JP2008533063A5 - - Google Patents
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- JP2008533063A5 JP2008533063A5 JP2008501193A JP2008501193A JP2008533063A5 JP 2008533063 A5 JP2008533063 A5 JP 2008533063A5 JP 2008501193 A JP2008501193 A JP 2008501193A JP 2008501193 A JP2008501193 A JP 2008501193A JP 2008533063 A5 JP2008533063 A5 JP 2008533063A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- alkoxy
- hydrogen
- compound
- 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.)
- Pending
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims 26
- 239000001257 hydrogen Substances 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 15
- 150000002431 hydrogen Chemical class 0.000 claims 15
- 229910052731 fluorine Inorganic materials 0.000 claims 14
- 239000011737 fluorine Substances 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 239000012453 solvate Substances 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 9
- 229910052801 chlorine Inorganic materials 0.000 claims 9
- 239000000460 chlorine Substances 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 4
- 239000003112 inhibitor Substances 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- -1 nitro, cyano, amino Chemical group 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 206010003210 Arteriosclerosis Diseases 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- 208000032928 Dyslipidaemia Diseases 0.000 claims 3
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 3
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 239000012442 inert solvent Substances 0.000 claims 3
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 239000003613 bile acid Substances 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 239000005495 thyroid hormone Substances 0.000 claims 2
- 229940036555 thyroid hormone Drugs 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 claims 1
- KCJKKFMNAXDVEL-UHFFFAOYSA-N 2-phenyl-4-(2,4,5-trichlorophenoxy)pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC(Cl)=C(Cl)C=C1Cl KCJKKFMNAXDVEL-UHFFFAOYSA-N 0.000 claims 1
- BUAKMFBGWYVGCD-UHFFFAOYSA-N 4-(2,3-dimethylphenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound CC1=CC=CC(OC=2C(=CN=C(N=2)C=2C=CC=CC=2)C(O)=O)=C1C BUAKMFBGWYVGCD-UHFFFAOYSA-N 0.000 claims 1
- WDZBQJRINYWGMV-UHFFFAOYSA-N 4-(2-methylphenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound CC1=CC=CC=C1OC1=NC(C=2C=CC=CC=2)=NC=C1C(O)=O WDZBQJRINYWGMV-UHFFFAOYSA-N 0.000 claims 1
- 239000005541 ACE inhibitor Substances 0.000 claims 1
- 102000015427 Angiotensins Human genes 0.000 claims 1
- 108010064733 Angiotensins Proteins 0.000 claims 1
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 1
- 102100033868 Cannabinoid receptor 1 Human genes 0.000 claims 1
- 101710187010 Cannabinoid receptor 1 Proteins 0.000 claims 1
- 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- 102000004877 Insulin Human genes 0.000 claims 1
- 108090001061 Insulin Proteins 0.000 claims 1
- 229940127470 Lipase Inhibitors Drugs 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 102100031545 Microsomal triglyceride transfer protein large subunit Human genes 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 1
- 108010016731 PPAR gamma Proteins 0.000 claims 1
- 102100038824 Peroxisome proliferator-activated receptor delta Human genes 0.000 claims 1
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 claims 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims 1
- AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical class IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000003463 adsorbent Substances 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 239000003146 anticoagulant agent Substances 0.000 claims 1
- 229940127219 anticoagulant drug Drugs 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 claims 1
- 229940125708 antidiabetic agent Drugs 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 229940127218 antiplatelet drug Drugs 0.000 claims 1
- 239000002876 beta blocker Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 claims 1
- 229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000002934 diuretic Substances 0.000 claims 1
- 229940030606 diuretics Drugs 0.000 claims 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims 1
- WWXARJSFXLLRPG-UHFFFAOYSA-N ethyl 2-phenyl-4-(2,4,5-trichlorophenoxy)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC(Cl)=C(Cl)C=C1Cl WWXARJSFXLLRPG-UHFFFAOYSA-N 0.000 claims 1
- BMUIXCLLFWRJOQ-UHFFFAOYSA-N ethyl 4-(2,3-dimethylphenoxy)-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC=CC(C)=C1C BMUIXCLLFWRJOQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229940125753 fibrate Drugs 0.000 claims 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 229940125396 insulin Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 108091008765 peroxisome proliferator-activated receptors β/δ Proteins 0.000 claims 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 229940031439 squalene Drugs 0.000 claims 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 0 *c1cc(-c(nc2)nc(CC3=C(*)C=C*C=C3)c2C(O)=O)c(*)c(*)c1* Chemical compound *c1cc(-c(nc2)nc(CC3=C(*)C=C*C=C3)c2C(O)=O)c(*)c(*)c1* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005011447 | 2005-03-12 | ||
| DE102005027150A DE102005027150A1 (de) | 2005-03-12 | 2005-06-11 | Pyrimidincarbonsäure-Derivate und ihre Verwendung |
| PCT/EP2006/002054 WO2006097220A1 (de) | 2005-03-12 | 2006-03-07 | Pyrimidincarbonsäure-derivate und ihre verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008533063A JP2008533063A (ja) | 2008-08-21 |
| JP2008533063A5 true JP2008533063A5 (https=) | 2009-04-23 |
Family
ID=36218368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008501193A Pending JP2008533063A (ja) | 2005-03-12 | 2006-03-07 | ピリミジンカルボン酸誘導体およびそれらの使用 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20080194598A1 (https=) |
| EP (1) | EP1866289A1 (https=) |
| JP (1) | JP2008533063A (https=) |
| KR (1) | KR20070116876A (https=) |
| AR (1) | AR055744A1 (https=) |
| AU (1) | AU2006224812A1 (https=) |
| BR (1) | BRPI0609207A2 (https=) |
| CA (1) | CA2600681A1 (https=) |
| DE (1) | DE102005027150A1 (https=) |
| DO (1) | DOP2006000062A (https=) |
| GT (1) | GT200600109A (https=) |
| IL (1) | IL185895A0 (https=) |
| MX (1) | MX2007011070A (https=) |
| PE (1) | PE20061348A1 (https=) |
| TW (1) | TW200724532A (https=) |
| UY (1) | UY29416A1 (https=) |
| WO (1) | WO2006097220A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1877384T3 (da) | 2005-05-06 | 2011-08-15 | Du Pont | Fremgangsmåde til fremstilling af eventuelt 2-substituerede 1,6-dihydro-6-oxo-4-pyrimidincarboxylsyrer |
| DE102006043520A1 (de) * | 2006-09-12 | 2008-03-27 | Bayer Healthcare Ag | 2-Phenoxynikotinsäure-Derivate und ihre Verwendung |
| DE102006043519A1 (de) * | 2006-09-12 | 2008-03-27 | Bayer Healthcare Ag | 4-Phenoxynikotinsäure-Derivate und ihre Verwendung |
| EA020531B1 (ru) * | 2007-04-13 | 2014-11-28 | Милленниум Фармасьютикалз, Инк. | КОМБИНИРОВАННАЯ ТЕРАПИЯ АНТИКОАГУЛИРУЮЩЕГО СРЕДСТВА С СОЕДИНЕНИЕМ, КОТОРОЕ ДЕЙСТВУЕТ КАК ИНГИБИТОР ФАКТОРА Ха |
| DE102007042754A1 (de) | 2007-09-07 | 2009-03-12 | Bayer Healthcare Ag | Substituierte 6-Phenylnikotinsäuren und ihre Verwendung |
| DE102007061757A1 (de) | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Substituierte 2-Phenylpyrimidin-5-carbonsäuren und ihre Verwendung |
| DE102007061756A1 (de) | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Substituierte 4-Aminopyrimidin-5-carbonsäuren und ihre Verwendung |
| ES2552657T3 (es) | 2010-05-26 | 2015-12-01 | Satiogen Pharmaceuticals, Inc. | Inhibidores del reciclado de ácidos biliares y saciógenos para el tratamiento de diabetes, obesidad, y afecciones gastrointestinales inflamatorias |
| EP2612669A4 (en) | 2010-08-31 | 2014-05-14 | Snu R&Db Foundation | USING THE FÖTAL REPROGRAMMING OF A PPAR AGONIST |
| AU2012328526B2 (en) | 2011-10-28 | 2017-05-25 | Shire Human Genetic Therapies, Inc. | Bile acid recycling inhibitors for treatment of pediatric cholestatic liver diseases |
| US20130108573A1 (en) | 2011-10-28 | 2013-05-02 | Lumena Pharmaceuticals, Inc. | Bile Acid Recycling Inhibitors for Treatment of Hypercholemia and Cholestatic Liver Disease |
| AU2014229050A1 (en) | 2013-03-15 | 2015-10-22 | Lumena Pharmaceuticals Llc | Bile acid recycling inhibitors for treatment of Barrett's esophagus and gastroesophageal reflux disease |
| CA2907230A1 (en) | 2013-03-15 | 2014-09-18 | Lumena Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of primary sclerosing cholangitis and inflammatory bowel disease |
| EP3923943B1 (en) | 2019-02-12 | 2024-07-31 | Mirum Pharmaceuticals, Inc. | Genotype and dose-dependent response to an asbti in patients with bile salt export pump deficiency |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU72201A (sh) * | 1999-04-28 | 2005-07-19 | Aventis Pharma Deutschland Gmbh. | Derivati di-aril kiseline kao ppar receptorski ligandi |
| YU39503A (sh) * | 2000-11-22 | 2006-05-25 | F. Hoffmann-La Roche Ag. | Derivati pirimidina |
-
2005
- 2005-06-11 DE DE102005027150A patent/DE102005027150A1/de not_active Withdrawn
-
2006
- 2006-03-07 US US11/886,289 patent/US20080194598A1/en not_active Abandoned
- 2006-03-07 WO PCT/EP2006/002054 patent/WO2006097220A1/de not_active Ceased
- 2006-03-07 EP EP06707442A patent/EP1866289A1/de not_active Withdrawn
- 2006-03-07 AU AU2006224812A patent/AU2006224812A1/en not_active Abandoned
- 2006-03-07 BR BRPI0609207-1A patent/BRPI0609207A2/pt not_active Application Discontinuation
- 2006-03-07 CA CA002600681A patent/CA2600681A1/en not_active Abandoned
- 2006-03-07 JP JP2008501193A patent/JP2008533063A/ja active Pending
- 2006-03-07 KR KR1020077023311A patent/KR20070116876A/ko not_active Withdrawn
- 2006-03-07 MX MX2007011070A patent/MX2007011070A/es not_active Application Discontinuation
- 2006-03-09 AR ARP060100888A patent/AR055744A1/es not_active Application Discontinuation
- 2006-03-10 GT GT200600109A patent/GT200600109A/es unknown
- 2006-03-10 PE PE2006000274A patent/PE20061348A1/es not_active Application Discontinuation
- 2006-03-10 UY UY29416A patent/UY29416A1/es not_active Application Discontinuation
- 2006-03-10 TW TW095108034A patent/TW200724532A/zh unknown
- 2006-03-10 DO DO2006000062A patent/DOP2006000062A/es unknown
-
2007
- 2007-09-11 IL IL185895A patent/IL185895A0/en unknown
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