BG104602A - Производни на арилтиазолидиндион - Google Patents

Производни на арилтиазолидиндион Download PDF

Info

Publication number: BG104602A
Authority: BG; Bulgaria
Prior art keywords: propyl; phenyl; alkyl; optionally substituted; aryl
Prior art date: 1997-12-19

Application number

BG104602A

Other languages

Bulgarian (bg)

English (en)

Inventor

Soumya Sahoo

Richard Tolman

Wei Han

Jeffrey Bergmann

Conrad Santini

Vicki LOMBARDO

Ranjit Desai

Julia BOUERES

Dominick GRATALE

Original Assignee

Merck & Co., Inc

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.)

1997-12-19

Filing date

2000-07-13

Publication date

2001-01-31

1998-07-27 Priority claimed from GBGB9816279.5A external-priority patent/GB9816279D0/en

2000-07-13 Application filed by Merck & Co., Inc filed Critical Merck & Co., Inc

2001-01-31 Publication of BG104602A publication Critical patent/BG104602A/bg

Links

150000001875 compounds Chemical class 0.000 claims description 267
-1 alkynyl halogen Chemical class 0.000 claims description 151
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
125000003118 aryl group Chemical group 0.000 claims description 57
125000000217 alkyl group Chemical group 0.000 claims description 49
125000001072 heteroaryl group Chemical group 0.000 claims description 28
229910052736 halogen Inorganic materials 0.000 claims description 21
150000002367 halogens Chemical class 0.000 claims description 20
125000003342 alkenyl group Chemical group 0.000 claims description 19
229910052717 sulfur Inorganic materials 0.000 claims description 19
125000000304 alkynyl group Chemical group 0.000 claims description 16
229910052760 oxygen Inorganic materials 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
125000000753 cycloalkyl group Chemical group 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000005842 heteroatom Chemical group 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 10
125000001589 carboacyl group Chemical group 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000000732 arylene group Chemical group 0.000 claims description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 5
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
125000005549 heteroarylene group Chemical group 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
229930192474 thiophene Natural products 0.000 claims description 2
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 7
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 abstract description 16
108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 abstract description 16
239000000556 agonist Substances 0.000 abstract description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 12
238000011282 treatment Methods 0.000 abstract description 12
206010012601 diabetes mellitus Diseases 0.000 abstract description 11
108010016731 PPAR gamma Proteins 0.000 abstract description 10
102000023984 PPAR alpha Human genes 0.000 abstract description 7
201000001421 hyperglycemia Diseases 0.000 abstract description 7
201000010099 disease Diseases 0.000 abstract description 6
208000035475 disorder Diseases 0.000 abstract description 6
201000001320 Atherosclerosis Diseases 0.000 abstract description 4
208000008589 Obesity Diseases 0.000 abstract description 4
208000006575 hypertriglyceridemia Diseases 0.000 abstract description 4
235000020824 obesity Nutrition 0.000 abstract description 4
230000003389 potentiating effect Effects 0.000 abstract description 4
230000001404 mediated effect Effects 0.000 abstract description 3
208000037803 restenosis Diseases 0.000 abstract description 3
230000002792 vascular Effects 0.000 abstract description 3
108010044210 PPAR-beta Proteins 0.000 abstract description 2
108010028924 PPAR alpha Proteins 0.000 abstract 1
230000002265 prevention Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 173
238000002360 preparation method Methods 0.000 description 138
238000000034 method Methods 0.000 description 133
239000007858 starting material Substances 0.000 description 119
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 84
239000000243 solution Substances 0.000 description 81
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 70
IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 67
229940049953 phenylacetate Drugs 0.000 description 67
235000019439 ethyl acetate Nutrition 0.000 description 58
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 56
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
239000011541 reaction mixture Substances 0.000 description 51
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
239000003921 oil Substances 0.000 description 48
235000019198 oils Nutrition 0.000 description 48
239000000741 silica gel Substances 0.000 description 47
229910002027 silica gel Inorganic materials 0.000 description 47
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 42
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 38
239000000203 mixture Substances 0.000 description 38
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 34
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 28
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 27
229910052938 sodium sulfate Inorganic materials 0.000 description 27
235000011152 sodium sulphate Nutrition 0.000 description 27
239000012074 organic phase Substances 0.000 description 26
239000012044 organic layer Substances 0.000 description 25
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
239000000047 product Substances 0.000 description 21
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
102000004877 Insulin Human genes 0.000 description 19
108090001061 Insulin Proteins 0.000 description 19
229940125396 insulin Drugs 0.000 description 19
229910052943 magnesium sulfate Inorganic materials 0.000 description 18
235000019341 magnesium sulphate Nutrition 0.000 description 18
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
239000007787 solid Substances 0.000 description 17
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
239000000460 chlorine Substances 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 13
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 13
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 13
229910000024 caesium carbonate Inorganic materials 0.000 description 13
239000008103 glucose Substances 0.000 description 13
SUOCNBAOIPRDIA-UHFFFAOYSA-N 4-phenoxy-2-propylphenol Chemical compound C1=C(O)C(CCC)=CC(OC=2C=CC=CC=2)=C1 SUOCNBAOIPRDIA-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000012267 brine Substances 0.000 description 12
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 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
239000002904 solvent Substances 0.000 description 12
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 11
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 description 11
239000004480 active ingredient Substances 0.000 description 11
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 11
230000000694 effects Effects 0.000 description 11
238000001704 evaporation Methods 0.000 description 11
230000008020 evaporation Effects 0.000 description 11
208000001072 type 2 diabetes mellitus Diseases 0.000 description 11
WTGPITKQSNYMJM-UHFFFAOYSA-N 3-phenyl-1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1C1=CC=CC=C1 WTGPITKQSNYMJM-UHFFFAOYSA-N 0.000 description 10
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
239000000543 intermediate Substances 0.000 description 10
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 10
229940011051 isopropyl acetate Drugs 0.000 description 10
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 10
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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108020003175 receptors Proteins 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
238000012360 testing method Methods 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
102000005962 receptors Human genes 0.000 description 8
239000011734 sodium Substances 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
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206010022489 Insulin Resistance Diseases 0.000 description 7
239000002253 acid Substances 0.000 description 7
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229910000027 potassium carbonate Inorganic materials 0.000 description 7
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229920006395 saturated elastomer Polymers 0.000 description 7
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YDJKOERQQLYGDN-UHFFFAOYSA-N 5-[4-[2-(1,3-benzoxazol-2-ylmethylamino)ethoxy]phenyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1C(C=C1)=CC=C1OCCNCC1=NC2=CC=CC=C2O1 YDJKOERQQLYGDN-UHFFFAOYSA-N 0.000 description 6
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YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 6
102100039556 Galectin-4 Human genes 0.000 description 6
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235000019502 Orange oil Nutrition 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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239000003054 catalyst Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
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235000012000 cholesterol Nutrition 0.000 description 6
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CRWVOXFUXPYTRK-UHFFFAOYSA-N pent-4-yn-1-ol Chemical compound OCCCC#C CRWVOXFUXPYTRK-UHFFFAOYSA-N 0.000 description 6
239000003614 peroxisome proliferator Substances 0.000 description 6
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AMDDOQIUPAINLH-UHFFFAOYSA-N methyl 2-(3-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC=CC(O)=C1 AMDDOQIUPAINLH-UHFFFAOYSA-N 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
210000002824 peroxisome Anatomy 0.000 description 5
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 5
VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 4
MQFNMOXZRKQSDW-UHFFFAOYSA-N 3-(2-phenylethyl)-7-propyl-1-benzothiophene Chemical compound C1(=CC=CC=C1)CCC1=CSC2=C1C=CC=C2CCC MQFNMOXZRKQSDW-UHFFFAOYSA-N 0.000 description 4
ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 4
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ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol 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)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
229950005143 sitosterol Drugs 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical class [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 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
239000007901 soft capsule Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
229960004559 theobromine Drugs 0.000 description 1
230000004797 therapeutic response Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000007944 thiolates Chemical class 0.000 description 1
108090000721 thyroid hormone receptors Proteins 0.000 description 1
102000004217 thyroid hormone receptors Human genes 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
229960001641 troglitazone Drugs 0.000 description 1
GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
241001529453 unidentified herpesvirus Species 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
239000013598 vector Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000010792 warming Methods 0.000 description 1
101150069452 z gene Proteins 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 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
- C07D263/34—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 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
- C07D263/44—Two oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/34—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Diabetes (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Obesity (AREA)
Hematology (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Child & Adolescent Psychology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Thiazole And Isothizaole Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

BG104602A 1997-12-19 2000-07-13 Производни на арилтиазолидиндион BG104602A (bg)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US6827197P	1997-12-19	1997-12-19
GBGB9816279.5A GB9816279D0 (en)	1998-07-27	1998-07-27	Arylthiazolidinedione derivatives
US10523898P	1998-10-22	1998-10-22
PCT/US1998/027139 WO1999032465A1 (en)	1997-12-19	1998-12-18	Arylthiazolidinedione derivatives

Publications (1)

Publication Number	Publication Date
BG104602A true BG104602A (bg)	2001-01-31

Family

ID=27269416

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG104602A BG104602A (bg)	1997-12-19	2000-07-13	Производни на арилтиазолидиндион

Country Status (21)

Country	Link
EP (1)	EP1040102B1 (id)
JP (1)	JP3373198B2 (id)
KR (1)	KR20010033355A (id)
CN (1)	CN1282325A (id)
AT (1)	ATE352545T1 (id)
AU (1)	AU740733B2 (id)
BG (1)	BG104602A (id)
BR (1)	BR9813801A (id)
CA (1)	CA2315397C (id)
DE (1)	DE69836980T2 (id)
EA (1)	EA200000687A1 (id)
ES (1)	ES2281146T3 (id)
HU (1)	HUP0101366A2 (id)
ID (1)	ID24878A (id)
IL (1)	IL136138A0 (id)
IS (1)	IS5506A (id)
NO (1)	NO20003112L (id)
PL (1)	PL340958A1 (id)
SK (1)	SK9212000A3 (id)
TR (1)	TR200001753T2 (id)
WO (1)	WO1999032465A1 (id)

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GB9824614D0 (en) *	1998-11-11	1999-01-06	Glaxo Group Ltd	Chemical compounds
EP1053989B1 (en) *	1999-05-20	2007-07-25	Ciba SC Holding AG	Hydroxydiphenyl ether compounds
EP1194146B1 (en) *	1999-06-18	2006-07-19	Merck & Co., Inc.	Arylthiazolidinedione and aryloxazolidinedione derivatives
AU5876900A (en) *	1999-06-18	2001-01-09	Merck & Co., Inc.	Process for making arylthiazolidinedione derivatives
US7041691B1 (en)	1999-06-30	2006-05-09	Amgen Inc.	Compounds for the modulation of PPARγ activity
WO2001016120A1 (en)	1999-08-27	2001-03-08	Eli Lilly And Company	Biaryl-oxa(thia)zole derivatives and their use as ppars modulators
AU1303301A (en) *	1999-11-10	2001-06-06	Takeda Chemical Industries Ltd.	Body weight gain inhibitors
US20030171399A1 (en)	2000-06-28	2003-09-11	Tularik Inc.	Quinolinyl and benzothiazolyl modulators
AU2001298065A1 (en) *	2001-01-12	2003-09-02	Abbott Laboratories	Process for the preparation of matrix metalloproteinase inhibitors
WO2002087580A1 (en) *	2001-04-25	2002-11-07	Takeda Chemical Industries, Ltd.	Abc expression promoters
AU2003256655A1 (en) *	2002-07-25	2004-02-16	Merck And Co., Inc.	Therapeutic compounds for treating dyslipidemic conditions
ATE483699T1 (de) *	2002-08-30	2010-10-15	Hoffmann La Roche	Neue 2-arylthiazolverbindungen als ppar-alpha und gamma agonisten
DK1567493T3 (da) *	2002-11-26	2009-06-08	Pfizer Prod Inc	Phenyl-substituerede piperidin-forbindelser til anvendelse som PPAR-aktivatorer
CN1319956C (zh) *	2003-09-12	2007-06-06	深圳市海粤门生物科技开发有限公司	一种噻唑烷二酮的衍生物及其药用制剂的制备方法和应用
UA87467C2 (xx) *	2003-09-19	2009-07-27	Янссен Фармацевтика Н.В	4-((феноксіалкіл)тіо)феноксіоцтова кислота та її аналоги$4-((феноксиалкил)тио)феноксиуксусная кислота и ее аналоги
CA2539403C (en) *	2003-09-19	2013-11-19	Janssen Pharmaceutica N.V.	4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs
DE602005001265T2 (de) *	2004-01-20	2008-01-31	Merck & Co., Inc.	Antidiabetische oxazolidindione und thiazolidindione
WO2006138328A1 (en) *	2005-06-14	2006-12-28	Merck & Co., Inc.	Process for the production of antidiabetic oxazolidinediones
CA2612765A1 (en) *	2005-07-06	2007-01-18	Merck And Co., Inc.	Antidiabetic oxazolidinediones and thiazolidinediones
JP2009502783A (ja) *	2005-07-20	2009-01-29	メルクエンドカムパニーインコーポレーテッド	抗糖尿病性オキサゾリジンジオン及びチアゾリジンジオン
ES2569660T3 (es)	2007-06-08	2016-05-12	Mannkind Corporation	Inhibidores de la IRE-1alfa
CN105001174A (zh) *	2015-07-14	2015-10-28	佛山市赛维斯医药科技有限公司	含苯并异恶唑和末端腈基苄基类结构的化合物及其用途
CN104987314A (zh) *	2015-07-14	2015-10-21	佛山市赛维斯医药科技有限公司	含苯并异恶唑和末端硝基苄基类结构的化合物及其用途

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Publication number	Priority date	Publication date	Assignee	Title
JP3053490B2 (ja) *	1991-02-25	2000-06-19	杏林製薬株式会社	チアゾリジン−２，４−ジオン誘導体とその塩及び製造法
JP3906935B2 (ja) *	1995-12-18	2007-04-18	杏林製薬株式会社	Ｎ−置換ジオキソチアゾリジルベンズアミド誘導体及びその製造法
CA2245524A1 (en) *	1996-02-02	1997-08-07	Wei Han	Antidiabetic agents
JP2002503202A (ja) *	1996-02-02	2002-01-29	メルクエンドカンパニーインコーポレーテッド	抗糖尿病薬
ATE236137T1 (de) *	1996-02-02	2003-04-15	Merck & Co Inc	Heterocyclische verbindungen als antidiabetische mittel und für die behandlung von fettleibigkeit
US5801173A (en) *	1996-05-06	1998-09-01	Dr. Reddy's Research Foundation	Heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them

1998
- 1998-12-18 ID IDW20001163A patent/ID24878A/id unknown
- 1998-12-18 BR BR9813801-4A patent/BR9813801A/pt not_active Application Discontinuation
- 1998-12-18 TR TR2000/01753T patent/TR200001753T2/xx unknown
- 1998-12-18 AU AU18334/99A patent/AU740733B2/en not_active Ceased
- 1998-12-18 CN CN98812229A patent/CN1282325A/zh active Pending
- 1998-12-18 DE DE69836980T patent/DE69836980T2/de not_active Expired - Fee Related
- 1998-12-18 SK SK921-2000A patent/SK9212000A3/sk unknown
- 1998-12-18 JP JP2000525402A patent/JP3373198B2/ja not_active Expired - Fee Related
- 1998-12-18 IL IL13613898A patent/IL136138A0/xx unknown
- 1998-12-18 KR KR1020007006820A patent/KR20010033355A/ko not_active Withdrawn
- 1998-12-18 ES ES98963283T patent/ES2281146T3/es not_active Expired - Lifetime
- 1998-12-18 CA CA002315397A patent/CA2315397C/en not_active Expired - Fee Related
- 1998-12-18 HU HU0101366A patent/HUP0101366A2/hu unknown
- 1998-12-18 WO PCT/US1998/027139 patent/WO1999032465A1/en not_active Ceased
- 1998-12-18 AT AT98963283T patent/ATE352545T1/de not_active IP Right Cessation
- 1998-12-18 PL PL98340958A patent/PL340958A1/xx not_active Application Discontinuation
- 1998-12-18 EP EP98963283A patent/EP1040102B1/en not_active Expired - Lifetime
- 1998-12-18 EA EA200000687A patent/EA200000687A1/ru unknown
2000
- 2000-05-23 IS IS5506A patent/IS5506A/is unknown
- 2000-06-16 NO NO20003112A patent/NO20003112L/no not_active Application Discontinuation
- 2000-07-13 BG BG104602A patent/BG104602A/bg unknown

Also Published As

Publication number	Publication date
JP3373198B2 (ja)	2003-02-04
ID24878A (id)	2000-08-31
EA200000687A1 (ru)	2000-12-25
DE69836980T2 (de)	2007-11-15
EP1040102B1 (en)	2007-01-24
IL136138A0 (en)	2001-05-20
CA2315397A1 (en)	1999-07-01
ATE352545T1 (de)	2007-02-15
PL340958A1 (en)	2001-03-12
NO20003112D0 (no)	2000-06-16
JP2001526278A (ja)	2001-12-18
BR9813801A (pt)	2000-10-03
DE69836980D1 (de)	2007-03-15
ES2281146T3 (es)	2007-09-16
CN1282325A (zh)	2001-01-31
AU1833499A (en)	1999-07-12
HUP0101366A2 (hu)	2001-09-28
IS5506A (is)	2000-05-23
WO1999032465A1 (en)	1999-07-01
TR200001753T2 (tr)	2000-11-21
SK9212000A3 (en)	2001-02-12
AU740733B2 (en)	2001-11-15
EP1040102A4 (en)	2002-11-27
CA2315397C (en)	2007-08-07
EP1040102A1 (en)	2000-10-04
NO20003112L (no)	2000-08-18
KR20010033355A (ko)	2001-04-25

Publication	Publication Date	Title
US6008237A (en)	1999-12-28	Arylthiazolidinedione derivatives
EP1194146B1 (en)	2006-07-19	Arylthiazolidinedione and aryloxazolidinedione derivatives
EP1040102B1 (en)	2007-01-24	Arylthiazolidinedione derivatives
US6465497B2 (en)	2002-10-15	Arylthiazolidinedione derivatives
US6645997B2 (en)	2003-11-11	Benzopyrancarboxylic acid derivatives for the treatment of diabetes and lipid disorders
DE60128475T2 (de)	2008-02-07	N-substituierte indole mit anwendung in der behandlung von diabetes
US6569879B2 (en)	2003-05-27	Aryloxyacetic acids for diabetes and lipid disorders
AU2003260085B2 (en)	2008-09-11	Indoles having anti-diabetic activity
JP2003523336A (ja)	2003-08-05	糖尿病及び脂質障害のためのアリールオキシ酢酸
DE602005001265T2 (de)	2008-01-31	Antidiabetische oxazolidindione und thiazolidindione
MXPA00006035A (en)	2001-07-03	Arylthiazolidinedione derivatives
CZ20002286A3 (cs)	2000-11-15	Arylthiazolidindionové deriváty