HRP20140025T1 - N1-PIRAZOLOSPIROKETONSKI INHIBITORI ACETIL-CoA-KARBOKSILAZE - Google Patents
N1-PIRAZOLOSPIROKETONSKI INHIBITORI ACETIL-CoA-KARBOKSILAZE Download PDFInfo
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- HRP20140025T1 HRP20140025T1 HRP20140025AT HRP20140025T HRP20140025T1 HR P20140025 T1 HRP20140025 T1 HR P20140025T1 HR P20140025A T HRP20140025A T HR P20140025AT HR P20140025 T HRP20140025 T HR P20140025T HR P20140025 T1 HRP20140025 T1 HR P20140025T1
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- Prior art keywords
- compound according
- pharmaceutically acceptable
- acceptable salt
- compound
- formula
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- 229940121373 acetyl-coa carboxylase inhibitor Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 24
- -1 hydroxy, fluoro, phenyl Chemical group 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 229940125708 antidiabetic agent Drugs 0.000 claims 2
- 239000003472 antidiabetic agent Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 229960004580 glibenclamide Drugs 0.000 claims 2
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 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 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 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
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims 1
- FOZFSEMFCIPOSZ-SPCKQMHLSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-[[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]piperidine-3,4,5-triol;trihydrate Chemical compound O.O.O.O[C@H]1[C@H](O)[C@@H](O)[C@@H](OC)O[C@@H]1CN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1.O[C@H]1[C@H](O)[C@@H](O)[C@@H](OC)O[C@@H]1CN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1 FOZFSEMFCIPOSZ-SPCKQMHLSA-N 0.000 claims 1
- QJLPWVUZFKETMK-LLVKDONJSA-N (5r)-1,5,7,9,11,14-hexahydroxy-3-methyl-8,13-dioxo-5,6-dihydrobenzo[a]tetracene-2-carboxylic acid Chemical compound O=C1C2=C(O)C=C(O)C=C2C(=O)C2=C1C(O)=C1C[C@@H](O)C(C=C(C(=C3O)C(O)=O)C)=C3C1=C2O QJLPWVUZFKETMK-LLVKDONJSA-N 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- BDXXSFOJPYSYOC-UHFFFAOYSA-N 1'-(2-methyl-3h-benzimidazole-5-carbonyl)-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-7-one Chemical compound C1=C2NC(C)=NC2=CC(C(=O)N2CCC3(CC=4C=NN(C=4C(=O)C3)C(C)C)CC2)=C1 BDXXSFOJPYSYOC-UHFFFAOYSA-N 0.000 claims 1
- BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 claims 1
- QOPWTEZWCHPGGC-UHFFFAOYSA-N 1-propan-2-yl-1'-(1h-pyrrolo[3,2-b]pyridine-6-carbonyl)spiro[4,6-dihydroindazole-5,4'-piperidine]-7-one Chemical compound N1=C2C=CNC2=CC(C(=O)N2CCC3(CC=4C=NN(C=4C(=O)C3)C(C)C)CC2)=C1 QOPWTEZWCHPGGC-UHFFFAOYSA-N 0.000 claims 1
- MVDXXGIBARMXSA-PYUWXLGESA-N 5-[[(2r)-2-benzyl-3,4-dihydro-2h-chromen-6-yl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC1=CC=C(O[C@@H](CC=2C=CC=CC=2)CC2)C2=C1 MVDXXGIBARMXSA-PYUWXLGESA-N 0.000 claims 1
- IETKPTYAGKZLKY-UHFFFAOYSA-N 5-[[4-[(3-methyl-4-oxoquinazolin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=CC=C2C(=O)N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O IETKPTYAGKZLKY-UHFFFAOYSA-N 0.000 claims 1
- KDOPAZIWBAHVJB-UHFFFAOYSA-N 5h-pyrrolo[3,2-d]pyrimidine Chemical group C1=NC=C2NC=CC2=N1 KDOPAZIWBAHVJB-UHFFFAOYSA-N 0.000 claims 1
- 108010011459 Exenatide Proteins 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 claims 1
- QJLPWVUZFKETMK-UHFFFAOYSA-N Pradimicin Q Natural products O=C1C2=C(O)C=C(O)C=C2C(=O)C2=C1C(O)=C1CC(O)C(C=C(C(=C3O)C(O)=O)C)=C3C1=C2O QJLPWVUZFKETMK-UHFFFAOYSA-N 0.000 claims 1
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 claims 1
- OCTNNXHKAOLDJL-BMGYQPLYSA-N Salbostatin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)OC[C@@H]1N[C@@H]1[C@H](O)[C@@H](O)[C@H](O)C(CO)=C1 OCTNNXHKAOLDJL-BMGYQPLYSA-N 0.000 claims 1
- OCTNNXHKAOLDJL-UHFFFAOYSA-N Salbostatin Natural products OC1C(O)C(CO)OCC1NC1C(O)C(O)C(O)C(CO)=C1 OCTNNXHKAOLDJL-UHFFFAOYSA-N 0.000 claims 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 claims 1
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 claims 1
- 229930186167 Trestatin Natural products 0.000 claims 1
- FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 claims 1
- 229960002632 acarbose Drugs 0.000 claims 1
- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 claims 1
- 229960001466 acetohexamide Drugs 0.000 claims 1
- VGZSUPCWNCWDAN-UHFFFAOYSA-N acetohexamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 VGZSUPCWNCWDAN-UHFFFAOYSA-N 0.000 claims 1
- 229960001667 alogliptin Drugs 0.000 claims 1
- ZSBOMTDTBDDKMP-OAHLLOKOSA-N alogliptin Chemical compound C=1C=CC=C(C#N)C=1CN1C(=O)N(C)C(=O)C=C1N1CCC[C@@H](N)C1 ZSBOMTDTBDDKMP-OAHLLOKOSA-N 0.000 claims 1
- 229950010663 balaglitazone Drugs 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 229950001261 camiglibose Drugs 0.000 claims 1
- JUFFVKRROAPVBI-PVOYSMBESA-N chembl1210015 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(=O)N[C@H]1[C@@H]([C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO[C@]3(O[C@@H](C[C@H](O)[C@H](O)CO)[C@H](NC(C)=O)[C@@H](O)C3)C(O)=O)O2)O)[C@@H](CO)O1)NC(C)=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 JUFFVKRROAPVBI-PVOYSMBESA-N 0.000 claims 1
- 229960001761 chlorpropamide Drugs 0.000 claims 1
- YZFWTZACSRHJQD-UHFFFAOYSA-N ciglitazone Chemical compound C=1C=C(CC2C(NC(=O)S2)=O)C=CC=1OCC1(C)CCCCC1 YZFWTZACSRHJQD-UHFFFAOYSA-N 0.000 claims 1
- 229950009226 ciglitazone Drugs 0.000 claims 1
- QQKNSPHAFATFNQ-UHFFFAOYSA-N darglitazone Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCC(=O)C(C=C1)=CC=C1CC1SC(=O)NC1=O QQKNSPHAFATFNQ-UHFFFAOYSA-N 0.000 claims 1
- 229950006689 darglitazone Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229950002375 englitazone Drugs 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229960001519 exenatide Drugs 0.000 claims 1
- 108010015174 exendin 3 Proteins 0.000 claims 1
- LMHMJYMCGJNXRS-IOPUOMRJSA-N exendin-3 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](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@H](C)O)[C@H](C)O)C(C)C)C1=CC=CC=C1 LMHMJYMCGJNXRS-IOPUOMRJSA-N 0.000 claims 1
- 229960000346 gliclazide Drugs 0.000 claims 1
- 229960004346 glimepiride Drugs 0.000 claims 1
- WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 claims 1
- 229960001381 glipizide Drugs 0.000 claims 1
- ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 claims 1
- 229950008402 glisentide Drugs 0.000 claims 1
- NSJYMFYVNWVGON-UHFFFAOYSA-N glisentide Chemical compound COC1=CC=CC=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCC2)C=C1 NSJYMFYVNWVGON-UHFFFAOYSA-N 0.000 claims 1
- 230000002440 hepatic effect Effects 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 229960003105 metformin Drugs 0.000 claims 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims 1
- 229960001110 miglitol Drugs 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
- PKWDZWYVIHVNKS-UHFFFAOYSA-N netoglitazone Chemical compound FC1=CC=CC=C1COC1=CC=C(C=C(CC2C(NC(=O)S2)=O)C=C2)C2=C1 PKWDZWYVIHVNKS-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229960005095 pioglitazone Drugs 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 229940016667 resveratrol Drugs 0.000 claims 1
- 235000021283 resveratrol Nutrition 0.000 claims 1
- 229960004586 rosiglitazone Drugs 0.000 claims 1
- 229960004937 saxagliptin Drugs 0.000 claims 1
- QGJUIPDUBHWZPV-SGTAVMJGSA-N saxagliptin Chemical compound C1C(C2)CC(C3)CC2(O)CC13[C@H](N)C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21 QGJUIPDUBHWZPV-SGTAVMJGSA-N 0.000 claims 1
- 108010033693 saxagliptin Proteins 0.000 claims 1
- 229960004034 sitagliptin Drugs 0.000 claims 1
- 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 1
- 229950001790 tendamistat Drugs 0.000 claims 1
- 108010037401 tendamistate Proteins 0.000 claims 1
- 229960002277 tolazamide Drugs 0.000 claims 1
- OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 claims 1
- 229960005371 tolbutamide Drugs 0.000 claims 1
- 229960001641 troglitazone Drugs 0.000 claims 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 claims 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 claims 1
- 229960001254 vildagliptin Drugs 0.000 claims 1
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 claims 1
- 229960001729 voglibose Drugs 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/438—The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
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Claims (19)
1. Spoj Formule (I)
[image]
,
naznačen time što
R1 je (C1-C6)alkil, (C3-C7)cikloalkil, tetrahidrofuranil ili oksetanil; gdje je navedeni (C1-C6)alkil izborno supstituiran s 1 do 2 supstituenta, koje se neovisno bira između (C1-C3)alkoksi, hidroksi, fluora, fenila, tetrahidrofuranila ili oksetanila;
R2 je vodik, halogen, (C1-C3)alkil ili cijano;
R3 su svaki neovisno vodik ili (C1-C3)alkil;
R4 je (C6-C10)aril, 5- do 12-eročlani heteroaril ili 8- do 12-eročlani kondenzirani heterociklički aril; gdje je svaki od navedenih (C6-C10)arila, 5- do 12-eročlanog heteroarila ili 8- do 12-eročlanog kondenziranog heterocikličkog arila izborno supstituiran s jednim do tri supstituenta, koje se neovisno bira između (C1-C3)alkila, (C1-C3)alkoksi, halogena, amino, (C1-C3)alkilamino, di(C1-C3)alkilamino, hidroksi, cijano, amido, fenila, 5- do 6-eročlanog heteroarila ili 5- do 6-eročlanog heterociklila;
ili njegova farmaceutski prihvatljiva sol.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je R1 (C1-C6)alkil, (C3-C7)cikloalkil ili tetrahidrofuranil; a R2 je vodik ili metil; ili njegova farmaceutski prihvatljiva sol.
3. Spoj u skladu s patentnim zahtjevom 2, naznačen time što je R1 etil, izopropil ili t-butil; svaki R3 je vodik; a R4 je fenil, pirazolil, imidazolil, triazolil, piridinil, pirimidinil, indolil, benzopirazinil, benzoimidazolil, benzoimidazolonil, pirolopiridinil, pirolopirimidinil, pirazolopiridinil, pirazolopirimidinil, indazolil, indolinonil, naftiridinil, kinolinil, kinolinonil, dihidrokinolinonil, oksodihidrokinolinonil, izokinolinil, izokinolinonil, dihidroizokinonil ili oksodihidroizokinonil, od kojih je svaki izborno supstituiran s jednim do tri supstituenta, koje se neovisno bira između fluora, klora, metila, metoksi, amino, metilamino, dimetilamino, amido, cijano, fenila, imidazolila, pirazolila, triazolila, piridinila ili morfolinila; ili njegova farmaceutski prihvatljiva sol.
4. Spoj u skladu s patentnim zahtjevom 3, naznačen time što je R1 izopropil ili t-butil; a R2 je vodik; ili njegova farmaceutski prihvatljiva sol.
5. Spoj u skladu s patentnim zahtjevom 4, naznačen time što je R4 indazolil, benzoimidazolil, 1-okso-1,2-dihidroizokinolinil, 1H-pirolo[3,2-b]piridinil, 2-okso-2,3-dihidro-1H-benzo[d]imidazolil, 1H-pirazolilfenil, 1H-pirazolilpiridinil ili 1H-imidazolilfenil; od kojih je svaki izborno supstituiran s jednim do dva metila, klora ili fluora; ili njegova farmaceutski prihvatljiva sol.
6. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je 1-izopropil-1′-(1H-pirolo[3,2-b]piridin-6-karbonil)-4,6-dihidrospiro[indazol-5,4′-piperidin]-7(1H)-on, ili njegova farmaceutski prihvatljiva sol.
7. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je spoj formule
[image]
.
8. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je 1-izopropil-1′-(2-metil-1H-benzo[d]imidazol-6-karbonil)-4,6-dihidrospiro[indazol-5,4′-piperidin]-7(1H)-on, ili njegova farmaceutski prihvatljiva sol.
9. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je spoj formule
[image]
.
10. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je spoj formule
[image]
,
ili njegova farmaceutski prihvatljiva sol.
11. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je spoj formule
[image]
,
ili njegova farmaceutski prihvatljiva sol.
12. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je spoj formule
[image]
,
ili njegova farmaceutski prihvatljiva sol.
13. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je spoj formule
[image]
,
ili njegova farmaceutski prihvatljiva sol.
14. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je spoj formule
[image]
,
ili njegova farmaceutski prihvatljiva sol.
15. Farmaceutski pripravak, naznačen time što sadrži terapijski djelotvornu količinu spoja u skladu s bilo kojim od patentnih zahtjeva 1 do 14, ili njegove farmaceutski prihvatljive soli, i farmaceutski prihvatljivu pomoćnu tvar, razrjeđivač ili podlogu.
16. Pripravak u skladu s patentnim zahtjevom 15, naznačen time što dodatno sadrži najmanje jedno dodatno antidijabetično sredstvo.
17. Pripravak u skladu s patentnim zahtjevom 16, naznačen time što se navedeno antidijabetično sredstvo bira iz skupine koju čine metformin, acetoheksamid, klorpropamid, Diabinese, glibenklamid, glipizid, gliburid, glimepirid, gliklazid, glipentid, glikvidon, glizolamid, tolazamid, tolbutamid, tendamistat, trestatin, akarboza, adipozin, kamigliboza, emiglitat, miglitol, vogliboza, pradimicin-Q, salbostatin, balaglitazon, ciglitazon, darglitazon, englitazon, izaglitazon, pioglitazon, roziglitazon, troglitazon, eksendin-3, eksendin-4, troduskvemin, rezveratrol, hirtiosalni ekstrakt, sitagliptin, vildagliptin, alogliptin i saksagliptin.
18. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 14, ili pripravak u skladu s bilo kojim od patentnih zahtjeva 15 do 17, naznačeni time što su namijenjeni upotrebi u liječenju ili odgađanju napredovanja ili početka dijabetesa tip 2.
19. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 14, ili pripravak u skladu s bilo kojim od patentnih zahtjeva 15 do 17, naznačeni time što su namijenjeni upotrebi u liječenju nealkoholne bolesti masne jetre (NAFLD) ili jetrene otpornosti na inzulin.
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| US25982309P | 2009-11-10 | 2009-11-10 | |
| PCT/IB2010/054908 WO2011058474A1 (en) | 2009-11-10 | 2010-10-29 | N1-pyrazolospiroketone acetyl-coa carboxylase inhibitors |
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| PT2699576E (pt) * | 2011-04-22 | 2016-03-09 | Pfizer | Derivados de pirazoloespirocetona para utilização como inibidores de acetil-coa carboxilase |
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