SG189830A1 - 4- (5-cyano-pyrazol-1-yl) -piperidine derivatives as gpr 119 modulators - Google Patents

Info

Publication number

SG189830A1

SG189830A1 SG2013023189A SG2013023189A SG189830A1 SG 189830 A1 SG189830 A1 SG 189830A1 SG 2013023189 A SG2013023189 A SG 2013023189A SG 2013023189 A SG2013023189 A SG 2013023189A SG 189830 A1 SG189830 A1 SG 189830A1

Authority

SG

Singapore

Prior art keywords

methyl

cyano

carboxylate

pyrazol

piperidine

Prior art date

2010-11-23

Links

• Espacenet
• Global Dossier
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• ZCSHWKPISDXCIB-UHFFFAOYSA-N 2-piperidin-4-ylpyrazole-3-carbonitrile Chemical class N#CC1=CC=NN1C1CCNCC1 ZCSHWKPISDXCIB-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 245
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 34
• 201000010099 disease Diseases 0.000 claims abstract description 23
• 238000011282 treatment Methods 0.000 claims abstract description 16
• 239000000203 mixture Substances 0.000 claims description 173
• 238000000034 method Methods 0.000 claims description 78
• -1 2,3-difluorophenoxy Chemical group 0.000 claims description 70
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 62
• 206010012601 diabetes mellitus Diseases 0.000 claims description 45
• 239000000284 extract Substances 0.000 claims description 36
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 36
• 150000003839 salts Chemical class 0.000 claims description 34
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 32
• 239000008103 glucose Substances 0.000 claims description 30
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 29
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
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• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
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• GVIYUKXRXPXMQM-BPXGDYAESA-N 221231-10-3 Chemical compound C([C@H](N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]1C(N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CSSC1)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C(C)C)=O)C1=CC=C(O)C=C1 GVIYUKXRXPXMQM-BPXGDYAESA-N 0.000 claims description 6
• RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 claims description 6
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• HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims description 6
• MFFMDFFZMYYVKS-SECBINFHSA-N sitagliptin Chemical compound C([C@H](CC(=O)N1CC=2N(C(=NN=2)C(F)(F)F)CC1)N)C1=CC(F)=C(F)C=C1F MFFMDFFZMYYVKS-SECBINFHSA-N 0.000 claims description 6
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• AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims description 5
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• PRBNKVOYFVGRLP-UHFFFAOYSA-N tert-butyl 4-[5-cyano-4-[(4-cyano-2-fluorophenoxy)methyl]pyrazol-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1C(C#N)=C(COC=2C(=CC(=CC=2)C#N)F)C=N1 PRBNKVOYFVGRLP-UHFFFAOYSA-N 0.000 claims description 5
• ZENUALSPCNSGOP-UHFFFAOYSA-N (1-methylcyclopropyl) 4-[4-[(4-carbamoyl-2-fluorophenoxy)methyl]-5-cyanopyrazol-1-yl]piperidine-1-carboxylate Chemical compound C1CC(N2C(=C(COC=3C(=CC(=CC=3)C(N)=O)F)C=N2)C#N)CCN1C(=O)OC1(C)CC1 ZENUALSPCNSGOP-UHFFFAOYSA-N 0.000 claims description 4
• BEPRAFMCMXKWSI-UHFFFAOYSA-N (1-methylcyclopropyl) 4-[5-cyano-4-[(2,3,6-trifluorophenoxy)methyl]pyrazol-1-yl]piperidine-1-carboxylate Chemical compound C1CC(N2C(=C(COC=3C(=C(F)C=CC=3F)F)C=N2)C#N)CCN1C(=O)OC1(C)CC1 BEPRAFMCMXKWSI-UHFFFAOYSA-N 0.000 claims description 4
• XGPVGJMQYAJJKL-UHFFFAOYSA-N (1-methylcyclopropyl) 4-[5-cyano-4-[(2,5-difluorophenoxy)methyl]pyrazol-1-yl]piperidine-1-carboxylate Chemical compound C1CC(N2C(=C(COC=3C(=CC=C(F)C=3)F)C=N2)C#N)CCN1C(=O)OC1(C)CC1 XGPVGJMQYAJJKL-UHFFFAOYSA-N 0.000 claims description 4
• SFWORIUDBFNINU-UHFFFAOYSA-N 4-[(4-cyano-2-fluorophenoxy)methyl]-2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]pyrazole-3-carbonitrile Chemical compound N1=CC(CC)=CN=C1N1CCC(N2C(=C(COC=3C(=CC(=CC=3)C#N)F)C=N2)C#N)CC1 SFWORIUDBFNINU-UHFFFAOYSA-N 0.000 claims description 4
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• HTQBXNHDCUEHJF-XWLPCZSASA-N Exenatide Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 HTQBXNHDCUEHJF-XWLPCZSASA-N 0.000 claims description 4
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