OA10896A - Indole derivatives useful as endothelin receptor antagonists - Google Patents

Indole derivatives useful as endothelin receptor antagonists Download PDF

Info

Publication number: OA10896A
Authority: OA; OAPI
Prior art keywords: compound; iii; alkyl; formula; nmr
Prior art date: 1996-05-09

Application number

OA9800192A

Other languages

English (en)

Inventor

David James Rawson

Kevin Neil Dack

Roger Peter Dickinson

Kim James

Original Assignee

Pfizer

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.)

1996-05-09

Filing date

1998-10-09

Publication date

2001-10-11

1998-10-09 Application filed by Pfizer filed Critical Pfizer

2001-10-11 Publication of OA10896A publication Critical patent/OA10896A/en

Links

239000002308 endothelin receptor antagonist Substances 0.000 title description 7
229940118365 Endothelin receptor antagonist Drugs 0.000 title description 6
150000002475 indoles Chemical class 0.000 title description 3
229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 191
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
150000002367 halogens Chemical class 0.000 claims abstract description 9
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 7
208000002815 pulmonary hypertension Diseases 0.000 claims abstract description 7
208000037803 restenosis Diseases 0.000 claims abstract description 6
125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
125000001424 substituent group Chemical group 0.000 claims abstract description 3
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims abstract 4
238000000034 method Methods 0.000 claims description 53
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 44
125000000217 alkyl group Chemical group 0.000 claims description 41
229910052757 nitrogen Inorganic materials 0.000 claims description 41
238000006243 chemical reaction Methods 0.000 claims description 35
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 30
-1 C2.( Chemical group 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
229910002092 carbon dioxide Chemical group 0.000 claims description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 11
229910052740 iodine Inorganic materials 0.000 claims description 10
239000002841 Lewis acid Substances 0.000 claims description 9
150000007517 lewis acids Chemical class 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
229910052763 palladium Inorganic materials 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
206010007559 Cardiac failure congestive Diseases 0.000 claims description 5
206010019280 Heart failures Diseases 0.000 claims description 5
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 5
239000007789 gas Substances 0.000 claims description 5
229910000077 silane Inorganic materials 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
206010002383 Angina Pectoris Diseases 0.000 claims description 4
206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 4
208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
239000002585 base Substances 0.000 claims description 4
150000004795 grignard reagents Chemical class 0.000 claims description 4
208000031225 myocardial ischemia Diseases 0.000 claims description 4
201000001320 Atherosclerosis Diseases 0.000 claims description 3
PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 3
229930105110 Cyclosporin A Natural products 0.000 claims description 3
108010036949 Cyclosporine Proteins 0.000 claims description 3
208000006011 Stroke Diseases 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
239000001569 carbon dioxide Substances 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
229960001265 ciclosporin Drugs 0.000 claims description 3
229930182912 cyclosporin Natural products 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
238000010791 quenching Methods 0.000 claims description 3
230000000171 quenching effect Effects 0.000 claims description 3
239000007818 Grignard reagent Substances 0.000 claims description 2
239000002671 adjuvant Substances 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
230000008878 coupling Effects 0.000 claims description 2
238000010168 coupling process Methods 0.000 claims description 2
238000005859 coupling reaction Methods 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
230000000269 nucleophilic effect Effects 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
208000028867 ischemia Diseases 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
208000001647 Renal Insufficiency Diseases 0.000 abstract 1
201000006370 kidney failure Diseases 0.000 abstract 1
125000005010 perfluoroalkyl group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 153
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 132
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 129
239000000243 solution Substances 0.000 description 125
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 74
239000000203 mixture Substances 0.000 description 72
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 60
101150041968 CDC13 gene Proteins 0.000 description 58
239000000047 product Substances 0.000 description 54
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
229940093499 ethyl acetate Drugs 0.000 description 44
235000019439 ethyl acetate Nutrition 0.000 description 44
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
239000002904 solvent Substances 0.000 description 43
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
238000003818 flash chromatography Methods 0.000 description 30
239000007787 solid Substances 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
239000003921 oil Substances 0.000 description 27
235000019198 oils Nutrition 0.000 description 27
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 26
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
239000012044 organic layer Substances 0.000 description 25
238000010828 elution Methods 0.000 description 24
238000010992 reflux Methods 0.000 description 24
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 22
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 21
229910021653 sulphate ion Inorganic materials 0.000 description 21
235000011167 hydrochloric acid Nutrition 0.000 description 19
229960000443 hydrochloric acid Drugs 0.000 description 19
229910052943 magnesium sulfate Inorganic materials 0.000 description 18
235000019341 magnesium sulphate Nutrition 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 18
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 18
238000004458 analytical method Methods 0.000 description 17
239000012267 brine Substances 0.000 description 17
101800004490 Endothelin-1 Proteins 0.000 description 16
102400000686 Endothelin-1 Human genes 0.000 description 16
238000003756 stirring Methods 0.000 description 16
108050009340 Endothelin Proteins 0.000 description 15
102000002045 Endothelin Human genes 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 description 15
239000006260 foam Substances 0.000 description 15
238000012360 testing method Methods 0.000 description 15
229960004132 diethyl ether Drugs 0.000 description 14
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 14
229940124530 sulfonamide Drugs 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 13
229960000583 acetic acid Drugs 0.000 description 13
241000206607 Porphyra umbilicalis Species 0.000 description 12
125000001041 indolyl group Chemical group 0.000 description 12
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
102000005962 receptors Human genes 0.000 description 11
108020003175 receptors Proteins 0.000 description 11
210000001519 tissue Anatomy 0.000 description 11
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 10
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
230000002411 adverse Effects 0.000 description 10
238000001816 cooling Methods 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
238000001914 filtration Methods 0.000 description 7
210000000056 organ Anatomy 0.000 description 7
239000012312 sodium hydride Substances 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
239000000725 suspension Substances 0.000 description 7
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 6
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
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KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000005557 antagonist Substances 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
238000000746 purification Methods 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 5
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical group CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 5
GFQPTVGPUTXTBG-UHFFFAOYSA-N 6-bromo-1-ethylindole Chemical compound C1=C(Br)C=C2N(CC)C=CC2=C1 GFQPTVGPUTXTBG-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
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QCVIFBRTTLMEOV-FUKQNADPSA-M sodium;(2r)-2-[[(2r)-2-[[(2s)-2-[[(2s,6r)-2,6-dimethylpiperidine-1-carbonyl]amino]-4,4-dimethylpentanoyl]amino]-3-(1-methoxycarbonylindol-3-yl)propanoyl]amino]hexanoate Chemical compound [Na+].N([C@@H](CC(C)(C)C)C(=O)N[C@H](CC=1C2=CC=CC=C2N(C(=O)OC)C=1)C(=O)N[C@H](CCCC)C([O-])=O)C(=O)N1[C@@H](C)CCC[C@H]1C QCVIFBRTTLMEOV-FUKQNADPSA-M 0.000 description 4
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MAWGHOPSCKCTPA-UHFFFAOYSA-N 6-bromo-1h-indole Chemical compound BrC1=CC=C2C=CNC2=C1 MAWGHOPSCKCTPA-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
102000052567 Anaphase-Promoting Complex-Cyclosome Apc1 Subunit Human genes 0.000 description 3
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BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
102000010180 Endothelin receptor Human genes 0.000 description 2
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NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000007574 infarction Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
201000004332 intermediate coronary syndrome Diseases 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
YTJXGDYAEOTOCG-UHFFFAOYSA-N lithium;di(propan-2-yl)azanide;oxolane Chemical compound [Li+].C1CCOC1.CC(C)[N-]C(C)C YTJXGDYAEOTOCG-UHFFFAOYSA-N 0.000 description 1
230000004807 localization Effects 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
239000006210 lotion Substances 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
NMILWYUYIFMKTE-UHFFFAOYSA-N methyl 1-methylindole-6-carboxylate Chemical compound COC(=O)C1=CC=C2C=CN(C)C2=C1 NMILWYUYIFMKTE-UHFFFAOYSA-N 0.000 description 1
NPKATACLAVJRPB-UHFFFAOYSA-N methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetate Chemical compound COC(=O)C(Br)C1=CC=C2OCOC2=C1 NPKATACLAVJRPB-UHFFFAOYSA-N 0.000 description 1
ZJXPBEXOGWFULD-UHFFFAOYSA-N methyl 2-(1,3-benzodioxol-5-yl)-2-hydroxyacetate Chemical compound COC(=O)C(O)C1=CC=C2OCOC2=C1 ZJXPBEXOGWFULD-UHFFFAOYSA-N 0.000 description 1
QDTUVODPKVRHRC-UHFFFAOYSA-N methyl 2-(6-chloro-1,3-benzodioxol-5-yl)-2-hydroxyacetate Chemical compound C1=C(Cl)C(C(O)C(=O)OC)=CC2=C1OCO2 QDTUVODPKVRHRC-UHFFFAOYSA-N 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
230000008692 neointimal formation Effects 0.000 description 1
230000016273 neuron death Effects 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910000489 osmium tetroxide Inorganic materials 0.000 description 1
239000012285 osmium tetroxide Substances 0.000 description 1
ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 description 1
125000000160 oxazolidinyl group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 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
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229940081310 piperonal Drugs 0.000 description 1
239000011505 plaster Substances 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
201000011461 pre-eclampsia Diseases 0.000 description 1
230000036584 pressor response Effects 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
239000003380 propellant Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
210000001147 pulmonary artery Anatomy 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000004291 sulphur dioxide Substances 0.000 description 1
235000010269 sulphur dioxide Nutrition 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000011273 tar residue Substances 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
QPDUQKTYZRXRBC-UHFFFAOYSA-N triazole-4-thione Chemical compound S=C1C=NN=N1 QPDUQKTYZRXRBC-UHFFFAOYSA-N 0.000 description 1
UOHDZXTWPSGQLO-UHFFFAOYSA-N tributyl(methoxymethyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)COC UOHDZXTWPSGQLO-UHFFFAOYSA-N 0.000 description 1
MKBQBFPNTLPOIV-UHFFFAOYSA-N tributylstannylmethanol Chemical compound CCCC[Sn](CO)(CCCC)CCCC MKBQBFPNTLPOIV-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 1
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Urology & Nephrology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pulmonology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)

OA9800192A 1996-05-09 1998-10-09 Indole derivatives useful as endothelin receptor antagonists OA10896A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB9609641.7A GB9609641D0 (en)	1996-05-09	1996-05-09	Compounds useful in therapy

Publications (1)

Publication Number	Publication Date
OA10896A true OA10896A (en)	2001-10-11

Family

ID=10793387

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9800192A OA10896A (en)	1996-05-09	1998-10-09	Indole derivatives useful as endothelin receptor antagonists

Country Status (42)

Country	Link
US (4)	US6017945A (de)
EP (1)	EP0901470B1 (de)
JP (1)	JP3245179B2 (de)
KR (1)	KR100331217B1 (de)
CN (1)	CN1124262C (de)
AP (1)	AP830A (de)
AR (1)	AR007030A1 (de)
AT (1)	ATE263151T1 (de)
AU (1)	AU717849B2 (de)
BG (1)	BG102873A (de)
BR (1)	BR9709072A (de)
CA (1)	CA2253876A1 (de)
CO (1)	CO4650036A1 (de)
CZ (1)	CZ292928B6 (de)
DE (1)	DE69728392T2 (de)
DK (1)	DK0901470T3 (de)
DZ (1)	DZ2227A1 (de)
EA (1)	EA001471B1 (de)
ES (1)	ES2218675T3 (de)
GB (1)	GB9609641D0 (de)
HN (1)	HN1997000058A (de)
HR (1)	HRP970249B1 (de)
HU (1)	HUP9901245A3 (de)
ID (1)	ID16878A (de)
IL (1)	IL125903A0 (de)
IS (1)	IS1856B (de)
MA (1)	MA26428A1 (de)
NO (1)	NO312547B1 (de)
NZ (1)	NZ332640A (de)
OA (1)	OA10896A (de)
PE (1)	PE65098A1 (de)
PL (1)	PL329725A1 (de)
PT (1)	PT901470E (de)
SI (1)	SI0901470T1 (de)
SK (1)	SK150398A3 (de)
TN (1)	TNSN97078A1 (de)
TR (1)	TR199802269T2 (de)
TW (1)	TW491838B (de)
UA (1)	UA50767C2 (de)
UY (1)	UY24546A1 (de)
WO (1)	WO1997043260A1 (de)
ZA (1)	ZA973963B (de)

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* Cited by examiner, † Cited by third party
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GB9722287D0 (en) *	1997-10-22	1997-12-17	Pfizer Ltd	Compounds useful in therapy
EE05345B1 (et)	1999-02-10	2010-10-15	Astrazeneca Ab	Kinasoliini derivaadid angiogeneesi inhibiitoritena
GB0016162D0 (en) *	2000-06-30	2000-08-23	Cancer Res Campaign Tech	Indole-3-acetic acid derivatives
US20050203166A1 (en) *	2000-06-30	2005-09-15	Cancer Research Technology Limited	Indole-3-acetic acid derivatives
US7074817B2 (en)	2001-06-20	2006-07-11	Wyeth	Substituted indole acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)
TWI224101B (en)	2001-06-20	2004-11-21	Wyeth Corp	Substituted naphthyl indole derivatives as inhibitors of plasminogen activator inhibitor type-1 (PAI-1)
AR037097A1 (es)	2001-10-05	2004-10-20	Novartis Ag	Compuestos acilsulfonamidas, composiciones farmaceuticas y el uso de dichos compuestos para la preparacion de un medicamento
EP1569899B1 (de)	2002-12-10	2006-06-28	Wyeth	Substituierte 3-alkyl- und 3-arylalkyl-1h-indol-1-yl-essigsäure-derivate als plasminogen aktivator inhibitor-1 (pai-1) inhibitoren
US7078429B2 (en)	2002-12-10	2006-07-18	Wyeth	Substituted 3-carbonyl-1H-indol-1-yl acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)
WO2004052854A2 (en)	2002-12-10	2004-06-24	Wyeth	Aryl, aryloxy, and alkyloxy substituted 1h-indol-3-yl glyoxylic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1)
WO2004052856A1 (en)	2002-12-10	2004-06-24	Wyeth	Substituted indole oxo-acetyl amino acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1)
UA80453C2 (en)	2002-12-10	2007-09-25		Derivatives of substituted dyhydropyranoindol-3,4-dion as inhibitors of plasminogen activator inhibitor-1 (pai-1)
BRPI0406883A (pt) *	2003-01-22	2006-01-03	Lilly Co Eli	Composto, composição farmacêutica, método de tratar um distúrbio, e, uso de um composto
US7342039B2 (en)	2003-09-25	2008-03-11	Wyeth	Substituted indole oximes
US7163954B2 (en)	2003-09-25	2007-01-16	Wyeth	Substituted naphthyl benzothiophene acids
US7420083B2 (en)	2003-09-25	2008-09-02	Wyeth	Substituted aryloximes
US7351726B2 (en)	2003-09-25	2008-04-01	Wyeth	Substituted oxadiazolidinediones
US7332521B2 (en)	2003-09-25	2008-02-19	Wyeth	Substituted indoles
US7265148B2 (en)	2003-09-25	2007-09-04	Wyeth	Substituted pyrrole-indoles
US7534894B2 (en)	2003-09-25	2009-05-19	Wyeth	Biphenyloxy-acids
US7442805B2 (en)	2003-09-25	2008-10-28	Wyeth	Substituted sulfonamide-indoles
US7582773B2 (en)	2003-09-25	2009-09-01	Wyeth	Substituted phenyl indoles
US7268159B2 (en)	2003-09-25	2007-09-11	Wyeth	Substituted indoles
US7446201B2 (en)	2003-09-25	2008-11-04	Wyeth	Substituted heteroaryl benzofuran acids
US7141592B2 (en)	2003-09-25	2006-11-28	Wyeth	Substituted oxadiazolidinediones
US7411083B2 (en)	2003-09-25	2008-08-12	Wyeth	Substituted acetic acid derivatives
JP2005109006A (ja) *	2003-09-29	2005-04-21	Tdk Corp	高電圧貫通型コンデンサ及びマグネトロン
HN2004000536A (es) *	2003-12-16	2009-02-18	Wyeth Corp	Un procediemiento de sintesis para la alquilacion reductiva de la posicon c-3 de indoles
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1996
- 1996-05-09 GB GBGB9609641.7A patent/GB9609641D0/en active Pending
1997
- 1997-04-01 TW TW086104171A patent/TW491838B/zh not_active IP Right Cessation
- 1997-04-11 EP EP97920690A patent/EP0901470B1/de not_active Expired - Lifetime
- 1997-04-11 KR KR1019980709023A patent/KR100331217B1/ko not_active Expired - Fee Related
- 1997-04-11 WO PCT/EP1997/001882 patent/WO1997043260A1/en not_active Ceased
- 1997-04-11 DK DK97920690T patent/DK0901470T3/da active
- 1997-04-11 BR BR9709072A patent/BR9709072A/pt active Search and Examination
- 1997-04-11 AU AU26978/97A patent/AU717849B2/en not_active Ceased
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- 1997-04-11 ES ES97920690T patent/ES2218675T3/es not_active Expired - Lifetime
- 1997-04-11 DE DE1997628392 patent/DE69728392T2/de not_active Expired - Fee Related
- 1997-04-11 JP JP54042397A patent/JP3245179B2/ja not_active Expired - Fee Related
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1999
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2000
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Also Published As

Publication number	Publication date
AR007030A1 (es)	1999-10-13
ID16878A (id)	1997-11-20
TNSN97078A1 (fr)	2005-03-15
ATE263151T1 (de)	2004-04-15
ZA973963B (en)	1998-11-09
CN1124262C (zh)	2003-10-15
US6384070B2 (en)	2002-05-07
HRP970249B1 (en)	2003-06-30
HRP970249A2 (en)	1998-06-30
CZ358298A3 (cs)	1999-08-11
HUP9901245A2 (hu)	1999-08-30
SK150398A3 (en)	1999-03-12
KR100331217B1 (ko)	2002-05-09
EP0901470B1 (de)	2004-03-31
IL125903A0 (en)	1999-04-11
DE69728392T2 (de)	2005-01-13
HN1997000058A (es)	1997-06-26
HUP9901245A3 (en)	2002-01-28
CN1216531A (zh)	1999-05-12
EP0901470A1 (de)	1999-03-17
UY24546A1 (es)	2000-09-29
ES2218675T3 (es)	2004-11-16
EA199800908A1 (ru)	1999-06-24
IS4838A (is)	1998-08-28
US20010014677A1 (en)	2001-08-16
PL329725A1 (en)	1999-04-12
AU717849B2 (en)	2000-04-06
DE69728392D1 (de)	2004-05-06
HK1019149A1 (en)	2000-01-14
AU2697897A (en)	1997-12-05
KR20000010879A (ko)	2000-02-25
JP3245179B2 (ja)	2002-01-07
BG102873A (en)	1999-11-30
DZ2227A1 (fr)	2002-12-25
AP9700982A0 (en)	1997-07-31
AP830A (en)	2000-05-03
DK0901470T3 (da)	2004-07-12
CZ292928B6 (cs)	2004-01-14
MA26428A1 (fr)	2004-12-20
NO985225D0 (no)	1998-11-09
SI0901470T1 (en)	2004-08-31
CO4650036A1 (es)	1998-09-03
US6017945A (en)	2000-01-25
EA001471B1 (ru)	2001-04-23
NO312547B1 (no)	2002-05-27
TR199802269T2 (xx)	2001-12-21
PT901470E (pt)	2004-07-30
JPH11508285A (ja)	1999-07-21
TW491838B (en)	2002-06-21
PE65098A1 (es)	1998-10-29
IS1856B (is)	2003-02-21
US6306852B1 (en)	2001-10-23
WO1997043260A1 (en)	1997-11-20
UA50767C2 (uk)	2002-11-15
US6136843A (en)	2000-10-24
CA2253876A1 (en)	1997-11-20
BR9709072A (pt)	1999-08-03
GB9609641D0 (en)	1996-07-10
NO985225L (no)	1998-11-09
NZ332640A (en)	2001-03-30

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