KR19990083234A - 치환된 삼환식 화합물 - Google Patents
치환된 삼환식 화합물 Download PDFInfo
- Publication number
- KR19990083234A KR19990083234A KR1019990013439A KR19990013439A KR19990083234A KR 19990083234 A KR19990083234 A KR 19990083234A KR 1019990013439 A KR1019990013439 A KR 1019990013439A KR 19990013439 A KR19990013439 A KR 19990013439A KR 19990083234 A KR19990083234 A KR 19990083234A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- phenyl
- arthritis
- formula
- nitrogen
- 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.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims abstract description 127
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 32
- 238000011282 treatment Methods 0.000 claims abstract description 32
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- 239000000194 fatty acid Substances 0.000 claims abstract description 14
- 229930195729 fatty acid Natural products 0.000 claims abstract description 14
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 14
- 230000001404 mediated effect Effects 0.000 claims abstract description 13
- 206010040070 Septic Shock Diseases 0.000 claims abstract description 10
- 230000036303 septic shock Effects 0.000 claims abstract description 10
- -1 phenoxy Phenyl Chemical group 0.000 claims description 125
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 109
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 101
- 239000002253 acid Substances 0.000 claims description 83
- 229910052757 nitrogen Inorganic materials 0.000 claims description 58
- 125000005843 halogen group Chemical group 0.000 claims description 44
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 28
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 239000001301 oxygen Substances 0.000 claims description 28
- 239000011593 sulfur Substances 0.000 claims description 28
- 230000002452 interceptive effect Effects 0.000 claims description 27
- 125000004076 pyridyl group Chemical group 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
- 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 claims description 20
- 125000005647 linker group Chemical group 0.000 claims description 20
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 18
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
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- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000001544 thienyl group Chemical group 0.000 claims description 13
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- 125000002541 furyl group Chemical group 0.000 claims description 12
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- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 11
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
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- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 7
- RERZNCLIYCABFS-UHFFFAOYSA-N harmaline Chemical compound C1CN=C(C)C2=C1C1=CC=C(OC)C=C1N2 RERZNCLIYCABFS-UHFFFAOYSA-N 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
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- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
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- 230000001684 chronic effect Effects 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 6
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 6
- 230000001575 pathological effect Effects 0.000 claims description 6
- 230000035939 shock Effects 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
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- 239000011575 calcium Substances 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- KYZMWHSKQSAKMW-UHFFFAOYSA-N methyl 10-benzyl-4-methoxy-6,7,8,9-tetrahydropyrido[1,2-a]indole-6-carboxylate Chemical compound C12=CC=CC(OC)=C2N2C(C(=O)OC)CCCC2=C1CC1=CC=CC=C1 KYZMWHSKQSAKMW-UHFFFAOYSA-N 0.000 claims description 5
- 230000008733 trauma Effects 0.000 claims description 5
- YKFOLURXVRADNC-UHFFFAOYSA-N 2-[(2,9-dibenzyl-4-carbamoyl-3,4-dihydro-1h-pyrido[3,4-b]indol-5-yl)oxy]acetic acid Chemical compound C1C(N(C2=CC=CC(OCC(O)=O)=C22)CC=3C=CC=CC=3)=C2C(C(=O)N)CN1CC1=CC=CC=C1 YKFOLURXVRADNC-UHFFFAOYSA-N 0.000 claims description 4
- MHXZVTNDXLWWNN-UHFFFAOYSA-N 2-[(9-benzyl-1-carbamoyl-3,4-dihydro-2h-pyrido[2,3-b]indol-8-yl)oxy]acetic acid Chemical compound NC(=O)N1CCCC(C2=CC=CC(OCC(O)=O)=C22)=C1N2CC1=CC=CC=C1 MHXZVTNDXLWWNN-UHFFFAOYSA-N 0.000 claims description 4
- 206010000599 Acromegaly Diseases 0.000 claims description 4
- 206010003256 Arthritis gonococcal Diseases 0.000 claims description 4
- 206010003267 Arthritis reactive Diseases 0.000 claims description 4
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- 206010006811 Bursitis Diseases 0.000 claims description 4
- 201000011275 Epicondylitis Diseases 0.000 claims description 4
- 206010016207 Familial Mediterranean fever Diseases 0.000 claims description 4
- 206010017533 Fungal infection Diseases 0.000 claims description 4
- 208000018565 Hemochromatosis Diseases 0.000 claims description 4
- 102000001554 Hemoglobins Human genes 0.000 claims description 4
- 108010054147 Hemoglobins Proteins 0.000 claims description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
- 208000012659 Joint disease Diseases 0.000 claims description 4
- 208000016604 Lyme disease Diseases 0.000 claims description 4
- 208000000112 Myalgia Diseases 0.000 claims description 4
- 206010036030 Polyarthritis Diseases 0.000 claims description 4
- 206010065159 Polychondritis Diseases 0.000 claims description 4
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 4
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 4
- 206010037549 Purpura Diseases 0.000 claims description 4
- 241001672981 Purpura Species 0.000 claims description 4
- 206010037660 Pyrexia Diseases 0.000 claims description 4
- 201000002661 Spondylitis Diseases 0.000 claims description 4
- 208000002240 Tennis Elbow Diseases 0.000 claims description 4
- 208000027418 Wounds and injury Diseases 0.000 claims description 4
- 208000021240 acute bronchiolitis Diseases 0.000 claims description 4
- 210000004369 blood Anatomy 0.000 claims description 4
- 239000008280 blood Substances 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 208000024386 fungal infectious disease Diseases 0.000 claims description 4
- 230000002008 hemorrhagic effect Effects 0.000 claims description 4
- 208000020346 hyperlipoproteinemia Diseases 0.000 claims description 4
- 230000001969 hypertrophic effect Effects 0.000 claims description 4
- 230000002458 infectious effect Effects 0.000 claims description 4
- 208000030428 polyarticular arthritis Diseases 0.000 claims description 4
- 230000000306 recurrent effect Effects 0.000 claims description 4
- 201000001223 septic arthritis Diseases 0.000 claims description 4
- 208000007056 sickle cell anemia Diseases 0.000 claims description 4
- 208000006379 syphilis Diseases 0.000 claims description 4
- 201000008827 tuberculosis Diseases 0.000 claims description 4
- 208000034624 Leukocytoclastic Cutaneous Vasculitis Diseases 0.000 claims description 3
- 208000032514 Leukocytoclastic vasculitis Diseases 0.000 claims description 3
- 108010031873 Secretory Phospholipases A2 Proteins 0.000 claims description 3
- 208000006045 Spondylarthropathies Diseases 0.000 claims description 3
- 201000006362 hypersensitivity vasculitis Diseases 0.000 claims description 3
- 201000005671 spondyloarthropathy Diseases 0.000 claims description 3
- 231100000331 toxic Toxicity 0.000 claims description 3
- 230000002588 toxic effect Effects 0.000 claims description 3
- 206010008690 Chondrocalcinosis pyrophosphate Diseases 0.000 claims description 2
- 208000033464 Reiter syndrome Diseases 0.000 claims description 2
- 102000005473 Secretory Phospholipases A2 Human genes 0.000 claims description 2
- 208000002849 chondrocalcinosis Diseases 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims 8
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 3
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 3
- 208000017442 Retinal disease Diseases 0.000 claims 3
- 206010038923 Retinopathy Diseases 0.000 claims 3
- 210000003797 carpal joint Anatomy 0.000 claims 3
- 208000003906 hydrocephalus Diseases 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 3
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 claims 2
- 201000002980 Hyperparathyroidism Diseases 0.000 claims 2
- 206010021143 Hypoxia Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 230000006907 apoptotic process Effects 0.000 claims 2
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- 206010039083 rhinitis Diseases 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 270
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 121
- 229960000583 acetic acid Drugs 0.000 description 94
- 239000000243 solution Substances 0.000 description 87
- 125000001041 indolyl group Chemical group 0.000 description 83
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- 239000000203 mixture Substances 0.000 description 75
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
- 238000002360 preparation method Methods 0.000 description 49
- 239000000047 product Substances 0.000 description 44
- 235000019439 ethyl acetate Nutrition 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 24
- 238000000921 elemental analysis Methods 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 23
- 150000003254 radicals Chemical class 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
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- 239000012267 brine Substances 0.000 description 22
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
- 150000002148 esters Chemical class 0.000 description 21
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 18
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- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 7
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- LUNOXNMCFPFPMO-UHFFFAOYSA-N 4-methoxy-1h-indole Chemical compound COC1=CC=CC2=C1C=CN2 LUNOXNMCFPFPMO-UHFFFAOYSA-N 0.000 description 5
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- 239000000375 suspending agent Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 201000004415 tendinitis Diseases 0.000 description 1
- 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 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 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
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- ROUYSXBEYWORTN-UHFFFAOYSA-N thiopyrano[2,3-g]indole Chemical compound S1C=CC=C2C3=NC=CC3=CC=C21 ROUYSXBEYWORTN-UHFFFAOYSA-N 0.000 description 1
- VLZVXVNGVZTXEI-UHFFFAOYSA-N thiopyrano[3,4-b]indole Chemical compound S1C=CC2=C3C=CC=CC3=NC2=C1 VLZVXVNGVZTXEI-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 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
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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 | |
| US9/062,165 | 1998-04-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR19990083234A true KR19990083234A (ko) | 1999-11-25 |
Family
ID=22040624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019990013439A Withdrawn KR19990083234A (ko) | 1998-04-17 | 1999-04-16 | 치환된 삼환식 화합물 |
Country Status (27)
| Country | Link |
|---|---|
| EP (2) | EP0950661B1 (https=) |
| 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=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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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Legal Events
| Date | Code | Title | Description |
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| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19990416 |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |