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- Withdrawn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 (https=) | 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 (https=) |
| JP (1) | JP2004520393A (https=) |
| CA (1) | CA2436738A1 (https=) |
| WO (1) | WO2002062798A2 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7041691B1 (en) | 1999-06-30 | 2006-05-09 | Amgen Inc. | Compounds for the modulation of PPARγ activity |
| WO2001082916A2 (en) | 2000-05-03 | 2001-11-08 | Tularik Inc. | Combination therapeutic compositions and methods of use |
| US20030171399A1 (en) | 2000-06-28 | 2003-09-11 | Tularik Inc. | Quinolinyl and benzothiazolyl modulators |
| 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 |
| JP4691988B2 (ja) * | 2002-10-03 | 2011-06-01 | 小野薬品工業株式会社 | Ｌｐａ受容体拮抗剤 |
| US7550590B2 (en) * | 2003-03-25 | 2009-06-23 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7223761B2 (en) | 2003-10-03 | 2007-05-29 | Amgen Inc. | Salts and polymorphs of a potent antidiabetic compound |
| EA201491749A1 (ru) * | 2012-03-22 | 2015-01-30 | ТРАНСТЕК ФАРМА, ЭлЭлСи | Трис-(гидроксиметил)аминометановые соли низкомолекулярного агониста glp1r, их фармацевтические композиции и применение |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL127296A (en) * | 1996-12-31 | 2003-01-12 | Reddy Research Foundation | Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them |
| ATE286032T1 (de) * | 1998-04-23 | 2005-01-15 | Reddys Lab Ltd Dr | Heterozyklische verbindungen,und deren verwendung in arzneimittel,verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammenstellungen |
-
2002
- 2002-02-05 JP JP2002563151A patent/JP2004520393A/ja not_active Withdrawn
- 2002-02-05 WO PCT/IB2002/000312 patent/WO2002062798A2/en not_active Ceased
- 2002-02-05 EP EP02711124A patent/EP1363913A2/en not_active Withdrawn
- 2002-02-05 CA CA002436738A patent/CA2436738A1/en not_active Abandoned
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