition 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
238000001819 mass spectrum Methods 0.000 description 20
239000000243 solution Substances 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
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WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
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238000009472 formulation Methods 0.000 description 15
239000012044 organic layer Substances 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
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OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000010410 layer Substances 0.000 description 12
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 11
239000003814 drug Substances 0.000 description 11
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 11
239000002775 capsule Substances 0.000 description 10
239000006260 foam Substances 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 9
239000000843 powder Substances 0.000 description 9
239000005977 Ethylene Substances 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
108090000190 Thrombin Proteins 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
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239000004480 active ingredient Substances 0.000 description 7
210000004369 blood Anatomy 0.000 description 7
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150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
229940125898 compound 5 Drugs 0.000 description 7
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230000000694 effects Effects 0.000 description 7
235000019441 ethanol Nutrition 0.000 description 7
210000004623 platelet-rich plasma Anatomy 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
102000008186 Collagen Human genes 0.000 description 6
108010035532 Collagen Proteins 0.000 description 6
230000002776 aggregation Effects 0.000 description 6
238000004220 aggregation Methods 0.000 description 6
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239000000969 carrier Substances 0.000 description 6
229920001436 collagen Polymers 0.000 description 6
239000011521 glass Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 6
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000010898 silica gel chromatography Methods 0.000 description 6
IYMAXBFPHPZYIK-BQBZGAKWSA-N Arg-Gly-Asp Chemical compound NC(N)=NCCC[C@H](N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(O)=O IYMAXBFPHPZYIK-BQBZGAKWSA-N 0.000 description 5
101000621371 Homo sapiens WD and tetratricopeptide repeats protein 1 Proteins 0.000 description 5
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238000005481 NMR spectroscopy Methods 0.000 description 5
101000820656 Rattus norvegicus Seminal vesicle secretory protein 4 Proteins 0.000 description 5
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125000001424 substituent group Chemical group 0.000 description 5
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
241000282472 Canis lupus familiaris Species 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 4
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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

SK134-2001A 1998-07-27 1999-07-21 Triazolopyridine, method and intermediates for the preparation thereof and pharmaceutical composition based thereon SK1342001A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US9423198P	1998-07-27	1998-07-27
US09/354,032 US6303625B1 (en)	1998-07-27	1999-07-15	Triazolopyridines for the treatment of thrombosis disorders
PCT/US1999/016572 WO2000006570A1 (fr)	1998-07-27	1999-07-21	Triazolopyridines pour traiter les dysfonctionnements thrombotiques

Publications (1)

Publication Number	Publication Date
SK1342001A3 true SK1342001A3 (en)	2002-04-04

Family

ID=22243910

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK134-2001A SK1342001A3 (en)	1998-07-27	1999-07-21	Triazolopyridine, method and intermediates for the preparation thereof and pharmaceutical composition based thereon

Country Status (21)

Country	Link
US (1)	US6303625B1 (fr)
EP (1)	EP1102766B1 (fr)
JP (1)	JP2003527306A (fr)
KR (1)	KR20010079576A (fr)
CN (1)	CN1320125A (fr)
AR (1)	AR019477A1 (fr)
AT (1)	ATE263169T1 (fr)
AU (1)	AU757512B2 (fr)
BR (1)	BR9912556A (fr)
CA (1)	CA2338654A1 (fr)
CZ (1)	CZ2001347A3 (fr)
DE (1)	DE69916073T2 (fr)
ES (1)	ES2219042T3 (fr)
HU (1)	HUP0103832A3 (fr)
ID (1)	ID27214A (fr)
MX (1)	MXPA01001099A (fr)
NO (1)	NO20010456L (fr)
PL (1)	PL345769A1 (fr)
SK (1)	SK1342001A3 (fr)
WO (1)	WO2000006570A1 (fr)
ZA (1)	ZA200100783B (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6306909B1 (en)	1997-03-12	2001-10-23	Queen's University At Kingston	Anti-epileptogenic agents
BR0013248A (pt) *	1999-08-13	2002-07-23	Biogen Inc	Inibidores da adesão celular
TWI288745B (en) *	2000-04-05	2007-10-21	Daiichi Seiyaku Co	Ethylenediamine derivatives
EP1397136A1 (fr) *	2001-05-25	2004-03-17	Queen's University At Kingston	Beta-acides amines heterocycliques et leur utilisation en tant qu'agents anti-epileptogenes
WO2003000657A1 (fr)	2001-06-20	2003-01-03	Daiichi Pharmaceutical Co., Ltd.	Derives de diamine
CA2577648A1 (fr) *	2004-08-18	2006-02-23	Pharmacia & Upjohn Company Llc	Nouveaux composes de triazolopyridine pour le traitement d'inflammation
US7618983B2 (en) *	2004-11-10	2009-11-17	Janssen Pharmaceutica, N.V.	Bicyclic triazole α4 integrin inhibitors
ES2569398T3 (es) *	2005-09-16	2016-05-10	Daiichi Sankyo Company, Limited	Derivado de diamina ópticamente activo y proceso para producir el mismo
AU2007307031B2 (en) *	2006-10-11	2011-11-24	Amgen Inc.	Imidazo- and triazolo-pyridine compounds and methods of use therof
EP2417135A1 (fr) *	2009-04-07	2012-02-15	Schering Corporation	Triazolopyridines substituées et leurs analogues
US8871760B2 (en) *	2009-09-21	2014-10-28	Roche Palo Alto Llc	[1,2,4]triazolo[3,4-C][1,4]oxazines as P2X7 modulators
KR20140077916A (ko)	2011-09-15	2014-06-24	노파르티스 아게	티로신 키나제로서의 6-치환된 3-(퀴놀린-6-일티오)-[1,2,4]트리아졸로[4,3-a]피라딘
JP2016520113A (ja) *	2013-06-03	2016-07-11	バイエルファーマアクチエンゲゼルシャフト	血栓塞栓疾患の治療のためのトロンビン阻害薬としてのトリアゾロピリジン類
GB201511382D0 (en)	2015-06-29	2015-08-12	Imp Innovations Ltd	Novel compounds and their use in therapy

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3050525A (en)	1960-12-14	1962-08-21	John B Bicking	Certain derivatives of s-triazolo [4, 3-a]-pyridine
PL310386A1 (en)	1993-02-22	1995-12-11	Merck & Co Inc	Antagonists of factor i receptors
DE4326758A1 (de) *	1993-08-10	1995-02-16	Basf Ag	[1,3,4]Triazolo[1,5-a]pyridine
CA2134192A1 (fr)	1993-11-12	1995-05-13	Michael L. Denney	Antagonistes iib/iiia de la glycoproteine 5, 6-bicyclique

1999
- 1999-07-15 US US09/354,032 patent/US6303625B1/en not_active Expired - Lifetime
- 1999-07-21 JP JP2000562372A patent/JP2003527306A/ja active Pending
- 1999-07-21 EP EP99937373A patent/EP1102766B1/fr not_active Expired - Lifetime
- 1999-07-21 PL PL99345769A patent/PL345769A1/xx not_active Application Discontinuation
- 1999-07-21 AU AU52218/99A patent/AU757512B2/en not_active Ceased
- 1999-07-21 CA CA002338654A patent/CA2338654A1/fr not_active Abandoned
- 1999-07-21 CN CN99811380A patent/CN1320125A/zh active Pending
- 1999-07-21 CZ CZ2001347A patent/CZ2001347A3/cs unknown
- 1999-07-21 SK SK134-2001A patent/SK1342001A3/sk unknown
- 1999-07-21 ES ES99937373T patent/ES2219042T3/es not_active Expired - Lifetime
- 1999-07-21 MX MXPA01001099A patent/MXPA01001099A/es unknown
- 1999-07-21 AT AT99937373T patent/ATE263169T1/de not_active IP Right Cessation
- 1999-07-21 DE DE69916073T patent/DE69916073T2/de not_active Expired - Fee Related
- 1999-07-21 ID IDW20010365A patent/ID27214A/id unknown
- 1999-07-21 HU HU0103832A patent/HUP0103832A3/hu unknown
- 1999-07-21 WO PCT/US1999/016572 patent/WO2000006570A1/fr not_active Application Discontinuation
- 1999-07-21 BR BR9912556-0A patent/BR9912556A/pt not_active Application Discontinuation
- 1999-07-21 KR KR1020017001183A patent/KR20010079576A/ko not_active Withdrawn
- 1999-07-26 AR ARP990103671A patent/AR019477A1/es unknown
2001
- 2001-01-26 NO NO20010456A patent/NO20010456L/no not_active Application Discontinuation
- 2001-01-26 ZA ZA200100783A patent/ZA200100783B/en unknown

Also Published As

Publication number	Publication date
WO2000006570A1 (fr)	2000-02-10
ZA200100783B (en)	2002-01-28
CN1320125A (zh)	2001-10-31
ID27214A (id)	2001-03-08
NO20010456D0 (no)	2001-01-26
EP1102766A1 (fr)	2001-05-30
HUP0103832A3 (en)	2002-12-28
EP1102766B1 (fr)	2004-03-31
CZ2001347A3 (cs)	2001-12-12
AU5221899A (en)	2000-02-21
AR019477A1 (es)	2002-02-20
KR20010079576A (ko)	2001-08-22
ES2219042T3 (es)	2004-11-16
ATE263169T1 (de)	2004-04-15
HUP0103832A2 (hu)	2002-04-29
PL345769A1 (en)	2002-01-02
BR9912556A (pt)	2002-01-15
JP2003527306A (ja)	2003-09-16
NO20010456L (no)	2001-03-26
MXPA01001099A (es)	2002-04-24
DE69916073T2 (de)	2004-12-30
CA2338654A1 (fr)	2000-02-10
DE69916073D1 (de)	2004-05-06
US6303625B1 (en)	2001-10-16
AU757512B2 (en)	2003-02-20

Publication	Publication Date	Title
US6069254A (en)	2000-05-30	Carboxamide derivatives of piperidine for the treatment of thrombosis disorders
US6303625B1 (en)	2001-10-16	Triazolopyridines for the treatment of thrombosis disorders
AU703397B2 (en)	1999-03-25	Nipecotic acid derivatives as antithrombic compounds
US6191145B1 (en)	2001-02-20	Orally-active nipecotamide glycolamide esters for the treatment of thrombosis disorders
EP1133489B9 (fr)	2006-05-03	Isonipecotamides destinees au traitement de maladies provoquees par l'integrine
MXPA00004201A (en)	2001-12-13	Orally-active nipecotamide glycolamide esters for the treatment of thrombosis disorders
MXPA01005347A (en)	2002-05-09	Isonipecotamides for the treatment of integrinmediated disorders
EP1533310A1 (fr)	2005-05-25	isonipecotamides destinées au traitement de maladies provoquées par l'integrine
EP1184374A1 (fr)	2002-03-06	Derivés carboxamide de pyrrolidine, pipéridine et hexahydroazépine utilisés dans le traitement de troubles thrombotiques