SK4132003A3 - Propionic acid derivatives, the process for their preparation, pharmaceutical composition comprising them, use thereof and intermediates for producing them - Google Patents

Propionic acid derivatives, the process for their preparation, pharmaceutical composition comprising them, use thereof and intermediates for producing them Download PDF

Info

Publication number: SK4132003A3
Authority: SK; Slovakia
Prior art keywords: group; methyl; amino; carbon atoms; hydrogen atom
Prior art date: 2000-10-05

Application number

SK413-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Klaus Urbahns

Michael Woltering

Susanne Nikolic

Josef Pernerstorfer

Berthold Hinzen

Elke Dittrich-Wengenroth

Hilmar Bischoff

Claudia Hirth-Dietrich

Klemens Lustig

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

2000-10-05

Filing date

2001-09-24

Publication date

2004-02-03

2001-05-22 Priority claimed from DE10124905A external-priority patent/DE10124905A1/de

2001-09-24 Application filed by Bayer Ag filed Critical Bayer Ag

2004-02-03 Publication of SK4132003A3 publication Critical patent/SK4132003A3/sk

Links

238000000034 method Methods 0.000 title claims description 31
150000005599 propionic acid derivatives Chemical class 0.000 title claims description 22
229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 title claims description 21
238000002360 preparation method Methods 0.000 title claims description 10
230000008569 process Effects 0.000 title claims description 10
239000000543 intermediate Substances 0.000 title description 4
239000008194 pharmaceutical composition Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 126
238000004519 manufacturing process Methods 0.000 claims abstract description 10
230000003213 activating effect Effects 0.000 claims abstract description 3
-1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 226
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 167
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 166
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
125000004432 carbon atom Chemical group C* 0.000 claims description 76
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 67
239000002904 solvent Substances 0.000 claims description 45
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 40
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 33
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 29
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 23
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 22
229910052736 halogen Inorganic materials 0.000 claims description 22
150000002367 halogens Chemical class 0.000 claims description 22
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 22
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
229910052760 oxygen Inorganic materials 0.000 claims description 19
239000001301 oxygen Substances 0.000 claims description 19
229910052717 sulfur Inorganic materials 0.000 claims description 19
239000011593 sulfur Chemical group 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 18
229910052799 carbon Inorganic materials 0.000 claims description 17
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 16
150000001721 carbon Chemical group 0.000 claims description 16
239000000126 substance Substances 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 14
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 12
238000011282 treatment Methods 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
150000004677 hydrates Chemical class 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
239000012453 solvate Substances 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 8
125000004122 cyclic group Chemical group 0.000 claims description 8
125000001153 fluoro group Chemical group F* 0.000 claims description 8
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
241001465754 Metazoa Species 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Chemical group 0.000 claims description 6
238000010532 solid phase synthesis reaction Methods 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
150000003626 triacylglycerols Chemical class 0.000 claims description 5
206010003210 Arteriosclerosis Diseases 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
208000011775 arteriosclerosis disease Diseases 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
239000002270 dispersing agent Substances 0.000 claims description 3
239000003995 emulsifying agent Substances 0.000 claims description 3
125000001072 heteroaryl group Chemical group 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
208000035150 Hypercholesterolemia Diseases 0.000 claims description 2
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 2
238000005804 alkylation reaction Methods 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
230000002829 reductive effect Effects 0.000 claims description 2
239000003981 vehicle Substances 0.000 claims description 2
230000002265 prevention Effects 0.000 claims 2
239000002552 dosage form Substances 0.000 claims 1
239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 claims 1
102000023984 PPAR alpha Human genes 0.000 abstract description 5
108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 abstract description 5
208000029078 coronary artery disease Diseases 0.000 abstract description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 289
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 213
238000005160 1H NMR spectroscopy Methods 0.000 description 145
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 127
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 121
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 99
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 94
239000000243 solution Substances 0.000 description 85
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 78
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 70
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 52
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 51
125000000446 sulfanediyl group Chemical group *S* 0.000 description 51
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
239000011541 reaction mixture Substances 0.000 description 46
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 40
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 38
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 36
239000011347 resin Substances 0.000 description 33
229920005989 resin Polymers 0.000 description 33
239000000203 mixture Substances 0.000 description 32
239000012074 organic phase Substances 0.000 description 32
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
235000019441 ethanol Nutrition 0.000 description 25
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 25
238000004587 chromatography analysis Methods 0.000 description 23
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 22
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
239000000741 silica gel Substances 0.000 description 22
229910002027 silica gel Inorganic materials 0.000 description 22
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
229910052943 magnesium sulfate Inorganic materials 0.000 description 21
235000019341 magnesium sulphate Nutrition 0.000 description 21
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 20
239000000047 product Substances 0.000 description 19
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 17
235000019260 propionic acid Nutrition 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 14
238000003756 stirring Methods 0.000 description 14
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 13
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
239000002585 base Substances 0.000 description 12
238000003818 flash chromatography Methods 0.000 description 12
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
229960000583 acetic acid Drugs 0.000 description 11
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 10
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 9
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
238000011097 chromatography purification Methods 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
239000011734 sodium Substances 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
238000012360 testing method Methods 0.000 description 9
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 8
WLYPBMBWKYALCG-UHFFFAOYSA-N [2,4-bis(trifluoromethyl)phenyl]boronic acid Chemical group OB(O)C1=CC=C(C(F)(F)F)C=C1C(F)(F)F WLYPBMBWKYALCG-UHFFFAOYSA-N 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
235000019253 formic acid Nutrition 0.000 description 8
230000007062 hydrolysis Effects 0.000 description 8
238000006460 hydrolysis reaction Methods 0.000 description 8
WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 8
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 7
239000012230 colorless oil Substances 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 7
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
JGMMSFZTDYOQQQ-UHFFFAOYSA-N 2-[n-[[4-[2,2-dimethyl-3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]phenyl]methyl]anilino]acetic acid Chemical compound C1=CC(CC(C)(C)C(=O)OC(C)(C)C)=CC=C1CN(CC(O)=O)C1=CC=CC=C1 JGMMSFZTDYOQQQ-UHFFFAOYSA-N 0.000 description 6
JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 6
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 6
239000007821 HATU Substances 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 6
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
238000000746 purification Methods 0.000 description 6
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
CBMYWVHNQLSNEJ-UHFFFAOYSA-N tert-butyl 3-(4-formylphenyl)-2,2-dimethylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)CC1=CC=C(C=O)C=C1 CBMYWVHNQLSNEJ-UHFFFAOYSA-N 0.000 description 6
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 6
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 5
ZCKVENPXPQNFSH-UHFFFAOYSA-N 4-methoxy-2,5-dimethylaniline Chemical compound COC1=CC(C)=C(N)C=C1C ZCKVENPXPQNFSH-UHFFFAOYSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
150000001413 amino acids Chemical class 0.000 description 5
210000004369 blood Anatomy 0.000 description 5
239000008280 blood Substances 0.000 description 5
150000001733 carboxylic acid esters Chemical class 0.000 description 5
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 5
238000003776 cleavage reaction Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
235000011181 potassium carbonates Nutrition 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
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229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000001294 propane Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
230000005180 public health Effects 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000011002 quantification Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
239000011435 rock Substances 0.000 description 1
238000003118 sandwich ELISA Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000008275 solid aerosol Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000010972 statistical evaluation Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
OEZVHZLBAZDRLT-UHFFFAOYSA-N tert-butyl 2-(3-bromophenoxy)-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)OC1=CC=CC(Br)=C1 OEZVHZLBAZDRLT-UHFFFAOYSA-N 0.000 description 1
PZHWEJYUWGFECQ-UHFFFAOYSA-N tert-butyl 2-(3-bromophenyl)sulfanyl-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)SC1=CC=CC(Br)=C1 PZHWEJYUWGFECQ-UHFFFAOYSA-N 0.000 description 1
JGFMUCPMULJPQX-UHFFFAOYSA-N tert-butyl 2-(3-formylphenoxy)-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)OC1=CC=CC(C=O)=C1 JGFMUCPMULJPQX-UHFFFAOYSA-N 0.000 description 1
XDUDZEJYXMAQEA-UHFFFAOYSA-N tert-butyl 2-(4-aminophenoxy)-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)OC1=CC=C(N)C=C1 XDUDZEJYXMAQEA-UHFFFAOYSA-N 0.000 description 1
SYNUPKFIWSYGPA-UHFFFAOYSA-N tert-butyl 2-(4-bromophenyl)sulfanyl-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)SC1=CC=C(Br)C=C1 SYNUPKFIWSYGPA-UHFFFAOYSA-N 0.000 description 1
TZONEPGXYVZUKR-UHFFFAOYSA-N tert-butyl 2-(4-formylphenoxy)acetate Chemical compound CC(C)(C)OC(=O)COC1=CC=C(C=O)C=C1 TZONEPGXYVZUKR-UHFFFAOYSA-N 0.000 description 1
GHUBDCMJYAHSOE-UHFFFAOYSA-N tert-butyl 2-[3-(2-aminoethyl)phenoxy]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)OC1=CC=CC(CCN)=C1 GHUBDCMJYAHSOE-UHFFFAOYSA-N 0.000 description 1
ALIRSOWNPPWYFJ-UHFFFAOYSA-N tert-butyl 2-[3-[2-(1,3-dioxoisoindol-2-yl)ethenyl]phenoxy]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)OC1=CC=CC(C=CN2C(C3=CC=CC=C3C2=O)=O)=C1 ALIRSOWNPPWYFJ-UHFFFAOYSA-N 0.000 description 1
MEXFXLOIVPBQLF-UHFFFAOYSA-N tert-butyl 2-[3-[2-(1,3-dioxoisoindol-2-yl)ethyl]phenoxy]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)OC1=CC=CC(CCN2C(C3=CC=CC=C3C2=O)=O)=C1 MEXFXLOIVPBQLF-UHFFFAOYSA-N 0.000 description 1
AXFWSWUXEROATH-UHFFFAOYSA-N tert-butyl 2-[4-(1,3-dioxoisoindol-2-yl)phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)(C)C)=CC=C1N1C(=O)C2=CC=CC=C2C1=O AXFWSWUXEROATH-UHFFFAOYSA-N 0.000 description 1
RBWSVDKKZKPEHT-UHFFFAOYSA-N tert-butyl 2-[4-(2-aminoethyl)phenyl]sulfanyl-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)SC1=CC=C(CCN)C=C1 RBWSVDKKZKPEHT-UHFFFAOYSA-N 0.000 description 1
KVMPTLLCCVLFJI-UHFFFAOYSA-N tert-butyl 2-[4-(furan-2-ylmethylamino)phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)(C)C)=CC=C1NCC1=CC=CO1 KVMPTLLCCVLFJI-UHFFFAOYSA-N 0.000 description 1
XBMFHBLYZLGJNH-UHFFFAOYSA-N tert-butyl 2-[4-[(2-methoxyethylamino)methyl]phenoxy]-2-methylpropanoate Chemical compound COCCNCC1=CC=C(OC(C)(C)C(=O)OC(C)(C)C)C=C1 XBMFHBLYZLGJNH-UHFFFAOYSA-N 0.000 description 1
UMNAURYKWHDKSF-UHFFFAOYSA-N tert-butyl 2-[4-[(2-methoxyethylamino)methyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound COCCNCC1=CC=C(SC(C)(C)C(=O)OC(C)(C)C)C=C1 UMNAURYKWHDKSF-UHFFFAOYSA-N 0.000 description 1
IJKNBZZGHWILJE-UHFFFAOYSA-N tert-butyl 2-[4-[(furan-2-ylmethylamino)methyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)(C)C)=CC=C1CNCC1=CC=CO1 IJKNBZZGHWILJE-UHFFFAOYSA-N 0.000 description 1
PHMVAJCBKCCHHG-UHFFFAOYSA-N tert-butyl 2-[4-[(furan-2-ylmethylamino)methyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound C1=CC(SC(C)(C)C(=O)OC(C)(C)C)=CC=C1CNCC1=CC=CO1 PHMVAJCBKCCHHG-UHFFFAOYSA-N 0.000 description 1
MQQRKABUJLEZFH-UHFFFAOYSA-N tert-butyl 2-[4-[2-(furan-2-ylmethylamino)ethyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound C1=CC(SC(C)(C)C(=O)OC(C)(C)C)=CC=C1CCNCC1=CC=CO1 MQQRKABUJLEZFH-UHFFFAOYSA-N 0.000 description 1
MLZUUQKOKXAMJZ-UHFFFAOYSA-N tert-butyl 2-[4-[2-[[2-(2,4-dimethylanilino)-2-oxoethyl]-(furan-2-ylmethyl)amino]ethyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound CC1=CC(C)=CC=C1NC(=O)CN(CC=1OC=CC=1)CCC1=CC=C(SC(C)(C)C(=O)OC(C)(C)C)C=C1 MLZUUQKOKXAMJZ-UHFFFAOYSA-N 0.000 description 1
MYZPSDPMRKDBAI-UHFFFAOYSA-N tert-butyl 2-[4-[2-[furan-2-ylmethyl-[2-(4-methoxy-2,5-dimethylanilino)-2-oxoethyl]amino]ethyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound C1=C(C)C(OC)=CC(C)=C1NC(=O)CN(CC=1OC=CC=1)CCC1=CC=C(SC(C)(C)C(=O)OC(C)(C)C)C=C1 MYZPSDPMRKDBAI-UHFFFAOYSA-N 0.000 description 1
UGOVKCGIQZCHQO-UHFFFAOYSA-N tert-butyl 2-[4-[[2-(2,4-dimethylanilino)ethyl-(furan-2-ylmethyl)amino]methyl]phenoxy]-2-methylpropanoate Chemical compound CC1=CC(C)=CC=C1NCCN(CC=1C=CC(OC(C)(C)C(=O)OC(C)(C)C)=CC=1)CC1=CC=CO1 UGOVKCGIQZCHQO-UHFFFAOYSA-N 0.000 description 1
FJPJKRBCOLGDPL-UHFFFAOYSA-N tert-butyl 2-[4-[[[2-(2,4-dichloroanilino)-2-oxoethyl]-(2-methoxyethyl)amino]methyl]phenoxy]-2-methylpropanoate Chemical compound C=1C=C(OC(C)(C)C(=O)OC(C)(C)C)C=CC=1CN(CCOC)CC(=O)NC1=CC=C(Cl)C=C1Cl FJPJKRBCOLGDPL-UHFFFAOYSA-N 0.000 description 1
SQXGFIGDSMWRQE-UHFFFAOYSA-N tert-butyl 2-[4-[[[2-(2,4-dimethylanilino)-2-oxoethyl]-(furan-2-ylmethyl)amino]methyl]phenoxy]-2-methylpropanoate Chemical compound CC1=CC(C)=CC=C1NC(=O)CN(CC=1C=CC(OC(C)(C)C(=O)OC(C)(C)C)=CC=1)CC1=CC=CO1 SQXGFIGDSMWRQE-UHFFFAOYSA-N 0.000 description 1
ZNWKQQDVBIQYGZ-UHFFFAOYSA-N tert-butyl 2-[4-[[[2-(2,4-dimethylanilino)-2-oxoethyl]-(furan-2-ylmethyl)amino]methyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound CC1=CC(C)=CC=C1NC(=O)CN(CC=1C=CC(SC(C)(C)C(=O)OC(C)(C)C)=CC=1)CC1=CC=CO1 ZNWKQQDVBIQYGZ-UHFFFAOYSA-N 0.000 description 1
NGZQIAZXJVNMFF-UHFFFAOYSA-N tert-butyl 2-[4-[[[2-(4-cyclohexyl-2-methylanilino)-2-oxoethyl]-(2-methoxyethyl)amino]methyl]phenoxy]-2-methylpropanoate Chemical compound C=1C=C(OC(C)(C)C(=O)OC(C)(C)C)C=CC=1CN(CCOC)CC(=O)NC(C(=C1)C)=CC=C1C1CCCCC1 NGZQIAZXJVNMFF-UHFFFAOYSA-N 0.000 description 1
NXCVDUJNJBXFNQ-UHFFFAOYSA-N tert-butyl 2-[4-[[[2-(4-cyclohexyl-2-methylanilino)-2-oxoethyl]-(2-methoxyethyl)amino]methyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound C=1C=C(SC(C)(C)C(=O)OC(C)(C)C)C=CC=1CN(CCOC)CC(=O)NC(C(=C1)C)=CC=C1C1CCCCC1 NXCVDUJNJBXFNQ-UHFFFAOYSA-N 0.000 description 1
VBZYBGZTADHUOI-UHFFFAOYSA-N tert-butyl 2-[4-[[[2-[2,4-bis(trifluoromethyl)anilino]-2-oxoethyl]-(2-methoxyethyl)amino]methyl]phenoxy]-2-methylpropanoate Chemical compound C=1C=C(OC(C)(C)C(=O)OC(C)(C)C)C=CC=1CN(CCOC)CC(=O)NC1=CC=C(C(F)(F)F)C=C1C(F)(F)F VBZYBGZTADHUOI-UHFFFAOYSA-N 0.000 description 1
AVPQVDQNMIVAOQ-UHFFFAOYSA-N tert-butyl 2-[4-[[[2-[2,4-bis(trifluoromethyl)anilino]-2-oxoethyl]-(furan-2-ylmethyl)amino]methyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)(C)C)=CC=C1CN(CC=1OC=CC=1)CC(=O)NC1=CC=C(C(F)(F)F)C=C1C(F)(F)F AVPQVDQNMIVAOQ-UHFFFAOYSA-N 0.000 description 1
MVCSVLHANBOQLN-UHFFFAOYSA-N tert-butyl 3-[4-[(furan-2-ylmethylamino)methyl]phenyl]-2,2-dimethylpropanoate Chemical compound C1=CC(CC(C)(C)C(=O)OC(C)(C)C)=CC=C1CNCC1=CC=CO1 MVCSVLHANBOQLN-UHFFFAOYSA-N 0.000 description 1
IPDNBBAIBFXFJE-UHFFFAOYSA-N tert-butyl 3-[4-[[furan-2-ylmethyl-[2-(4-methoxy-2,5-dimethylanilino)-2-oxoethyl]amino]methyl]phenyl]-2,2-dimethylpropanoate Chemical compound C1=C(C)C(OC)=CC(C)=C1NC(=O)CN(CC=1C=CC(CC(C)(C)C(=O)OC(C)(C)C)=CC=1)CC1=CC=CO1 IPDNBBAIBFXFJE-UHFFFAOYSA-N 0.000 description 1
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
230000009261 transgenic effect Effects 0.000 description 1
238000011830 transgenic mouse model Methods 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000011995 wilkinson's catalyst Substances 0.000 description 1
UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/18—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

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Health & Medical Sciences (AREA)
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Bioinformatics & Cheminformatics (AREA)
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Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
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Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
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Heart & Thoracic Surgery (AREA)
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Child & Adolescent Psychology (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Gastroenterology & Hepatology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Furan Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

SK413-2003A 2000-10-05 2001-09-24 Propionic acid derivatives, the process for their preparation, pharmaceutical composition comprising them, use thereof and intermediates for producing them SK4132003A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE10049208		2000-10-05
DE10124905A DE10124905A1 (de)	2000-10-05	2001-05-22	Propionsäurederivate
PCT/EP2001/011005 WO2002028821A2 (de)	2000-10-05	2001-09-24	Propionsäurederivate mit ppar-alpha aktivierenden eigenschaften.

Publications (1)

Publication Number	Publication Date
SK4132003A3 true SK4132003A3 (en)	2004-02-03

Family

ID=26007267

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK413-2003A SK4132003A3 (en)	2000-10-05	2001-09-24	Propionic acid derivatives, the process for their preparation, pharmaceutical composition comprising them, use thereof and intermediates for producing them

Country Status (22)

Country	Link
EP (1)	EP1328508A2 (no)
JP (1)	JP2004510757A (no)
CN (1)	CN1479716A (no)
AU (1)	AU2001293838A1 (no)
BG (1)	BG107684A (no)
BR (1)	BR0114437A (no)
CA (1)	CA2424540A1 (no)
CZ (1)	CZ2003964A3 (no)
EE (1)	EE200300140A (no)
HN (1)	HN2001000223A (no)
HR (1)	HRP20030346A2 (no)
HU (1)	HUP0302306A3 (no)
IL (1)	IL155125A0 (no)
MA (1)	MA25917A1 (no)
MX (1)	MXPA03002901A (no)
NO (1)	NO20031517L (no)
NZ (1)	NZ525119A (no)
PL (1)	PL361162A1 (no)
RU (1)	RU2003112968A (no)
SK (1)	SK4132003A3 (no)
UY (1)	UY26951A1 (no)
WO (1)	WO2002028821A2 (no)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10151390A1 (de) *	2001-10-18	2003-05-08	Bayer Ag	Essigsäurederivate
GB0214254D0 (en)	2002-06-20	2002-07-31	Glaxo Group Ltd	Chemical compounds
KR20050055773A (ko) *	2002-10-21	2005-06-13	얀센 파마슈티카 엔.브이.	치환된 테트라린 및 인단
AU2003279996B2 (en) *	2002-10-21	2009-07-09	Janssen Pharmaceutica, N.V.	Substituted tetralins and indanes and their use
CA2503405A1 (en) *	2002-10-21	2004-05-06	Janssen Pharmaceutica, N.V.	Treating syndrome x with substituted tetralins and indanes
AU2003296402A1 (en) *	2003-01-06	2004-08-10	Eli Lilly And Company	Thiophene derivative ppar modulators
KR20110140139A (ko)	2003-08-29	2011-12-30	오노 야꾸힝 고교 가부시키가이샤	Ｓ１ｐ 수용체 결합능을 갖는 화합물 및 그 의약 용도
AR048931A1 (es)	2004-04-21	2006-06-14	Janssen Pharmaceutica Nv	Proceso para la preparacion de derivados de tetralina sustituida e indano sustituido y preparacion de intermediarios de sintesis
CN100344618C (zh) *	2004-05-24	2007-10-24	北京摩力克科技有限公司	作为hPPARα和hPPARγ激动剂的N－芳丙烯酰基取代的酪氨酸衍生物
KR100699928B1 (ko) *	2004-10-05	2007-03-26	재단법인서울대학교산학협력재단	퍼록시솜 증식자 활성화 수용체 알파 리간드를 제조하기위한 중간체의 제조방법
BRPI0519012A2 (pt)	2004-12-13	2008-12-23	Ono Pharmaceutical Co	derivado do Ácido aminocarboxÍlico e seu uso medicinal
CN101054372B (zh) *	2006-04-11	2010-10-13	中国科学院上海药物研究所	嘧啶取代苯丙酸衍生化合物、其制法和在治疗多囊肾疾病中的用途
TW201022221A (en)	2008-12-01	2010-06-16	Mitsubishi Tanabe Pharma Corp	Carboxylic acid derivatives containing thiazole ring and pharmaceutical use thereof
JP5436941B2 (ja) *	2009-06-03	2014-03-05	あすか製薬株式会社	ラクタム化合物又はその塩及びｐｐａｒ活性化剤
UY34200A (es)	2011-07-21	2013-02-28	Bayer Ip Gmbh	3-(fluorovinil)pirazoles y su uso
EP3230304B1 (en) *	2014-12-11	2020-01-01	Centrient Pharmaceuticals Netherlands B.V.	Method for acylating a cyclic peptide

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Publication number	Priority date	Publication date	Assignee	Title
DE2320387A1 (de) *	1973-04-21	1974-10-31	Boehringer Mannheim Gmbh	Phenoxyalkylcarbonsaeurederivate und verfahren zur herstellung derselben
GB9822473D0 (en) *	1998-10-16	1998-12-09	Glaxo Group Ltd	Chemical compounds

2001
- 2001-09-24 HU HU0302306A patent/HUP0302306A3/hu unknown
- 2001-09-24 PL PL01361162A patent/PL361162A1/xx not_active Application Discontinuation
- 2001-09-24 EE EEP200300140A patent/EE200300140A/xx unknown
- 2001-09-24 MX MXPA03002901A patent/MXPA03002901A/es unknown
- 2001-09-24 IL IL15512501A patent/IL155125A0/xx unknown
- 2001-09-24 SK SK413-2003A patent/SK4132003A3/sk not_active Application Discontinuation
- 2001-09-24 BR BR0114437-5A patent/BR0114437A/pt not_active IP Right Cessation
- 2001-09-24 NZ NZ525119A patent/NZ525119A/en unknown
- 2001-09-24 EP EP01974287A patent/EP1328508A2/de not_active Withdrawn
- 2001-09-24 AU AU2001293838A patent/AU2001293838A1/en not_active Abandoned
- 2001-09-24 WO PCT/EP2001/011005 patent/WO2002028821A2/de not_active Ceased
- 2001-09-24 CN CNA018200885A patent/CN1479716A/zh active Pending
- 2001-09-24 CA CA002424540A patent/CA2424540A1/en not_active Abandoned
- 2001-09-24 JP JP2002532408A patent/JP2004510757A/ja active Pending
- 2001-09-24 CZ CZ2003964A patent/CZ2003964A3/cs unknown
- 2001-09-24 RU RU2003112968/04A patent/RU2003112968A/ru not_active Application Discontinuation
- 2001-09-24 HR HR20030346A patent/HRP20030346A2/hr not_active Application Discontinuation
- 2001-10-03 UY UY26951A patent/UY26951A1/es not_active Application Discontinuation
- 2001-10-04 HN HN2001000223A patent/HN2001000223A/es unknown
2003
- 2003-03-28 BG BG107684A patent/BG107684A/bg unknown
- 2003-04-03 NO NO20031517A patent/NO20031517L/no not_active Application Discontinuation
- 2003-04-04 MA MA27091A patent/MA25917A1/fr unknown

Also Published As

Publication number	Publication date
AU2001293838A1 (en)	2002-04-15
HN2001000223A (es)	2001-10-25
RU2003112968A (ru)	2004-09-20
MXPA03002901A (es)	2003-10-15
CZ2003964A3 (cs)	2003-08-13
EP1328508A2 (de)	2003-07-23
CN1479716A (zh)	2004-03-03
BR0114437A (pt)	2003-07-01
HUP0302306A3 (en)	2005-02-28
IL155125A0 (en)	2003-10-31
EE200300140A (et)	2003-08-15
HRP20030346A2 (en)	2005-04-30
NO20031517D0 (no)	2003-04-03
BG107684A (bg)	2003-10-31
PL361162A1 (en)	2004-09-20
NZ525119A (en)	2005-04-29
JP2004510757A (ja)	2004-04-08
WO2002028821A2 (de)	2002-04-11
NO20031517L (no)	2003-05-28
UY26951A1 (es)	2002-06-20
HUP0302306A2 (hu)	2003-10-28
MA25917A1 (fr)	2003-10-01
WO2002028821A3 (de)	2002-08-15
CA2424540A1 (en)	2003-04-02

Legal Events

Date	Code	Title	Description
2010-12-07	FC9A	Refused patent application

Publication	Publication Date	Title
US6548538B2 (en)	2003-04-15	Propionic acid derivatives
SK4132003A3 (en)	2004-02-03	Propionic acid derivatives, the process for their preparation, pharmaceutical composition comprising them, use thereof and intermediates for producing them
EP1553075B1 (en)	2013-08-14	Lpa receptor antagonists
US7553867B2 (en)	2009-06-30	Furan or thiophene derivative and medicinal use thereof
JP4345230B2 (ja)	2009-10-14	カルボン酸誘導体およびその誘導体を有効成分として含有する薬剤
US20070149595A1 (en)	2007-06-28	Compounds having lysophosphatidic acid receptor antagonism and uses thereof
AU2005304962A1 (en)	2006-05-18	Glycogen phosphorylase inhibitor compounds and pharmaceutical compositions thereof
SK14922003A3 (sk)	2005-04-01	Modulátory receptorov aktivovaných proliferátormi peroxizómov (PPAR)
US20120029034A1 (en)	2012-02-02	Novel calcium salts of Compound as Anti-Inflammatory, Immunomodulatory and Anti-Proliferatory Agents
US20070219261A1 (en)	2007-09-20	Anthranilamide and 2-amino-heteroarene-carboxamide compounds
JPWO2002046176A1 (ja)	2004-04-08	ペルオキシソーム増殖剤応答性受容体の活性化剤
US6828446B2 (en)	2004-12-07	Aromatic thioether liver X-receptor modulators
US20060287304A1 (en)	2006-12-21	Dihydronaphthalene derivative compounds and agent comprising the derivative as active ingredient
ES2279310T3 (es)	2007-08-16	Derivados de oximas heterociclicas, su procedimiento de preparacion y su utilizacion en el tratamiento de la diabetes tipo ii.
KR20030059175A (ko)	2003-07-07	Ｐｐａｒ-알파 활성화 성질을 갖는 프로피온산 유도체
ES2352071T3 (es)	2011-02-15	Derivados de tirosina sustituidos con n-fenilacroloilo como agonostas de hppar alfa y de hppar gama.
JP2005035966A (ja)	2005-02-10	フランまたはチオフェン誘導体およびその医薬用途
HK1063460A (en)	2004-12-31	Propionic acid derivatives with pparalpha activating properties
WO2008069611A1 (en)	2008-06-12	N-phenylamide derivative, process for the preparation thereof, and composition for preventing or treating ischemic diseases comprising same
JP4062204B2 (ja)	2008-03-19	ジヒドロナフタレン誘導体化合物およびその化合物を有効成分とする薬剤
KR20110077018A (ko)	2011-07-06	갑상선 수용체 리간드
JPH01156974A (ja)	1989-06-20	ベンゾジオキソール誘導体