HRP20000739A2 - sPLA<->2<P> INHIBITOR COMPOUNDS FOR TREATMENT OF DISEASE - Google Patents
sPLA<->2<P> INHIBITOR COMPOUNDS FOR TREATMENT OF DISEASE Download PDFInfo
- Publication number
- HRP20000739A2 HRP20000739A2 HR20000739A HRP20000739A HRP20000739A2 HR P20000739 A2 HRP20000739 A2 HR P20000739A2 HR 20000739 A HR20000739 A HR 20000739A HR P20000739 A HRP20000739 A HR P20000739A HR P20000739 A2 HRP20000739 A2 HR P20000739A2
- Authority
- HR
- Croatia
- Prior art keywords
- amino
- oxy
- indol
- dioxoethyl
- group
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 54
- 239000003112 inhibitor Substances 0.000 title claims description 40
- 238000011282 treatment Methods 0.000 title claims description 36
- 201000010099 disease Diseases 0.000 title description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 6
- AWMLDBKLOPNOAR-UHFFFAOYSA-N indole-3-glyoxylamide Natural products C1=CC=C2C(C(=O)C(=O)N)=CNC2=C1 AWMLDBKLOPNOAR-UHFFFAOYSA-N 0.000 claims description 48
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 43
- 102000005473 Secretory Phospholipases A2 Human genes 0.000 claims description 38
- 108010031873 Secretory Phospholipases A2 Proteins 0.000 claims description 38
- -1 carbalkoxy Chemical group 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 12
- 239000000651 prodrug Substances 0.000 claims description 12
- 229940002612 prodrug Drugs 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 230000002452 interceptive effect Effects 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 6
- 229910006069 SO3H Inorganic materials 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- BHLXTPHDSZUFHR-UHFFFAOYSA-N varespladib Chemical compound CCC1=C(C(=O)C(N)=O)C2=C(OCC(O)=O)C=CC=C2N1CC1=CC=CC=C1 BHLXTPHDSZUFHR-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 3
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- UWZIPJAIHVSDQU-UHFFFAOYSA-N 2-(1-benzyl-2-cyclopropyl-3-oxamoylindol-4-yl)oxyacetic acid Chemical compound C=1C=CC=CC=1CN1C2=CC=CC(OCC(O)=O)=C2C(C(=O)C(=O)N)=C1C1CC1 UWZIPJAIHVSDQU-UHFFFAOYSA-N 0.000 claims description 3
- FBGWHCFPQBQYNU-UHFFFAOYSA-N 2-(1-benzyl-2-methyl-3-oxamoylindol-4-yl)oxyacetic acid Chemical compound CC1=C(C(=O)C(N)=O)C2=C(OCC(O)=O)C=CC=C2N1CC1=CC=CC=C1 FBGWHCFPQBQYNU-UHFFFAOYSA-N 0.000 claims description 3
- GWHFRTCCSTUDBC-UHFFFAOYSA-N 2-(1-benzyl-2-methyl-3-oxamoylindol-4-yl)oxypropanoic acid Chemical compound CC1=C(C(=O)C(N)=O)C=2C(OC(C)C(O)=O)=CC=CC=2N1CC1=CC=CC=C1 GWHFRTCCSTUDBC-UHFFFAOYSA-N 0.000 claims description 3
- AXRTZAZDPVBRMQ-UHFFFAOYSA-N 2-[1-[(2,6-dichlorophenyl)methyl]-2-methyl-3-oxamoylindol-4-yl]oxyacetic acid Chemical compound CC1=C(C(=O)C(N)=O)C2=C(OCC(O)=O)C=CC=C2N1CC1=C(Cl)C=CC=C1Cl AXRTZAZDPVBRMQ-UHFFFAOYSA-N 0.000 claims description 3
- NFFDUBFVBHVZQY-UHFFFAOYSA-N 2-[1-[(3-chlorophenyl)methyl]-2-ethyl-3-oxamoylindol-4-yl]oxyacetic acid Chemical compound CCC1=C(C(=O)C(N)=O)C2=C(OCC(O)=O)C=CC=C2N1CC1=CC=CC(Cl)=C1 NFFDUBFVBHVZQY-UHFFFAOYSA-N 0.000 claims description 3
- YWJZXUKVOVNLBZ-UHFFFAOYSA-N 2-[2-cyclopropyl-3-oxamoyl-1-[(2-phenylphenyl)methyl]indol-4-yl]oxyacetic acid Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1CN1C2=CC=CC(OCC(O)=O)=C2C(C(=O)C(=O)N)=C1C1CC1 YWJZXUKVOVNLBZ-UHFFFAOYSA-N 0.000 claims description 3
- IMGOQYQYSLHFKI-UHFFFAOYSA-N 2-[2-ethyl-3-oxamoyl-1-[(2-phenylphenyl)methyl]indol-4-yl]oxyacetic acid Chemical compound CCC1=C(C(=O)C(N)=O)C2=C(OCC(O)=O)C=CC=C2N1CC1=CC=CC=C1C1=CC=CC=C1 IMGOQYQYSLHFKI-UHFFFAOYSA-N 0.000 claims description 3
- OCZWKLXXLNWSDH-UHFFFAOYSA-N 2-[2-methyl-1-(naphthalen-1-ylmethyl)-3-oxamoylindol-4-yl]oxyacetic acid Chemical compound C1=CC=C2C(CN3C4=CC=CC(OCC(O)=O)=C4C(C(=O)C(N)=O)=C3C)=CC=CC2=C1 OCZWKLXXLNWSDH-UHFFFAOYSA-N 0.000 claims description 3
- KFJOAXDOAYZVOY-UHFFFAOYSA-N 2-[2-methyl-3-oxamoyl-1-[(2-phenylphenyl)methyl]indol-4-yl]oxyacetic acid Chemical compound CC1=C(C(=O)C(N)=O)C2=C(OCC(O)=O)C=CC=C2N1CC1=CC=CC=C1C1=CC=CC=C1 KFJOAXDOAYZVOY-UHFFFAOYSA-N 0.000 claims description 3
- CXAFWBHDYGONMZ-UHFFFAOYSA-N 2-[2-methyl-3-oxamoyl-1-[(3-phenylphenyl)methyl]indol-4-yl]oxyacetic acid Chemical compound CC1=C(C(=O)C(N)=O)C2=C(OCC(O)=O)C=CC=C2N1CC(C=1)=CC=CC=1C1=CC=CC=C1 CXAFWBHDYGONMZ-UHFFFAOYSA-N 0.000 claims description 3
- VGOLBSXVJJOMNA-UHFFFAOYSA-N 2-[2-methyl-3-oxamoyl-1-[(4-phenylphenyl)methyl]indol-4-yl]oxyacetic acid Chemical compound CC1=C(C(=O)C(N)=O)C2=C(OCC(O)=O)C=CC=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1 VGOLBSXVJJOMNA-UHFFFAOYSA-N 0.000 claims description 3
- PCSBUIIMXNYHLA-UHFFFAOYSA-N 2-[3-oxamoyl-1-[(2-phenylphenyl)methyl]-2-propylindol-4-yl]oxyacetic acid Chemical compound CCCC1=C(C(=O)C(N)=O)C2=C(OCC(O)=O)C=CC=C2N1CC1=CC=CC=C1C1=CC=CC=C1 PCSBUIIMXNYHLA-UHFFFAOYSA-N 0.000 claims description 3
- CUSWQJGVEIICPH-UHFFFAOYSA-N 4-(1-benzyl-2-ethyl-3-oxamoylindol-5-yl)oxybutanoic acid Chemical compound CCC1=C(C(=O)C(N)=O)C2=CC(OCCCC(O)=O)=CC=C2N1CC1=CC=CC=C1 CUSWQJGVEIICPH-UHFFFAOYSA-N 0.000 claims description 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 206010012735 Diarrhoea Diseases 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
- 238000001990 intravenous administration Methods 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000003555 thioacetals Chemical class 0.000 claims description 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 3
- 125000005425 toluyl group Chemical group 0.000 claims description 3
- 125000002256 xylenyl group Chemical group C1(C(C=CC=C1)C)(C)* 0.000 claims description 3
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
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- 239000008280 blood Substances 0.000 claims description 2
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- 229940125721 immunosuppressive agent Drugs 0.000 claims description 2
- 239000003018 immunosuppressive agent Substances 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 239000012453 solvate Chemical class 0.000 claims description 2
- 150000003431 steroids Chemical class 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 6
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- 159000000000 sodium salts Chemical class 0.000 description 6
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/22—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an aralkyl radical attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8387498P | 1998-05-01 | 1998-05-01 | |
| PCT/US1999/008654 WO1999057100A1 (en) | 1998-05-01 | 1999-04-20 | Spla2 inhibitor compounds for treatment of disease |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20000739A2 true HRP20000739A2 (en) | 2001-10-31 |
Family
ID=22181224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20000739A HRP20000739A2 (en) | 1998-05-01 | 2000-10-31 | sPLA<->2<P> INHIBITOR COMPOUNDS FOR TREATMENT OF DISEASE |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6340699B1 (zh) |
| EP (1) | EP1084108A4 (zh) |
| JP (1) | JP2002513783A (zh) |
| KR (1) | KR20010043190A (zh) |
| CN (1) | CN1299348A (zh) |
| AU (1) | AU3656299A (zh) |
| BR (1) | BR9910095A (zh) |
| CA (1) | CA2330856A1 (zh) |
| CZ (1) | CZ20004052A3 (zh) |
| EA (1) | EA200001140A1 (zh) |
| HR (1) | HRP20000739A2 (zh) |
| HU (1) | HUP0102243A2 (zh) |
| ID (1) | ID27153A (zh) |
| IL (1) | IL139019A0 (zh) |
| NO (1) | NO20005479L (zh) |
| PL (1) | PL343708A1 (zh) |
| SK (1) | SK16342000A3 (zh) |
| TR (1) | TR200003194T2 (zh) |
| WO (1) | WO1999057100A1 (zh) |
| ZA (1) | ZA200005563B (zh) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19962300A1 (de) * | 1999-12-23 | 2001-06-28 | Asta Medica Ag | Substituierte N-Benzyl-Indol-3-yl-glyoxylsäure-Derivate mit Antitumorwirkung |
| WO2001055108A2 (en) * | 2000-01-25 | 2001-08-02 | Eli Lilly And Company | Use of spl a2 inhibitors for the treatment of inflammation |
| JPWO2002000621A1 (ja) * | 2000-06-29 | 2004-04-22 | 塩野義製薬株式会社 | Ｘ型ｓＰＬＡ２阻害作用を有する化合物 |
| US20020039869A1 (en) * | 2000-07-24 | 2002-04-04 | Felix Achille | Thermoplastic superabsorbent polymer blend compositions and their preparation |
| AU2006311766A1 (en) * | 2005-11-03 | 2007-05-18 | Ilypsa, Inc. | Indole compounds having C4-acidic substituents and use thereof as phospholipase-A2 inhibitors |
| JPWO2009123080A1 (ja) * | 2008-04-01 | 2011-07-28 | アステラス製薬株式会社 | インドリノン化合物 |
| NZ624963A (en) | 2009-04-29 | 2016-07-29 | Amarin Pharmaceuticals Ie Ltd | Pharmaceutical compositions comprising epa and a cardiovascular agent and methods of using the same |
| US9290752B2 (en) | 2013-03-13 | 2016-03-22 | Sunny Delight Beverages Co. | Process for enhancing the amylase inhibitory efficacy from phaseolus vulgaris extracts |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5356919A (en) | 1991-05-30 | 1994-10-18 | G. D. Searle & Co. | Leukotriene B4 synthesis inhibitors |
| DE4218096A1 (de) | 1992-06-02 | 1993-12-09 | Boehringer Mannheim Gmbh | Spiro-oxetane, Verfahren zu ihrer Herstellung und Arzneimittel |
| DE4323409A1 (de) | 1993-07-13 | 1995-01-19 | Boehringer Mannheim Gmbh | Verwendung von Cumarinen und Carbostyrilen als PLA¶2¶-Inhibitoren, neue Cumarine und Carbostyrile, Verfahren zu ihrer Herstellung und Arzneimittel |
| RU2128169C1 (ru) | 1994-04-01 | 1999-03-27 | Эли Лилли Энд Компани | Iн-индол-3-глиоксиламиды, ингибирующие spla2-медиируемое выделение жирных кислот, фармацевтическая композиция |
| WO1995033462A1 (en) * | 1994-06-02 | 1995-12-14 | Smithkline Beecham Corporation | Anti-inflammatory compounds |
| NZ298145A (en) * | 1994-12-29 | 1998-08-26 | Yamanouchi Pharma Co Ltd | Monoclonal antibodies having inhibitory effect on type ii phospholipase a2, proteins forming part thereof, cells producing them, dna encoding them, recombinant vector comprising the dna and medicament |
| KR20000049210A (ko) | 1996-10-30 | 2000-07-25 | 피터 지. 스트링거 | 치환된 트리시클릭류 |
| TR200002447T2 (tr) * | 1998-02-25 | 2000-11-21 | Genetics Institute, Inc. | Fosfolinaz enzimlerinin inhibitörleri |
-
1999
- 1999-04-20 US US09/673,675 patent/US6340699B1/en not_active Expired - Fee Related
- 1999-04-20 HU HU0102243A patent/HUP0102243A2/hu unknown
- 1999-04-20 CN CN99805675A patent/CN1299348A/zh active Pending
- 1999-04-20 ID IDW20002214A patent/ID27153A/id unknown
- 1999-04-20 WO PCT/US1999/008654 patent/WO1999057100A1/en not_active Application Discontinuation
- 1999-04-20 CZ CZ20004052A patent/CZ20004052A3/cs unknown
- 1999-04-20 EP EP99918711A patent/EP1084108A4/en not_active Withdrawn
- 1999-04-20 IL IL13901999A patent/IL139019A0/xx unknown
- 1999-04-20 KR KR1020007012113A patent/KR20010043190A/ko not_active Application Discontinuation
- 1999-04-20 TR TR2000/03194T patent/TR200003194T2/xx unknown
- 1999-04-20 PL PL99343708A patent/PL343708A1/xx unknown
- 1999-04-20 SK SK1634-2000A patent/SK16342000A3/sk unknown
- 1999-04-20 JP JP2000547070A patent/JP2002513783A/ja not_active Withdrawn
- 1999-04-20 AU AU36562/99A patent/AU3656299A/en not_active Abandoned
- 1999-04-20 EA EA200001140A patent/EA200001140A1/ru unknown
- 1999-04-20 CA CA002330856A patent/CA2330856A1/en not_active Abandoned
- 1999-04-20 BR BR9910095-9A patent/BR9910095A/pt not_active Application Discontinuation
-
2000
- 2000-10-10 ZA ZA200005563A patent/ZA200005563B/en unknown
- 2000-10-31 NO NO20005479A patent/NO20005479L/no not_active Application Discontinuation
- 2000-10-31 HR HR20000739A patent/HRP20000739A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PL343708A1 (en) | 2001-08-27 |
| SK16342000A3 (sk) | 2002-04-04 |
| TR200003194T2 (tr) | 2001-03-21 |
| NO20005479D0 (no) | 2000-10-31 |
| WO1999057100A1 (en) | 1999-11-11 |
| EA200001140A1 (ru) | 2001-04-23 |
| CA2330856A1 (en) | 1999-11-11 |
| JP2002513783A (ja) | 2002-05-14 |
| AU3656299A (en) | 1999-11-23 |
| ZA200005563B (en) | 2002-01-10 |
| KR20010043190A (ko) | 2001-05-25 |
| NO20005479L (no) | 2000-12-20 |
| CN1299348A (zh) | 2001-06-13 |
| EP1084108A4 (en) | 2005-01-12 |
| EP1084108A1 (en) | 2001-03-21 |
| ID27153A (id) | 2001-03-08 |
| US6340699B1 (en) | 2002-01-22 |
| CZ20004052A3 (cs) | 2002-05-15 |
| IL139019A0 (en) | 2001-11-25 |
| BR9910095A (pt) | 2000-12-26 |
| HUP0102243A2 (hu) | 2001-10-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| OBST | Application withdrawn |