JP2004520393A5 - - Google Patents
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- Publication number
- JP2004520393A5 JP2004520393A5 JP2002563151A JP2002563151A JP2004520393A5 JP 2004520393 A5 JP2004520393 A5 JP 2004520393A5 JP 2002563151 A JP2002563151 A JP 2002563151A JP 2002563151 A JP2002563151 A JP 2002563151A JP 2004520393 A5 JP2004520393 A5 JP 2004520393A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- ethoxy
- oxo
- salt
- ethyl
- 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.)
- Withdrawn
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- -1 monoalkylamino Chemical group 0.000 claims 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 57
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 55
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims 48
- UAPQKLTXQPVJGQ-UHFFFAOYSA-N 3-[4-[2-(1,5-dimethyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound CCCC1=NN(C)C(C2=O)=C1N=C(C)N2CCOC1=CC=C(CC(OCC)C(O)=O)C=C1 UAPQKLTXQPVJGQ-UHFFFAOYSA-N 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 12
- 239000003814 drug Substances 0.000 claims 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 9
- 201000010099 disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 8
- 206010022489 Insulin Resistance Diseases 0.000 claims 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 5
- ZRRNJJURLBXWLL-REWJHTLYSA-N (2r,3r,4r,5s)-6-(octylamino)hexane-1,2,3,4,5-pentol Chemical compound CCCCCCCCNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO ZRRNJJURLBXWLL-REWJHTLYSA-N 0.000 claims 4
- 208000002705 Glucose Intolerance Diseases 0.000 claims 4
- 206010020772 Hypertension Diseases 0.000 claims 4
- 208000008589 Obesity Diseases 0.000 claims 4
- 208000001132 Osteoporosis Diseases 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 208000017169 kidney disease Diseases 0.000 claims 4
- 229910003002 lithium salt Inorganic materials 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 235000020824 obesity Nutrition 0.000 claims 4
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 4
- 201000009104 prediabetes syndrome Diseases 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 208000011580 syndromic disease Diseases 0.000 claims 4
- BHNOABDGWRVNFJ-ZSCHJXSPSA-N (2s)-2,6-diaminohexanoic acid;2-ethoxy-3-[4-[2-(2-ethyl-6-oxo-4-phenylpyrimidin-1-yl)ethoxy]phenyl]propanoic acid Chemical compound NCCCC[C@H](N)C(O)=O.C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(=O)C=C(C=2C=CC=CC=2)N=C1CC BHNOABDGWRVNFJ-ZSCHJXSPSA-N 0.000 claims 3
- LSTOEDCJTSIOHJ-ZSCHJXSPSA-N (2s)-2,6-diaminohexanoic acid;3-[4-[2-(1,5-dimethyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound NCCCC[C@H](N)C(O)=O.CCCC1=NN(C)C(C2=O)=C1N=C(C)N2CCOC1=CC=C(CC(OCC)C(O)=O)C=C1 LSTOEDCJTSIOHJ-ZSCHJXSPSA-N 0.000 claims 3
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 claims 3
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 claims 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- DRJWRWKPEAMGKN-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;2-ethoxy-3-[4-[2-(2-ethyl-6-oxo-4-phenylpyrimidin-1-yl)ethoxy]phenyl]propanoic acid Chemical compound OCC(N)(CO)CO.C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(=O)C=C(C=2C=CC=CC=2)N=C1CC DRJWRWKPEAMGKN-UHFFFAOYSA-N 0.000 claims 3
- WJRONFWTXGGIFO-UHFFFAOYSA-N 2-aminoguanidine;2-ethoxy-3-[4-[2-(2-ethyl-6-oxo-4-phenylpyrimidin-1-yl)ethoxy]phenyl]propanoic acid Chemical compound NN=C(N)N.C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(=O)C=C(C=2C=CC=CC=2)N=C1CC WJRONFWTXGGIFO-UHFFFAOYSA-N 0.000 claims 3
- WRUKUEDMHMSEJH-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(2-ethyl-4-oxoquinazolin-3-yl)ethoxy]phenyl]propanoic acid;n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1.C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(=O)C2=CC=CC=C2N=C1CC WRUKUEDMHMSEJH-UHFFFAOYSA-N 0.000 claims 3
- XLDQCIVDPJEVRX-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(2-ethyl-6-oxo-4-phenylpyrimidin-1-yl)ethoxy]phenyl]propanoic acid;n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1.C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(=O)C=C(C=2C=CC=CC=2)N=C1CC XLDQCIVDPJEVRX-UHFFFAOYSA-N 0.000 claims 3
- CEDOJTDGYCORRG-DDAWSSNUSA-N 3-[4-[2-(1,5-dimethyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]-2-ethoxypropanoic acid (2R,3R,4R,5S)-6-(octylamino)hexane-1,2,3,4,5-pentol Chemical compound CCCCCCCCNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCC1=NN(C)C(C2=O)=C1N=C(C)N2CCOC1=CC=C(CC(OCC)C(O)=O)C=C1 CEDOJTDGYCORRG-DDAWSSNUSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- 239000004475 Arginine Substances 0.000 claims 3
- VTOAMBIACMEITR-UHFFFAOYSA-L CCOC(CC1=CC=C(C=C1)OCCN2C(=O)C3=CC=CC=C3N=C2N4CCCCC4)C(=O)[O-].CCOC(CC1=CC=C(C=C1)OCCN2C(=O)C3=CC=CC=C3N=C2N4CCCCC4)C(=O)[O-].[Mg+2] Chemical compound CCOC(CC1=CC=C(C=C1)OCCN2C(=O)C3=CC=CC=C3N=C2N4CCCCC4)C(=O)[O-].CCOC(CC1=CC=C(C=C1)OCCN2C(=O)C3=CC=CC=C3N=C2N4CCCCC4)C(=O)[O-].[Mg+2] VTOAMBIACMEITR-UHFFFAOYSA-L 0.000 claims 3
- FWPKZPBXZJYCCE-UHFFFAOYSA-L CCOC(CC1=CC=C(C=C1)OCCN2C(=O)C3=CC=CC=C3N=C2N4CCOCC4)C(=O)[O-].CCOC(CC1=CC=C(C=C1)OCCN2C(=O)C3=CC=CC=C3N=C2N4CCOCC4)C(=O)[O-].[Mg+2] Chemical compound CCOC(CC1=CC=C(C=C1)OCCN2C(=O)C3=CC=CC=C3N=C2N4CCOCC4)C(=O)[O-].CCOC(CC1=CC=C(C=C1)OCCN2C(=O)C3=CC=CC=C3N=C2N4CCOCC4)C(=O)[O-].[Mg+2] FWPKZPBXZJYCCE-UHFFFAOYSA-L 0.000 claims 3
- 229920001268 Cholestyramine Polymers 0.000 claims 3
- 229920002911 Colestipol Polymers 0.000 claims 3
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 3
- 239000004472 Lysine Substances 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 3
- 235000009697 arginine Nutrition 0.000 claims 3
- FPRSPUHXEPWUBZ-HNNXBMFYSA-N benzyl (2s)-2-amino-3-phenylpropanoate Chemical compound C([C@H](N)C(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 FPRSPUHXEPWUBZ-HNNXBMFYSA-N 0.000 claims 3
- KHCBJBPASPAHCS-UHFFFAOYSA-L calcium;2-ethoxy-3-[4-[2-(2-ethyl-6-oxo-4-phenylpyrimidin-1-yl)ethoxy]phenyl]propanoate Chemical compound [Ca+2].C1=CC(CC(OCC)C([O-])=O)=CC=C1OCCN1C(=O)C=C(C=2C=CC=CC=2)N=C1CC.C1=CC(CC(OCC)C([O-])=O)=CC=C1OCCN1C(=O)C=C(C=2C=CC=CC=2)N=C1CC KHCBJBPASPAHCS-UHFFFAOYSA-L 0.000 claims 3
- KCWVTLRNXPDNBW-UHFFFAOYSA-L calcium;3-[4-[2-(1,5-dimethyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]-2-ethoxypropanoate Chemical compound [Ca+2].CCCC1=NN(C)C(C2=O)=C1N=C(C)N2CCOC1=CC=C(CC(OCC)C([O-])=O)C=C1.CCCC1=NN(C)C(C2=O)=C1N=C(C)N2CCOC1=CC=C(CC(OCC)C([O-])=O)C=C1 KCWVTLRNXPDNBW-UHFFFAOYSA-L 0.000 claims 3
- GMRWGQCZJGVHKL-UHFFFAOYSA-N colestipol Chemical compound ClCC1CO1.NCCNCCNCCNCCN GMRWGQCZJGVHKL-UHFFFAOYSA-N 0.000 claims 3
- 229960002604 colestipol Drugs 0.000 claims 3
- 239000012971 dimethylpiperazine Substances 0.000 claims 3
- 229940125753 fibrate Drugs 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- YAJFHRPDYSJOTM-UHFFFAOYSA-M lithium;2-ethoxy-3-[4-[2-(2-ethyl-4-oxoquinazolin-3-yl)ethoxy]phenyl]propanoate Chemical compound [Li+].C1=CC(CC(OCC)C([O-])=O)=CC=C1OCCN1C(=O)C2=CC=CC=C2N=C1CC YAJFHRPDYSJOTM-UHFFFAOYSA-M 0.000 claims 3
- PAZMPIHKBIZHBL-UHFFFAOYSA-M lithium;2-ethoxy-3-[4-[2-(2-ethyl-6-oxo-4-phenylpyrimidin-1-yl)ethoxy]phenyl]propanoate Chemical compound [Li+].C1=CC(CC(OCC)C([O-])=O)=CC=C1OCCN1C(=O)C=C(C=2C=CC=CC=2)N=C1CC PAZMPIHKBIZHBL-UHFFFAOYSA-M 0.000 claims 3
- 235000018977 lysine Nutrition 0.000 claims 3
- IDLFHYIDADWWPH-UHFFFAOYSA-L magnesium;2-ethoxy-3-[4-[2-(2-ethyl-4-oxoquinazolin-3-yl)ethoxy]phenyl]propanoate Chemical compound [Mg+2].C1=CC(CC(OCC)C([O-])=O)=CC=C1OCCN1C(=O)C2=CC=CC=C2N=C1CC.C1=CC(CC(OCC)C([O-])=O)=CC=C1OCCN1C(=O)C2=CC=CC=C2N=C1CC IDLFHYIDADWWPH-UHFFFAOYSA-L 0.000 claims 3
- CWKXCPCLKVHOBR-UHFFFAOYSA-L magnesium;2-ethoxy-3-[4-[2-(2-ethyl-6-oxo-4-phenylpyrimidin-1-yl)ethoxy]phenyl]propanoate Chemical compound [Mg+2].C1=CC(CC(OCC)C([O-])=O)=CC=C1OCCN1C(=O)C=C(C=2C=CC=CC=2)N=C1CC.C1=CC(CC(OCC)C([O-])=O)=CC=C1OCCN1C(=O)C=C(C=2C=CC=CC=2)N=C1CC CWKXCPCLKVHOBR-UHFFFAOYSA-L 0.000 claims 3
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims 3
- 229960003105 metformin Drugs 0.000 claims 3
- SZJUWKPNWWCOPG-UHFFFAOYSA-N methyl 2-anilinoacetate Chemical compound COC(=O)CNC1=CC=CC=C1 SZJUWKPNWWCOPG-UHFFFAOYSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- OVXHMIWSVYZPEY-UHFFFAOYSA-N n-cyclohexylcyclohexanamine;2-ethoxy-3-[4-[2-(2-ethyl-6-oxo-4-phenylpyrimidin-1-yl)ethoxy]phenyl]propanoic acid Chemical compound C1CCCCC1NC1CCCCC1.C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(=O)C=C(C=2C=CC=CC=2)N=C1CC OVXHMIWSVYZPEY-UHFFFAOYSA-N 0.000 claims 3
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 claims 3
- 229960003512 nicotinic acid Drugs 0.000 claims 3
- 235000001968 nicotinic acid Nutrition 0.000 claims 3
- 239000011664 nicotinic acid Substances 0.000 claims 3
- FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 claims 3
- 229960003912 probucol Drugs 0.000 claims 3
- KYFZPRNJKCLFBX-UHFFFAOYSA-M sodium;2-ethoxy-3-[4-[2-(2-ethyl-6-oxo-4-phenylpyrimidin-1-yl)ethoxy]phenyl]propanoate Chemical compound [Na+].C1=CC(CC(OCC)C([O-])=O)=CC=C1OCCN1C(=O)C=C(C=2C=CC=CC=2)N=C1CC KYFZPRNJKCLFBX-UHFFFAOYSA-M 0.000 claims 3
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims 3
- JRZWZCNPHDSCRM-ZSCHJXSPSA-N (2s)-2,6-diaminohexanoic acid;2-ethoxy-3-[4-[2-(2-ethyl-4-oxoquinazolin-3-yl)ethoxy]phenyl]propanoic acid Chemical compound NCCCC[C@H](N)C(O)=O.C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(=O)C2=CC=CC=C2N=C1CC JRZWZCNPHDSCRM-ZSCHJXSPSA-N 0.000 claims 2
- LTLZYEVVBNYXJJ-VWMHFEHESA-N (2s)-2-amino-5-(diaminomethylideneamino)pentanoic acid;2-ethoxy-3-[4-[2-(2-ethyl-6-oxo-4-phenylpyrimidin-1-yl)ethoxy]phenyl]propanoic acid Chemical compound OC(=O)[C@@H](N)CCCNC(N)=N.C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(=O)C=C(C=2C=CC=CC=2)N=C1CC LTLZYEVVBNYXJJ-VWMHFEHESA-N 0.000 claims 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- XWSBPADOZLNAHB-UHFFFAOYSA-N 2-aminoguanidine;carbonic acid;2-ethoxy-3-[4-[2-(2-ethyl-4-oxoquinazolin-3-yl)ethoxy]phenyl]propanoic acid Chemical compound OC(O)=O.NNC(N)=N.C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(=O)C2=CC=CC=C2N=C1CC XWSBPADOZLNAHB-UHFFFAOYSA-N 0.000 claims 2
- XAWRDWCILPXSAR-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(5-ethyl-1-methyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]propanoic acid Chemical compound CCCC1=NN(C)C(C2=O)=C1N=C(CC)N2CCOC1=CC=C(CC(OCC)C(O)=O)C=C1 XAWRDWCILPXSAR-UHFFFAOYSA-N 0.000 claims 2
- 206010003210 Arteriosclerosis Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 208000002249 Diabetes Complications Diseases 0.000 claims 2
- 206010012655 Diabetic complications Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 208000030814 Eating disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- 206010018364 Glomerulonephritis Diseases 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
- QMXOFBXZEKTJIK-UHFFFAOYSA-N Glycinol Natural products C1=C(O)C=C2OCC3(O)C4=CC=C(O)C=C4OC3C2=C1 QMXOFBXZEKTJIK-UHFFFAOYSA-N 0.000 claims 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 108010028554 LDL Cholesterol Proteins 0.000 claims 2
- 102000016267 Leptin Human genes 0.000 claims 2
- 108010092277 Leptin Proteins 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 206010068871 Myotonic dystrophy Diseases 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010029164 Nephrotic syndrome Diseases 0.000 claims 2
- 206010033645 Pancreatitis Diseases 0.000 claims 2
- 206010036049 Polycystic ovaries Diseases 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000017442 Retinal disease Diseases 0.000 claims 2
- 206010038923 Retinopathy Diseases 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 108010069201 VLDL Cholesterol Proteins 0.000 claims 2
- 206010048214 Xanthoma Diseases 0.000 claims 2
- 206010048215 Xanthomatosis Diseases 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 2
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 2
- 239000011575 calcium Chemical group 0.000 claims 2
- 229910052791 calcium Inorganic materials 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims 2
- 230000020411 cell activation Effects 0.000 claims 2
- 208000029078 coronary artery disease Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 210000002889 endothelial cell Anatomy 0.000 claims 2
- BQUDLWUEXZTHGM-UHFFFAOYSA-N ethyl propaneperoxoate Chemical compound CCOOC(=O)CC BQUDLWUEXZTHGM-UHFFFAOYSA-N 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 235000021588 free fatty acids Nutrition 0.000 claims 2
- 206010061989 glomerulosclerosis Diseases 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 2
- 201000001421 hyperglycemia Diseases 0.000 claims 2
- 230000001631 hypertensive effect Effects 0.000 claims 2
- 150000002500 ions Chemical class 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims 2
- 229940039781 leptin Drugs 0.000 claims 2
- 229910052744 lithium Inorganic materials 0.000 claims 2
- 239000011777 magnesium Chemical group 0.000 claims 2
- KGFHYUURPKAYFP-UHFFFAOYSA-L magnesium 3-[4-[2-(2-azido-4-oxoquinazolin-3-yl)ethoxy]phenyl]-2-ethoxypropanoate Chemical compound [Mg++].CCOC(Cc1ccc(OCCn2c(N=[N+]=[N-])nc3ccccc3c2=O)cc1)C([O-])=O.CCOC(Cc1ccc(OCCn2c(N=[N+]=[N-])nc3ccccc3c2=O)cc1)C([O-])=O KGFHYUURPKAYFP-UHFFFAOYSA-L 0.000 claims 2
- 201000009925 nephrosclerosis Diseases 0.000 claims 2
- 230000008289 pathophysiological mechanism Effects 0.000 claims 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 239000011591 potassium Chemical group 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- RHLNBHVQUCRNKI-UHFFFAOYSA-M potassium;2-ethoxy-3-[4-[2-(2-ethyl-6-oxo-4-phenylpyrimidin-1-yl)ethoxy]phenyl]propanoate Chemical compound [K+].C1=CC(CC(OCC)C([O-])=O)=CC=C1OCCN1C(=O)C=C(C=2C=CC=CC=2)N=C1CC RHLNBHVQUCRNKI-UHFFFAOYSA-M 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 150000003626 triacylglycerols Chemical class 0.000 claims 2
- 229960000281 trometamol Drugs 0.000 claims 2
- FSDGNAWXVDJFPV-WCCKRBBISA-N (2s)-2-amino-5-(diaminomethylideneamino)pentanoic acid;propanoic acid Chemical compound CCC(O)=O.OC(=O)[C@@H](N)CCCNC(N)=N FSDGNAWXVDJFPV-WCCKRBBISA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims 1
- MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical compound OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 229940123934 Reductase inhibitor Drugs 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 1
- 239000000920 calcium hydroxide Substances 0.000 claims 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims 1
- 239000000347 magnesium hydroxide Substances 0.000 claims 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- IPIQBVLYAZBZSC-UHFFFAOYSA-N n-cyclohexylcyclohexanamine;2-ethoxy-3-[4-[2-(2-ethyl-4-oxoquinazolin-3-yl)ethoxy]phenyl]propanoic acid Chemical compound C1CCCCC1NC1CCCCC1.C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(=O)C2=CC=CC=C2N=C1CC IPIQBVLYAZBZSC-UHFFFAOYSA-N 0.000 claims 1
- ZRASGWZMJQFFPK-UHFFFAOYSA-N n-cyclohexylcyclohexanamine;2-ethoxy-3-[4-[2-(5-ethyl-1-methyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]propanoic acid Chemical compound C1CCCCC1NC1CCCCC1.CCCC1=NN(C)C(C2=O)=C1N=C(CC)N2CCOC1=CC=C(CC(OCC)C(O)=O)C=C1 ZRASGWZMJQFFPK-UHFFFAOYSA-N 0.000 claims 1
- BWILYWWHXDGKQA-UHFFFAOYSA-M potassium propanoate Chemical compound [K+].CCC([O-])=O BWILYWWHXDGKQA-UHFFFAOYSA-M 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26659501P | 2001-02-05 | 2001-02-05 | |
| IN813CH2001 | 2001-10-04 | ||
| PCT/IB2002/000312 WO2002062798A2 (en) | 2001-02-05 | 2002-02-05 | Salts of pyrimidine derivatives for use against coronary heart disease and atherosclerose |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004520393A JP2004520393A (ja) | 2004-07-08 |
| JP2004520393A5 true JP2004520393A5 (ko) | 2005-12-22 |
Family
ID=26324876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002563151A Withdrawn JP2004520393A (ja) | 2001-02-05 | 2002-02-05 | ヘテロ環化号物の薬学的に許容可能な塩 |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1363913A2 (ko) |
| JP (1) | JP2004520393A (ko) |
| CA (1) | CA2436738A1 (ko) |
| WO (1) | WO2002062798A2 (ko) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6653332B2 (en) | 2000-05-03 | 2003-11-25 | Tularik Inc. | Combination therapeutic compositions and method of use |
| EP1398032A1 (en) * | 2002-09-10 | 2004-03-17 | PheneX Pharmaceuticals AG | 4-Oxo-quinazolines as LXR nuclear receptor binding compounds |
| EP1407774A1 (en) * | 2002-09-10 | 2004-04-14 | LION Bioscience AG | 2-Amino-4-quinazolinones as LXR nuclear receptor binding compounds |
| AU2003241836A1 (en) | 2002-10-03 | 2004-04-23 | Ono Pharmaceutical Co., Ltd. | Lpa receptor antagonists |
| US20040242568A1 (en) * | 2003-03-25 | 2004-12-02 | Syrrx, Inc. | Dipeptidyl peptidase inhibitors |
| KR102158992B1 (ko) * | 2012-03-22 | 2020-09-23 | 브이티브이 테라퓨틱스 엘엘씨 | 소-분자 ｇｌｐ1ｒ 아고니스트의 트리스(하이드록시메틸)아미노메탄 염과 그것의 제약 조성물 및 사용 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1190434C (zh) * | 1996-12-31 | 2005-02-23 | 雷迪实验室有限公司 | 新的杂环化合物、其制备方法和含有它们的药物组合物及其在治疗糖尿病和相关疾病中的应用 |
| CN1208326C (zh) * | 1998-04-23 | 2005-06-29 | 雷迪实验室有限公司 | 杂环化合物及其在医药方面的应用、其制备方法及含有它们的药物组合物 |
-
2002
- 2002-02-05 CA CA002436738A patent/CA2436738A1/en not_active Abandoned
- 2002-02-05 WO PCT/IB2002/000312 patent/WO2002062798A2/en not_active Application Discontinuation
- 2002-02-05 EP EP02711124A patent/EP1363913A2/en not_active Withdrawn
- 2002-02-05 JP JP2002563151A patent/JP2004520393A/ja not_active Withdrawn
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