ZA200005561B - sPLA2 inhibitor ester. - Google Patents

sPLA2 inhibitor ester. Download PDF

Info

Publication number: ZA200005561B
Authority: ZA; South Africa
Prior art keywords: methyl; compound; phenylmethyl; indol; oxy
Prior art date: 1998-05-01

Application number

ZA200005561A

Other languages

English (en)

Inventor

Michael Lyle Denney

John Michael Morin Jr

Daniel Jon Sall

Jason Scott Sawyer

Original Assignee

Lilly Co Eli

Priority date (The priority date 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 date listed.)

1998-05-01

Filing date

2000-10-10

Publication date

2002-01-10

2000-10-10 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

2002-01-10 Publication of ZA200005561B publication Critical patent/ZA200005561B/en

Links

239000003112 inhibitor Substances 0.000 title description 14
150000002148 esters Chemical class 0.000 title description 7
102000005473 Secretory Phospholipases A2 Human genes 0.000 title description 4
108010031873 Secretory Phospholipases A2 Proteins 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 21
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 10
238000000034 method Methods 0.000 claims description 8
238000012261 overproduction Methods 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
239000000126 substance Substances 0.000 claims 5
238000009472 formulation Methods 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
235000019439 ethyl acetate Nutrition 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
-1 (3-(2-amino- 1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4- vl)oxy Chemical group 0.000 description 7
239000000243 solution Substances 0.000 description 7
239000002253 acid Substances 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
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
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 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
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-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
102000015439 Phospholipases Human genes 0.000 description 2
108010064785 Phospholipases 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
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
DHXSYOYHFRZWFU-UHFFFAOYSA-N methyl 2-(1-benzyl-2-methyl-3-oxamoylindol-4-yl)oxyacetate Chemical compound CC1=C(C(=O)C(N)=O)C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 DHXSYOYHFRZWFU-UHFFFAOYSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 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
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
229910015845 BBr3 Inorganic materials 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
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
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
OSQPUMRCKZAIOZ-UHFFFAOYSA-N carbon dioxide;ethanol Chemical compound CCO.O=C=O OSQPUMRCKZAIOZ-UHFFFAOYSA-N 0.000 description 1
125000000068 chlorophenyl group Chemical group 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
229910052500 inorganic mineral Inorganic materials 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
LSPWMIBSUHRLAP-UHFFFAOYSA-N methyl 2-(1-benzyl-2-methylindol-4-yl)oxyacetate Chemical compound CC1=CC=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 LSPWMIBSUHRLAP-UHFFFAOYSA-N 0.000 description 1
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
JRSZILYPLFWDTJ-UHFFFAOYSA-N n-methoxy-n-methyl-2-oxoacetamide Chemical compound CON(C)C(=O)C=O JRSZILYPLFWDTJ-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 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
230000003248 secreting effect Effects 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
CBURBMSJVXTVGO-UHFFFAOYSA-N tert-butyl n-[3-methoxy-2-(2-oxopropyl)phenyl]carbamate Chemical compound COC1=CC=CC(NC(=O)OC(C)(C)C)=C1CC(C)=O CBURBMSJVXTVGO-UHFFFAOYSA-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)

ZA200005561A 1998-05-01 2000-10-10 sPLA2 inhibitor ester. ZA200005561B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US8387398P	1998-05-01	1998-05-01

Publications (1)

Publication Number	Publication Date
ZA200005561B true ZA200005561B (en)	2002-01-10

Family

ID=22181214

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200005561A ZA200005561B (en)	1998-05-01	2000-10-10	sPLA2 inhibitor ester.

Country Status (22)

Country	Link
EP (1)	EP1073440B1 (fr)
JP (1)	JP4459441B2 (fr)
KR (1)	KR20010071197A (fr)
CN (1)	CN1303290A (fr)
AT (1)	ATE280155T1 (fr)
AU (1)	AU755901B2 (fr)
BR (1)	BR9910149A (fr)
CA (1)	CA2331036A1 (fr)
DE (1)	DE69921314T2 (fr)
EA (1)	EA003277B1 (fr)
ES (1)	ES2230847T3 (fr)
HR (1)	HRP20000738A2 (fr)
HU (1)	HUP0201636A1 (fr)
ID (1)	ID27812A (fr)
IL (1)	IL139203A0 (fr)
NO (1)	NO315940B1 (fr)
NZ (1)	NZ507391A (fr)
PL (1)	PL344571A1 (fr)
SK (1)	SK16332000A3 (fr)
TR (1)	TR200003198T2 (fr)
WO (1)	WO1999056752A1 (fr)
ZA (1)	ZA200005561B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
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
CN1450893A (zh) *	2000-07-14	2003-10-22	伊莱利利公司	治疗脓毒症的方法
EA200971020A1 (ru) *	2007-05-03	2010-10-29	Антера Фармасьютикалз, Инк.	Лечение сердечно-сосудистого заболевания и дислипидемии с использованием ингибиторов секреторной фосфолипазы а(spla) и способы комбинированного лечения с ингибитором spla
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
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
BR112018009100A8 (pt)	2015-11-04	2019-02-26	Procter & Gamble	estrutura absorvente
WO2017079601A1 (fr)	2015-11-04	2017-05-11	The Procter & Gamble Company	Structure absorbante
WO2017079599A1 (fr)	2015-11-04	2017-05-11	The Procter & Gamble Company	Structure absorbante

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2036307C (fr) *	1990-03-08	2002-07-09	Susan Jean Ward	Compositions anti-glaucome, a base de 3-arylcarbonyl-1-aminoalkyl-1h-indole; methode d'utilisation
PL180523B1 (pl) *	1994-04-01	2001-02-28	Eli Lilly & Co	Nowy zwiazek, pochodna 1H-indolo-3-glioksylamidu i srodek farmaceutyczny PL PL PL PL PL PL PL PL PL PL
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
AU1940800A (en) *	1998-12-21	2000-07-12	Eli Lilly And Company	Combination therapy for the treatment of sepsis

1999
- 1999-04-20 PL PL99344571A patent/PL344571A1/xx not_active IP Right Cessation
- 1999-04-20 CA CA002331036A patent/CA2331036A1/fr not_active Abandoned
- 1999-04-20 ES ES99918666T patent/ES2230847T3/es not_active Expired - Lifetime
- 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 SK SK1633-2000A patent/SK16332000A3/sk unknown
- 1999-04-20 NZ NZ507391A patent/NZ507391A/en unknown
- 1999-04-20 DE DE69921314T patent/DE69921314T2/de not_active Expired - Lifetime
- 1999-04-20 WO PCT/US1999/008538 patent/WO1999056752A1/fr not_active Ceased
- 1999-04-20 BR BR9910149-1A patent/BR9910149A/pt not_active IP Right Cessation
- 1999-04-20 HU HU0201636A patent/HUP0201636A1/hu unknown
- 1999-04-20 EP EP99918666A patent/EP1073440B1/fr not_active Expired - Lifetime
- 1999-04-20 TR TR2000/03198T patent/TR200003198T2/xx unknown
- 1999-04-20 EA EA200001141A patent/EA003277B1/ru not_active IP Right Cessation
- 1999-04-20 HR HR20000738A patent/HRP20000738A2/hr not_active Application Discontinuation
- 1999-04-20 ID IDW20002216A patent/ID27812A/id unknown
- 1999-04-20 IL IL13920399A patent/IL139203A0/xx unknown
- 1999-04-20 CN CN99805672A patent/CN1303290A/zh active Pending
- 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
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
IL139203A0 (en)	2001-11-25
ES2230847T3 (es)	2005-05-01
ATE280155T1 (de)	2004-11-15
TR200003198T2 (tr)	2001-03-21
AU755901B2 (en)	2003-01-02
NO20005477D0 (no)	2000-10-31
EA003277B1 (ru)	2003-04-24
JP4459441B2 (ja)	2010-04-28
EP1073440B1 (fr)	2004-10-20
EP1073440A1 (fr)	2001-02-07
CN1303290A (zh)	2001-07-11
HUP0201636A1 (en)	2002-09-28
NZ507391A (en)	2003-12-19
BR9910149A (pt)	2001-10-02
CA2331036A1 (fr)	1999-11-11
PL344571A1 (en)	2001-11-05
NO20005477L (no)	2000-10-31
SK16332000A3 (sk)	2001-06-11
EP1073440A4 (fr)	2002-07-17
EA200001141A1 (ru)	2001-04-23
AU3652599A (en)	1999-11-23
WO1999056752A1 (fr)	1999-11-11
HRP20000738A2 (en)	2001-10-31
DE69921314D1 (de)	2004-11-25
JP2002513761A (ja)	2002-05-14
KR20010071197A (ko)	2001-07-28
DE69921314T2 (de)	2006-02-09
NO315940B1 (no)	2003-11-17
ID27812A (id)	2001-04-26

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US6177426B1 (en)	2001-01-23	Morpholino-N-ethyl ester prodrugs of indole sPLA2 inhibitors
AU755901B2 (en)	2003-01-02	sPLA2 inhibitor ester
US6274616B1 (en)	2001-08-14	N,N-diethylglycolamido ester prodrugs of indole sPLA2 inhibitors
EP1202963B1 (fr)	2007-01-03	Inhibiteurs de spla2
US6274578B1 (en)	2001-08-14	sPLA2 inhibitor ester
US6140327A (en)	2000-10-31	Morpholino-n-ethyl ester derivative of an indole sPLA2 inhibitor
WO1999021545A1 (fr)	1999-05-06	PROMEDICAMENTS D'ESTER D'ISOPROPYLE D'INHIBITEURS INDOLIQUES DE sPLA¿2?
MXPA00010465A (en)	2001-07-31	sPLA2
CZ20004051A3 (cs)	2001-06-13	Ester jako inhibitor sPLA2