JP2013507366A5 - - Google Patents

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Publication number: JP2013507366A5
Authority: JP; Japan
Prior art keywords: methyl; phenyl; azetidin; trifluoromethyl; difluoro
Prior art date: 2010-10-01
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.): Pending

Application number

JP2012533226A

Other languages

English (en)

Japanese (ja)

Other versions

JP2013507366A (ja

Filing date

2010-10-01

Publication date

2013-11-14

2010-10-01 Application filed filed Critical

2010-10-01 Priority claimed from PCT/US2010/051186 external-priority patent/WO2011044001A1/en

2013-03-04 Publication of JP2013507366A publication Critical patent/JP2013507366A/ja

2013-11-14 Publication of JP2013507366A5 publication Critical patent/JP2013507366A5/ja

Status Pending legal-status Critical Current

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BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 49
125000001475 halogen functional group Chemical group 0.000 claims 46
229910052739 hydrogen Inorganic materials 0.000 claims 27
239000001257 hydrogen Substances 0.000 claims 27
125000003545 alkoxy group Chemical group 0.000 claims 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
150000001875 compounds Chemical class 0.000 claims 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
-1 hydroxypropyl Chemical group 0.000 claims 11
125000003118 aryl group Chemical group 0.000 claims 9
150000002431 hydrogen Chemical class 0.000 claims 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
125000002947 alkylene group Chemical group 0.000 claims 5
125000004093 cyano group Chemical group *C#N 0.000 claims 5
201000010099 disease Diseases 0.000 claims 5
102100033839 Glucose-dependent insulinotropic receptor Human genes 0.000 claims 4
101000996752 Homo sapiens Glucose-dependent insulinotropic receptor Proteins 0.000 claims 4
125000001072 heteroaryl group Chemical group 0.000 claims 4
125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 3
206010012601 diabetes mellitus Diseases 0.000 claims 3
230000000694 effects Effects 0.000 claims 3
150000003839 salts Chemical class 0.000 claims 3
208000001072 type 2 diabetes mellitus Diseases 0.000 claims 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
KREHFNPASISMLT-UHFFFAOYSA-N 1-[3,5-difluoro-4-[1-[[4-(trifluoromethyl)phenyl]methyl]azetidin-3-yl]oxyphenyl]-4-methylsulfonylpiperazin-2-one Chemical compound O=C1CN(S(=O)(=O)C)CCN1C(C=C1F)=CC(F)=C1OC1CN(CC=2C=CC(=CC=2)C(F)(F)F)C1 KREHFNPASISMLT-UHFFFAOYSA-N 0.000 claims 2
XDZADSVOHSQVTC-UHFFFAOYSA-N 1-[3,5-difluoro-4-[1-[[4-(trifluoromethyl)phenyl]methyl]azetidin-3-yl]oxyphenyl]-4-methylsulfonylpiperazine Chemical compound C1CN(S(=O)(=O)C)CCN1C(C=C1F)=CC(F)=C1OC1CN(CC=2C=CC(=CC=2)C(F)(F)F)C1 XDZADSVOHSQVTC-UHFFFAOYSA-N 0.000 claims 2
WUKRSOYOPHKYHF-UHFFFAOYSA-N 1-[3-fluoro-4-[1-[[4-(trifluoromethyl)phenyl]methyl]azetidin-3-yl]oxyphenyl]-4-methylsulfonylpiperazine Chemical compound C1CN(S(=O)(=O)C)CCN1C(C=C1F)=CC=C1OC1CN(CC=2C=CC(=CC=2)C(F)(F)F)C1 WUKRSOYOPHKYHF-UHFFFAOYSA-N 0.000 claims 2
QDMSPBCJVABTJI-UHFFFAOYSA-N 1-[4-[3,5-difluoro-4-[1-[[4-(trifluoromethyl)phenyl]methyl]azetidin-3-yl]oxyphenyl]-3,6-dihydro-2h-pyridin-1-yl]-2,2,2-trifluoroethanone Chemical compound FC1=CC(C=2CCN(CC=2)C(=O)C(F)(F)F)=CC(F)=C1OC(C1)CN1CC1=CC=C(C(F)(F)F)C=C1 QDMSPBCJVABTJI-UHFFFAOYSA-N 0.000 claims 2
MVXRMNLRWSEVMF-UHFFFAOYSA-N 2-(4-methylsulfonylpiperazin-1-yl)-5-[1-[[4-(trifluoromethyl)phenyl]methyl]azetidin-3-yl]oxypyrimidine Chemical compound C1CN(S(=O)(=O)C)CCN1C(N=C1)=NC=C1OC1CN(CC=2C=CC(=CC=2)C(F)(F)F)C1 MVXRMNLRWSEVMF-UHFFFAOYSA-N 0.000 claims 2
WXMFKKPOVWUMBQ-UHFFFAOYSA-N 2-[3-[2,6-difluoro-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]azetidin-1-yl]-2-[4-(trifluoromethyl)phenyl]ethanol Chemical compound C1CN(S(=O)(=O)C)CCC1C(C=C1F)=CC(F)=C1OC1CN(C(CO)C=2C=CC(=CC=2)C(F)(F)F)C1 WXMFKKPOVWUMBQ-UHFFFAOYSA-N 0.000 claims 2
JKCDGKXUOWITEV-UHFFFAOYSA-N 2-[[3-[2,6-difluoro-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]azetidin-1-yl]methyl]-4-(trifluoromethyl)-1,3-thiazole Chemical compound C1CN(S(=O)(=O)C)CCC1C(C=C1F)=CC(F)=C1OC1CN(CC=2SC=C(N=2)C(F)(F)F)C1 JKCDGKXUOWITEV-UHFFFAOYSA-N 0.000 claims 2
MFXBTDYTCIKRNZ-UHFFFAOYSA-N 2-[[3-[2,6-difluoro-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]azetidin-1-yl]methyl]-5-(trifluoromethyl)pyrimidine Chemical compound C1CN(S(=O)(=O)C)CCC1C(C=C1F)=CC(F)=C1OC1CN(CC=2N=CC(=CN=2)C(F)(F)F)C1 MFXBTDYTCIKRNZ-UHFFFAOYSA-N 0.000 claims 2
NZLZVERJPBTXAH-UHFFFAOYSA-N 2-[[4-[2,6-difluoro-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]piperidin-1-yl]methyl]-4-(trifluoromethyl)-1,3-thiazole Chemical compound C1CN(S(=O)(=O)C)CCC1C(C=C1F)=CC(F)=C1OC1CCN(CC=2SC=C(N=2)C(F)(F)F)CC1 NZLZVERJPBTXAH-UHFFFAOYSA-N 0.000 claims 2
TZQUXHRMXLPNIR-UHFFFAOYSA-N 3-(1,1-difluoroethyl)-5-[[3-[2,6-difluoro-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]azetidin-1-yl]methyl]-1,2,4-oxadiazole Chemical compound CC(F)(F)C1=NOC(CN2CC(C2)OC=2C(=CC(=CC=2F)C2CCN(CC2)S(C)(=O)=O)F)=N1 TZQUXHRMXLPNIR-UHFFFAOYSA-N 0.000 claims 2
YRYBUIINEVJSKD-UHFFFAOYSA-N 3-[[3-[2,6-difluoro-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]azetidin-1-yl]methyl]-5-propan-2-yl-1,2,4-oxadiazole Chemical compound O1C(C(C)C)=NC(CN2CC(C2)OC=2C(=CC(=CC=2F)C2CCN(CC2)S(C)(=O)=O)F)=N1 YRYBUIINEVJSKD-UHFFFAOYSA-N 0.000 claims 2
BPYCLQDOGIWCMA-UHFFFAOYSA-N 3-chloro-2-[[3-[2,6-difluoro-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]azetidin-1-yl]methyl]-5-(trifluoromethyl)pyridine Chemical compound C1CN(S(=O)(=O)C)CCC1C(C=C1F)=CC(F)=C1OC1CN(CC=2C(=CC(=CN=2)C(F)(F)F)Cl)C1 BPYCLQDOGIWCMA-UHFFFAOYSA-N 0.000 claims 2
BMLWMQDZZOGTFR-UHFFFAOYSA-N 3-cyclopropyl-5-[[3-[2,6-difluoro-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]azetidin-1-yl]methyl]-1,2,4-oxadiazole Chemical compound C1CN(S(=O)(=O)C)CCC1C(C=C1F)=CC(F)=C1OC1CN(CC=2ON=C(N=2)C2CC2)C1 BMLWMQDZZOGTFR-UHFFFAOYSA-N 0.000 claims 2
ZEZKZGIIBXPWHM-UHFFFAOYSA-N 4-[3,5-difluoro-4-[1-(naphthalen-1-ylmethyl)azetidin-3-yl]oxyphenyl]-1-methylsulfonylpiperidine Chemical compound C1CN(S(=O)(=O)C)CCC1C(C=C1F)=CC(F)=C1OC1CN(CC=2C3=CC=CC=C3C=CC=2)C1 ZEZKZGIIBXPWHM-UHFFFAOYSA-N 0.000 claims 2
YWPPYASFWVKDTH-UHFFFAOYSA-N 4-[3,5-difluoro-4-[1-(naphthalen-2-ylmethyl)azetidin-3-yl]oxyphenyl]-1-methylsulfonylpiperidine Chemical compound C1CN(S(=O)(=O)C)CCC1C(C=C1F)=CC(F)=C1OC1CN(CC=2C=C3C=CC=CC3=CC=2)C1 YWPPYASFWVKDTH-UHFFFAOYSA-N 0.000 claims 2
ZJOQZCRDOIEZFS-UHFFFAOYSA-N 4-[3,5-difluoro-4-[1-[1-[4-(trifluoromethyl)phenyl]propyl]azetidin-3-yl]oxyphenyl]-1-methylsulfonylpiperidine Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(CC)N(C1)CC1OC(C(=C1)F)=C(F)C=C1C1CCN(S(C)(=O)=O)CC1 ZJOQZCRDOIEZFS-UHFFFAOYSA-N 0.000 claims 2
HTGDOFSBHIEUIX-UHFFFAOYSA-N 4-[3,5-difluoro-4-[1-[[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]methyl]azetidin-3-yl]oxyphenyl]-1-methylsulfonylpiperidine Chemical compound CN1N=C(C(F)(F)F)C=C1CN1CC(OC=2C(=CC(=CC=2F)C2CCN(CC2)S(C)(=O)=O)F)C1 HTGDOFSBHIEUIX-UHFFFAOYSA-N 0.000 claims 2
ZVDDYYQIYSBLBM-UHFFFAOYSA-N 4-[3,5-difluoro-4-[1-[[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]methyl]piperidin-4-yl]oxyphenyl]-1-methylsulfonylpiperidine Chemical compound CN1N=C(C(F)(F)F)C=C1CN1CCC(OC=2C(=CC(=CC=2F)C2CCN(CC2)S(C)(=O)=O)F)CC1 ZVDDYYQIYSBLBM-UHFFFAOYSA-N 0.000 claims 2
IXJJEYBHRVETLG-UHFFFAOYSA-N 4-[3,5-difluoro-4-[1-[[4-(3-fluorooxetan-3-yl)phenyl]methyl]azetidin-3-yl]oxyphenyl]-1-methylsulfonylpiperidine Chemical compound C1CN(S(=O)(=O)C)CCC1C(C=C1F)=CC(F)=C1OC1CN(CC=2C=CC(=CC=2)C2(F)COC2)C1 IXJJEYBHRVETLG-UHFFFAOYSA-N 0.000 claims 2
XFIYFKJEPMUAMR-UHFFFAOYSA-N 4-[3,5-difluoro-4-[1-[[4-(trifluoromethyl)phenyl]methyl]azetidin-3-yl]oxyphenyl]-1-(oxan-4-ylsulfonyl)piperidine Chemical compound FC1=CC(C2CCN(CC2)S(=O)(=O)C2CCOCC2)=CC(F)=C1OC(C1)CN1CC1=CC=C(C(F)(F)F)C=C1 XFIYFKJEPMUAMR-UHFFFAOYSA-N 0.000 claims 2
UUDSTMMLSWAHBI-UHFFFAOYSA-N 4-[3,5-difluoro-4-[1-[[4-(trifluoromethyl)phenyl]methyl]azetidin-3-yl]oxyphenyl]-1-methylsulfonylpiperidine Chemical compound C1CN(S(=O)(=O)C)CCC1C(C=C1F)=CC(F)=C1OC1CN(CC=2C=CC(=CC=2)C(F)(F)F)C1 UUDSTMMLSWAHBI-UHFFFAOYSA-N 0.000 claims 2
TXVWVMBVTQWPLT-UHFFFAOYSA-N 4-[3,5-difluoro-4-[1-[[4-(trifluoromethyl)phenyl]methyl]azetidin-3-yl]oxyphenyl]-1-piperidin-4-ylsulfonylpiperidine Chemical compound FC1=CC(C2CCN(CC2)S(=O)(=O)C2CCNCC2)=CC(F)=C1OC(C1)CN1CC1=CC=C(C(F)(F)F)C=C1 TXVWVMBVTQWPLT-UHFFFAOYSA-N 0.000 claims 2
FKZSXTNYXOBXQG-UHFFFAOYSA-N 4-[3,5-difluoro-4-[1-[[4-(trifluoromethyl)phenyl]methyl]azetidin-3-yl]oxyphenyl]-1-pyrrolidin-3-ylsulfonylpiperidine Chemical compound FC1=CC(C2CCN(CC2)S(=O)(=O)C2CNCC2)=CC(F)=C1OC(C1)CN1CC1=CC=C(C(F)(F)F)C=C1 FKZSXTNYXOBXQG-UHFFFAOYSA-N 0.000 claims 2
UINQQGMFVPCBAR-UHFFFAOYSA-N 4-[3,5-difluoro-4-[1-[[4-(trifluoromethyl)phenyl]methyl]pyrrolidin-3-yl]oxyphenyl]-1-methylsulfonylpiperidine Chemical compound C1CN(S(=O)(=O)C)CCC1C(C=C1F)=CC(F)=C1OC1CN(CC=2C=CC(=CC=2)C(F)(F)F)CC1 UINQQGMFVPCBAR-UHFFFAOYSA-N 0.000 claims 2
ZQGKERQYOVCALX-UHFFFAOYSA-N 4-[[3-[2,6-difluoro-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]azetidin-1-yl]methyl]-2-(trifluoromethyl)-1,3-thiazole Chemical compound C1CN(S(=O)(=O)C)CCC1C(C=C1F)=CC(F)=C1OC1CN(CC=2N=C(SC=2)C(F)(F)F)C1 ZQGKERQYOVCALX-UHFFFAOYSA-N 0.000 claims 2
ILEKSOWVIGRTLK-UHFFFAOYSA-N 4-[[4-[2,6-difluoro-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]piperidin-1-yl]methyl]-2-(trifluoromethyl)-1,3-thiazole Chemical compound C1CN(S(=O)(=O)C)CCC1C(C=C1F)=CC(F)=C1OC1CCN(CC=2N=C(SC=2)C(F)(F)F)CC1 ILEKSOWVIGRTLK-UHFFFAOYSA-N 0.000 claims 2
FYPGJSOVVLGRIC-UHFFFAOYSA-N 4-methylsulfonyl-1-[5-[1-[[4-(trifluoromethoxy)phenyl]methyl]azetidin-3-yl]oxypyrazin-2-yl]piperazin-2-one Chemical compound O=C1CN(S(=O)(=O)C)CCN1C(N=C1)=CN=C1OC1CN(CC=2C=CC(OC(F)(F)F)=CC=2)C1 FYPGJSOVVLGRIC-UHFFFAOYSA-N 0.000 claims 2
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical group C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 2
UHXGRLNXXIPHAK-UHFFFAOYSA-N 5-[[3-[2,6-difluoro-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]azetidin-1-yl]methyl]-3-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound C1CN(S(=O)(=O)C)CCC1C(C=C1F)=CC(F)=C1OC1CN(CC=2ON=C(N=2)C(F)(F)F)C1 UHXGRLNXXIPHAK-UHFFFAOYSA-N 0.000 claims 2
PLROFIMLUNJEBN-UHFFFAOYSA-N 5-[[3-[2,6-difluoro-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]azetidin-1-yl]methyl]-3-propan-2-yl-1,2,4-oxadiazole Chemical compound CC(C)C1=NOC(CN2CC(C2)OC=2C(=CC(=CC=2F)C2CCN(CC2)S(C)(=O)=O)F)=N1 PLROFIMLUNJEBN-UHFFFAOYSA-N 0.000 claims 2
RPZNXQJFTNRLGS-UHFFFAOYSA-N 5-[[4-[2,6-difluoro-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]piperidin-1-yl]methyl]-3-propan-2-yl-1,2,4-oxadiazole Chemical compound CC(C)C1=NOC(CN2CCC(CC2)OC=2C(=CC(=CC=2F)C2CCN(CC2)S(C)(=O)=O)F)=N1 RPZNXQJFTNRLGS-UHFFFAOYSA-N 0.000 claims 2
WTIDTULUJMMFPP-UHFFFAOYSA-N 5-[[4-[2,6-difluoro-4-(4-fluoro-1-methylsulfonylpiperidin-4-yl)phenoxy]piperidin-1-yl]methyl]-3-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound C1CN(S(=O)(=O)C)CCC1(F)C(C=C1F)=CC(F)=C1OC1CCN(CC=2ON=C(N=2)C(F)(F)F)CC1 WTIDTULUJMMFPP-UHFFFAOYSA-N 0.000 claims 2
AEZSSFAWPPJUOE-UHFFFAOYSA-N 5-[[4-[2-fluoro-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]piperidin-1-yl]methyl]-3-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound C1CN(S(=O)(=O)C)CCC1C(C=C1F)=CC=C1OC1CCN(CC=2ON=C(N=2)C(F)(F)F)CC1 AEZSSFAWPPJUOE-UHFFFAOYSA-N 0.000 claims 2
FPPYBKDYHACVIJ-UHFFFAOYSA-N 5-[[4-[3-fluoro-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]piperidin-1-yl]methyl]-3-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound C1CN(S(=O)(=O)C)CCC1C(C(=C1)F)=CC=C1OC1CCN(CC=2ON=C(N=2)C(F)(F)F)CC1 FPPYBKDYHACVIJ-UHFFFAOYSA-N 0.000 claims 2
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 2
208000002705 Glucose Intolerance Diseases 0.000 claims 2
208000031226 Hyperlipidaemia Diseases 0.000 claims 2
239000003795 chemical substances by application Substances 0.000 claims 2
208000029078 coronary artery disease Diseases 0.000 claims 2
125000000753 cycloalkyl group Chemical group 0.000 claims 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
125000006001 difluoroethyl group Chemical group 0.000 claims 2
208000035475 disorder Diseases 0.000 claims 2
239000008103 glucose Substances 0.000 claims 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
230000000366 juvenile effect Effects 0.000 claims 2
238000000034 method Methods 0.000 claims 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
208000010125 myocardial infarction Diseases 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 claims 2
201000009104 prediabetes syndrome Diseases 0.000 claims 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
125000000335 thiazolyl group Chemical group 0.000 claims 2
AHJAFRIFZRLGQO-UHFFFAOYSA-N 1-[5-[1-[(4-chlorophenyl)methyl]azetidin-3-yl]oxypyridin-2-yl]-4-methylsulfonylpiperazine Chemical compound C1CN(S(=O)(=O)C)CCN1C(N=C1)=CC=C1OC1CN(CC=2C=CC(Cl)=CC=2)C1 AHJAFRIFZRLGQO-UHFFFAOYSA-N 0.000 claims 1
FTMFVDNBRISMBM-UHFFFAOYSA-N 1-[5-[1-[(4-methoxyphenyl)methyl]azetidin-3-yl]oxypyridin-2-yl]-4-methylsulfonylpiperazine Chemical compound C1=CC(OC)=CC=C1CN1CC(OC=2C=NC(=CC=2)N2CCN(CC2)S(C)(=O)=O)C1 FTMFVDNBRISMBM-UHFFFAOYSA-N 0.000 claims 1
OOIYQDIPUYOXRM-UHFFFAOYSA-N 1-[5-[1-[(4-methylphenyl)methyl]azetidin-3-yl]oxypyridin-2-yl]-4-methylsulfonylpiperazine Chemical compound C1=CC(C)=CC=C1CN1CC(OC=2C=NC(=CC=2)N2CCN(CC2)S(C)(=O)=O)C1 OOIYQDIPUYOXRM-UHFFFAOYSA-N 0.000 claims 1
JADXFOZAJSMQAV-UHFFFAOYSA-N 1-[5-[1-[[4-(difluoromethoxy)phenyl]methyl]azetidin-3-yl]oxypyridin-2-yl]-4-methylsulfonylpiperazine Chemical compound C1CN(S(=O)(=O)C)CCN1C(N=C1)=CC=C1OC1CN(CC=2C=CC(OC(F)F)=CC=2)C1 JADXFOZAJSMQAV-UHFFFAOYSA-N 0.000 claims 1
ZRKXJHNZKJRJIG-UHFFFAOYSA-N 1-methylsulfonyl-4-[4-[1-[(4-propan-2-ylphenyl)methyl]azetidin-3-yl]oxyphenyl]piperazine Chemical compound C1=CC(C(C)C)=CC=C1CN1CC(OC=2C=CC(=CC=2)N2CCN(CC2)S(C)(=O)=O)C1 ZRKXJHNZKJRJIG-UHFFFAOYSA-N 0.000 claims 1
CRFIRNYALDVCNH-UHFFFAOYSA-N 1-methylsulfonyl-4-[5-[1-[(4-propan-2-ylphenyl)methyl]azetidin-3-yl]oxypyridin-2-yl]piperazine Chemical compound C1=CC(C(C)C)=CC=C1CN1CC(OC=2C=NC(=CC=2)N2CCN(CC2)S(C)(=O)=O)C1 CRFIRNYALDVCNH-UHFFFAOYSA-N 0.000 claims 1
HJJNFIZAVLVPRN-UHFFFAOYSA-N 1-methylsulfonyl-4-[5-[1-[[3-(trifluoromethyl)phenyl]methyl]azetidin-3-yl]oxypyridin-2-yl]piperazine Chemical compound C1CN(S(=O)(=O)C)CCN1C(N=C1)=CC=C1OC1CN(CC=2C=C(C=CC=2)C(F)(F)F)C1 HJJNFIZAVLVPRN-UHFFFAOYSA-N 0.000 claims 1
HTIAOECCZOFYCU-UHFFFAOYSA-N 1-methylsulfonyl-4-[5-[1-[[4-(trifluoromethoxy)phenyl]methyl]azetidin-3-yl]oxypyridin-2-yl]piperazine Chemical compound C1CN(S(=O)(=O)C)CCN1C(N=C1)=CC=C1OC1CN(CC=2C=CC(OC(F)(F)F)=CC=2)C1 HTIAOECCZOFYCU-UHFFFAOYSA-N 0.000 claims 1
NROQZUOLYKYDRH-UHFFFAOYSA-N 1-methylsulfonyl-4-[5-[1-[[4-(trifluoromethyl)phenyl]methyl]azetidin-3-yl]oxypyridin-2-yl]piperazine Chemical compound C1CN(S(=O)(=O)C)CCN1C(N=C1)=CC=C1OC1CN(CC=2C=CC(=CC=2)C(F)(F)F)C1 NROQZUOLYKYDRH-UHFFFAOYSA-N 0.000 claims 1
FWNKUZCWCKOGKM-UHFFFAOYSA-N 1-propylsulfonyl-4-[5-[1-[[4-(trifluoromethyl)phenyl]methyl]azetidin-3-yl]oxypyridin-2-yl]piperazine Chemical compound C1CN(S(=O)(=O)CCC)CCN1C(N=C1)=CC=C1OC1CN(CC=2C=CC(=CC=2)C(F)(F)F)C1 FWNKUZCWCKOGKM-UHFFFAOYSA-N 0.000 claims 1
VUYPYGJFILRODH-UHFFFAOYSA-N 2-(4-methylsulfonylpiperazin-1-yl)-5-[1-[(4-propan-2-ylphenyl)methyl]azetidin-3-yl]oxypyrazine Chemical compound C1=CC(C(C)C)=CC=C1CN1CC(OC=2N=CC(=NC=2)N2CCN(CC2)S(C)(=O)=O)C1 VUYPYGJFILRODH-UHFFFAOYSA-N 0.000 claims 1
BLPPBPZPVXKRKW-UHFFFAOYSA-N 2-(4-methylsulfonylpiperazin-1-yl)-5-[1-[[4-(trifluoromethyl)phenyl]methyl]azetidin-3-yl]oxypyrazine Chemical compound C1CN(S(=O)(=O)C)CCN1C(N=C1)=CN=C1OC1CN(CC=2C=CC(=CC=2)C(F)(F)F)C1 BLPPBPZPVXKRKW-UHFFFAOYSA-N 0.000 claims 1
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JP2012533226A 2009-10-09 2010-10-01 Ｇｐｒ１１９活性モジュレーターとしての化合物および組成物 Pending JP2013507366A (ja)

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PCT/US2010/051186 WO2011044001A1 (en)	2009-10-09	2010-10-01	Compounds and compositions as modulators of gpr119 activity

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EA018703B1 (ru) *	2008-04-07	2013-10-30	Айрм Ллк	Соединения и композиции в качестве модуляторов активности gpr119
GB201114389D0 (en)	2011-08-22	2011-10-05	Prosidion Ltd	Novel compounds
WO2012066077A1 (en)	2010-11-18	2012-05-24	Prosidion Limited	1,4 di substituted pyrrolidine - 3 - yl -amine derivatives and their use for the treatment of metabolic disorders
KR101913619B1 (ko)	2011-06-09	2018-12-28	리젠 파마슈티컬스 소시에떼 아노님	Gpr-119의 조절제로서의 신규한 화합물
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