CA2666149A1

CA2666149A1 - Substituted indoles

Substituted indoles Download PDF

Info

Publication number: CA2666149A1
Authority: CA; Canada
Prior art keywords: compound; weight; group; deuterium; enantiomer
Prior art date: 2006-10-19
Legal status : Abandoned

Application number

CA002666149A

Other languages

English (en)

French (fr)

Inventor

Thomas G. Gant

Sepehr Sarshar

Current Assignee

Auspex Pharmaceuticals Inc

Original Assignee

Individual

Priority date

2006-10-19

Filing date

2007-10-19

Publication date

2008-04-24

2007-10-19 Application filed by Individual filed Critical Individual

2008-04-24 Publication of CA2666149A1 publication Critical patent/CA2666149A1/en

Status Abandoned legal-status Critical Current

Links

150000002475 indoles Chemical class 0.000 title abstract description 7
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 105
238000000034 method Methods 0.000 claims abstract description 81
-1 CYP39 Proteins 0.000 claims description 448
150000001875 compounds Chemical class 0.000 claims description 266
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 136
229910052805 deuterium Inorganic materials 0.000 claims description 102
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 98
239000000203 mixture Substances 0.000 claims description 93
150000003839 salts Chemical class 0.000 claims description 71
208000035475 disorder Diseases 0.000 claims description 69
229910052739 hydrogen Inorganic materials 0.000 claims description 60
239000001257 hydrogen Substances 0.000 claims description 58
229940002612 prodrug Drugs 0.000 claims description 43
239000000651 prodrug Substances 0.000 claims description 43
102000010909 Monoamine Oxidase Human genes 0.000 claims description 36
108010062431 Monoamine oxidase Proteins 0.000 claims description 36
239000012453 solvate Substances 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
102000001708 Protein Isoforms Human genes 0.000 claims description 30
108010029485 Protein Isoforms Proteins 0.000 claims description 30
230000003247 decreasing effect Effects 0.000 claims description 30
230000036470 plasma concentration Effects 0.000 claims description 27
102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 claims description 26
239000002207 metabolite Substances 0.000 claims description 26
150000002431 hydrogen Chemical class 0.000 claims description 22
208000019695 Migraine disease Diseases 0.000 claims description 20
KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 claims description 19
239000003937 drug carrier Substances 0.000 claims description 19
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238000001990 intravenous administration Methods 0.000 claims description 6
102100027518 1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial Human genes 0.000 claims description 5
102100036285 25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial Human genes 0.000 claims description 5
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101000875401 Homo sapiens Sterol 26-hydroxylase, mitochondrial Proteins 0.000 claims description 5
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108010058254 Steroid 12-alpha-Hydroxylase Proteins 0.000 claims description 5
108010015330 Steroid 17-alpha-Hydroxylase Proteins 0.000 claims description 5
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108010064377 prostacyclin synthetase Proteins 0.000 claims description 5
108010073030 25-Hydroxyvitamin D3 1-alpha-Hydroxylase Proteins 0.000 claims description 4
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102100021695 Lanosterol 14-alpha demethylase Human genes 0.000 claims description 4
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108010049356 Steroid 11-beta-Hydroxylase Proteins 0.000 claims description 4
102100026523 Vitamin D 25-hydroxylase Human genes 0.000 claims description 4
108010084976 Cholesterol Side-Chain Cleavage Enzyme Proteins 0.000 claims 3
102100027516 Cholesterol side-chain cleavage enzyme, mitochondrial Human genes 0.000 claims 3
102100039205 Cytochrome P450 3A4 Human genes 0.000 claims 3
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XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
229940003675 zomig Drugs 0.000 description 1