SK22195A3 - Imidazo £1,2-a| pyridine derivatives, method of their production, pharmaceutical agents on their base, method of their production and their using - Google Patents

Imidazo £1,2-a| pyridine derivatives, method of their production, pharmaceutical agents on their base, method of their production and their using Download PDF

Info

Publication number: SK22195A3
Authority: SK; Slovakia
Prior art keywords: pyridin; imidazo; acid; group; tert
Prior art date: 1994-02-19

Application number

SK221-95A

Other languages

English (en)

Slovak (sk)

Inventor

Horst Juraszyk

Joachim Gante

Hans Wurziger

Sabine Bernstat-Danielowski

Guido Melzer

Original Assignee

Merck Patent Gmbh

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.)

1994-02-19

Filing date

1995-02-17

Publication date

1995-09-13

1995-02-17 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

1995-09-13 Publication of SK22195A3 publication Critical patent/SK22195A3/sk

Links

238000000034 method Methods 0.000 title claims description 26
238000004519 manufacturing process Methods 0.000 title claims description 9
150000003222 pyridines Chemical class 0.000 title claims description 6
239000008177 pharmaceutical agent Substances 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 20
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 16
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims abstract description 10
QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims abstract description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
150000001413 amino acids Chemical class 0.000 claims abstract description 6
239000012453 solvate Substances 0.000 claims abstract description 5
PPRGXYWEHFENBY-UHFFFAOYSA-N 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine Chemical compound C1CCCN2C=CN=C21 PPRGXYWEHFENBY-UHFFFAOYSA-N 0.000 claims abstract description 4
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
125000002947 alkylene group Chemical group 0.000 claims abstract 2
-1 amino, amidino Chemical group 0.000 claims description 117
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 90
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 75
150000001875 compounds Chemical class 0.000 claims description 60
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IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 44
239000002253 acid Substances 0.000 claims description 23
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239000008194 pharmaceutical composition Substances 0.000 claims description 6
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125000000539 amino acid group Chemical group 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
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WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 4
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KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 4
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
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UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
BXTWRMNZAGYXQQ-UHFFFAOYSA-N 1,2,4-oxadiazol-3-one Chemical group O=C1N=CON1 BXTWRMNZAGYXQQ-UHFFFAOYSA-N 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
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JHOOLESFPPLXJW-UHFFFAOYSA-N 3-[[4-(6-carbamimidoylimidazo[1,2-a]pyridin-2-yl)benzoyl]amino]propanoic acid Chemical compound C=1N2C=C(C(=N)N)C=CC2=NC=1C1=CC=C(C(=O)NCCC(O)=O)C=C1 JHOOLESFPPLXJW-UHFFFAOYSA-N 0.000 claims 1
235000001014 amino acid Nutrition 0.000 abstract description 5
KDHWCFCNNGUJCP-UHFFFAOYSA-N 2-phenylimidazo[1,2-a]pyridine Chemical compound N1=C2C=CC=CN2C=C1C1=CC=CC=C1 KDHWCFCNNGUJCP-UHFFFAOYSA-N 0.000 abstract 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 52
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FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 5
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NWHLEFPGIKYNCT-UHFFFAOYSA-N tert-butyl 3-[4-[7-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]imidazo[1,2-a]pyridin-2-yl]benzoyl]piperidine-4-carboxylate Chemical compound N1=C2C=C(CNC(=O)OC(C)(C)C)C=CN2C=C1C(C=C1)=CC=C1C(=O)C1CNCCC1C(=O)OC(C)(C)C NWHLEFPGIKYNCT-UHFFFAOYSA-N 0.000 description 1
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KBGZIGSVDNWBOI-UHFFFAOYSA-N tert-butyl 3-[[4-(7-carbamimidoylimidazo[1,2-a]pyridin-2-yl)benzoyl]amino]propanoate Chemical compound C1=CC(C(=O)NCCC(=O)OC(C)(C)C)=CC=C1C1=CN(C=CC(=C2)C(N)=N)C2=N1 KBGZIGSVDNWBOI-UHFFFAOYSA-N 0.000 description 1
VGNXGEHKUVCCKJ-UHFFFAOYSA-N tert-butyl 3-[[4-(7-carbamothioylimidazo[1,2-a]pyridin-2-yl)benzoyl]amino]propanoate Chemical compound C1=CC(C(=O)NCCC(=O)OC(C)(C)C)=CC=C1C1=CN(C=CC(=C2)C(N)=S)C2=N1 VGNXGEHKUVCCKJ-UHFFFAOYSA-N 0.000 description 1
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IQCXGFVYVGOCMN-UHFFFAOYSA-N tert-butyl 3-[[4-[7-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]imidazo[1,2-a]pyridin-2-yl]benzoyl]amino]propanoate Chemical compound C1=CC(C(=O)NCCC(=O)OC(C)(C)C)=CC=C1C1=CN(C=CC(CNC(=O)OC(C)(C)C)=C2)C2=N1 IQCXGFVYVGOCMN-UHFFFAOYSA-N 0.000 description 1
CLFZQNODXISNPX-UHFFFAOYSA-N tert-butyl 3-amino-2-[3-[[3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]carbamoyl]phenyl]imidazo[1,2-a]pyridine-8-carboxylate Chemical compound CC(C)(C)OC(=O)CCNC(=O)C1=CC=CC(C2=C(N3C=CC=C(C3=N2)C(=O)OC(C)(C)C)N)=C1 CLFZQNODXISNPX-UHFFFAOYSA-N 0.000 description 1
QNIGXPWXKHGYPL-UHFFFAOYSA-N tert-butyl 3-amino-2-[4-[[3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]carbamoyl]phenyl]imidazo[1,2-a]pyridine-8-carboxylate Chemical compound C1=CC(C(=O)NCCC(=O)OC(C)(C)C)=CC=C1C1=C(N)N2C=CC=C(C(=O)OC(C)(C)C)C2=N1 QNIGXPWXKHGYPL-UHFFFAOYSA-N 0.000 description 1
ULZPJLHOZYXJIB-UHFFFAOYSA-N tert-butyl 4-[6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl]benzoate Chemical compound C=1N2CC(CNC(=O)OC(C)(C)C)CCC2=NC=1C1=CC=C(C(=O)OC(C)(C)C)C=C1 ULZPJLHOZYXJIB-UHFFFAOYSA-N 0.000 description 1
SDGLBJILLIMZLH-UHFFFAOYSA-N tert-butyl 4-[7-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl]benzoate Chemical compound N1=C2CC(CNC(=O)OC(C)(C)C)CCN2C=C1C1=CC=C(C(=O)OC(C)(C)C)C=C1 SDGLBJILLIMZLH-UHFFFAOYSA-N 0.000 description 1
FYDYLYYDIQVCFV-UHFFFAOYSA-N tert-butyl 4-[7-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]imidazo[1,2-a]pyridin-2-yl]benzoate Chemical compound N1=C2C=C(CNC(=O)OC(C)(C)C)C=CN2C=C1C1=CC=C(C(=O)OC(C)(C)C)C=C1 FYDYLYYDIQVCFV-UHFFFAOYSA-N 0.000 description 1
CSACLJQPVDSNGM-UHFFFAOYSA-N tert-butyl 4-[8-(aminomethyl)imidazo[1,2-a]pyridin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC(C)(C)C)=CC=C1C1=CN(C=CC=C2CN)C2=N1 CSACLJQPVDSNGM-UHFFFAOYSA-N 0.000 description 1
WSFLNHZNUMPWHV-UHFFFAOYSA-N tert-butyl 4-[8-[2-amino-1-[[4-[(2-methylpropan-2-yl)oxycarbonyl]benzoyl]amino]ethyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC(C)(C)C)=CC=C1C(=O)NC(CN)C1C2=NC(C=3C=CC(=CC=3)C(=O)OC(C)(C)C)=CN2CCC1 WSFLNHZNUMPWHV-UHFFFAOYSA-N 0.000 description 1
OPQVQUKUKXYPMC-UHFFFAOYSA-N tert-butyl 4-[8-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl]benzoate Chemical compound N1=C2C(CNC(=O)OC(C)(C)C)CCCN2C=C1C1=CC=C(C(=O)OC(C)(C)C)C=C1 OPQVQUKUKXYPMC-UHFFFAOYSA-N 0.000 description 1
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WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
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235000010487 tragacanth Nutrition 0.000 description 1
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YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
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125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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239000004474 valine Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
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GSQBIOQCECCMOQ-UHFFFAOYSA-N β-alanine ethyl ester Chemical compound CCOC(=O)CCN GSQBIOQCECCMOQ-UHFFFAOYSA-N 0.000 description 1

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
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Diabetes (AREA)
Hematology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Orthopedic Medicine & Surgery (AREA)
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Obesity (AREA)
Pain & Pain Management (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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SK221-95A 1994-02-19 1995-02-17 Imidazo £1,2-a| pyridine derivatives, method of their production, pharmaceutical agents on their base, method of their production and their using SK22195A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4405378A DE4405378A1 (de)	1994-02-19	1994-02-19	Adhäsionsrezeptor-Antagonisten

Publications (1)

Publication Number	Publication Date
SK22195A3 true SK22195A3 (en)	1995-09-13

Family

ID=6510687

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK221-95A SK22195A3 (en)	1994-02-19	1995-02-17	Imidazo £1,2-a\| pyridine derivatives, method of their production, pharmaceutical agents on their base, method of their production and their using

Country Status (15)

Country	Link
US (1)	US5614531A (zh)
EP (1)	EP0668278A1 (zh)
JP (1)	JPH07252254A (zh)
KR (1)	KR950032197A (zh)
CN (1)	CN1111630A (zh)
AU (1)	AU1230795A (zh)
CA (1)	CA2142741A1 (zh)
CZ (1)	CZ42495A3 (zh)
DE (1)	DE4405378A1 (zh)
HU (1)	HUT71806A (zh)
NO (1)	NO950606L (zh)
PL (1)	PL307328A1 (zh)
RU (1)	RU95102323A (zh)
SK (1)	SK22195A3 (zh)
ZA (1)	ZA951345B (zh)

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AR011057A1 (es) *	1997-01-08	2000-08-02	Smithkline Beecham Corp	Uso de bis-acridinas sustituidas y compuestos afines para la preparacion de medicamentos y dichos compuestos
US5902797A (en) *	1997-11-10	1999-05-11	Beth Israel Deaconess Medical Center	Nutritional supplement for use in the treatment of attention deficit
IL143901A0 (en)	1998-12-23	2002-04-21	Searle & Co	Use of cyclooxygenase-2- inhibitor, a matrix metallaproteinase inhibitor, an antineoplastic agent and optionally radiation as a combination treatment of neoplasia
DE10117184A1 (de) *	2001-04-05	2002-10-17	Gruenenthal Gmbh	Substituierte Imidazol[1,2-a]-pyridin-3-yl-amid- und -aminverbindungen
DE10117183A1 (de) *	2001-04-05	2002-10-10	Gruenenthal Gmbh	Verwendung von substituierten Imidazo[1,2-a]-pyridinverbindungen als Arzneimittel
PT2484365E (pt)	2004-06-04	2013-12-12	Scripps Research Inst	Composições e métodos para o tratamento de doenças neovasculares
US7566701B2 (en) *	2004-09-07	2009-07-28	Archemix Corp.	Aptamers to von Willebrand Factor and their use as thrombotic disease therapeutics
KR20070101226A (ko) *	2004-09-07	2007-10-16	아케믹스 코포레이션	앱타머의 약화학
SG156618A1 (en)	2004-09-07	2009-11-26	Archemix Corp	Aptamers to von willebrand factor and their use as thrombotic disease therapeutics
US7919519B2 (en) *	2005-11-23	2011-04-05	Epix Pharmaceuticals Inc.	S1P receptor modulating compounds and use thereof
JP2009520688A (ja) *	2005-11-23	2009-05-28	エピックスデラウェア，インコーポレイテッド	Ｓ１ｐ受容体調節化合物およびそれらの使用
US20080293947A1 (en) *	2005-11-28	2008-11-27	Halvachs Robert E	Method of Preparation for Imidazolepyridines
WO2007109330A2 (en) *	2006-03-21	2007-09-27	Epix Delaware, Inc.	S1p receptor modulating compounds
WO2008027812A2 (en) *	2006-08-28	2008-03-06	Forest Laboratories Holdings Limited	Imidazopyridine and imidazopyrimidine derivatives
EP1964840A1 (en)	2007-02-28	2008-09-03	sanofi-aventis	Imidazo[1,2-a]pyridines and their use as pharmaceuticals
MX2009010060A (es) *	2007-03-21	2010-01-20	Epix Pharm Inc	Compuestos moduladores del receptor de esfingosin-1-fosfato y uso de los mismos.
US20090203766A1 (en) *	2007-06-01	2009-08-13	Archemix Corp.	vWF aptamer formulations and methods for use
ES2360929T3 (es) *	2007-09-20	2011-06-10	Amgen Inc.	Derivados del ácido 1-(4-(4-bencilbenzamido)-bencil)azetidin-3-carboxílico y compuestos relacionados como moduladores del receptor s1p para el tratamiento de trastornos inmunitarios.
US7868001B2 (en) *	2007-11-02	2011-01-11	Hutchison Medipharma Enterprises Limited	Cytokine inhibitors

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FR2593818B1 (fr) *	1986-02-05	1988-04-29	Synthelabo	Derives d'acylaminomethyl-3 imidazo(1,2-a)pyridine, leur preparation et leur application en therapeutique
ATE62687T1 (de) *	1986-01-22	1991-05-15	Synthelabo	Acylaminomethylimidazo(1,2-a>pyrimidinderivate, ihre herstellung und therapeutische verwendung.
US4990506A (en) *	1986-02-05	1991-02-05	Synthelabo	3-(acylaminomethyl)imidazo[1,2-a]pyridine derivatives and their application in therapy
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1994
- 1994-02-19 DE DE4405378A patent/DE4405378A1/de not_active Withdrawn
1995
- 1995-02-14 EP EP95101992A patent/EP0668278A1/de not_active Withdrawn
- 1995-02-15 CN CN95101977A patent/CN1111630A/zh active Pending
- 1995-02-16 AU AU12307/95A patent/AU1230795A/en not_active Abandoned
- 1995-02-17 RU RU95102323/04A patent/RU95102323A/ru unknown
- 1995-02-17 NO NO950606A patent/NO950606L/no unknown
- 1995-02-17 HU HU9500479A patent/HUT71806A/hu unknown
- 1995-02-17 JP JP7029649A patent/JPH07252254A/ja active Pending
- 1995-02-17 ZA ZA951345A patent/ZA951345B/xx unknown
- 1995-02-17 PL PL95307328A patent/PL307328A1/xx unknown
- 1995-02-17 CZ CZ95424A patent/CZ42495A3/cs unknown
- 1995-02-17 US US08/390,669 patent/US5614531A/en not_active Expired - Fee Related
- 1995-02-17 CA CA002142741A patent/CA2142741A1/en not_active Abandoned
- 1995-02-17 SK SK221-95A patent/SK22195A3/sk unknown
- 1995-02-18 KR KR1019950003141A patent/KR950032197A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
KR950032197A (ko)	1995-12-20
EP0668278A1 (de)	1995-08-23
RU95102323A (ru)	1997-03-20
AU1230795A (en)	1995-08-31
ZA951345B (en)	1995-10-24
CA2142741A1 (en)	1995-08-20
HU9500479D0 (en)	1995-04-28
CZ42495A3 (en)	1995-10-18
PL307328A1 (en)	1995-08-21
NO950606D0 (no)	1995-02-17
CN1111630A (zh)	1995-11-15
JPH07252254A (ja)	1995-10-03
US5614531A (en)	1997-03-25
NO950606L (no)	1995-08-21
DE4405378A1 (de)	1995-08-24
HUT71806A (en)	1996-02-28

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DE19620041A1 (de)	1998-01-29	Adhäsionsrezeptor-Antagonisten
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PL177772B1 (pl)	2000-01-31	Nowe związki, cyklopeptydy, sposób ich wytwarzania oraz preparat farmaceutyczny
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