JPH06502145A - チアゾリジンジオン誘導体 - Google Patents

チアゾリジンジオン誘導体

Info

Publication number: JPH06502145A
Authority: JP; Japan
Prior art keywords: formula; group; pharmaceutically acceptable; substituted; unsubstituted
Prior art date: 1990-10-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP3516912A

Other languages

English (en)

Japanese (ja)

Inventor

ハイ，デイビッド

ベル，デイビッド

Original Assignee

ビーチャム・グループ・パブリック・リミテッド・カンパニー

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.)

1990-10-30

Filing date

1991-10-18

Publication date

1994-03-10

1991-10-18 Application filed by ビーチャム・グループ・パブリック・リミテッド・カンパニー filed Critical ビーチャム・グループ・パブリック・リミテッド・カンパニー

1994-03-10 Publication of JPH06502145A publication Critical patent/JPH06502145A/ja

Status Pending legal-status Critical Current

Links

150000001467 thiazolidinediones Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 150
-1 polymethylene group Polymers 0.000 claims description 43
125000000217 alkyl group Chemical group 0.000 claims description 40
150000003839 salts Chemical class 0.000 claims description 38
238000000034 method Methods 0.000 claims description 36
239000000203 mixture Substances 0.000 claims description 35
125000003118 aryl group Chemical group 0.000 claims description 31
239000012453 solvate Substances 0.000 claims description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
125000003710 aryl alkyl group Chemical group 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 16
239000003153 chemical reaction reagent Substances 0.000 claims description 12
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
201000001421 hyperglycemia Diseases 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
208000024172 Cardiovascular disease Diseases 0.000 claims description 8
208000030814 Eating disease Diseases 0.000 claims description 8
208000019454 Feeding and Eating disease Diseases 0.000 claims description 8
208000031226 Hyperlipidaemia Diseases 0.000 claims description 8
206010020772 Hypertension Diseases 0.000 claims description 8
235000014632 disordered eating Nutrition 0.000 claims description 8
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
230000001225 therapeutic effect Effects 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
238000009472 formulation Methods 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
239000004472 Lysine Substances 0.000 claims description 2
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
150000004677 hydrates Chemical class 0.000 claims description 2
SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
229940043274 prophylactic drug Drugs 0.000 claims description 2
238000011321 prophylaxis Methods 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims 1
WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical group COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 claims 1
OBMIBLCOLDQZGP-UHFFFAOYSA-N 2-phenylethyl n-[2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]ethyl]-n-methylcarbamate Chemical compound C=1C=CC=CC=1CCOC(=O)N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O OBMIBLCOLDQZGP-UHFFFAOYSA-N 0.000 claims 1
RBQZIAQNAZTDGE-UHFFFAOYSA-N 5-[[4-[2-(2-oxo-1,3-benzoxazol-3-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC(C=C1)=CC=C1OCCN1C(=O)OC2=CC=CC=C21 RBQZIAQNAZTDGE-UHFFFAOYSA-N 0.000 claims 1
HJKZAEPVTVPOID-UHFFFAOYSA-N benzyl n-[2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]ethyl]-n-methylcarbamate Chemical compound C=1C=CC=CC=1COC(=O)N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O HJKZAEPVTVPOID-UHFFFAOYSA-N 0.000 claims 1
238000010276 construction Methods 0.000 claims 1
MZHPCLNGIDSGNX-UHFFFAOYSA-N phenyl n-[2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]ethyl]-n-phenylcarbamate Chemical compound C=1C=C(CC2C(NC(=O)S2)=O)C=CC=1OCCN(C=1C=CC=CC=1)C(=O)OC1=CC=CC=C1 MZHPCLNGIDSGNX-UHFFFAOYSA-N 0.000 claims 1
229920000642 polymer Polymers 0.000 claims 1
229940126585 therapeutic drug Drugs 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 38
239000002904 solvent Substances 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
229910052739 hydrogen Inorganic materials 0.000 description 18
239000001257 hydrogen Substances 0.000 description 17
239000000243 solution Substances 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical class O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
238000010992 reflux Methods 0.000 description 12
238000001228 spectrum Methods 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
238000004587 chromatography analysis Methods 0.000 description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
239000003921 oil Substances 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
238000000746 purification Methods 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 7
239000010410 layer Substances 0.000 description 7
230000002265 prevention Effects 0.000 description 7
238000003756 stirring Methods 0.000 description 7
230000009466 transformation Effects 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
239000000047 product Substances 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000003814 drug Substances 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
150000002431 hydrogen Chemical group 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
238000006722 reduction reaction Methods 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
241000282412 Homo Species 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
239000012267 brine Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
229960001701 chloroform Drugs 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
229920001971 elastomer Polymers 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
239000006260 foam Substances 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
229910052721 tungsten Inorganic materials 0.000 description 3
VNDKJSXWQMXNGB-UHFFFAOYSA-N 2-phenylethyl n-(2-hydroxyethyl)-n-methylcarbamate Chemical compound OCCN(C)C(=O)OCCC1=CC=CC=C1 VNDKJSXWQMXNGB-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241000195493 Cryptophyta Species 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
125000003172 aldehyde group Chemical group 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 2
125000004448 alkyl carbonyl group Chemical group 0.000 description 2
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
125000002768 hydroxyalkyl group Chemical group 0.000 description 2
230000000055 hyoplipidemic effect Effects 0.000 description 2
230000002218 hypoglycaemic effect Effects 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000000463 material Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 2
QJIJQNUQORKBKY-UHFFFAOYSA-N piperidin-1-ium;benzoate Chemical compound C1CCNCC1.OC(=O)C1=CC=CC=C1 QJIJQNUQORKBKY-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
238000000844 transformation Methods 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
239000000052 vinegar Substances 0.000 description 2
235000021419 vinegar Nutrition 0.000 description 2
OYNIIKHNXNPSAG-UHFFFAOYSA-N 2-(4-formylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(C=O)C=C1 OYNIIKHNXNPSAG-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical compound OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 description 1
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 1
LRLBEYAFJPUHME-UHFFFAOYSA-N 3-(2-hydroxyethyl)-1,3-benzoxazol-2-one Chemical compound C1=CC=C2OC(=O)N(CCO)C2=C1 LRLBEYAFJPUHME-UHFFFAOYSA-N 0.000 description 1
UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
102100034744 Cell division cycle 7-related protein kinase Human genes 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
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102100028138 F-box/WD repeat-containing protein 7 Human genes 0.000 description 1
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101000945740 Homo sapiens Cell division cycle 7-related protein kinase Proteins 0.000 description 1
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239000005909 Kieselgur Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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241001465754 Metazoa Species 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
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ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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108010057464 Prolactin Proteins 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
244000028419 Styrax benzoin Species 0.000 description 1
235000000126 Styrax benzoin Nutrition 0.000 description 1
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CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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235000008411 Sumatra benzointree Nutrition 0.000 description 1
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JBVNMOALBOAVRM-UHFFFAOYSA-N [N].O=C1CSC(=O)N1 Chemical compound [N].O=C1CSC(=O)N1 JBVNMOALBOAVRM-UHFFFAOYSA-N 0.000 description 1
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150000001408 amides Chemical class 0.000 description 1
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HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229960002130 benzoin Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
244000309464 bull Species 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
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230000002301 combined effect Effects 0.000 description 1
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238000005859 coupling reaction Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
HALQELOKLVRWRI-VDBOFHIQSA-N doxycycline hyclate Chemical group O.[Cl-].[Cl-].CCO.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O HALQELOKLVRWRI-VDBOFHIQSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
LBGWCDQCRMORLC-UHFFFAOYSA-N ethanol methane Chemical compound C[H].[H]C([H])[H].[H]CC([H])O LBGWCDQCRMORLC-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
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235000013355 food flavoring agent Nutrition 0.000 description 1
239000000499 gel Substances 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
239000010931 gold Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
235000019382 gum benzoic Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000003345 hyperglycaemic effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
239000004137 magnesium phosphate Substances 0.000 description 1
229960002261 magnesium phosphate Drugs 0.000 description 1
229910000157 magnesium phosphate Inorganic materials 0.000 description 1
235000010994 magnesium phosphates Nutrition 0.000 description 1
239000011572 manganese Substances 0.000 description 1
238000003328 mesylation reaction Methods 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
IMTLAYIUCUAVRM-UHFFFAOYSA-N phenyl n-(2-hydroxyethyl)-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(CCO)C(=O)OC1=CC=CC=C1 IMTLAYIUCUAVRM-UHFFFAOYSA-N 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
239000001253 polyvinylpolypyrrolidone Substances 0.000 description 1
235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
229940097325 prolactin Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 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
238000007070 tosylation reaction Methods 0.000 description 1
239000002966 varnish Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- 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
- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Diabetes (AREA)
General Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Obesity (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

JP3516912A 1990-10-30 1991-10-18 チアゾリジンジオン誘導体 Pending JPH06502145A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB909023583A GB9023583D0 (en)	1990-10-30	1990-10-30	Novel compounds
GB9023583.9		1990-10-30
PCT/GB1991/001834 WO1992007838A1 (en)	1990-10-30	1991-10-18	Thiazolidine dione derivatives

Publications (1)

Publication Number	Publication Date
JPH06502145A true JPH06502145A (ja)	1994-03-10

Family

ID=10684574

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3516912A Pending JPH06502145A (ja)	1990-10-30	1991-10-18	チアゾリジンジオン誘導体

Country Status (5)

Country	Link
EP (1)	EP0555251A1 (de)
JP (1)	JPH06502145A (de)
AU (1)	AU8734791A (de)
GB (1)	GB9023583D0 (de)
WO (1)	WO1992007838A1 (de)

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* Cited by examiner, † Cited by third party
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ES2139633T3 (es) *	1992-08-31	2000-02-16	Sankyo Co	Derivados de oxazolidina con propiedades anti-diabetica y anti-obesidad, su preparacion y su utilizacion terapeutica.
GB9218830D0 (en) *	1992-09-05	1992-10-21	Smithkline Beecham Plc	Novel compounds
AU668818B2 (en) *	1993-04-07	1996-05-16	Taiho Pharmaceutical Co., Ltd.	Thiazolidine derivative and pharmaceutical composition containing the same
US6046222A (en) *	1993-09-15	2000-04-04	Warner-Lambert Company	Use of thiazolidinedione derivatives in the treatment of polycystic ovary syndrome, gestational diabetes and disease states at risk for progressing to noninsulin-dependent diabetes mellitus
NZ274346A (en) *	1993-09-15	1997-06-24	Sankyo Co	Use of various thiazolidine-2,4-dione and oxazolidine-2,4-dione derivatives to prevent or delay onset of non-insulin dependent diabetes mellitus
US5874454A (en) *	1993-09-15	1999-02-23	Warner-Lambert Company	Use of thiazolidinedione derivatives in the treatment of polycystic ovary syndrome, gestational diabetes and disease states at risk for progressing to noninsulin-dependent diabetes mellitus
US5478852C1 (en) *	1993-09-15	2001-03-13	Sankyo Co	Use of thiazolidinedione derivatives and related antihyperglycemic agents in the treatment of impaired glucose tolerance in order to prevent or delay the onset of noninsulin-dependent diabetes mellitus
IL113084A (en) *	1994-03-23	1999-01-26	Sankyo Co	Thiazolidine and oxazolidine derivatives processes for the preparation thereof and pharmaceutical compositions containing the same
CZ261095A3 (en) *	1994-10-07	1996-04-17	Sankyo Co	Oxime derivatives, process of their preparation, pharmaceutical composition containing thereof and their use
US5925656A (en) *	1995-04-10	1999-07-20	Dr. Reddy's Research Foundation	Compounds having antidiabetic, hypolipidemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them
TW399051B (en) *	1996-01-31	2000-07-21	Ssp Co Ltd	A novel benzoazine thiazolidinedione derivative and pharmaceutical composition for reducing blood glucose
ZA973848B (en) *	1996-05-06	1997-12-02	Reddy Research Foundation	Novel heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them.
US5919782A (en) *	1996-05-06	1999-07-06	Dr. Reddy's Research Foundation	Heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them
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
US5889025A (en) *	1996-05-06	1999-03-30	Reddy's Research Foundation	Antidiabetic compounds having hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them
US5885997A (en) *	1996-07-01	1999-03-23	Dr. Reddy's Research Foundation	Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
USRE39266E1 (en) *	1996-07-01	2006-09-05	Dr. Reddy's Laboratories, Limited	Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
CA2258949C (en)	1996-07-01	2008-05-06	Reddy-Cheminor, Inc.	Novel heterocyclic compounds process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
US6114526A (en) *	1996-07-01	2000-09-05	Dr. Reddy's Research Foundation	Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
US6372750B2 (en)	1996-07-01	2002-04-16	Dr. Reddy's Research Foundation	Heterocyclic compounds, process for their preparation and pharmaceutical compounds containing them and their use in the treatment of diabetes and related diseases
JP2000514041A (ja) *	1996-07-26	2000-10-24	ドクター・レディーズ・リサーチ・ファウンデーション	抗糖尿病、低脂血、抗高血圧特性を有するチアゾリジンジオン化合物、それらの調製法、及びその薬学的組成物
US5814647A (en)	1997-03-04	1998-09-29	Board Of Regents, The University Of Texas System	Use of troglitazone and related compounds for the treatment of the climacteric symptoms
US6313113B1 (en)	1997-04-15	2001-11-06	Reddy-Cheminor, Inc.	Heterocyclic compounds having antidiabetic, hypolipidemic and antihypertensive properties, process for their preparation and pharmaceutical compositions containing them
US6011031A (en) *	1997-05-30	2000-01-04	Dr. Reddy's Research Foundation	Azolidinediones useful for the treatment of diabetes, dyslipidemia and hypertension: process for their preparation and pharmaceutical compositions containing them
GB9723295D0 (en) *	1997-11-04	1998-01-07	Smithkline Beecham Plc	Novel process
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GB8820389D0 (en) *	1988-08-26	1988-09-28	Beecham Group Plc	Novel compounds

1990
- 1990-10-30 GB GB909023583A patent/GB9023583D0/en active Pending
1991
- 1991-10-18 JP JP3516912A patent/JPH06502145A/ja active Pending
- 1991-10-18 WO PCT/GB1991/001834 patent/WO1992007838A1/en not_active Ceased
- 1991-10-18 AU AU87347/91A patent/AU8734791A/en not_active Abandoned
- 1991-10-18 EP EP91918092A patent/EP0555251A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
AU8734791A (en)	1992-05-26
WO1992007838A1 (en)	1992-05-14
GB9023583D0 (en)	1990-12-12
EP0555251A1 (de)	1993-08-18

Publication	Publication Date	Title
JPH06502145A (ja)	1994-03-10	チアゾリジンジオン誘導体
JPH06502144A (ja)	1994-03-10	新規化合物
EP1680418B1 (de)	2007-05-09	Derivate von n-[heteroaryl(piperidin-2-yl)methyl]benzamid, verfahren zu deren herstellung und deren anwendung in therapeutika
CA2143849C (en)	2000-04-25	Substituted thiazolidinedione derivatives
US4918091A (en)	1990-04-17	Novel thiazolidinediones
JPH06502146A (ja)	1994-03-10	チアゾリジンジオン誘導体
US5132317A (en)	1992-07-21	Compounds
JPH06500538A (ja)	1994-01-20	オキサゾリジンジオン誘導体
JPH0283384A (ja)	1990-03-23	新規化合物、その製法及びそれを含む医薬組成物
JPH07505647A (ja)	1995-06-22	複素環化合物および２型糖尿病の治療におけるそれらの使用
CA2107223C (en)	2005-02-15	Crystalline tiagabine hydrochloride monohydrate, its preparation and use
CA2731789A1 (fr)	2010-01-28	Derives de carbamates d'alkylthiazoles, leur preparation et leur application en therapeutique
EP0734379B1 (de)	2001-03-07	Derivate von 2-arylalkenyl-azacyclo alkan als sigma rezeptor-liganden, verfahren zu ihrer herstellung und ihrer therapeutischer anwendung
JPH03287584A (ja)	1991-12-18	置換アリルアミン誘導体
TWI865700B (zh)	2024-12-11	用於製備呔酮衍生物及其中間體之製程
JPH06247850A (ja)	1994-09-06	１２−リポキシゲナーゼ阻害剤
AU2004291257B2 (en)	2008-06-19	Process for preparing thiazolidinediones
EP0475214B1 (de)	1995-06-07	Derivate der Kaffeinsäure und sie enthaltende pharmazeutische Zusammensetzungen
EP2283007A2 (de)	2011-02-16	Pyrrolderivate, ihre herstellung und ihre therapeutische verwendung
EP1773823B1 (de)	2013-08-21	4-arylmorpholin-3-onderivate, herstellung und therapeutische verwendung dafür
JPH0859638A (ja)	1996-03-05	新規なヘテロ環誘導体又はその塩
JPH02138218A (ja)	1990-05-28	血糖降下剤
JPH05194222A (ja)	1993-08-03	血糖降下剤
SK391691A3 (sk)	2000-12-11	Tiazolidindiónové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie
KR19990079559A (ko)	1999-11-05	4-치환된 피페리디노테레프탈산 유도체