ZA200101632B - Substituted imidazo[1,2A]azines as selective inhibitors of cox-2. - Google Patents
Substituted imidazo[1,2A]azines as selective inhibitors of cox-2. Download PDFInfo
- Publication number
- ZA200101632B ZA200101632B ZA200101632A ZA200101632A ZA200101632B ZA 200101632 B ZA200101632 B ZA 200101632B ZA 200101632 A ZA200101632 A ZA 200101632A ZA 200101632 A ZA200101632 A ZA 200101632A ZA 200101632 B ZA200101632 B ZA 200101632B
- Authority
- ZA
- South Africa
- Prior art keywords
- imidazo
- methylsulfonylphenyl
- aminosulfonylphenyl
- pyrimidine
- compound
- Prior art date
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
- 229940124639 Selective inhibitor Drugs 0.000 title 1
- -1 4-methylsulfonylphenyl Chemical group 0.000 claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 35
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 20
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 6
- INSWZAQOISIYDT-UHFFFAOYSA-N imidazo[1,2-a]pyrimidine Chemical compound C1=CC=NC2=NC=CN21 INSWZAQOISIYDT-UHFFFAOYSA-N 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims description 4
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims description 4
- 239000002253 acid Substances 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 229940111134 coxibs Drugs 0.000 claims description 3
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000001562 ulcerogenic effect Effects 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 78
- 102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 6
- 108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 230000001939 inductive effect Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229940124599 anti-inflammatory drug Drugs 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003180 prostaglandins Chemical class 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- RBHURFRUCSUMPN-UHFFFAOYSA-N 2-bromo-2-(4-methylsulfonylphenyl)-1-phenylethanone Chemical class C1=CC(S(=O)(=O)C)=CC=C1C(Br)C(=O)C1=CC=CC=C1 RBHURFRUCSUMPN-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 206010059024 Gastrointestinal toxicity Diseases 0.000 description 1
- 108010044467 Isoenzymes Proteins 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 208000038016 acute inflammation Diseases 0.000 description 1
- 230000006022 acute inflammation Effects 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical class BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000033077 cellular process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000011903 deuterated solvents Substances 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 231100000414 gastrointestinal toxicity Toxicity 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 150000003815 prostacyclins Chemical class 0.000 description 1
- 229940127293 prostanoid Drugs 0.000 description 1
- 150000003814 prostanoids Chemical class 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000004206 stomach function Effects 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003595 thromboxanes Chemical class 0.000 description 1
- 230000002792 vascular 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)
Applications Claiming Priority (1)
| 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. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200101632B true ZA200101632B (en) | 2001-08-30 |
Family
ID=8304755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200101632A ZA200101632B (en) | 1998-08-03 | 2001-02-27 | Substituted imidazo[1,2A]azines as selective inhibitors of cox-2. |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6670365B1 (xx) |
| EP (1) | EP1104762B1 (xx) |
| JP (1) | JP2002522438A (xx) |
| KR (1) | KR20010079602A (xx) |
| CN (1) | CN1131865C (xx) |
| AP (1) | AP2001002082A0 (xx) |
| AT (1) | ATE224391T1 (xx) |
| AU (1) | AU749770B2 (xx) |
| BG (1) | BG105299A (xx) |
| BR (1) | BR9912968A (xx) |
| CA (1) | CA2339187A1 (xx) |
| CZ (1) | CZ291783B6 (xx) |
| DE (1) | DE69903046T2 (xx) |
| DK (1) | DK1104762T3 (xx) |
| EA (1) | EA003399B1 (xx) |
| ES (2) | ES2140354B1 (xx) |
| HK (1) | HK1037629A1 (xx) |
| HU (1) | HUP0103004A3 (xx) |
| ID (1) | ID28539A (xx) |
| IL (1) | IL141242A0 (xx) |
| MX (1) | MXPA01001332A (xx) |
| NO (1) | NO20010568L (xx) |
| NZ (1) | NZ510196A (xx) |
| OA (1) | OA11592A (xx) |
| PL (1) | PL345804A1 (xx) |
| PT (1) | PT1104762E (xx) |
| SK (1) | SK1662001A3 (xx) |
| TR (1) | TR200100359T2 (xx) |
| WO (1) | WO2000008024A1 (xx) |
| YU (1) | YU7401A (xx) |
| ZA (1) | ZA200101632B (xx) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CA2519189C (en) | 2003-05-07 | 2012-07-17 | Osteologix A/S | Water-soluble strontium salts for use in treatment of cartilage and/or bone conditions |
| KR20060034303A (ko) * | 2003-07-30 | 2006-04-21 | 라보라토리오스 에스.에이.엘.브이.에이.티., 에스.에이. | 암을 예방하고 치료하기 위한 치환된 이미다조피리미딘 |
| WO2007034278A2 (en) * | 2005-09-19 | 2007-03-29 | Pfizer Products Inc. | Fused imidazole derivatives as c3a receptor antagonists |
| US20070265350A1 (en) * | 2005-12-30 | 2007-11-15 | 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 |
| MX2010005110A (es) * | 2007-11-14 | 2010-09-09 | Ortho Mcneil Janssen Pharm | Derivados de imidazo[1,2-a]piridina y su uso como moduladores alostericos positivos de los receptores de glutamato metabotropico 2. |
| JP2012504605A (ja) * | 2008-10-01 | 2012-02-23 | シンタ ファーマシューティカルズ コーポレーション | 炎症および免疫関連使用のための化合物 |
| 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 |
| AU2017229347A1 (en) | 2016-03-07 | 2018-11-01 | University Of Iowa Research Foundation | AAV-mediated expression using a synthetic promoter and enhancer |
| US11142775B2 (en) | 2017-01-13 | 2021-10-12 | University Of Iowa Research Foundation | Bocaparvovirus small noncoding RNA and uses thereof |
| IL305573A (en) | 2021-03-15 | 2023-10-01 | Saul Yedgar | Hyaluronic acid conjugated with dipalmitoyl phosphatidyl ethanolamine in combination with non-steroidal anti-inflammatory drugs (NSAIDs) for the treatment or suppression of inflammatory diseases |
Family Cites Families (7)
| 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 |
| CA2098177A1 (en) | 1990-12-13 | 1992-06-13 | Jerry L. Adams | Csaids |
| AU3648993A (en) * | 1992-03-17 | 1993-10-21 | Nippon Shinyaku Co. Ltd. | Imidazopyridine derivative and medicine |
| US5620999A (en) * | 1994-07-28 | 1997-04-15 | Weier; Richard M. | Benzenesulfonamide subtituted imidazolyl compounds for the treatment of inflammation |
| NZ304886A (en) * | 1995-04-04 | 1998-11-25 | Glaxo Group Ltd | Imidazo [1,2a] pyridine derivatives, preparation and pharmaceutical compositions thereof |
| 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 OA OA1200100033A patent/OA11592A/en unknown
- 1999-07-23 JP JP2000563657A patent/JP2002522438A/ja active Pending
- 1999-07-23 DE DE69903046T patent/DE69903046T2/de not_active Expired - Fee Related
- 1999-07-23 AT AT99931266T patent/ATE224391T1/de not_active IP Right Cessation
- 1999-07-23 SK SK166-2001A patent/SK1662001A3/sk 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 MX MXPA01001332A patent/MXPA01001332A/es unknown
- 1999-07-23 CA CA002339187A patent/CA2339187A1/en not_active Abandoned
- 1999-07-23 WO PCT/ES1999/000235 patent/WO2000008024A1/es not_active Application Discontinuation
- 1999-07-23 EA EA200100212A patent/EA003399B1/ru not_active IP Right Cessation
- 1999-07-23 DK DK99931266T patent/DK1104762T3/da active
- 1999-07-23 ES ES99931266T patent/ES2182546T3/es not_active Expired - Lifetime
- 1999-07-23 BR BR9912968-0A patent/BR9912968A/pt not_active IP Right Cessation
- 1999-07-23 NZ NZ510196A patent/NZ510196A/xx unknown
- 1999-07-23 ID IDW20010517A patent/ID28539A/id unknown
- 1999-07-23 AU AU47824/99A patent/AU749770B2/en not_active Ceased
- 1999-07-23 HU HU0103004A patent/HUP0103004A3/hu unknown
- 1999-07-23 CZ CZ2001433A patent/CZ291783B6/cs not_active IP Right Cessation
- 1999-07-23 US US09/762,146 patent/US6670365B1/en not_active Expired - Fee Related
- 1999-07-23 EP EP99931266A patent/EP1104762B1/en not_active Expired - Lifetime
- 1999-07-23 CN CN998116750A patent/CN1131865C/zh not_active Expired - Fee Related
- 1999-07-23 TR TR2001/00359T patent/TR200100359T2/xx unknown
- 1999-07-23 IL IL14124299A patent/IL141242A0/xx unknown
- 1999-07-23 YU YU7401A patent/YU7401A/sh unknown
- 1999-07-23 PT PT99931266T patent/PT1104762E/pt unknown
- 1999-07-23 KR KR1020017001453A patent/KR20010079602A/ko not_active Application Discontinuation
-
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
- 2001-12-04 HK HK01108500A patent/HK1037629A1/xx not_active IP Right Cessation
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