SK1662001A3 - Substituted imidazo[1,2a]azines as selective inhibotors of cox-2 - Google Patents

Substituted imidazo[1,2a]azines as selective inhibotors of cox-2 Download PDF

Info

Publication number: SK1662001A3
Authority: SK; Slovakia
Prior art keywords: imidazo; methylsulfonylphenyl; aminosulfonylphenyl; pyridine; pyrimidine
Prior art date: 1998-08-03

Application number

SK166-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Gallemi Carles Farrerons

Bono Ignacio-Jose Miquel

Serrat Ana Maria Fernandez

Vidal Carlos Monserrat

Arnal Carmen Lagunas

Guasch Ferran Gimenez

Garcia Andres Fernandez

Original Assignee

S A L V A T Lab Sa

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.)

1998-08-03

Filing date

1999-07-23

Publication date

2001-08-06

1999-07-23 Application filed by S A L V A T Lab Sa filed Critical S A L V A T Lab Sa

2001-08-06 Publication of SK1662001A3 publication Critical patent/SK1662001A3/sk

Links

101150071146 COX2 gene Proteins 0.000 title 1
101100114534 Caenorhabditis elegans ctc-2 gene Proteins 0.000 title 1
101150000187 PTGS2 gene Proteins 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 84
102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims abstract description 28
238000011282 treatment Methods 0.000 claims abstract description 23
229910052794 bromium Inorganic materials 0.000 claims abstract description 15
229910052801 chlorine Inorganic materials 0.000 claims abstract description 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 claims abstract description 11
229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims abstract description 8
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims abstract description 8
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 8
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract description 7
201000010099 disease Diseases 0.000 claims abstract description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 6
230000001404 mediated effect Effects 0.000 claims abstract description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
239000002798 polar solvent Substances 0.000 claims abstract description 5
-1 CH 3 Inorganic materials 0.000 claims description 83
238000002360 preparation method Methods 0.000 claims description 56
108010037462 Cyclooxygenase 2 Proteins 0.000 claims description 27
FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 23
238000000034 method Methods 0.000 claims description 21
239000003814 drug Substances 0.000 claims description 9
230000004054 inflammatory process Effects 0.000 claims description 9
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
206010061218 Inflammation Diseases 0.000 claims description 7
230000005764 inhibitory process Effects 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
WZFGZCSDTVNFST-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C2N1C=CC=N2 WZFGZCSDTVNFST-UHFFFAOYSA-N 0.000 claims description 5
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
MGGFNZWFWJBUPD-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OCC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=NC2=N1 MGGFNZWFWJBUPD-UHFFFAOYSA-N 0.000 claims description 4
SSARXDLPJGIOOC-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=NC2=N1 SSARXDLPJGIOOC-UHFFFAOYSA-N 0.000 claims description 4
RBPODQILINHERL-UHFFFAOYSA-N 2-(4-methylphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=NC2=N1 RBPODQILINHERL-UHFFFAOYSA-N 0.000 claims description 4
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
206010028980 Neoplasm Diseases 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 4
INSWZAQOISIYDT-UHFFFAOYSA-N imidazo[1,2-a]pyrimidine Chemical compound C1=CC=NC2=NC=CN21 INSWZAQOISIYDT-UHFFFAOYSA-N 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
YSWWOBKIEHJRSO-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=CC2=N1 YSWWOBKIEHJRSO-UHFFFAOYSA-N 0.000 claims description 3
XYKLNISORGVGKQ-UHFFFAOYSA-N 3-(4-methylsulfonylphenyl)-2-phenylimidazo[1,2-a]pyrimidine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)N=C2N1C=CC=N2 XYKLNISORGVGKQ-UHFFFAOYSA-N 0.000 claims description 3
ZOOSVGJPCPYFPD-UHFFFAOYSA-N 4-[2-(3-fluoro-4-methoxyphenyl)imidazo[1,2-a]pyrimidin-3-yl]benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(N)(=O)=O)N2C=CC=NC2=N1 ZOOSVGJPCPYFPD-UHFFFAOYSA-N 0.000 claims description 3
CWUMBAHPFHBIKG-UHFFFAOYSA-N 4-[2-(3-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=C(F)C=CC=2)N=C2N1C=CC=C2 CWUMBAHPFHBIKG-UHFFFAOYSA-N 0.000 claims description 3
NVQBSOYZAFELAK-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)imidazo[1,2-a]pyrimidin-3-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C2N1C=CC=N2 NVQBSOYZAFELAK-UHFFFAOYSA-N 0.000 claims description 3
JNAXQNHUQGWGDO-UHFFFAOYSA-N C1=C(Cl)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(N)(=O)=O)N2C=CC=CC2=N1 Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(N)(=O)=O)N2C=CC=CC2=N1 JNAXQNHUQGWGDO-UHFFFAOYSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
MMTGPHUVVVBSCZ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=NC2=N1 MMTGPHUVVVBSCZ-UHFFFAOYSA-N 0.000 claims description 2
BQXLYTBWPCTAHG-UHFFFAOYSA-N 2-(3,4-dimethylphenyl)-7-methyl-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound N1=C2N=C(C)C=CN2C(C=2C=CC(=CC=2)S(C)(=O)=O)=C1C1=CC=C(C)C(C)=C1 BQXLYTBWPCTAHG-UHFFFAOYSA-N 0.000 claims description 2
OTDGVNZPSWUFLR-UHFFFAOYSA-N 2-(3-chloro-4-methoxyphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=CC2=N1 OTDGVNZPSWUFLR-UHFFFAOYSA-N 0.000 claims description 2
VHQYBEUFSFJFDF-UHFFFAOYSA-N 2-(3-chloro-4-methoxyphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=NC2=N1 VHQYBEUFSFJFDF-UHFFFAOYSA-N 0.000 claims description 2
NHPRLAQNUKVNHP-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(F)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=NC2=N1 NHPRLAQNUKVNHP-UHFFFAOYSA-N 0.000 claims description 2
KWEALESHUQSTJZ-UHFFFAOYSA-N 2-(4-bromophenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Br)=CC=2)N=C2N1C=CC=N2 KWEALESHUQSTJZ-UHFFFAOYSA-N 0.000 claims description 2
HEDBESBDRYVCHB-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N=C2N1C=CC=N2 HEDBESBDRYVCHB-UHFFFAOYSA-N 0.000 claims description 2
JYDDSTQRHWLFIB-UHFFFAOYSA-N 2-(4-methoxy-3-methylphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine Chemical compound C1=C(C)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=CC2=N1 JYDDSTQRHWLFIB-UHFFFAOYSA-N 0.000 claims description 2
QDBAZWLKCAGRRY-UHFFFAOYSA-N 2-(4-methoxy-3-methylphenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(C)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=NC2=N1 QDBAZWLKCAGRRY-UHFFFAOYSA-N 0.000 claims description 2
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
ZWDGRLFZEYPOCN-UHFFFAOYSA-N 3-(4-methylsulfonylphenyl)-2-(4-propan-2-yloxyphenyl)imidazo[1,2-a]pyridine Chemical compound C1=CC(OC(C)C)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=CC2=N1 ZWDGRLFZEYPOCN-UHFFFAOYSA-N 0.000 claims description 2
SEACWJRYTNUDEN-UHFFFAOYSA-N 4-[2-(2-methylphenyl)imidazo[1,2-a]pyrimidin-3-yl]benzenesulfonamide Chemical compound CC1=CC=CC=C1C1=C(C=2C=CC(=CC=2)S(N)(=O)=O)N2C=CC=NC2=N1 SEACWJRYTNUDEN-UHFFFAOYSA-N 0.000 claims description 2
RFTDNQNEPOMKPT-UHFFFAOYSA-N 4-[2-(3-chlorophenyl)imidazo[1,2-a]pyrimidin-3-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=C(Cl)C=CC=2)N=C2N1C=CC=N2 RFTDNQNEPOMKPT-UHFFFAOYSA-N 0.000 claims description 2
MAEYYMYEBKENNO-UHFFFAOYSA-N 4-[2-(3-fluoro-4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl]benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(N)(=O)=O)N2C=CC=CC2=N1 MAEYYMYEBKENNO-UHFFFAOYSA-N 0.000 claims description 2
XESYGYPYDBLPIL-UHFFFAOYSA-N 4-[2-(3-methylphenyl)imidazo[1,2-a]pyridin-3-yl]benzenesulfonamide Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2C=CC(=CC=2)S(N)(=O)=O)=C1 XESYGYPYDBLPIL-UHFFFAOYSA-N 0.000 claims description 2
206010009944 Colon cancer Diseases 0.000 claims description 2
108010037464 Cyclooxygenase 1 Proteins 0.000 claims description 2
208000029742 colonic neoplasm Diseases 0.000 claims description 2
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
239000012453 solvate Substances 0.000 claims description 2
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239000012044 organic layer Substances 0.000 description 24
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229910000030 sodium bicarbonate Inorganic materials 0.000 description 20
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239000012267 brine Substances 0.000 description 9
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HSXSJJWWKGGAKE-UHFFFAOYSA-N 2-(4-methylsulfanylphenyl)acetyl chloride Chemical compound CSC1=CC=C(CC(Cl)=O)C=C1 HSXSJJWWKGGAKE-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
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LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 4
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206010043778 thyroiditis Diseases 0.000 description 1
230000000451 tissue damage Effects 0.000 description 1
231100000827 tissue damage Toxicity 0.000 description 1
208000004371 toothache Diseases 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
230000005747 tumor angiogenesis Effects 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
230000002792 vascular Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000009385 viral infection Effects 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
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- 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
- A61P35/00—Antineoplastic agents
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SK166-2001A 1998-08-03 1999-07-23 Substituted imidazo[1,2a]azines as selective inhibotors of cox-2 SK1662001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ES009801652A ES2140354B1 (es)	1998-08-03	1998-08-03	Imidazo (1,2a) azinas sustituidas como inhibidores selectivos de la cox-2.
PCT/ES1999/000235 WO2000008024A1 (es)	1998-08-03	1999-07-23	IMIDAZO[1,2a]AZINAS SUSTITUIDAS COMO INHIBIDORES SELECTIVOS DE LA COX-2

Publications (1)

Publication Number	Publication Date
SK1662001A3 true SK1662001A3 (en)	2001-08-06

Family

ID=8304755

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK166-2001A SK1662001A3 (en)	1998-08-03	1999-07-23	Substituted imidazo[1,2a]azines as selective inhibotors of cox-2

Country Status (30)

Country	Link
US (1)	US6670365B1 (de)
EP (1)	EP1104762B1 (de)
JP (1)	JP2002522438A (de)
KR (1)	KR20010079602A (de)
CN (1)	CN1131865C (de)
AP (1)	AP2001002082A0 (de)
AT (1)	ATE224391T1 (de)
AU (1)	AU749770B2 (de)
BG (1)	BG105299A (de)
BR (1)	BR9912968A (de)
CA (1)	CA2339187A1 (de)
CZ (1)	CZ291783B6 (de)
DE (1)	DE69903046T2 (de)
DK (1)	DK1104762T3 (de)
EA (1)	EA003399B1 (de)
ES (2)	ES2140354B1 (de)
HU (1)	HUP0103004A3 (de)
ID (1)	ID28539A (de)
IL (1)	IL141242A0 (de)
MX (1)	MXPA01001332A (de)
NO (1)	NO20010568L (de)
NZ (1)	NZ510196A (de)
OA (1)	OA11592A (de)
PL (1)	PL345804A1 (de)
PT (1)	PT1104762E (de)
SK (1)	SK1662001A3 (de)
TR (1)	TR200100359T2 (de)
WO (1)	WO2000008024A1 (de)
YU (1)	YU7401A (de)
ZA (1)	ZA200101632B (de)

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ATE283048T1 (de)	1999-12-08	2004-12-15	Pharmacia Corp	Cyclooxygenase-2 hemmer enthaltende zusammensetzungen mit schnellem wirkungseintritt
US8241622B2 (en) *	2001-07-13	2012-08-14	University Of Iowa Research Foundation	Adeno-associated virus vectors with intravector heterologous terminal palindromic sequences
US20030100594A1 (en) *	2001-08-10	2003-05-29	Pharmacia Corporation	Carbonic anhydrase inhibitor
DE10247271A1 (de) *	2002-10-10	2004-08-26	Grünenthal GmbH	Substituierte C-Imidazo[1,2-a]pyridin-3-yle
DE10256881A1 (de) *	2002-12-05	2004-06-24	Beiersdorf Ag	Neue topische Verwendung von Bis-Arylimidazo[1,2-a]thiolanderivaten
EP1745791B1 (de)	2003-05-07	2013-06-26	Osteologix A/S	Behandlung von Knorpel/Knochen-Erkrankungen mit wasserlöslichen Strontiumsalzen
EP1660500B1 (de) *	2003-07-30	2007-12-12	Laboratorios S.A.L.V.A.T., S.A.	Substituierte imidazopyrimidine zur prävention und behandlung von krebs
WO2007034278A2 (en) *	2005-09-19	2007-03-29	Pfizer Products Inc.	Fused imidazole derivatives as c3a receptor antagonists
CA2634670A1 (en) *	2005-12-30	2007-07-12	University Of Iowa Research Foundation	Method of identifying compounds useful to treat neuronal degenerative diseases
WO2007096764A2 (en) *	2006-02-27	2007-08-30	Glenmark Pharmaceuticals S.A.	Bicyclic heteroaryl derivatives as cannabinoid receptor modulators
RU2492170C9 (ru) *	2007-11-14	2013-12-27	Орто-Макнейл-Янссен Фармасьютикалз, Инк.	Имидазо[1,2-а]пиридиновые производные и их применение в качестве положительных аллостерических модуляторов рецепторов mglur2
EP2350006A1 (de) *	2008-10-01	2011-08-03	Synta Pharmaceuticals Corp.	Verbindungen gegen entzündungen und immun-relevante verwendungen
GB201321732D0 (en) *	2013-12-09	2014-01-22	Ucb Pharma Sa	Therapeutic agents
WO2017139381A1 (en)	2016-02-08	2017-08-17	University Of Iowa Research Foundation	Methods to produce chimeric adeno-associated virus/bocavirus parvovirus
CA3198936A1 (en)	2016-03-07	2017-09-14	University Of Iowa Research Foundation	Aav-mediated expression using a synthetic promoter and enhancer
US12173305B2 (en)	2016-05-26	2024-12-24	University Of Iowa Research Foundation	cis and trans requirements for terminal resolution of human bocavirus 1
US11142775B2 (en)	2017-01-13	2021-10-12	University Of Iowa Research Foundation	Bocaparvovirus small noncoding RNA and uses thereof
WO2022195579A1 (en)	2021-03-15	2022-09-22	Saul Yedgar	Hyaluronic acid-conjugated dipalmitoyl phosphatidyl ethanolamine in combination with non-steroidal anti-inflammatory drugs (nsaids) for treating or alleviating inflammatory diseases

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Publication number	Priority date	Publication date	Assignee	Title
US2785133A (en) *	1954-03-26	1957-03-12	Gen Aniline & Film Corp	Compositions for a method of whitening fine fabrics
US3455924A (en) *	1967-02-08	1969-07-15	Upjohn Co	Dianisylimidazoles
JPH06504779A (ja) *	1990-12-13	1994-06-02	スミスクライン・ビーチャム・コーポレイション	新規ｃｓａｉｄｓ
WO1993019066A1 (fr) *	1992-03-17	1993-09-30	Nippon Shinyaku Co., Ltd.	Derive de l'imidazopyridine et medicament
US5620999A (en) *	1994-07-28	1997-04-15	Weier; Richard M.	Benzenesulfonamide subtituted imidazolyl compounds for the treatment of inflammation
EA199700209A1 (ru) *	1995-04-04	1998-04-30	Глаксо Груп Лимитед	ПРОИЗВОДНЫЕ ИМИДАЗО[1,2-a]ПИРИДИНА
UA57002C2 (uk) *	1995-10-13	2003-06-16	Мерк Фросст Кенада Енд Ко./Мерк Фросст Кенада Енд Сі.	Похідне (метилсульфоніл)феніл-2-(5н)-фуранону, фармацевтична композиція та спосіб лікування

1998
- 1998-08-03 ES ES009801652A patent/ES2140354B1/es not_active Expired - Lifetime
1999
- 1999-07-23 TR TR2001/00359T patent/TR200100359T2/xx unknown
- 1999-07-23 CN CN998116750A patent/CN1131865C/zh not_active Expired - Fee Related
- 1999-07-23 PT PT99931266T patent/PT1104762E/pt unknown
- 1999-07-23 SK SK166-2001A patent/SK1662001A3/sk unknown
- 1999-07-23 JP JP2000563657A patent/JP2002522438A/ja active Pending
- 1999-07-23 ID IDW20010517A patent/ID28539A/id unknown
- 1999-07-23 US US09/762,146 patent/US6670365B1/en not_active Expired - Fee Related
- 1999-07-23 OA OA1200100033A patent/OA11592A/en unknown
- 1999-07-23 DK DK99931266T patent/DK1104762T3/da active
- 1999-07-23 NZ NZ510196A patent/NZ510196A/xx unknown
- 1999-07-23 AP APAP/P/2001/002082A patent/AP2001002082A0/en unknown
- 1999-07-23 PL PL99345804A patent/PL345804A1/xx not_active IP Right Cessation
- 1999-07-23 AU AU47824/99A patent/AU749770B2/en not_active Ceased
- 1999-07-23 DE DE69903046T patent/DE69903046T2/de not_active Expired - Fee Related
- 1999-07-23 BR BR9912968-0A patent/BR9912968A/pt not_active IP Right Cessation
- 1999-07-23 KR KR1020017001453A patent/KR20010079602A/ko not_active Ceased
- 1999-07-23 EP EP99931266A patent/EP1104762B1/de not_active Expired - Lifetime
- 1999-07-23 CZ CZ2001433A patent/CZ291783B6/cs not_active IP Right Cessation
- 1999-07-23 EA EA200100212A patent/EA003399B1/ru not_active IP Right Cessation
- 1999-07-23 WO PCT/ES1999/000235 patent/WO2000008024A1/es not_active Ceased
- 1999-07-23 ES ES99931266T patent/ES2182546T3/es not_active Expired - Lifetime
- 1999-07-23 MX MXPA01001332A patent/MXPA01001332A/es unknown
- 1999-07-23 HU HU0103004A patent/HUP0103004A3/hu unknown
- 1999-07-23 YU YU7401A patent/YU7401A/sh unknown
- 1999-07-23 CA CA002339187A patent/CA2339187A1/en not_active Abandoned
- 1999-07-23 AT AT99931266T patent/ATE224391T1/de not_active IP Right Cessation
- 1999-07-23 IL IL14124299A patent/IL141242A0/xx unknown
2001
- 2001-02-02 NO NO20010568A patent/NO20010568L/no not_active Application Discontinuation
- 2001-02-27 ZA ZA200101632A patent/ZA200101632B/en unknown
- 2001-02-28 BG BG105299A patent/BG105299A/xx unknown

Also Published As

Publication number	Publication date
IL141242A0 (en)	2002-03-10
CZ2001433A3 (cs)	2001-08-15
PT1104762E (pt)	2002-11-29
HUP0103004A2 (hu)	2002-01-28
WO2000008024A1 (es)	2000-02-17
ATE224391T1 (de)	2002-10-15
ES2182546T3 (es)	2003-03-01
YU7401A (sh)	2003-10-31
CN1131865C (zh)	2003-12-24
EP1104762A1 (de)	2001-06-06
AP2001002082A0 (en)	2001-03-31
ES2140354A1 (es)	2000-02-16
DE69903046D1 (de)	2002-10-24
NO20010568L (no)	2001-04-02
EA200100212A1 (ru)	2001-08-27
CN1321157A (zh)	2001-11-07
ID28539A (id)	2001-05-31
EA003399B1 (ru)	2003-04-24
DK1104762T3 (da)	2002-10-21
HK1037629A1 (en)	2002-02-15
US6670365B1 (en)	2003-12-30
TR200100359T2 (tr)	2001-06-21
HUP0103004A3 (en)	2003-03-28
CA2339187A1 (en)	2000-02-17
AU749770B2 (en)	2002-07-04
AU4782499A (en)	2000-02-28
DE69903046T2 (de)	2003-05-22
OA11592A (en)	2004-07-30
NO20010568D0 (no)	2001-02-02
ZA200101632B (en)	2001-08-30
PL345804A1 (en)	2002-01-02
BG105299A (en)	2001-11-30
KR20010079602A (ko)	2001-08-22
JP2002522438A (ja)	2002-07-23
EP1104762B1 (de)	2002-09-18
ES2140354B1 (es)	2000-11-01
BR9912968A (pt)	2001-05-08
MXPA01001332A (es)	2002-11-29
NZ510196A (en)	2002-09-27
CZ291783B6 (cs)	2003-05-14

Publication	Publication Date	Title
SK1662001A3 (en)	2001-08-06	Substituted imidazo[1,2a]azines as selective inhibotors of cox-2
JP3270830B2 (ja)	2002-04-02	化合物
EP0521768B1 (de)	1994-02-02	Thiazolopyrimidinderivate als Angiotensin-II-Rezeptorantagonisten: Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
KR100808433B1 (ko)	2008-03-03	항-염증 활성을 갖는 신규 이미다졸
JP2000515162A (ja)	2000-11-14	Ｃｏｘ―２阻害剤としての１，２―ジアリールインドール
CZ20011058A3 (cs)	2001-08-15	Deriváty 2-fenylpyran-4-onu
JP2707936B2 (ja)	1998-02-04	β−オキソ−β−ベンゼンプロパンチオアミド誘導体
US3657242A (en)	1972-04-18	2 6-substituted - 4 5 - dihydropyridazin(2h)-3-ones and 1 3-substituted hexahydropyridazines
HUT62888A (en)	1993-06-28	Process for producing new oxazole derivatives and pharmaceutical compositions comprising same
JPS59116288A (ja)	1984-07-05	ピラゾロ〔４．３−ｂ〕〔１．４〕オキサジン類
HK1037629B (en)	2003-05-02	Substituted imidazo [1,2a]azines as selective inhibitors of cox-2
JPS6351374A (ja)	1988-03-04	イミダゾール誘導体、それらの製造法及び薬剤としての使用
FR2523972A1 (fr)	1983-09-30	Derives vinyliques substitues de la 1h-pyrazolo-(1,5-a) pyrimidine utiles notamment comme medicaments antiulcerigenes et antisecretoires gastriques et procede de leur preparation
MXPA01003679A (en)	2001-12-04	Novel imidazoles with anti-inflammatory activity
ZA200103344B (en)	2002-07-24	Pyrazolopyridine derivatives as selective COX-2 inhibitors.
HK1034961B (en)	2003-04-17	2-phenylpyran-4-one derivatives