AU755901B2 - sPLA2 inhibitor ester - Google Patents
sPLA2 inhibitor ester Download PDFInfo
- Publication number
- AU755901B2 AU755901B2 AU36525/99A AU3652599A AU755901B2 AU 755901 B2 AU755901 B2 AU 755901B2 AU 36525/99 A AU36525/99 A AU 36525/99A AU 3652599 A AU3652599 A AU 3652599A AU 755901 B2 AU755901 B2 AU 755901B2
- Authority
- AU
- Australia
- Prior art keywords
- compound
- methyl
- phenylmethyl
- oxy
- spla
- 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
- 239000003112 inhibitor Substances 0.000 title abstract description 15
- 102000005473 Secretory Phospholipases A2 Human genes 0.000 title abstract description 4
- 108010031873 Secretory Phospholipases A2 Proteins 0.000 title abstract description 4
- 150000002148 esters Chemical class 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 238000012261 overproduction Methods 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 4
- 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
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 25
- -1 3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl Chemical group 0.000 abstract description 15
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 37
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 235000019439 ethyl acetate Nutrition 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 238000003556 assay Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- XDYZMGCJQLDBQN-UHFFFAOYSA-N 1-benzyl-2-methylindol-4-ol Chemical compound CC1=CC2=C(O)C=CC=C2N1CC1=CC=CC=C1 XDYZMGCJQLDBQN-UHFFFAOYSA-N 0.000 description 3
- QFWNDWTXECQVOE-UHFFFAOYSA-N 4-methoxy-2-methyl-1h-indole Chemical compound COC1=CC=CC2=C1C=C(C)N2 QFWNDWTXECQVOE-UHFFFAOYSA-N 0.000 description 3
- 241000282693 Cercopithecidae Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RZZFTOJEHIRCRK-UHFFFAOYSA-N tert-butyl n-(3-methoxy-2-methylphenyl)carbamate Chemical compound COC1=CC=CC(NC(=O)OC(C)(C)C)=C1C RZZFTOJEHIRCRK-UHFFFAOYSA-N 0.000 description 3
- SUTVCLUFXXAFIP-UHFFFAOYSA-N 1-benzyl-4-methoxy-2-methylindole Chemical compound CC1=CC=2C(OC)=CC=CC=2N1CC1=CC=CC=C1 SUTVCLUFXXAFIP-UHFFFAOYSA-N 0.000 description 2
- 241000220479 Acacia Species 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 102000006447 Phospholipases A2 Human genes 0.000 description 2
- 108010058864 Phospholipases A2 Proteins 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229940114079 arachidonic acid Drugs 0.000 description 2
- 235000021342 arachidonic acid Nutrition 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- OPXLVWLFDKRYRB-UHFFFAOYSA-N 3-methoxy-2-methylaniline Chemical compound COC1=CC=CC(N)=C1C OPXLVWLFDKRYRB-UHFFFAOYSA-N 0.000 description 1
- NBJHDLKSWUDGJG-UHFFFAOYSA-N 4-(2-chloroethyl)morpholin-4-ium;chloride Chemical compound Cl.ClCCN1CCOCC1 NBJHDLKSWUDGJG-UHFFFAOYSA-N 0.000 description 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000019054 Group II Phospholipases A2 Human genes 0.000 description 1
- 108010026929 Group II Phospholipases A2 Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000282567 Macaca fascicularis Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- OSQPUMRCKZAIOZ-UHFFFAOYSA-N carbon dioxide;ethanol Chemical compound CCO.O=C=O OSQPUMRCKZAIOZ-UHFFFAOYSA-N 0.000 description 1
- 238000010367 cloning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- POCFBDFTJMJWLG-UHFFFAOYSA-N dihydrosinapic acid methyl ester Natural products COC(=O)CCC1=CC(OC)=C(O)C(OC)=C1 POCFBDFTJMJWLG-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- AWMLDBKLOPNOAR-UHFFFAOYSA-N indole-3-glyoxylamide Natural products C1=CC=C2C(C(=O)C(=O)N)=CNC2=C1 AWMLDBKLOPNOAR-UHFFFAOYSA-N 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Substances ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003259 recombinant expression Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 210000001179 synovial fluid Anatomy 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
Classifications
-
- 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
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8387398P | 1998-05-01 | 1998-05-01 | |
| US60/083873 | 1998-05-01 | ||
| PCT/US1999/008538 WO1999056752A1 (en) | 1998-05-01 | 1999-04-20 | sPLA2 INHIBITOR ESTER |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3652599A AU3652599A (en) | 1999-11-23 |
| AU755901B2 true AU755901B2 (en) | 2003-01-02 |
Family
ID=22181214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU36525/99A Ceased AU755901B2 (en) | 1998-05-01 | 1999-04-20 | sPLA2 inhibitor ester |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP1073440B1 (https=) |
| JP (1) | JP4459441B2 (https=) |
| KR (1) | KR20010071197A (https=) |
| CN (1) | CN1303290A (https=) |
| AT (1) | ATE280155T1 (https=) |
| AU (1) | AU755901B2 (https=) |
| BR (1) | BR9910149A (https=) |
| CA (1) | CA2331036A1 (https=) |
| DE (1) | DE69921314T2 (https=) |
| EA (1) | EA003277B1 (https=) |
| ES (1) | ES2230847T3 (https=) |
| HR (1) | HRP20000738A2 (https=) |
| HU (1) | HUP0201636A1 (https=) |
| ID (1) | ID27812A (https=) |
| IL (1) | IL139203A0 (https=) |
| NO (1) | NO315940B1 (https=) |
| NZ (1) | NZ507391A (https=) |
| PL (1) | PL344571A1 (https=) |
| SK (1) | SK16332000A3 (https=) |
| TR (1) | TR200003198T2 (https=) |
| WO (1) | WO1999056752A1 (https=) |
| ZA (1) | ZA200005561B (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6140327A (en) * | 1999-05-12 | 2000-10-31 | Eli Lilly And Company | Morpholino-n-ethyl ester derivative of an indole sPLA2 inhibitor |
| AU2252201A (en) * | 1999-12-16 | 2001-06-25 | Eli Lilly And Company | Carbon monoxide-based synthesis of spla2 inhibitors |
| DE19962300A1 (de) * | 1999-12-23 | 2001-06-28 | Asta Medica Ag | Substituierte N-Benzyl-Indol-3-yl-glyoxylsäure-Derivate mit Antitumorwirkung |
| EP1303262A2 (en) * | 2000-07-14 | 2003-04-23 | Eli Lilly And Company | Use of a spla2 inhibitor for the treatment of sepsis |
| US8048880B2 (en) | 2007-05-03 | 2011-11-01 | Anthera Pharmaceuticals, Inc. | Treatment of cardiovascular disease and dyslipidemia using secretory phospholipase A2 (SPLA2) inhibitors and SPLA2 inhibitor combination therapies |
| CN101742907A (zh) * | 2007-05-03 | 2010-06-16 | 安塞拉制药有限公司 | 采用分泌型磷脂酶a2（spla2）抑制剂和spla2抑制剂组合疗法治疗心血管疾病和血脂异常 |
| US20150335498A1 (en) * | 2014-05-22 | 2015-11-26 | The Procter & Gamble Company | Heterogenous mass containing foam |
| US10729600B2 (en) | 2015-06-30 | 2020-08-04 | The Procter & Gamble Company | Absorbent structure |
| CA3004313A1 (en) | 2015-11-04 | 2017-05-11 | The Procter & Gamble Company | Absorbent structure |
| US11173078B2 (en) | 2015-11-04 | 2021-11-16 | The Procter & Gamble Company | Absorbent structure |
| EP3370664B1 (en) | 2015-11-04 | 2022-01-26 | The Procter & Gamble Company | Absorbent article comprising an absorbent structure |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2036307C (en) * | 1990-03-08 | 2002-07-09 | Susan Jean Ward | 3-arylcarbonyl-1-aminoalkyl-1h-indole-containing antiglaucoma compositions and method |
| BR9501404A (pt) * | 1994-04-01 | 1996-03-05 | Lilly Co Eli | 1H-indol-3 glioxilamida e formulação farmacèutica |
| DE4435477A1 (de) * | 1994-10-04 | 1996-04-11 | Bayer Ag | Cycloalkano-indol- und -azaindol-derivate |
| FI974437A7 (fi) * | 1995-06-06 | 1997-12-05 | Pfizer | Substituoituja N-(indoli-2-karbonyyli)amideja ja johdannaisia glykogee nifosforylaasi-inhibiittoreina |
| JP2002542148A (ja) * | 1998-12-21 | 2002-12-10 | イーライ・リリー・アンド・カンパニー | 敗血症の処置のための組み合わせ療法 |
-
1999
- 1999-04-20 ID IDW20002216A patent/ID27812A/id unknown
- 1999-04-20 HU HU0201636A patent/HUP0201636A1/hu unknown
- 1999-04-20 AU AU36525/99A patent/AU755901B2/en not_active Ceased
- 1999-04-20 KR KR1020007012114A patent/KR20010071197A/ko not_active Withdrawn
- 1999-04-20 HR HR20000738A patent/HRP20000738A2/hr not_active Application Discontinuation
- 1999-04-20 DE DE69921314T patent/DE69921314T2/de not_active Expired - Lifetime
- 1999-04-20 BR BR9910149-1A patent/BR9910149A/pt not_active IP Right Cessation
- 1999-04-20 EP EP99918666A patent/EP1073440B1/en not_active Expired - Lifetime
- 1999-04-20 PL PL99344571A patent/PL344571A1/xx not_active IP Right Cessation
- 1999-04-20 CA CA002331036A patent/CA2331036A1/en not_active Abandoned
- 1999-04-20 TR TR2000/03198T patent/TR200003198T2/xx unknown
- 1999-04-20 ES ES99918666T patent/ES2230847T3/es not_active Expired - Lifetime
- 1999-04-20 WO PCT/US1999/008538 patent/WO1999056752A1/en not_active Ceased
- 1999-04-20 JP JP2000546777A patent/JP4459441B2/ja not_active Expired - Fee Related
- 1999-04-20 AT AT99918666T patent/ATE280155T1/de not_active IP Right Cessation
- 1999-04-20 CN CN99805672A patent/CN1303290A/zh active Pending
- 1999-04-20 EA EA200001141A patent/EA003277B1/ru not_active IP Right Cessation
- 1999-04-20 IL IL13920399A patent/IL139203A0/xx unknown
- 1999-04-20 NZ NZ507391A patent/NZ507391A/en unknown
- 1999-04-20 SK SK1633-2000A patent/SK16332000A3/sk unknown
-
2000
- 2000-10-10 ZA ZA200005561A patent/ZA200005561B/en unknown
- 2000-10-31 NO NO20005477A patent/NO315940B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE280155T1 (de) | 2004-11-15 |
| EA003277B1 (ru) | 2003-04-24 |
| JP2002513761A (ja) | 2002-05-14 |
| PL344571A1 (en) | 2001-11-05 |
| HRP20000738A2 (en) | 2001-10-31 |
| KR20010071197A (ko) | 2001-07-28 |
| BR9910149A (pt) | 2001-10-02 |
| ZA200005561B (en) | 2002-01-10 |
| IL139203A0 (en) | 2001-11-25 |
| CN1303290A (zh) | 2001-07-11 |
| CA2331036A1 (en) | 1999-11-11 |
| ID27812A (id) | 2001-04-26 |
| DE69921314T2 (de) | 2006-02-09 |
| WO1999056752A1 (en) | 1999-11-11 |
| NO315940B1 (no) | 2003-11-17 |
| EP1073440B1 (en) | 2004-10-20 |
| AU3652599A (en) | 1999-11-23 |
| SK16332000A3 (sk) | 2001-06-11 |
| EP1073440A4 (en) | 2002-07-17 |
| HUP0201636A1 (en) | 2002-09-28 |
| NO20005477D0 (no) | 2000-10-31 |
| JP4459441B2 (ja) | 2010-04-28 |
| NO20005477L (no) | 2000-10-31 |
| DE69921314D1 (de) | 2004-11-25 |
| NZ507391A (en) | 2003-12-19 |
| TR200003198T2 (tr) | 2001-03-21 |
| ES2230847T3 (es) | 2005-05-01 |
| EP1073440A1 (en) | 2001-02-07 |
| EA200001141A1 (ru) | 2001-04-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) |