SK5412003A3 - Triazole derivatives and their use as peroxisome proliferator activated receptor alpha agonists - Google Patents

Triazole derivatives and their use as peroxisome proliferator activated receptor alpha agonists Download PDF

Info

Publication number: SK5412003A3
Authority: SK; Slovakia
Prior art keywords: alkyl; optionally substituted; group; compound; compound according
Prior art date: 2000-11-10

Application number

SK541-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Ivan Collado Cano

Samuel James Dominianni

Garret Jay Junior Etgen

Cristina Garcia-Paredes

Richard Duane Johnston

Michael Edward Letourneau

Nathan Bryan Mantlo

Michael John Martinelli

Daniel Ray Mayhugh

Ashraf Saeed

Richard Craig Thompson

Xiadong Wang

David Scott Coffey

Christopher Randall Schmid

Jeffrey Thomas Vicenzi

Yanping Xu

Original Assignee

Lilly Co Eli

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.)

2000-11-10

Filing date

2001-11-09

Publication date

2004-01-08

2001-11-09 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

2004-01-08 Publication of SK5412003A3 publication Critical patent/SK5412003A3/sk

Links

229940127520 Peroxisome Proliferator-activated Receptor alpha Agonists Drugs 0.000 title 1
229940042055 systemic antimycotics triazole derivative Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 407
150000003839 salts Chemical class 0.000 claims abstract description 63
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 55
229910052799 carbon Inorganic materials 0.000 claims abstract description 53
229920006395 saturated elastomer Polymers 0.000 claims abstract description 52
229910052760 oxygen Inorganic materials 0.000 claims abstract description 46
229910052717 sulfur Inorganic materials 0.000 claims abstract description 40
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 37
239000012453 solvate Substances 0.000 claims abstract description 36
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 32
229940124530 sulfonamide Drugs 0.000 claims abstract description 27
150000003456 sulfonamides Chemical class 0.000 claims abstract description 27
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 21
150000004677 hydrates Chemical class 0.000 claims abstract description 19
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims abstract description 17
125000005647 linker group Chemical group 0.000 claims abstract description 17
150000003536 tetrazoles Chemical class 0.000 claims abstract description 15
150000003857 carboxamides Chemical group 0.000 claims abstract description 14
125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
125000000524 functional group Chemical group 0.000 claims abstract description 10
230000002378 acidificating effect Effects 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims abstract 11
-1 nitro, phenyl Chemical group 0.000 claims description 195
229910052739 hydrogen Inorganic materials 0.000 claims description 71
239000001257 hydrogen Substances 0.000 claims description 70
238000000034 method Methods 0.000 claims description 48
150000002431 hydrogen Chemical class 0.000 claims description 36
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
241000124008 Mammalia Species 0.000 claims description 33
229910052736 halogen Inorganic materials 0.000 claims description 33
150000002367 halogens Chemical class 0.000 claims description 33
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
229910052757 nitrogen Inorganic materials 0.000 claims description 20
239000008194 pharmaceutical composition Substances 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 19
238000011282 treatment Methods 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 15
125000005001 aminoaryl group Chemical group 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 13
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
125000003107 substituted aryl group Chemical group 0.000 claims description 13
208000011580 syndromic disease Diseases 0.000 claims description 13
125000005000 thioaryl group Chemical group 0.000 claims description 13
150000001408 amides Chemical class 0.000 claims description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
210000002966 serum Anatomy 0.000 claims description 12
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 11
108010010234 HDL Lipoproteins Proteins 0.000 claims description 10
102000015779 HDL Lipoproteins Human genes 0.000 claims description 10
125000005002 aryl methyl group Chemical group 0.000 claims description 10
125000001188 haloalkyl group Chemical group 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 10
208000024172 Cardiovascular disease Diseases 0.000 claims description 9
208000008589 Obesity Diseases 0.000 claims description 9
206010012601 diabetes mellitus Diseases 0.000 claims description 9
235000020824 obesity Nutrition 0.000 claims description 9
102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 8
108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
108010007622 LDL Lipoproteins Proteins 0.000 claims description 7
102000007330 LDL Lipoproteins Human genes 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 6
230000005855 radiation Effects 0.000 claims description 6
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 6
125000005596 alkyl carboxamido group Chemical group 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
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 description 4
229910052802 copper Inorganic materials 0.000 claims description 4
239000010949 copper Substances 0.000 claims description 4
239000008103 glucose Substances 0.000 claims description 4
125000004438 haloalkoxy group Chemical group 0.000 claims description 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 claims description 4
210000004369 blood Anatomy 0.000 claims description 3
239000008280 blood Substances 0.000 claims description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
238000002441 X-ray diffraction Methods 0.000 claims description 2
239000003614 peroxisome proliferator Substances 0.000 claims description 2
102000005962 receptors Human genes 0.000 claims 2
108020003175 receptors Proteins 0.000 claims 2
125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 1
230000007423 decrease Effects 0.000 claims 1
125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 780
235000019439 ethyl acetate Nutrition 0.000 description 260
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 259
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 249
239000000243 solution Substances 0.000 description 241
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 183
239000000203 mixture Substances 0.000 description 181
239000011541 reaction mixture Substances 0.000 description 179
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 128
238000002360 preparation method Methods 0.000 description 125
239000011734 sodium Substances 0.000 description 103
239000003921 oil Substances 0.000 description 100
235000019198 oils Nutrition 0.000 description 100
239000000047 product Substances 0.000 description 98
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 96
239000012267 brine Substances 0.000 description 91
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 91
239000012044 organic layer Substances 0.000 description 88
239000007787 solid Substances 0.000 description 88
239000002904 solvent Substances 0.000 description 86
238000004949 mass spectrometry Methods 0.000 description 83
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 73
238000000746 purification Methods 0.000 description 63
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
239000010410 layer Substances 0.000 description 60
238000003818 flash chromatography Methods 0.000 description 55
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 52
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 51
235000002639 sodium chloride Nutrition 0.000 description 50
238000005481 NMR spectroscopy Methods 0.000 description 48
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 44
239000000284 extract Substances 0.000 description 41
238000010992 reflux Methods 0.000 description 37
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
238000006243 chemical reaction Methods 0.000 description 34
238000003756 stirring Methods 0.000 description 34
239000012043 crude product Substances 0.000 description 33
238000001704 evaporation Methods 0.000 description 33
230000008020 evaporation Effects 0.000 description 33
239000004480 active ingredient Substances 0.000 description 31
150000004702 methyl esters Chemical class 0.000 description 28
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
239000012230 colorless oil Substances 0.000 description 27
125000004494 ethyl ester group Chemical group 0.000 description 24
239000000706 filtrate Substances 0.000 description 23
239000000463 material Substances 0.000 description 23
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
239000012074 organic phase Substances 0.000 description 21
238000001816 cooling Methods 0.000 description 20
239000000843 powder Substances 0.000 description 20
239000003826 tablet Substances 0.000 description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
150000001732 carboxylic acid derivatives Chemical class 0.000 description 19
238000001035 drying Methods 0.000 description 19
229910052938 sodium sulfate Inorganic materials 0.000 description 19
235000011152 sodium sulphate Nutrition 0.000 description 19
239000002775 capsule Substances 0.000 description 18
229910000027 potassium carbonate Inorganic materials 0.000 description 18
239000000725 suspension Substances 0.000 description 18
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 18
235000011181 potassium carbonates Nutrition 0.000 description 17
239000002002 slurry Substances 0.000 description 17
150000002148 esters Chemical class 0.000 description 16
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
238000004458 analytical method Methods 0.000 description 15
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 14
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 14
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 14
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
MHIYNVRNPVGJEI-UHFFFAOYSA-N C1=CC(C)=CC=C1CN1NC(=O)C=N1 Chemical compound C1=CC(C)=CC=C1CN1NC(=O)C=N1 MHIYNVRNPVGJEI-UHFFFAOYSA-N 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
229910004298 SiO 2 Inorganic materials 0.000 description 13
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
125000002252 acyl group Chemical group 0.000 description 12
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 12
229940125782 compound 2 Drugs 0.000 description 12
238000001914 filtration Methods 0.000 description 12
239000012299 nitrogen atmosphere Substances 0.000 description 12
238000002390 rotary evaporation Methods 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
229920002472 Starch Polymers 0.000 description 11
239000007864 aqueous solution Substances 0.000 description 11
238000004440 column chromatography Methods 0.000 description 11
239000003960 organic solvent Substances 0.000 description 11
235000019698 starch Nutrition 0.000 description 11
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
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 description 10
239000000377 silicon dioxide Substances 0.000 description 10
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125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 9
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
150000001350 alkyl halides Chemical class 0.000 description 9
IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 9
239000007788 liquid Substances 0.000 description 9
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
102000023984 PPAR alpha Human genes 0.000 description 8
239000013543 active substance Substances 0.000 description 8
239000013078 crystal Substances 0.000 description 8
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
229910052763 palladium Inorganic materials 0.000 description 8
108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 8
229960005235 piperonyl butoxide Drugs 0.000 description 8
239000000651 prodrug Substances 0.000 description 8
229940002612 prodrug Drugs 0.000 description 8
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 8
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208000001072 type 2 diabetes mellitus Diseases 0.000 description 8
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239000003054 catalyst Substances 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
201000010099 disease Diseases 0.000 description 7
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238000002844 melting Methods 0.000 description 7
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235000017557 sodium bicarbonate Nutrition 0.000 description 7
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WZRKSPFYXUXINF-UHFFFAOYSA-N 1-(bromomethyl)-4-methylbenzene Chemical compound CC1=CC=C(CBr)C=C1 WZRKSPFYXUXINF-UHFFFAOYSA-N 0.000 description 6
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
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125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 6
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
206010022489 Insulin Resistance Diseases 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
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150000001721 carbon Chemical group 0.000 description 6
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Classifications

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- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
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- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/22—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having nitrogen atoms of amidino groups further bound to nitrogen atoms, e.g. hydrazidines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
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- C07C281/04—Compounds containing any of the groups, e.g. carbazates the other nitrogen atom being further doubly-bound to a carbon atom
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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SK541-2003A 2000-11-10 2001-11-09 Triazole derivatives and their use as peroxisome proliferator activated receptor alpha agonists SK5412003A3 (en)

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AU2002347985A1 (en) *	2001-11-15	2003-06-10	Eli Lilly And Company	Peroxisome proliferator activated receptor alpha agonists
GB0314079D0 (en) *	2003-06-18	2003-07-23	Astrazeneca Ab	Therapeutic agents
WO2004000789A1 (en)	2002-06-19	2003-12-31	Eli Lilly And Company	Amide linker peroxisome proliferator activated receptor modulators
TW200505441A (en)	2003-03-24	2005-02-16	Hoffmann La Roche	Non-nucleoside reverse transcriptase inhibitorsⅠ
FR2866339B1 (fr) *	2004-02-18	2006-05-05	Pf Medicament	Derives de 1,2,4-triazines, leur preparation et leur application en therapeutique humaine
US7262318B2 (en)	2004-03-10	2007-08-28	Pfizer, Inc.	Substituted heteroaryl- and phenylsulfamoyl compounds
US20050288340A1 (en) *	2004-06-29	2005-12-29	Pfizer Inc	Substituted heteroaryl- and phenylsulfamoyl compounds
US8293778B2 (en)	2004-07-27	2012-10-23	Roche Palo Alto Llc	Heterocyclic antiviral compounds
MX2007000788A (es) *	2004-07-27	2007-03-23	Hoffmann La Roche	Compuestos de benciltriazolona como inhibidores no nucleosidos de transcriptasa inversa.
KR100803481B1 (ko) *	2004-07-27	2008-02-14	에프. 호프만-라 로슈 아게	비-뉴클레오사이드 역전사효소 억제제로서의벤질트라이아졸론 화합물
AU2005272389B2 (en) *	2004-08-11	2011-08-04	Kyorin Pharmaceutical Co., Ltd.	Novel cyclic aminobenzoic acid derivative
WO2006068199A1 (ja) *	2004-12-22	2006-06-29	Mochida Pharmaceutical Co., Ltd.	代謝的に安定な３－オキシ－１，２，４－トリアゾール誘導体
TW200640453A (en) *	2005-01-28	2006-12-01	Lilly Co Eli	Formulations and dosing regimen for PPAR-α modulators
FR2882750B1 (fr) *	2005-03-03	2007-05-11	Pierre Fabre Medicament Sa	Derives de 1,2,4-triazines, leur preparation et leur application en therapeutique humaine
WO2006101108A1 (ja) *	2005-03-23	2006-09-28	Kyorin Pharmaceutical Co., Ltd.	新規環状アミノフェニルアルカン酸誘導体
WO2006099978A1 (en) *	2005-03-24	2006-09-28	F.Hoffmann-La Roche Ag	1,2,4-triazole-5-one compounds as heterocyclic reverse transcriptase inhibitors
JP5225076B2 (ja) *	2006-04-27	2013-07-03	田辺三菱製薬株式会社	チアゾール環を含むカルボン酸誘導体の医薬用途
WO2008103574A2 (en) *	2007-02-23	2008-08-28	Eli Lilly And Company	Peroxisome proliferator activated receptor modulators
EP2142520A1 (en)	2007-03-29	2010-01-13	F. Hoffmann-Roche AG	Non-nucleoside reverse transcriptase inhibitors
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Also Published As

Publication number	Publication date
PT1335908E (pt)	2008-05-08
UA82048C2 (uk)	2008-03-11
PL362692A1 (en)	2004-11-02
CA2421154A1 (en)	2002-05-16
HUP0301655A2 (hu)	2003-12-29
NO20032059L (no)	2003-06-24
EA200300558A1 (ru)	2004-02-26
ZA200302517B (en)	2004-06-30
NO20032059D0 (no)	2003-05-08
MXPA03004141A (es)	2003-08-19
EP1335908A2 (en)	2003-08-20
WO2002038553A3 (en)	2003-05-01
AR031305A1 (es)	2003-09-17
AU2002228592B8 (en)	2006-08-24
JP4243101B2 (ja)	2009-03-25
PE20020693A1 (es)	2002-08-05
US20090044299A1 (en)	2009-02-12
ATE386026T1 (de)	2008-03-15
US7868225B2 (en)	2011-01-11
BR0114986A (pt)	2003-09-23
MY157884A (en)	2016-08-01
SI1335908T1 (sl)	2008-08-31
HK1058790A1 (en)	2004-06-04
EA006920B1 (ru)	2006-04-28
CY1107388T1 (el)	2012-12-19
IL154840A0 (en)	2003-10-31
DE60132799D1 (de)	2008-03-27
ECSP034595A (es)	2003-06-25
US20090062358A1 (en)	2009-03-05
US20040102500A1 (en)	2004-05-27
AU2006202811A1 (en)	2006-07-20
DK1335908T3 (da)	2008-06-02
AU2002228592B2 (en)	2006-04-27
NZ524569A (en)	2006-05-26
HRP20030365A2 (en)	2003-08-31
DE60132799T2 (de)	2009-03-19
CZ20031283A3 (cs)	2003-09-17
SV2003000727A (es)	2003-01-13
AU2859202A (en)	2002-05-21
IL154840A (en)	2009-09-22
KR100839705B1 (ko)	2008-06-19
EP1335908B1 (en)	2008-02-13
CN1479728A (zh)	2004-03-03
JP2004513166A (ja)	2004-04-30
US7304062B2 (en)	2007-12-04
ES2300378T3 (es)	2008-06-16
KR20030048133A (ko)	2003-06-18
WO2002038553A2 (en)	2002-05-16
TW200716572A (en)	2007-05-01

Publication	Publication Date	Title
SK5412003A3 (en)	2004-01-08	Triazole derivatives and their use as peroxisome proliferator activated receptor alpha agonists
AU2002228592A1 (en)	2002-07-25	Triazole derivatives and their use as peroxisome proliferator activated receptor alpha agonists
JP6861858B2 (ja)	2021-04-21	Ｓｓａｏ阻害剤
EP2027096B1 (de)	2012-05-23	Substituierte arylimidaz0l0ne und -triaz0l0ne als inhibitoren der vasopressin-rezeptoren
DE69935133T2 (de)	2007-11-22	Antagonisten zur behandlung von cd11/cd18 adhäsionsrezeptor-vermittelten krankheiten
EP1421078B1 (en)	2006-09-27	Indole derivatives as beta-3 adrenergic agonists for the treatment of type 2 diabetes
KR19990087321A (ko)	1999-12-27	Ppar-감마에 대한 효능제 활성을 갖는 치환된 4-히드록시-페닐알카논산 유도체
JP2005517643A (ja)	2005-06-16	ペルオキシソーム増殖因子活性化受容体アゴニスト
FR2552759A1 (fr)	1985-04-05	Composes de la 1,2,4-triazolone et leur application pharmacologique
HUP0300857A2 (hu)	2003-10-28	Peroxiszóma proliferátor aktivált agonisták
EA001217B1 (ru)	2000-12-25	СЕЛЕКТИВНЫЕ β-АДРЕНЕРГИЧЕСКИЕ АГОНИСТЫ
US20020025948A1 (en)	2002-02-28	3-azabicyclo[3.1.0]hexane derivatives useful in therapy
FR2477150A1 (fr)	1981-09-04	Nouveaux derives heterocycliques, procedes pour leur preparation et compositions pharmaceutiques les comportant
EP1395582A1 (fr)	2004-03-10	Nouveaux derives de piperidinecarboxamide, un procede pour leur preparation et les compositions pharmaceutiques les contenant
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US20020040023A1 (en)	2002-04-04	Substituted arylsulfides, arylsulfoxides and arylsulfones as beta-3 adrenergic receptor agonists
WO2002006272A1 (fr)	2002-01-24	Derives de polyfluoroalkyltriazole, leur preparation et leur utilisation en therapeutique
HK1058790B (en)	2008-08-01	Peroxisome proliferator activated receptor alpha agonists
NZ542242A (en)	2007-04-27	Triazole derivatives and their use as peroxisome proliferator activated receptor alpha agonists
FR2542741A1 (fr)	1984-09-21	3,4-diamino-1,2,5-thiadiazoles substitues possedant une activite antagoniste du recepteur-h2 de l'histamine
CN108558784A (zh)	2018-09-21	咪唑-氨基酸衍生物和相关化合物的合成方法

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