DE69912670T2 - Substituierte tricyclische Verbindungen und deren Verwendung zur Behandlung von sPLA2-bedingten Erkrankungen - Google Patents
Substituierte tricyclische Verbindungen und deren Verwendung zur Behandlung von sPLA2-bedingten Erkrankungen Download PDFInfo
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- DE69912670T2 DE69912670T2 DE69912670T DE69912670T DE69912670T2 DE 69912670 T2 DE69912670 T2 DE 69912670T2 DE 69912670 T DE69912670 T DE 69912670T DE 69912670 T DE69912670 T DE 69912670T DE 69912670 T2 DE69912670 T2 DE 69912670T2
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- LOJLUPOAZRYZLD-UHFFFAOYSA-N ethyl 2-(1-benzyl-4-methoxyindol-3-yl)-3-methoxypropanoate Chemical compound C12=CC=CC(OC)=C2C(C(COC)C(=O)OCC)=CN1CC1=CC=CC=C1 LOJLUPOAZRYZLD-UHFFFAOYSA-N 0.000 description 1
- JHUNUOOWAUAGQO-UHFFFAOYSA-N ethyl 2-(4-methoxy-1h-indol-3-yl)acetate Chemical compound C1=CC(OC)=C2C(CC(=O)OCC)=CNC2=C1 JHUNUOOWAUAGQO-UHFFFAOYSA-N 0.000 description 1
- GOULDOSPVBOJGE-UHFFFAOYSA-N ethyl 9-benzyl-5-methoxy-3,4-dihydro-1h-pyrano[3,4-b]indole-4-carboxylate Chemical compound CCOC(=O)C1COCC2=C1C1=C(OC)C=CC=C1N2CC1=CC=CC=C1 GOULDOSPVBOJGE-UHFFFAOYSA-N 0.000 description 1
- MFFXVVHUKRKXCI-UHFFFAOYSA-N ethyl iodoacetate Chemical compound CCOC(=O)CI MFFXVVHUKRKXCI-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
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- 238000011597 hartley guinea pig Methods 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000013537 high throughput screening Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- HECSHXUNOVTAIJ-UHFFFAOYSA-N hydron;(2-methoxyphenyl)hydrazine;chloride Chemical compound Cl.COC1=CC=CC=C1NN HECSHXUNOVTAIJ-UHFFFAOYSA-N 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 1
- 201000004990 juvenile ankylosing spondylitis Diseases 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 1
- VTLKDNDBUKQFBR-UHFFFAOYSA-N methyl 2-(3-benzyl-7-methoxyindol-1-yl)-5-chloropentanoate Chemical compound C12=CC=CC(OC)=C2N(C(CCCCl)C(=O)OC)C=C1CC1=CC=CC=C1 VTLKDNDBUKQFBR-UHFFFAOYSA-N 0.000 description 1
- XPTYCSXFJJLTGH-UHFFFAOYSA-N methyl 2-(3-benzyl-7-methoxyindol-1-yl)pentanoate Chemical compound C12=CC=CC(OC)=C2N(C(C(=O)OC)CCC)C=C1CC1=CC=CC=C1 XPTYCSXFJJLTGH-UHFFFAOYSA-N 0.000 description 1
- SCBDYAJOMFFQIM-UHFFFAOYSA-N methyl 2-benzyl-4-oxo-3,9-dihydro-1h-pyrido[3,4-b]indole-5-carboxylate Chemical compound C1C(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2CN1CC1=CC=CC=C1 SCBDYAJOMFFQIM-UHFFFAOYSA-N 0.000 description 1
- HFRNWXMIMIPGQB-UHFFFAOYSA-N methyl 2-bromo-5-chloropentanoate Chemical compound COC(=O)C(Br)CCCCl HFRNWXMIMIPGQB-UHFFFAOYSA-N 0.000 description 1
- ZXUQEPZWVQIOJE-UHFFFAOYSA-N methyl 2-chloro-2-oxoacetate Chemical compound COC(=O)C(Cl)=O ZXUQEPZWVQIOJE-UHFFFAOYSA-N 0.000 description 1
- GLCZQTLCVLVFGV-UHFFFAOYSA-N methyl 4-methoxy-1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OC)=CC2=C1OC GLCZQTLCVLVFGV-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- YKNYRRVISWJDSR-UHFFFAOYSA-N methyl oxirane-2-carboxylate Chemical compound COC(=O)C1CO1 YKNYRRVISWJDSR-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003259 recombinant expression Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- FHHPUSMSKHSNKW-SMOYURAASA-M sodium deoxycholate Chemical compound [Na+].C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 FHHPUSMSKHSNKW-SMOYURAASA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 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
- DXWMQIPBFPYBTD-UHFFFAOYSA-N tert-butyl-(1h-indol-4-yloxy)-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C=CN2 DXWMQIPBFPYBTD-UHFFFAOYSA-N 0.000 description 1
- CAVZAVHPWLOMFW-UHFFFAOYSA-N tert-butyl-[(2,9-dibenzyl-1-ethyl-3,4-dihydro-1H-pyrido[3,4-b]indol-5-yl)oxy]-dimethylsilane Chemical compound C(C)C1N(CCC=2C3=C(C=CC=C3N(C1=2)CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1 CAVZAVHPWLOMFW-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
-
- 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
- A61P19/00—Drugs for skeletal disorders
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyridine Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6216598A | 1998-04-17 | 1998-04-17 | |
| US62165 | 1998-04-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69912670D1 DE69912670D1 (de) | 2003-12-18 |
| DE69912670T2 true DE69912670T2 (de) | 2004-08-12 |
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| DE69912670T Expired - Fee Related DE69912670T2 (de) | 1998-04-17 | 1999-04-16 | Substituierte tricyclische Verbindungen und deren Verwendung zur Behandlung von sPLA2-bedingten Erkrankungen |
| DE69914951T Expired - Fee Related DE69914951T2 (de) | 1998-04-17 | 1999-04-16 | Substituierte tricyclische Verbindungen und deren Verwendung zur Behandlung von sPLA2-bedingten Erkrankungen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
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| DE69914951T Expired - Fee Related DE69914951T2 (de) | 1998-04-17 | 1999-04-16 | Substituierte tricyclische Verbindungen und deren Verwendung zur Behandlung von sPLA2-bedingten Erkrankungen |
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| JP (1) | JP4435325B2 (https=) |
| KR (1) | KR19990083234A (https=) |
| CN (1) | CN1235968A (https=) |
| AR (1) | AR018185A1 (https=) |
| AT (2) | ATE254128T1 (https=) |
| AU (1) | AU757454B2 (https=) |
| BR (1) | BR9901275A (https=) |
| CA (1) | CA2269256A1 (https=) |
| CO (1) | CO5080728A1 (https=) |
| CZ (1) | CZ137199A3 (https=) |
| DE (2) | DE69912670T2 (https=) |
| EA (1) | EA003129B1 (https=) |
| ES (2) | ES2213668T3 (https=) |
| HU (1) | HUP9901219A1 (https=) |
| ID (1) | ID23219A (https=) |
| IL (1) | IL129484A0 (https=) |
| NO (1) | NO991823L (https=) |
| NZ (1) | NZ335252A (https=) |
| PE (1) | PE20000472A1 (https=) |
| PL (1) | PL332564A1 (https=) |
| SG (1) | SG106035A1 (https=) |
| SV (1) | SV1999000052A (https=) |
| TR (1) | TR199900842A2 (https=) |
| TW (1) | TW555760B (https=) |
| YU (1) | YU19099A (https=) |
| ZA (1) | ZA992773B (https=) |
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| CA2301586A1 (en) * | 1997-08-28 | 1999-03-04 | William Louis Macias | Method for treatment of non-rheumatoid arthritis |
| WO2001074817A1 (en) * | 2000-03-30 | 2001-10-11 | Yamanouchi Pharmaceutical Co., Ltd. | Hydrazide derivatives |
| EP1303262A2 (en) * | 2000-07-14 | 2003-04-23 | Eli Lilly And Company | Use of a spla2 inhibitor for the treatment of sepsis |
| WO2002050029A2 (en) * | 2000-12-18 | 2002-06-27 | Eli Lilly And Company | Tetracyclic derivatives as spla2 inhibitors |
| CA2441077A1 (en) | 2001-03-28 | 2002-10-10 | Eli Lilly And Company | Substituted carbazoles as inhibitors of spla2 |
| US7160909B2 (en) | 2001-08-09 | 2007-01-09 | Eli Lilly And Company | Cyclopenta[b]indole derivatives as sPLA2 inhibitors |
| US7109231B2 (en) | 2001-08-09 | 2006-09-19 | Eli Lilly And Company | Cyclohept[b]indole derivatives |
| US6992100B2 (en) | 2001-12-06 | 2006-01-31 | Eli Lilly And Company | sPLA2 inhibitors |
| WO2006050007A2 (en) | 2004-11-01 | 2006-05-11 | Wyeth | Substituted indolizines and derivatives as cns agents |
| US8716308B2 (en) | 2008-01-11 | 2014-05-06 | Albany Molecular Research, Inc. | (1-azinone)-substituted pyridoindoles |
| US9073925B2 (en) | 2009-07-01 | 2015-07-07 | Albany Molecular Research, Inc. | Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| US8993765B2 (en) | 2010-12-21 | 2015-03-31 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline MCH-1 antagonists, methods of making, and uses thereof |
| DK2697223T3 (en) * | 2011-04-14 | 2016-09-05 | Actelion Pharmaceuticals Ltd | 7- (heteroaryl-amino) -6,7,8,9-tetrahydro-pyrido [1,2-a] indole-acetic acid derivatives and their use as prostaglandin D2 receptor |
| SI2825541T1 (sl) | 2012-03-16 | 2016-10-28 | Vitae Pharmaceuticals, Inc. | Modulatorji jetrnega receptorja X |
| ES2607113T3 (es) | 2012-03-16 | 2017-03-29 | Vitae Pharmaceuticals, Inc. | Moduladores de los receptores X del hígado |
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|---|---|---|---|---|
| US3979391A (en) * | 1972-11-22 | 1976-09-07 | Sterling Drug Inc. | 1,2,3,4-Tetrahydrocarbazoles |
| PT95692A (pt) * | 1989-10-27 | 1991-09-13 | American Home Prod | Processo para a preparacao de derivados de acidos indole-,indeno-,piranoindole- e tetra-hidrocarbazole-alcanoicos, ou quais sao uteis como inibidores de pla2 e da lipoxigenase |
| IL109309A (en) * | 1993-04-16 | 2000-06-29 | Lilly Co Eli | 1-H-indole-3-acetic acid hydrazide SPLA2 inhibitors and pharmaceutical compositions containing them |
| IL109311A0 (en) * | 1993-04-16 | 1994-07-31 | Lilly Co Eli | 1H-indole-3-acetamide sPla2 inhibitors |
| BR9508298A (pt) * | 1994-07-21 | 1998-11-03 | Shionogi & Co | Inibidores de indolizina de spla2 |
| EP0779271B1 (en) * | 1995-12-13 | 2001-08-01 | Eli Lilly And Company | Naphthyl acetamides as sPLA2 inhibitors |
| CA2269203A1 (en) * | 1996-10-30 | 1998-05-07 | Nicholas James Bach | Substituted tricyclics |
| EP1007056A1 (en) * | 1997-09-26 | 2000-06-14 | Eli Lilly And Company | Method for the treatment of cystic fibrosis |
| WO1999025340A1 (en) * | 1997-11-14 | 1999-05-27 | Eli Lilly And Company | Treatment for alzheimer's disease |
-
1999
- 1999-04-15 IL IL12948499A patent/IL129484A0/xx unknown
- 1999-04-15 ID IDP990342D patent/ID23219A/id unknown
- 1999-04-16 NZ NZ335252A patent/NZ335252A/xx unknown
- 1999-04-16 PE PE1999000321A patent/PE20000472A1/es not_active Application Discontinuation
- 1999-04-16 AT AT99302969T patent/ATE254128T1/de not_active IP Right Cessation
- 1999-04-16 DE DE69912670T patent/DE69912670T2/de not_active Expired - Fee Related
- 1999-04-16 SV SV1999000052A patent/SV1999000052A/es not_active Application Discontinuation
- 1999-04-16 TW TW088106131A patent/TW555760B/zh not_active IP Right Cessation
- 1999-04-16 BR BR9901275-8A patent/BR9901275A/pt not_active IP Right Cessation
- 1999-04-16 CO CO99022891A patent/CO5080728A1/es unknown
- 1999-04-16 SG SG9901844A patent/SG106035A1/en unknown
- 1999-04-16 NO NO991823A patent/NO991823L/no not_active Application Discontinuation
- 1999-04-16 DE DE69914951T patent/DE69914951T2/de not_active Expired - Fee Related
- 1999-04-16 AR ARP990101769A patent/AR018185A1/es not_active Application Discontinuation
- 1999-04-16 ZA ZA9902773A patent/ZA992773B/xx unknown
- 1999-04-16 TR TR1999/00842A patent/TR199900842A2/xx unknown
- 1999-04-16 AU AU23818/99A patent/AU757454B2/en not_active Ceased
- 1999-04-16 EA EA199900304A patent/EA003129B1/ru not_active IP Right Cessation
- 1999-04-16 CZ CZ991371A patent/CZ137199A3/cs unknown
- 1999-04-16 CA CA002269256A patent/CA2269256A1/en not_active Abandoned
- 1999-04-16 EP EP99302969A patent/EP0950661B1/en not_active Expired - Lifetime
- 1999-04-16 PL PL99332564A patent/PL332564A1/xx not_active Application Discontinuation
- 1999-04-16 ES ES01203116T patent/ES2213668T3/es not_active Expired - Lifetime
- 1999-04-16 EP EP01203116A patent/EP1156050B1/en not_active Expired - Lifetime
- 1999-04-16 AT AT01203116T patent/ATE259818T1/de not_active IP Right Cessation
- 1999-04-16 CN CN99108097A patent/CN1235968A/zh active Pending
- 1999-04-16 ES ES99302969T patent/ES2210979T3/es not_active Expired - Lifetime
- 1999-04-16 JP JP10965699A patent/JP4435325B2/ja not_active Expired - Fee Related
- 1999-04-16 KR KR1019990013439A patent/KR19990083234A/ko not_active Withdrawn
- 1999-04-16 HU HU9901219A patent/HUP9901219A1/hu unknown
- 1999-04-16 YU YU19099A patent/YU19099A/sh unknown
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