SK133297A3 - Imidazo[1,2-a]pyridine derivatives, pharmaceutical composition containing same and their use - Google Patents
Imidazo[1,2-a]pyridine derivatives, pharmaceutical composition containing same and their use Download PDFInfo
- Publication number
- SK133297A3 SK133297A3 SK1332-97A SK133297A SK133297A3 SK 133297 A3 SK133297 A3 SK 133297A3 SK 133297 A SK133297 A SK 133297A SK 133297 A3 SK133297 A3 SK 133297A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- compound
- alkyl
- methyl
- pharmaceutically acceptable
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 13
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 156
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims abstract description 15
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 claims abstract description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 201000010099 disease Diseases 0.000 claims abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 5
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 230000005764 inhibitory process Effects 0.000 claims description 8
- KVVJDDVNYVCFDS-UHFFFAOYSA-N 1-[3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridin-8-yl]ethanone Chemical compound N1=C2C(C(=O)C)=CC=CN2C(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 KVVJDDVNYVCFDS-UHFFFAOYSA-N 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical class C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
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- 230000004054 inflammatory process Effects 0.000 abstract description 4
- 206010061218 Inflammation Diseases 0.000 abstract description 3
- 230000003389 potentiating effect Effects 0.000 abstract description 3
- 206010037660 Pyrexia Diseases 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 229940124639 Selective inhibitor Drugs 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
- 239000000243 solution Substances 0.000 description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 37
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- 238000003818 flash chromatography Methods 0.000 description 16
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- -1 chloro, bromo, methyl Chemical group 0.000 description 13
- MWSPVZXQINZJFP-UHFFFAOYSA-N 2-bromo-2-(4-fluorophenyl)-1-(4-methylsulfonylphenyl)ethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)C(Br)C1=CC=C(F)C=C1 MWSPVZXQINZJFP-UHFFFAOYSA-N 0.000 description 12
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- 238000010992 reflux Methods 0.000 description 12
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- 150000003839 salts Chemical class 0.000 description 11
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
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- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
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- 239000000047 product Substances 0.000 description 1
- 229960000786 propylhexedrine Drugs 0.000 description 1
- JCRIVQIOJSSCQD-UHFFFAOYSA-N propylhexedrine Chemical compound CNC(C)CC1CCCCC1 JCRIVQIOJSSCQD-UHFFFAOYSA-N 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 229940127293 prostanoid Drugs 0.000 description 1
- 150000003814 prostanoids Chemical class 0.000 description 1
- 229960003908 pseudoephedrine Drugs 0.000 description 1
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
- 229960000620 ranitidine Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000008327 renal blood flow Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229940083037 simethicone Drugs 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000016160 smooth muscle contraction Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229940126121 sodium channel inhibitor Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000003890 substance P antagonist Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 201000004595 synovitis Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 201000004415 tendinitis Diseases 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 208000037816 tissue injury Diseases 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 208000030401 vitamin deficiency disease Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 229960000833 xylometazoline Drugs 0.000 description 1
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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9506965.4A GB9506965D0 (en) | 1995-04-04 | 1995-04-04 | Chemical compounds |
| GBGB9512099.4A GB9512099D0 (en) | 1995-06-14 | 1995-06-14 | Chemical compounds |
| GBGB9516117.0A GB9516117D0 (en) | 1995-08-05 | 1995-08-05 | Chemical compounds |
| PCT/EP1996/001438 WO1996031509A1 (en) | 1995-04-04 | 1996-04-02 | IMIDAZO[1,2-a]PYRIDINE DERIVATIVES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK133297A3 true SK133297A3 (en) | 1998-07-08 |
Family
ID=27267657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1332-97A SK133297A3 (en) | 1995-04-04 | 1996-04-02 | Imidazo[1,2-a]pyridine derivatives, pharmaceutical composition containing same and their use |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0819127A1 (is) |
| JP (1) | JPH11501049A (is) |
| KR (1) | KR19980703559A (is) |
| CN (1) | CN1186492A (is) |
| AU (1) | AU5276696A (is) |
| BG (1) | BG101934A (is) |
| CA (1) | CA2216809A1 (is) |
| CZ (1) | CZ313397A3 (is) |
| EA (1) | EA199700209A1 (is) |
| HU (1) | HUP9801602A3 (is) |
| IS (1) | IS4570A (is) |
| NO (1) | NO974595L (is) |
| NZ (1) | NZ304886A (is) |
| PL (1) | PL322623A1 (is) |
| SK (1) | SK133297A3 (is) |
| TR (1) | TR199701105T1 (is) |
| WO (1) | WO1996031509A1 (is) |
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2764292B1 (fr) * | 1997-06-10 | 2000-12-29 | Innothera Lab Sa | Utilisation de derives de tetracycles dicetoniques, nouveaux composes obtenus et leur application en therapeutique |
| US6307047B1 (en) | 1997-08-22 | 2001-10-23 | Abbott Laboratories | Prostaglandin endoperoxide H synthase biosynthesis inhibitors |
| US6525053B1 (en) | 1997-08-22 | 2003-02-25 | Abbott Laboratories | Prostaglandin endoperoxide H synthase biosynthesis inhibitors |
| DE69816651T2 (de) | 1997-09-05 | 2004-04-01 | Glaxo Group Ltd., Greenford | 2,3-diaryl-pyrazolo[1,5-b]pyridazin derivate, deren herstellung und deren verwendung als cyclooxygenase 2 (cox-2) inhibitoren |
| FR2770131A1 (fr) * | 1997-10-27 | 1999-04-30 | Union Pharma Scient Appl | Nouvelle association pharmaceutique a activite analgesique |
| FR2771005B1 (fr) * | 1997-11-18 | 2002-06-07 | Union Pharma Scient Appl | Nouvelle association pharmaceutique a activite analgesique |
| GB9810920D0 (en) * | 1998-05-21 | 1998-07-22 | Merck Sharp & Dohme | Therapeutic use |
| ES2140354B1 (es) * | 1998-08-03 | 2000-11-01 | S A L V A T Lab Sa | Imidazo (1,2a) azinas sustituidas como inhibidores selectivos de la cox-2. |
| TW587079B (en) * | 1998-09-25 | 2004-05-11 | Almirall Prodesfarma Ag | 2-phenylpyran-4-one derivatives |
| DE69919887T2 (de) * | 1998-11-03 | 2005-09-15 | Glaxo Group Ltd., Greenford | Pyrazolopyridin derivative als selektive cox-2 inhibitoren |
| AU2661400A (en) * | 1999-02-27 | 2000-09-21 | Glaxo Group Limited | Pyrazolopyridines |
| EP1175214B1 (en) | 1999-12-08 | 2004-11-24 | Pharmacia Corporation | Cyclooxygenase-2 inhibitor compositions having rapid onset of therapeutic effect |
| GB9930358D0 (en) | 1999-12-22 | 2000-02-09 | Glaxo Group Ltd | Process for the preparation of chemical compounds |
| IL150368A0 (en) | 1999-12-23 | 2002-12-01 | Nitromed Inc | Nitrosated and nitrosylated cyclooxygenase-2-inhibitors, compositions and methods of use |
| GB0002312D0 (en) * | 2000-02-01 | 2000-03-22 | Glaxo Group Ltd | Medicaments |
| PE20011333A1 (es) | 2000-03-16 | 2002-01-16 | Almirall Prodesfarma Ag | Derivados de 2-fenilpiran-4-ona como inhibidores de ciclooxigenasa 2 |
| PE20020146A1 (es) * | 2000-07-13 | 2002-03-31 | Upjohn Co | Formulacion oftalmica que comprende un inhibidor de ciclooxigenasa-2 (cox-2) |
| NZ524252A (en) | 2000-07-20 | 2004-03-26 | Lauras As | Cox-2 inhibitors for treating HIV and AIDS |
| PE20020506A1 (es) * | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| GB0025449D0 (en) * | 2000-10-17 | 2000-11-29 | Glaxo Group Ltd | Chemical compounds |
| DE60112609T2 (de) | 2000-12-15 | 2006-01-19 | Glaxo Group Ltd., Greenford | Pyrazolopyridine |
| US7163940B2 (en) | 2000-12-15 | 2007-01-16 | Smithkline Beecham Corporation | Pyrazolopyridinyl pyrimidine therapeutic compounds |
| WO2002072581A2 (en) | 2001-03-08 | 2002-09-19 | Smithkline Beecham Corporation | Pyrazolopyriadine derivatives |
| JP4237497B2 (ja) | 2001-03-30 | 2009-03-11 | スミスクライン ビーチャム コーポレーション | ピラゾロピリジン類、その調製方法及びその治療用化合物としての使用 |
| PE20021017A1 (es) | 2001-04-03 | 2002-11-24 | Pharmacia Corp | Composicion parenteral reconstituible |
| JP4219171B2 (ja) | 2001-04-10 | 2009-02-04 | スミスクライン ビーチャム コーポレーション | 抗ウイルス性ピラゾロピリジン化合物 |
| US6756498B2 (en) | 2001-04-27 | 2004-06-29 | Smithkline Beecham Corporation | Process for the preparation of chemical compounds |
| JP2004527560A (ja) | 2001-04-27 | 2004-09-09 | スミスクライン ビーチャム コーポレーション | ピラゾロ［１，５−α］ピリジン誘導体 |
| WO2003000689A1 (en) | 2001-06-21 | 2003-01-03 | Smithkline Beecham Corporation | Imidazo`1,2-a!pyridine derivatives for the prophylaxis and treatment of herpes viral infections |
| AR038957A1 (es) | 2001-08-15 | 2005-02-02 | Pharmacia Corp | Terapia de combinacion para el tratamiento del cancer |
| WO2003031446A1 (en) | 2001-10-05 | 2003-04-17 | Smithkline Beecham Corporation | Imidazo-pyridine derivatives for use in the treatment of herpes viral infection |
| GB0124931D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124934D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124939D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124933D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124941D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124936D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124938D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| JP2005516916A (ja) | 2001-12-11 | 2005-06-09 | スミスクライン ビーチャム コーポレーション | 抗ヘルペス薬としてのピラゾロ−ピリジン誘導体 |
| EP2258687B1 (en) | 2002-02-12 | 2012-12-26 | Glaxosmithkline LLC | Nicotinamide derivates useful as P38 inhibitors |
| AU2003279622A1 (en) | 2002-06-28 | 2004-01-19 | Nitromed, Inc. | Oxime and/or hydrazone containing nitrosated and/or nitrosylated cyclooxigenase-2 selective inhibitors, compositions and methods of use |
| GB0217757D0 (en) | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Novel compounds |
| EP1546148A1 (en) | 2002-10-03 | 2005-06-29 | SmithKline Beecham Corporation | Therapeutic compounds based on pyrazolopyridine derivatives |
| KR20040072004A (ko) | 2003-02-07 | 2004-08-16 | 삼성에스디아이 주식회사 | 유기 전계 발광 소자용 발광 화합물 및 그를 이용한 유기전계발광 소자 |
| GB0308201D0 (en) | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
| GB0308185D0 (en) | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
| GB0308186D0 (en) | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
| PL2266585T3 (pl) | 2003-05-07 | 2013-10-31 | Osteologix As | Rozpuszczalne w wodzie sole stronktu do stosowania w leczeniu chorób chrząstki i/lub kości |
| GB0318814D0 (en) | 2003-08-11 | 2003-09-10 | Smithkline Beecham Corp | Novel compounds |
| WO2006041855A2 (en) | 2004-10-04 | 2006-04-20 | Nitromed, Inc. | Compositions and methods using apocynin compounds and nitric oxide donors |
| EP1915157A4 (en) | 2005-08-02 | 2010-09-01 | Nicox Sa | NICKEL OXYGENIZING ANTIMICROBIAL COMPOUNDS, COMPOSITIONS AND USE PROCESSES |
| CA2647859C (en) | 2006-03-29 | 2016-01-05 | Nitromed, Inc. | Nitric oxide enhancing prostaglandin compounds, compositions and methods of use |
| MX2009004700A (es) | 2006-11-06 | 2009-05-15 | Supergen Inc | Derivados de imidazo[1,2-b]piridazin y pirazolo[1,5-a] pirimidina y su uso como inhibidores de proteina cinasa. |
| PT3409278T (pt) | 2011-07-21 | 2020-12-18 | Sumitomo Dainippon Pharma Oncology Inc | Inibidores de proteína cinase heterocíclicos |
| EP3292213A1 (en) | 2015-05-04 | 2018-03-14 | Academisch Medisch Centrum | Biomarkers for the detection of aspirin insensitivity |
| NZ778055A (en) | 2019-02-12 | 2025-11-28 | Sumitomo Pharma America Inc | Formulations comprising heterocyclic protein kinase inhibitors |
| CA3209491A1 (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 disease |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3455924A (en) * | 1967-02-08 | 1969-07-15 | Upjohn Co | Dianisylimidazoles |
-
1996
- 1996-04-02 HU HU9801602A patent/HUP9801602A3/hu unknown
- 1996-04-02 PL PL96322623A patent/PL322623A1/xx unknown
- 1996-04-02 WO PCT/EP1996/001438 patent/WO1996031509A1/en not_active Ceased
- 1996-04-02 CZ CZ973133A patent/CZ313397A3/cs unknown
- 1996-04-02 EP EP96909164A patent/EP0819127A1/en not_active Withdrawn
- 1996-04-02 JP JP8529971A patent/JPH11501049A/ja active Pending
- 1996-04-02 NZ NZ304886A patent/NZ304886A/en unknown
- 1996-04-02 TR TR97/01105T patent/TR199701105T1/xx unknown
- 1996-04-02 AU AU52766/96A patent/AU5276696A/en not_active Abandoned
- 1996-04-02 SK SK1332-97A patent/SK133297A3/sk unknown
- 1996-04-02 KR KR1019970706963A patent/KR19980703559A/ko not_active Ceased
- 1996-04-02 CN CN96194403A patent/CN1186492A/zh active Pending
- 1996-04-02 CA CA002216809A patent/CA2216809A1/en not_active Abandoned
- 1996-04-02 EA EA199700209A patent/EA199700209A1/ru unknown
-
1997
- 1997-09-25 IS IS4570A patent/IS4570A/is unknown
- 1997-09-30 BG BG101934A patent/BG101934A/xx unknown
- 1997-10-03 NO NO974595A patent/NO974595L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO974595L (no) | 1997-12-03 |
| MX9707379A (es) | 1997-11-29 |
| AU5276696A (en) | 1996-10-23 |
| PL322623A1 (en) | 1998-02-02 |
| NZ304886A (en) | 1998-11-25 |
| EA199700209A1 (ru) | 1998-04-30 |
| NO974595D0 (no) | 1997-10-03 |
| KR19980703559A (ko) | 1998-11-05 |
| WO1996031509A1 (en) | 1996-10-10 |
| BG101934A (en) | 1999-04-30 |
| JPH11501049A (ja) | 1999-01-26 |
| CA2216809A1 (en) | 1996-10-10 |
| HUP9801602A3 (en) | 1999-01-28 |
| CZ313397A3 (cs) | 1998-03-18 |
| HUP9801602A2 (hu) | 1998-11-30 |
| CN1186492A (zh) | 1998-07-01 |
| IS4570A (is) | 1997-09-25 |
| EP0819127A1 (en) | 1998-01-21 |
| TR199701105T1 (xx) | 1998-02-21 |
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