JP2008534581A5 - - Google Patents
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- Publication number
- JP2008534581A5 JP2008534581A5 JP2008503954A JP2008503954A JP2008534581A5 JP 2008534581 A5 JP2008534581 A5 JP 2008534581A5 JP 2008503954 A JP2008503954 A JP 2008503954A JP 2008503954 A JP2008503954 A JP 2008503954A JP 2008534581 A5 JP2008534581 A5 JP 2008534581A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- trifluoromethyl
- dihydropyrido
- oxobutyl
- butyl
- Prior art date
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 45
- 150000003839 salts Chemical class 0.000 claims 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 30
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 30
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 30
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 15
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 15
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 15
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 15
- 239000011976 maleic acid Substances 0.000 claims 15
- 229940098779 methanesulfonic acid Drugs 0.000 claims 15
- 239000011975 tartaric acid Substances 0.000 claims 15
- 235000002906 tartaric acid Nutrition 0.000 claims 15
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- -1 3-furan Chemical compound 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 6
- IKBXXBXFEDIVJH-ZDUSSCGKSA-N 1-[(2s)-2-amino-4-[2-(furan-3-yl)-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5,5-difluoropiperidin-2-one Chemical compound C([C@@H](N)CC(=O)N1CC2=C(C(=NC(=N2)C2=COC=C2)C(F)(F)F)CC1)N1CC(F)(F)CCC1=O IKBXXBXFEDIVJH-ZDUSSCGKSA-N 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- VTAQGNVTOHRZRK-NEPJUHHUSA-N (5r)-1-[(2s)-2-amino-4-[2-(fluoromethyl)-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(CF)N=C2C(F)(F)F)=C2CC1 VTAQGNVTOHRZRK-NEPJUHHUSA-N 0.000 claims 2
- WALRTZHEUGUMEW-YPMHNXCESA-N (5r)-1-[(2s)-2-amino-4-[2-methyl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(C)N=C2C(F)(F)F)=C2CC1 WALRTZHEUGUMEW-YPMHNXCESA-N 0.000 claims 2
- VDKVOKNVOQJFHM-BBRMVZONSA-N (6s)-4-[(2s)-2-amino-4-[2-(4-fluorophenyl)-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-6-methylmorpholin-2-one Chemical compound C1C(=O)O[C@@H](C)CN1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C=3C=CC(F)=CC=3)=C2CC1 VDKVOKNVOQJFHM-BBRMVZONSA-N 0.000 claims 2
- QXBFXIKTQCKASH-AAEUAGOBSA-N (6s)-4-[(2s)-2-amino-4-[2-cyclopropyl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-6-methylmorpholin-3-one Chemical compound O=C1CO[C@@H](C)CN1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C3CC3)=C2CC1 QXBFXIKTQCKASH-AAEUAGOBSA-N 0.000 claims 2
- IZJNAQGFGRUTAK-JQWIXIFHSA-N (6s)-4-[(2s)-2-amino-4-[2-methyl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-6-methylmorpholin-3-one Chemical compound O=C1CO[C@@H](C)CN1C[C@@H](N)CC(=O)N1CC(N=C(C)N=C2C(F)(F)F)=C2CC1 IZJNAQGFGRUTAK-JQWIXIFHSA-N 0.000 claims 2
- PTJKFVGRURDHTO-STQMWFEESA-N (6s)-4-[(2s)-2-amino-4-[2-tert-butyl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-6-methylmorpholin-3-one Chemical compound O=C1CO[C@@H](C)CN1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C(C)(C)C)=C2CC1 PTJKFVGRURDHTO-STQMWFEESA-N 0.000 claims 2
- WDCJUKKLNWPYDU-JTQLQIEISA-N 1-[(2s)-2-amino-4-[2-(fluoromethyl)-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5,5-difluoropiperidin-2-one Chemical compound C([C@@H](N)CC(=O)N1CC2=C(C(=NC(CF)=N2)C(F)(F)F)CC1)N1CC(F)(F)CCC1=O WDCJUKKLNWPYDU-JTQLQIEISA-N 0.000 claims 2
- NEVACBBFMZPBCL-NSHDSACASA-N 1-[(2s)-2-amino-4-[2-methyl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5,5-difluoropiperidin-2-one Chemical compound C([C@@H](N)CC(=O)N1CC=2N=C(N=C(C=2CC1)C(F)(F)F)C)N1CC(F)(F)CCC1=O NEVACBBFMZPBCL-NSHDSACASA-N 0.000 claims 2
- NRUPLOOESZBVLS-VIFPVBQESA-N 1-[(2s)-2-amino-4-oxo-4-[2-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]butyl]-5,5-difluoropiperidin-2-one Chemical compound C([C@@H](N)CC(=O)N1CC2=C(C(=NC(=N2)C(F)(F)C(F)(F)F)C(F)(F)F)CC1)N1CC(F)(F)CCC1=O NRUPLOOESZBVLS-VIFPVBQESA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 claims 2
- ZWPRRQZNBDYKLH-VIFPVBQESA-N Gemigliptin Chemical compound C([C@@H](N)CC(=O)N1CC2=C(C(=NC(=N2)C(F)(F)F)C(F)(F)F)CC1)N1CC(F)(F)CCC1=O ZWPRRQZNBDYKLH-VIFPVBQESA-N 0.000 claims 2
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- LZXXYWRZDAGXSJ-MNOVXSKESA-N (5r)-1-[(2s)-2-amino-4-[2,4-bis(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C(F)(F)F)=C2CC1 LZXXYWRZDAGXSJ-MNOVXSKESA-N 0.000 claims 1
- ZMFRTOJDRJYDQC-KGLIPLIRSA-N (5r)-1-[(2s)-2-amino-4-[2-(2-methoxyethyl)-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5-methylpiperidin-2-one Chemical compound C([C@@H](N)CC(=O)N1CC=2N=C(N=C(C=2CC1)C(F)(F)F)CCOC)N1C[C@H](C)CCC1=O ZMFRTOJDRJYDQC-KGLIPLIRSA-N 0.000 claims 1
- GJAGXFGOQJDHMG-HIFRSBDPSA-N (5r)-1-[(2s)-2-amino-4-[2-(3,4-difluorophenyl)-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C=3C=C(F)C(F)=CC=3)=C2CC1 GJAGXFGOQJDHMG-HIFRSBDPSA-N 0.000 claims 1
- YTHMPIPXDYQIFH-PBHICJAKSA-N (5r)-1-[(2s)-2-amino-4-[2-(4-fluorophenyl)-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C=3C=CC(F)=CC=3)=C2CC1 YTHMPIPXDYQIFH-PBHICJAKSA-N 0.000 claims 1
- BBQAKAGYXGKXMJ-PBHICJAKSA-N (5r)-1-[(2s)-2-amino-4-[2-(4-fluorophenyl)-6,7-dihydro-4h-[1,3]thiazolo[4,5-c]pyridin-5-yl]-4-oxobutyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(S2)C=3C=CC(F)=CC=3)=C2CC1 BBQAKAGYXGKXMJ-PBHICJAKSA-N 0.000 claims 1
- HOZVRGBYSDXNDD-HIFRSBDPSA-N (5r)-1-[(2s)-2-amino-4-[2-(cyclopropylmethyl)-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(CC2CC2)N=C2C(F)(F)F)=C2CC1 HOZVRGBYSDXNDD-HIFRSBDPSA-N 0.000 claims 1
- GYATXFQPZVGGMJ-KGLIPLIRSA-N (5r)-1-[(2s)-2-amino-4-[2-(furan-2-yl)-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C=3OC=CC=3)=C2CC1 GYATXFQPZVGGMJ-KGLIPLIRSA-N 0.000 claims 1
- GHNBAWWYZOLGQW-HIFRSBDPSA-N (5r)-1-[(2s)-2-amino-4-[2-(furan-3-yl)-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C3=COC=C3)=C2CC1 GHNBAWWYZOLGQW-HIFRSBDPSA-N 0.000 claims 1
- NICJDAWRKKKROW-QAPCUYQASA-N (5r)-1-[(2s)-2-amino-4-[2-[(4-fluorophenyl)methyl]-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(CC=2C=CC(F)=CC=2)N=C2C(F)(F)F)=C2CC1 NICJDAWRKKKROW-QAPCUYQASA-N 0.000 claims 1
- ZLQXPIQSMPTOGU-HIFRSBDPSA-N (5r)-1-[(2s)-2-amino-4-[2-cyclobutyl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C3CCC3)=C2CC1 ZLQXPIQSMPTOGU-HIFRSBDPSA-N 0.000 claims 1
- DJNMQSVECLAYMK-ZBFHGGJFSA-N (5r)-1-[(2s)-2-amino-4-[2-cyclopentyl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C3CCCC3)=C2CC1 DJNMQSVECLAYMK-ZBFHGGJFSA-N 0.000 claims 1
- XIGSSFWYVCBXNQ-MNOVXSKESA-N (5r)-1-[(2s)-2-amino-4-oxo-4-[2-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]butyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C(F)(F)C(F)(F)F)=C2CC1 XIGSSFWYVCBXNQ-MNOVXSKESA-N 0.000 claims 1
- XZJSGVSUEMLGAD-PBHICJAKSA-N (5r)-1-[(2s)-2-amino-4-oxo-4-[2-[4-(trifluoromethyl)phenyl]-6,7-dihydro-4h-[1,3]thiazolo[4,5-c]pyridin-5-yl]butyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(S2)C=3C=CC(=CC=3)C(F)(F)F)=C2CC1 XZJSGVSUEMLGAD-PBHICJAKSA-N 0.000 claims 1
- KOARBUHQPKZLHB-WBVHZDCISA-N (5r)-1-[(2s)-2-amino-4-oxo-4-[2-phenyl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]butyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C=3C=CC=CC=3)=C2CC1 KOARBUHQPKZLHB-WBVHZDCISA-N 0.000 claims 1
- PTZUFFHRUUTPSB-KGLIPLIRSA-N (5r)-1-[(2s)-2-amino-4-oxo-4-[2-propyl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]butyl]-5-methylpiperidin-2-one Chemical compound C([C@@H](N)CC(=O)N1CC=2N=C(N=C(C=2CC1)C(F)(F)F)CCC)N1C[C@H](C)CCC1=O PTZUFFHRUUTPSB-KGLIPLIRSA-N 0.000 claims 1
- DIMNCOWKJPBZTI-ZBFHGGJFSA-N (5r)-1-[(2s)-2-amino-4-oxo-4-[2-pyridin-3-yl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]butyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C=3C=NC=CC=3)=C2CC1 DIMNCOWKJPBZTI-ZBFHGGJFSA-N 0.000 claims 1
- RNXARZUJEQCSDC-ZBFHGGJFSA-N (5r)-1-[(2s)-2-amino-4-oxo-4-[2-pyridin-4-yl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]butyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C=3C=CN=CC=3)=C2CC1 RNXARZUJEQCSDC-ZBFHGGJFSA-N 0.000 claims 1
- HVKRQGSOVNNKQT-KGLIPLIRSA-N (5r)-1-[(2s)-2-amino-4-oxo-4-[2-thiophen-2-yl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]butyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C=3SC=CC=3)=C2CC1 HVKRQGSOVNNKQT-KGLIPLIRSA-N 0.000 claims 1
- QTXOAUMQCVDJGC-HIFRSBDPSA-N (5r)-1-[(2s)-2-amino-4-oxo-4-[2-thiophen-3-yl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]butyl]-5-methylpiperidin-2-one Chemical compound C1[C@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C3=CSC=C3)=C2CC1 QTXOAUMQCVDJGC-HIFRSBDPSA-N 0.000 claims 1
- LZXXYWRZDAGXSJ-QWRGUYRKSA-N (5s)-1-[(2s)-2-amino-4-[2,4-bis(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5-methylpiperidin-2-one Chemical compound C1[C@@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C(F)(F)F)=C2CC1 LZXXYWRZDAGXSJ-QWRGUYRKSA-N 0.000 claims 1
- PNJOUWGUDCMGPW-QWRGUYRKSA-N (5s)-1-[(2s)-2-amino-4-oxo-4-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]butyl]-5-methylpiperidin-2-one Chemical compound C1[C@@H](C)CCC(=O)N1C[C@@H](N)CC(=O)N1CC2=NN=C(C(F)(F)F)N2CC1 PNJOUWGUDCMGPW-QWRGUYRKSA-N 0.000 claims 1
- DASWVISTCFTOIS-ZJUUUORDSA-N (6r)-4-[(2s)-2-amino-4-oxo-4-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]butyl]-6-methylmorpholin-3-one Chemical compound O=C1CO[C@H](C)CN1C[C@@H](N)CC(=O)N1CC2=NN=C(C(F)(F)F)N2CC1 DASWVISTCFTOIS-ZJUUUORDSA-N 0.000 claims 1
- QYTRYTQNQKXPRC-JSGCOSHPSA-N (6s)-4-[(2s)-2-amino-4-[2-(3,4-difluorophenyl)-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-6-methylmorpholin-3-one Chemical compound O=C1CO[C@@H](C)CN1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C=3C=C(F)C(F)=CC=3)=C2CC1 QYTRYTQNQKXPRC-JSGCOSHPSA-N 0.000 claims 1
- UOBNYVYEPQSIGK-BBRMVZONSA-N (6s)-4-[(2s)-2-amino-4-[2-(3-fluorophenyl)-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-6-methylmorpholin-3-one Chemical compound O=C1CO[C@@H](C)CN1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C=3C=C(F)C=CC=3)=C2CC1 UOBNYVYEPQSIGK-BBRMVZONSA-N 0.000 claims 1
- GZNNXRIBKPNKJU-BBRMVZONSA-N (6s)-4-[(2s)-2-amino-4-[2-(4-fluorophenyl)-6,7-dihydro-4h-[1,3]thiazolo[4,5-c]pyridin-5-yl]-4-oxobutyl]-6-methylmorpholin-3-one Chemical compound O=C1CO[C@@H](C)CN1C[C@@H](N)CC(=O)N1CC(N=C(S2)C=3C=CC(F)=CC=3)=C2CC1 GZNNXRIBKPNKJU-BBRMVZONSA-N 0.000 claims 1
- XALIVERBROSNTF-ZFWWWQNUSA-N (6s)-4-[(2s)-2-amino-4-[2-cyclopentyl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-6-methylmorpholin-3-one Chemical compound O=C1CO[C@@H](C)CN1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C3CCCC3)=C2CC1 XALIVERBROSNTF-ZFWWWQNUSA-N 0.000 claims 1
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- XVYVGRBMSDRCMF-NSHDSACASA-N 1-[(2s)-2-amino-4-[2-ethyl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5,5-difluoropiperidin-2-one Chemical compound C([C@@H](N)CC(=O)N1CC=2N=C(N=C(C=2CC1)C(F)(F)F)CC)N1CC(F)(F)CCC1=O XVYVGRBMSDRCMF-NSHDSACASA-N 0.000 claims 1
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- AGEBFSDHNBLHRV-KZUDCZAMSA-N 1-[(2s)-2-amino-4-oxo-4-[2-propan-2-yl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]butyl]-5-methylpiperidin-2-one Chemical compound C([C@@H](N)CC(=O)N1CC=2N=C(N=C(C=2CC1)C(F)(F)F)C(C)C)N1CC(C)CCC1=O AGEBFSDHNBLHRV-KZUDCZAMSA-N 0.000 claims 1
- BURQKBQMSLDOEB-LBPRGKRZSA-N 1-[(2s)-2-amino-4-oxo-4-[2-propyl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]butyl]-5,5-difluoropiperidin-2-one Chemical compound C([C@@H](N)CC(=O)N1CC=2N=C(N=C(C=2CC1)C(F)(F)F)CCC)N1CC(F)(F)CCC1=O BURQKBQMSLDOEB-LBPRGKRZSA-N 0.000 claims 1
- ASNFYBPTMBOSDI-AWEZNQCLSA-N 1-[(2s)-2-amino-4-oxo-4-[2-pyridin-4-yl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]butyl]-5,5-difluoropiperidin-2-one Chemical compound C([C@@H](N)CC(=O)N1CC2=C(C(=NC(=N2)C=2C=CN=CC=2)C(F)(F)F)CC1)N1CC(F)(F)CCC1=O ASNFYBPTMBOSDI-AWEZNQCLSA-N 0.000 claims 1
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- PNTXVMJPGXFQPQ-ZDUSSCGKSA-N 1-[(2s)-2-amino-4-oxo-4-[2-thiophen-3-yl-4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]butyl]-5,5-difluoropiperidin-2-one Chemical compound C([C@@H](N)CC(=O)N1CC2=C(C(=NC(=N2)C2=CSC=C2)C(F)(F)F)CC1)N1CC(F)(F)CCC1=O PNTXVMJPGXFQPQ-ZDUSSCGKSA-N 0.000 claims 1
- IGENXLFHZMEIHQ-VIFPVBQESA-N 1-[(2s)-2-amino-4-oxo-4-[3-(1,1,2,2,2-pentafluoroethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]butyl]-5,5-difluoropiperidin-2-one Chemical compound C([C@@H](N)CC(=O)N1CC=2N(C(=NN=2)C(F)(F)C(F)(F)F)CC1)N1CC(F)(F)CCC1=O IGENXLFHZMEIHQ-VIFPVBQESA-N 0.000 claims 1
- VCLHTXJUNLKZBG-JTQLQIEISA-N 1-[(2s)-2-amino-4-oxo-4-[4-(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]butyl]-5,5-difluoropiperidin-2-one Chemical compound C([C@@H](N)CC(=O)N1CC2=C(C(=NC=N2)C(F)(F)F)CC1)N1CC(F)(F)CCC1=O VCLHTXJUNLKZBG-JTQLQIEISA-N 0.000 claims 1
- PXRYTMICGFTIOG-ZDUSSCGKSA-N 1-[(2s)-2-amino-4-oxo-4-[5-(trifluoromethyl)-3,4-dihydro-1h-isoquinolin-2-yl]butyl]-5,5-difluoropiperidin-2-one Chemical compound C([C@@H](N)CC(=O)N1CC2=C(C(=CC=C2)C(F)(F)F)CC1)N1CC(F)(F)CCC1=O PXRYTMICGFTIOG-ZDUSSCGKSA-N 0.000 claims 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- PHZNOAYWNSJWFE-AXDSSHIGSA-N 4-[(2s)-2-amino-4-[2,4-bis(trifluoromethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-6-methylthiomorpholin-3-one Chemical compound O=C1CSC(C)CN1C[C@@H](N)CC(=O)N1CC(N=C(N=C2C(F)(F)F)C(F)(F)F)=C2CC1 PHZNOAYWNSJWFE-AXDSSHIGSA-N 0.000 claims 1
- HCXIAOCLLFTEPS-AXDSSHIGSA-N 4-[(2s)-2-amino-4-oxo-4-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]butyl]-6-methylthiomorpholin-3-one Chemical compound O=C1CSC(C)CN1C[C@@H](N)CC(=O)N1CC2=NN=C(C(F)(F)F)N2CC1 HCXIAOCLLFTEPS-AXDSSHIGSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 229910005965 SO 2 Chemical group 0.000 claims 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229910052757 nitrogen Chemical group 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003457 sulfones Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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| KR10-2005-0053761 | 2005-06-22 | ||
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| KR10-2005-0085980 | 2005-09-15 | ||
| KR20050085980 | 2005-09-15 | ||
| KR20050122361 | 2005-12-13 | ||
| KR10-2005-0122361 | 2005-12-13 | ||
| PCT/KR2006/001169 WO2006104356A1 (en) | 2005-04-01 | 2006-03-30 | Dipeptidyl peptidase-iv inhibiting compounds, methods of preparing the same, and pharmaceutical compositions containing the same as an active agent |
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| JP2008534581A JP2008534581A (ja) | 2008-08-28 |
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| CN101652147B (zh) | 2007-04-03 | 2013-07-24 | 田边三菱制药株式会社 | 二肽基肽酶iv抑制化合物和甜味剂的并用 |
| CN101357922B (zh) * | 2007-08-02 | 2011-05-18 | 山东轩竹医药科技有限公司 | 新的dpp-iv抑制剂 |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| MX2010006216A (es) * | 2007-12-05 | 2010-08-02 | Astrazeneca Ab | Nuevos compuestos iii. |
| JP5358585B2 (ja) * | 2007-12-21 | 2013-12-04 | エルジー ライフ サイエンス リミテッド | ジペプチジルペプチダーゼ−ｉｖ阻害化合物、同化合物を製造する方法、及び活性剤として同化合物を含む医薬組成物 |
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| CN101486689B (zh) * | 2008-01-18 | 2011-08-10 | 山东轩竹医药科技有限公司 | 具有磺酰胺基甲酰胺哌嗪结构的dpp-iv抑制剂 |
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| EP2683705B1 (de) | 2011-03-08 | 2015-04-22 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
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| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| WO2012120053A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
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| RU2018133288A (ru) | 2016-02-23 | 2020-03-24 | Индиана Юниверсити Рисерч Энд Текнолоджи Корпорейшн | Комбинированные терапии для лечения спинальной мышечной атрофии |
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| CN111537622B (zh) * | 2019-11-29 | 2021-11-26 | 杭州华东医药集团新药研究院有限公司 | 一种度格列汀及其盐的杂质的检测方法 |
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