SG189471A1 - Solid dispersions containing an apoptosis-inducing agent - Google Patents

Info

Publication number

SG189471A1

SG189471A1 SG2013029772A SG2013029772A SG189471A1 SG 189471 A1 SG189471 A1 SG 189471A1 SG 2013029772 A SG2013029772 A SG 2013029772A SG 2013029772 A SG2013029772 A SG 2013029772A SG 189471 A1 SG189471 A1 SG 189471A1

Authority

SG

Singapore

Prior art keywords

compound

pyridin

chlorophenyl

piperazin

yloxy

Prior art date

2010-10-29

Links

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• 239000007962 solid dispersion Substances 0.000 title claims abstract description 47
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• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 175
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• 239000000203 mixture Substances 0.000 claims description 145
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 98
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 51
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• 125000003342 alkenyl group Chemical group 0.000 claims description 4
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• JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims 4
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• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
• JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims 1
• ALNZQNVLDRMHKM-UHFFFAOYSA-N 2-(1h-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide Chemical compound NC(=O)C1=CC=CC=C1OC1=CN=C(NC=C2)C2=C1 ALNZQNVLDRMHKM-UHFFFAOYSA-N 0.000 claims 1
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• KTTSHOSENUGIEM-UHFFFAOYSA-N methyl 4-[4-[[2-(4-chlorophenyl)-5,5-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(1h-pyrrolo[2,3-b]pyridin-5-yloxy)benzoate Chemical compound C1=C(OC=2C=C3C=CNC3=NC=2)C(C(=O)OC)=CC=C1N(CC1)CCN1CC(CC(C)(C)CC1)=C1C1=CC=C(Cl)C=C1 KTTSHOSENUGIEM-UHFFFAOYSA-N 0.000 description 1
• CKDHJPHKWPRNNS-UHFFFAOYSA-N methyl 4-[4-[[2-(4-chlorophenyl)-6,6-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(1h-pyrrolo[2,3-b]pyridin-5-yloxy)benzoate Chemical compound C1=C(OC=2C=C3C=CNC3=NC=2)C(C(=O)OC)=CC=C1N(CC1)CCN1CC(C(CCC1)(C)C)=C1C1=CC=C(Cl)C=C1 CKDHJPHKWPRNNS-UHFFFAOYSA-N 0.000 description 1
• YSAIXVQUYBNVNP-UHFFFAOYSA-N methyl 4-[4-[[4-(4-chlorophenyl)-6,6-dimethyl-2,5-dihydropyran-3-yl]methyl]piperazin-1-yl]-2-(1h-pyrrolo[2,3-b]pyridin-5-yloxy)benzoate Chemical compound C1=C(OC=2C=C3C=CNC3=NC=2)C(C(=O)OC)=CC=C1N(CC1)CCN1CC(COC(C)(C)C1)=C1C1=CC=C(Cl)C=C1 YSAIXVQUYBNVNP-UHFFFAOYSA-N 0.000 description 1
• WQJIYOYCCGOQRX-UHFFFAOYSA-N methyl 4-[4-[[8-(4-chlorophenyl)spiro[4.5]dec-8-en-9-yl]methyl]piperazin-1-yl]-2-(1h-pyrrolo[2,3-b]pyridin-5-yloxy)benzoate Chemical compound C1=C(OC=2C=C3C=CNC3=NC=2)C(C(=O)OC)=CC=C1N(CC1)CCN1CC(C1)=C(C=2C=CC(Cl)=CC=2)CCC21CCCC2 WQJIYOYCCGOQRX-UHFFFAOYSA-N 0.000 description 1
• DTIHHPHJAJHJKC-UHFFFAOYSA-N methyl 4-piperazin-1-yl-2-(1h-pyrrolo[2,3-b]pyridin-5-yloxy)benzoate Chemical compound C1=C(OC=2C=C3C=CNC3=NC=2)C(C(=O)OC)=CC=C1N1CCNCC1 DTIHHPHJAJHJKC-UHFFFAOYSA-N 0.000 description 1
• RRQMBADXYALRFP-UHFFFAOYSA-N methyl 5,5-dimethyl-2-(trifluoromethylsulfonyloxy)cyclohexene-1-carboxylate Chemical compound COC(=O)C1=C(OS(=O)(=O)C(F)(F)F)CCC(C)(C)C1 RRQMBADXYALRFP-UHFFFAOYSA-N 0.000 description 1
• SFXQJROVECIHKO-UHFFFAOYSA-N methyl 5,5-dimethyl-2-oxocyclohexane-1-carboxylate Chemical group COC(=O)C1CC(C)(C)CCC1=O SFXQJROVECIHKO-UHFFFAOYSA-N 0.000 description 1
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• WIEJVMZWPIUWHO-MRVPVSSYSA-N tert-butyl n-[[(3r)-pyrrolidin-3-yl]methyl]carbamate Chemical group CC(C)(C)OC(=O)NC[C@@H]1CCNC1 WIEJVMZWPIUWHO-MRVPVSSYSA-N 0.000 description 1
• WIEJVMZWPIUWHO-QMMMGPOBSA-N tert-butyl n-[[(3s)-pyrrolidin-3-yl]methyl]carbamate Chemical group CC(C)(C)OC(=O)NC[C@H]1CCNC1 WIEJVMZWPIUWHO-QMMMGPOBSA-N 0.000 description 1
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• JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 238000011269 treatment regimen Methods 0.000 description 1
• JGWFUSVYECJQDT-UHFFFAOYSA-N trimethyl(2-trimethylsilyloxyethoxy)silane Chemical compound C[Si](C)(C)OCCO[Si](C)(C)C JGWFUSVYECJQDT-UHFFFAOYSA-N 0.000 description 1
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• IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
• 238000001665 trituration Methods 0.000 description 1
• 230000003827 upregulation Effects 0.000 description 1
• 238000005292 vacuum distillation Methods 0.000 description 1
• 238000001291 vacuum drying Methods 0.000 description 1
• 238000003828 vacuum filtration Methods 0.000 description 1
• GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1