JP2000503304A - 新規シクロアルキル置換イミダゾール - Google Patents
新規シクロアルキル置換イミダゾールInfo
- Publication number
- JP2000503304A JP2000503304A JP9525466A JP52546697A JP2000503304A JP 2000503304 A JP2000503304 A JP 2000503304A JP 9525466 A JP9525466 A JP 9525466A JP 52546697 A JP52546697 A JP 52546697A JP 2000503304 A JP2000503304 A JP 2000503304A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- imidazole
- pyrimidin
- substituted
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
Links
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims description 104
- 150000002460 imidazoles Chemical class 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 218
- -1 CHTwoOR12 Chemical group 0.000 claims description 132
- 238000000034 method Methods 0.000 claims description 98
- 238000006243 chemical reaction Methods 0.000 claims description 54
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 102000004127 Cytokines Human genes 0.000 claims description 39
- 108090000695 Cytokines Proteins 0.000 claims description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 37
- 239000002904 solvent Substances 0.000 claims description 37
- 201000010099 disease Diseases 0.000 claims description 36
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 35
- 241000124008 Mammalia Species 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- 238000011282 treatment Methods 0.000 claims description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 20
- 230000015572 biosynthetic process Effects 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 230000002401 inhibitory effect Effects 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 150000002466 imines Chemical class 0.000 claims description 19
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 18
- 239000011593 sulfur Substances 0.000 claims description 18
- 230000001404 mediated effect Effects 0.000 claims description 17
- 238000003786 synthesis reaction Methods 0.000 claims description 17
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 16
- 229950004696 flusalan Drugs 0.000 claims description 16
- 206010040070 Septic Shock Diseases 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 239000003153 chemical reaction reagent Substances 0.000 claims description 11
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 201000005569 Gout Diseases 0.000 claims description 9
- 108010084680 Heterogeneous-Nuclear Ribonucleoprotein K Proteins 0.000 claims description 9
- 102100023482 Mitogen-activated protein kinase 14 Human genes 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- 206010061218 Inflammation Diseases 0.000 claims description 8
- 206010040047 Sepsis Diseases 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 230000004054 inflammatory process Effects 0.000 claims description 8
- 230000005764 inhibitory process Effects 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 208000002193 Pain Diseases 0.000 claims description 7
- 206010037660 Pyrexia Diseases 0.000 claims description 7
- 206010044248 Toxic shock syndrome Diseases 0.000 claims description 7
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 201000008482 osteoarthritis Diseases 0.000 claims description 7
- 230000036407 pain Effects 0.000 claims description 7
- 208000001132 Osteoporosis Diseases 0.000 claims description 6
- 206010063837 Reperfusion injury Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 6
- 239000002243 precursor Substances 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 5
- SIXQRWZCONFXSS-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)-5-(2-methoxypyrimidin-4-yl)imidazol-1-yl]cyclohexan-1-one Chemical compound COC1=NC=CC(C=2N(C=NC=2C=2C=CC(F)=CC=2)C2CCC(=O)CC2)=N1 SIXQRWZCONFXSS-UHFFFAOYSA-N 0.000 claims description 5
- WTDHTMCTXLLUPX-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)-5-(2-propan-2-yloxypyrimidin-4-yl)imidazol-1-yl]cyclohexan-1-one Chemical compound CC(C)OC1=NC=CC(C=2N(C=NC=2C=2C=CC(F)=CC=2)C2CCC(=O)CC2)=N1 WTDHTMCTXLLUPX-UHFFFAOYSA-N 0.000 claims description 5
- YVIVYBRJUXAWNH-UHFFFAOYSA-N 6-[5-(4-fluorophenyl)-3-(4-oxocyclohexyl)imidazol-4-yl]-1h-pyrimidin-2-one Chemical compound OC1=NC=CC(C=2N(C=NC=2C=2C=CC(F)=CC=2)C2CCC(=O)CC2)=N1 YVIVYBRJUXAWNH-UHFFFAOYSA-N 0.000 claims description 5
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 5
- 206010018634 Gouty Arthritis Diseases 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 206010028289 Muscle atrophy Diseases 0.000 claims description 5
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims description 5
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 5
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 5
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 230000001684 chronic effect Effects 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
- NXOOHIFZUWBRJP-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)-5-(2-propan-2-yloxypyrimidin-4-yl)imidazol-1-yl]cyclohexan-1-ol Chemical compound CC(C)OC1=NC=CC(C=2N(C=NC=2C=2C=CC(F)=CC=2)C2CCC(O)CC2)=N1 NXOOHIFZUWBRJP-UHFFFAOYSA-N 0.000 claims description 4
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 4
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- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 4
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 4
- 206010042496 Sunburn Diseases 0.000 claims description 4
- 208000007536 Thrombosis Diseases 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
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- 230000024279 bone resorption Effects 0.000 claims description 4
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- 201000004595 synovitis Diseases 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- 206010063094 Cerebral malaria Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
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- XFXPMWWXUTWYJX-UHFFFAOYSA-N isonitrile group Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
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- CCOXWRVWKFVFDG-UHFFFAOYSA-N pyrimidine-2-carbaldehyde Chemical compound O=CC1=NC=CC=N1 CCOXWRVWKFVFDG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 claims description 2
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Classifications
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A61P17/00—Drugs for dermatological disorders
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- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
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- Diabetes (AREA)
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- Emergency Medicine (AREA)
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- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1001096P | 1996-01-11 | 1996-01-11 | |
| US60/010,010 | 1996-01-11 | ||
| PCT/US1997/000619 WO1997025048A1 (en) | 1996-01-11 | 1997-01-10 | Novel cycloalkyl substituted imidazoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000503304A true JP2000503304A (ja) | 2000-03-21 |
| JP2000503304A5 JP2000503304A5 (enExample) | 2004-11-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9525466A Ceased JP2000503304A (ja) | 1996-01-11 | 1997-01-10 | 新規シクロアルキル置換イミダゾール |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6329526B1 (enExample) |
| EP (1) | EP0889726B1 (enExample) |
| JP (1) | JP2000503304A (enExample) |
| CN (1) | CN1213305A (enExample) |
| AP (1) | AP9700912A0 (enExample) |
| AR (1) | AR005434A1 (enExample) |
| AT (1) | ATE276248T1 (enExample) |
| AU (1) | AU715315B2 (enExample) |
| BR (1) | BR9708149A (enExample) |
| CZ (1) | CZ218198A3 (enExample) |
| DE (1) | DE69730704T2 (enExample) |
| ES (1) | ES2229335T3 (enExample) |
| HU (1) | HUP9901233A2 (enExample) |
| ID (1) | ID18759A (enExample) |
| IL (1) | IL125224A0 (enExample) |
| MA (1) | MA24055A1 (enExample) |
| MX (1) | MX9805628A (enExample) |
| NO (1) | NO983182L (enExample) |
| NZ (1) | NZ330889A (enExample) |
| PL (1) | PL327939A1 (enExample) |
| TR (1) | TR199801350T2 (enExample) |
| UY (1) | UY24434A1 (enExample) |
| WO (1) | WO1997025048A1 (enExample) |
| ZA (1) | ZA97173B (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006062069A1 (ja) * | 2004-12-06 | 2006-06-15 | Santen Pharmaceutical Co., Ltd. | ｐ３８ＭＡＰキナーゼ阻害剤を有効成分とする掻痒治療剤 |
| JP2007145819A (ja) * | 2005-10-28 | 2007-06-14 | Tanabe Seiyaku Co Ltd | 医薬組成物 |
| WO2013100208A1 (ja) | 2011-12-28 | 2013-07-04 | 京都府公立大学法人 | 角膜内皮細胞の培養正常化 |
| WO2015072580A1 (ja) | 2013-11-14 | 2015-05-21 | 学校法人同志社 | 細胞増殖促進または細胞障害抑制による角膜内皮治療薬 |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5916891A (en) | 1992-01-13 | 1999-06-29 | Smithkline Beecham Corporation | Pyrimidinyl imidazoles |
| ZA9610687B (en) * | 1995-12-22 | 1997-09-29 | Smithkline Beecham Corp | Novel synthesis. |
| AP9700912A0 (en) | 1996-01-11 | 1997-01-31 | Smithkline Beecham Corp | Novel cycloalkyl substituted imidazoles |
| US6046208A (en) * | 1996-01-11 | 2000-04-04 | Smithkline Beecham Corporation | Substituted imidazole compounds |
| US5756499A (en) * | 1996-01-11 | 1998-05-26 | Smithkline Beecham Corporation | Substituted imidazole compounds |
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- 1997-01-08 MA MA24456A patent/MA24055A1/fr unknown
- 1997-01-08 UY UY24434A patent/UY24434A1/es unknown
- 1997-01-09 ZA ZA97173A patent/ZA97173B/xx unknown
- 1997-01-10 DE DE69730704T patent/DE69730704T2/de not_active Expired - Fee Related
- 1997-01-10 JP JP9525466A patent/JP2000503304A/ja not_active Ceased
- 1997-01-10 AT AT97905576T patent/ATE276248T1/de not_active IP Right Cessation
- 1997-01-10 CN CN97192881A patent/CN1213305A/zh active Pending
- 1997-01-10 ES ES97905576T patent/ES2229335T3/es not_active Expired - Lifetime
- 1997-01-10 BR BR9708149A patent/BR9708149A/pt unknown
- 1997-01-10 WO PCT/US1997/000619 patent/WO1997025048A1/en not_active Ceased
- 1997-01-10 HU HU9901233A patent/HUP9901233A2/hu unknown
- 1997-01-10 TR TR1998/01350T patent/TR199801350T2/xx unknown
- 1997-01-10 ID IDP970056A patent/ID18759A/id unknown
- 1997-01-10 PL PL97327939A patent/PL327939A1/xx unknown
- 1997-01-10 EP EP97905576A patent/EP0889726B1/en not_active Expired - Lifetime
- 1997-01-10 IL IL12522497A patent/IL125224A0/xx unknown
- 1997-01-10 AR ARP970100105A patent/AR005434A1/es unknown
- 1997-01-10 AU AU22425/97A patent/AU715315B2/en not_active Ceased
- 1997-01-10 NZ NZ330889A patent/NZ330889A/xx unknown
- 1997-01-10 CZ CZ982181A patent/CZ218198A3/cs unknown
- 1997-01-10 US US09/101,416 patent/US6329526B1/en not_active Expired - Fee Related
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1998
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006062069A1 (ja) * | 2004-12-06 | 2006-06-15 | Santen Pharmaceutical Co., Ltd. | ｐ３８ＭＡＰキナーゼ阻害剤を有効成分とする掻痒治療剤 |
| JP2007145819A (ja) * | 2005-10-28 | 2007-06-14 | Tanabe Seiyaku Co Ltd | 医薬組成物 |
| WO2013100208A1 (ja) | 2011-12-28 | 2013-07-04 | 京都府公立大学法人 | 角膜内皮細胞の培養正常化 |
| EP3553169A1 (en) | 2011-12-28 | 2019-10-16 | Kyoto Prefectural Public University Corporation | Normalization of culture of corneal endothelial cells |
| WO2015072580A1 (ja) | 2013-11-14 | 2015-05-21 | 学校法人同志社 | 細胞増殖促進または細胞障害抑制による角膜内皮治療薬 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE276248T1 (de) | 2004-10-15 |
| MA24055A1 (fr) | 1997-10-01 |
| PL327939A1 (en) | 1999-01-04 |
| NZ330889A (en) | 2000-03-27 |
| ZA97173B (en) | 1997-07-18 |
| AU715315B2 (en) | 2000-01-20 |
| WO1997025048A1 (en) | 1997-07-17 |
| ID18759A (id) | 1998-05-07 |
| ES2229335T3 (es) | 2005-04-16 |
| DE69730704T2 (de) | 2005-09-22 |
| TR199801350T2 (xx) | 1998-10-21 |
| EP0889726B1 (en) | 2004-09-15 |
| AR005434A1 (es) | 1999-06-23 |
| UY24434A1 (es) | 1997-06-06 |
| HUP9901233A2 (hu) | 2000-04-28 |
| AU2242597A (en) | 1997-08-01 |
| DE69730704D1 (de) | 2004-10-21 |
| NO983182L (no) | 1998-09-09 |
| MX9805628A (es) | 1998-11-29 |
| US6329526B1 (en) | 2001-12-11 |
| IL125224A0 (en) | 1999-03-12 |
| EP0889726A4 (en) | 1999-07-21 |
| CN1213305A (zh) | 1999-04-07 |
| BR9708149A (pt) | 1999-07-27 |
| CZ218198A3 (cs) | 1999-09-15 |
| EP0889726A1 (en) | 1999-01-13 |
| AP9700912A0 (en) | 1997-01-31 |
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