NO832146L - Fremgangsmaate ved fremstilling av oxazoleddiksyrederivater - Google Patents

Fremgangsmaate ved fremstilling av oxazoleddiksyrederivater

Info

Publication number: NO832146L
Authority: NO; Norway
Prior art keywords: methyl; carbon atoms; group; acid; yield
Prior art date: 1982-06-15

Application number

NO832146A

Other languages

English (en)

Norwegian (no)

Inventor

Kanji Meguro

Takeshi Fujita

Original Assignee

Takeda Chemical Industries Ltd

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.)

1982-06-15

Filing date

1983-06-14

Publication date

1983-12-16

1983-06-14 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1983-12-16 Publication of NO832146L publication Critical patent/NO832146L/no

Links

238000000034 method Methods 0.000 title claims description 30
238000002360 preparation method Methods 0.000 title claims description 4
239000002253 acid Substances 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims description 45
125000004432 carbon atom Chemical group C* 0.000 claims description 35
-1 benzyl ester Chemical class 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 17
125000000392 cycloalkenyl group Chemical group 0.000 claims description 14
125000000753 cycloalkyl group Chemical group 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
150000001602 bicycloalkyls Chemical group 0.000 claims description 7
150000001721 carbon Chemical group 0.000 claims description 7
239000012024 dehydrating agents‎ Substances 0.000 claims description 6
UZKFWBFLCWZXBJ-UHFFFAOYSA-N 2-[5-methyl-2-(1-methylcyclohexyl)-1,3-oxazol-4-yl]acetic acid Chemical compound OC(=O)CC1=C(C)OC(C2(C)CCCCC2)=N1 UZKFWBFLCWZXBJ-UHFFFAOYSA-N 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 4
230000009467 reduction Effects 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
HGPRKRZSJBCHIX-UHFFFAOYSA-N 2-(2-cyclohexyl-5-ethyl-1,3-oxazol-4-yl)acetic acid Chemical compound OC(=O)CC1=C(CC)OC(C2CCCCC2)=N1 HGPRKRZSJBCHIX-UHFFFAOYSA-N 0.000 claims description 3
XRWMYFZNIHLNJS-UHFFFAOYSA-N 2-(2-cyclohexyl-5-propyl-1,3-oxazol-4-yl)acetic acid Chemical compound OC(=O)CC1=C(CCC)OC(C2CCCCC2)=N1 XRWMYFZNIHLNJS-UHFFFAOYSA-N 0.000 claims description 3
FIEJOHZKHSVLST-UHFFFAOYSA-N 2-[5-methyl-2-(1-methylcyclohex-3-en-1-yl)-1,3-oxazol-4-yl]acetic acid Chemical compound OC(=O)CC1=C(C)OC(C2(C)CC=CCC2)=N1 FIEJOHZKHSVLST-UHFFFAOYSA-N 0.000 claims description 3
JXWBMJHCIPVTFX-UHFFFAOYSA-N 2-[5-methyl-2-(2-phenylethenyl)-1,3-oxazol-4-yl]acetic acid Chemical compound OC(=O)CC1=C(C)OC(C=CC=2C=CC=CC=2)=N1 JXWBMJHCIPVTFX-UHFFFAOYSA-N 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
KNYSULZXWSBQGQ-UHFFFAOYSA-N 2-(2-cycloheptyl-5-methyl-1,3-oxazol-4-yl)acetic acid Chemical compound OC(=O)CC1=C(C)OC(C2CCCCCC2)=N1 KNYSULZXWSBQGQ-UHFFFAOYSA-N 0.000 claims description 2
MMDWSADAQQWYMT-UHFFFAOYSA-N 2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)acetic acid Chemical compound OC(=O)CC1=C(C)OC(C2CCCCC2)=N1 MMDWSADAQQWYMT-UHFFFAOYSA-N 0.000 claims description 2
LUYVCGZEDWLKPQ-UHFFFAOYSA-N 2-(2-cyclopentyl-5-methyl-1,3-oxazol-4-yl)acetic acid Chemical compound OC(=O)CC1=C(C)OC(C2CCCC2)=N1 LUYVCGZEDWLKPQ-UHFFFAOYSA-N 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims 7
239000001257 hydrogen Substances 0.000 claims 7
150000002431 hydrogen Chemical class 0.000 claims 5
238000004519 manufacturing process Methods 0.000 claims 2
KZZNHZOPCOTXPM-UHFFFAOYSA-N 2-(2-cyclohex-3-en-1-yl-5-methyl-1,3-oxazol-4-yl)acetic acid Chemical compound OC(=O)CC1=C(C)OC(C2CC=CCC2)=N1 KZZNHZOPCOTXPM-UHFFFAOYSA-N 0.000 claims 1
SNMQOEVQYDYIIO-UHFFFAOYSA-N 2-[2-(cyclohexylmethyl)-5-methyl-1,3-oxazol-4-yl]acetic acid Chemical compound OC(=O)CC1=C(C)OC(CC2CCCCC2)=N1 SNMQOEVQYDYIIO-UHFFFAOYSA-N 0.000 claims 1
230000032050 esterification Effects 0.000 claims 1
230000007062 hydrolysis Effects 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 135
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 88
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239000002904 solvent Substances 0.000 description 67
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
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ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 37
238000000921 elemental analysis Methods 0.000 description 37
238000002844 melting Methods 0.000 description 34
230000008018 melting Effects 0.000 description 34
239000013078 crystal Substances 0.000 description 31
238000001953 recrystallisation Methods 0.000 description 31
238000001816 cooling Methods 0.000 description 29
238000006243 chemical reaction Methods 0.000 description 28
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 28
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
229910000030 sodium bicarbonate Inorganic materials 0.000 description 24
235000017557 sodium bicarbonate Nutrition 0.000 description 24
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 22
238000003756 stirring Methods 0.000 description 22
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
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 15
239000008103 glucose Substances 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
239000008280 blood Substances 0.000 description 12
210000004369 blood Anatomy 0.000 description 12
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 10
230000000694 effects Effects 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
150000008065 acid anhydrides Chemical class 0.000 description 8
238000012360 testing method Methods 0.000 description 8
241000699670 Mus sp. Species 0.000 description 7
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 7
239000003480 eluent Substances 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
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 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
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206010022489 Insulin Resistance Diseases 0.000 description 5
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 5
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125000004122 cyclic group Chemical group 0.000 description 5
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 5
238000002329 infrared spectrum Methods 0.000 description 5
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
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 4
244000215068 Acacia senegal Species 0.000 description 4
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229910052794 bromium Inorganic materials 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
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206010012601 diabetes mellitus Diseases 0.000 description 4
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230000002140 halogenating effect Effects 0.000 description 4
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235000011181 potassium carbonates Nutrition 0.000 description 3
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
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125000004093 cyano group Chemical group *C#N 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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 1
WEPUZBYKXNKSDH-UHFFFAOYSA-N cyclopentanecarbonyl chloride Chemical compound ClC(=O)C1CCCC1 WEPUZBYKXNKSDH-UHFFFAOYSA-N 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
SAFOISHPYBCUDA-UHFFFAOYSA-N ethyl 2-[2-(3-chlorophenyl)ethenyl]-5-methyl-1,3-oxazole-4-carboxylate Chemical compound O1C(C)=C(C(=O)OCC)N=C1C=CC1=CC=CC(Cl)=C1 SAFOISHPYBCUDA-UHFFFAOYSA-N 0.000 description 1
MNWJLVCUSPALOU-UHFFFAOYSA-N ethyl 2-[2-(4-chlorophenyl)ethenyl]-5-methyl-1,3-oxazole-4-carboxylate Chemical compound O1C(C)=C(C(=O)OCC)N=C1C=CC1=CC=C(Cl)C=C1 MNWJLVCUSPALOU-UHFFFAOYSA-N 0.000 description 1
YAZTZISFPWTGDM-UHFFFAOYSA-N ethyl 2-[3-(4-chlorophenyl)prop-2-enoylamino]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)NC(=O)C=CC1=CC=C(Cl)C=C1 YAZTZISFPWTGDM-UHFFFAOYSA-N 0.000 description 1
PFHQKHMMQHEPAC-UHFFFAOYSA-N ethyl 2-cyclopentyl-5-methyl-1,3-oxazole-4-carboxylate Chemical compound O1C(C)=C(C(=O)OCC)N=C1C1CCCC1 PFHQKHMMQHEPAC-UHFFFAOYSA-N 0.000 description 1
XVLZIZGPZPKXSQ-UHFFFAOYSA-N ethyl 5-methyl-2-[2-[3-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole-4-carboxylate Chemical compound O1C(C)=C(C(=O)OCC)N=C1C=CC1=CC=CC(C(F)(F)F)=C1 XVLZIZGPZPKXSQ-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
150000002303 glucose derivatives Chemical class 0.000 description 1
230000010030 glucose lowering effect Effects 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000000887 hydrating effect Effects 0.000 description 1
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 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
230000003914 insulin secretion Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
LHLYOQLDYCWXTB-UHFFFAOYSA-N methyl 2-[5-methyl-2-(1-methylcyclohexyl)-1,3-oxazol-4-yl]acetate Chemical compound O1C(C)=C(CC(=O)OC)N=C1C1(C)CCCCC1 LHLYOQLDYCWXTB-UHFFFAOYSA-N 0.000 description 1
VZENRNDPPYHVDU-UHFFFAOYSA-N methyl 2-amino-3-(cyclohexanecarbonyl)-4-oxohexanoate Chemical compound COC(=O)C(N)C(C(=O)CC)C(=O)C1CCCCC1 VZENRNDPPYHVDU-UHFFFAOYSA-N 0.000 description 1
KANXUEHAKKULKQ-UHFFFAOYSA-N methyl 3-(cycloheptanecarbonylamino)-4-oxopentanoate Chemical compound COC(=O)CC(C(C)=O)NC(=O)C1CCCCCC1 KANXUEHAKKULKQ-UHFFFAOYSA-N 0.000 description 1
GUVQJTNFUXKYJL-UHFFFAOYSA-N methyl 3-(cyclohexanecarbonylamino)-4-oxopentanoate Chemical compound COC(=O)CC(C(C)=O)NC(=O)C1CCCCC1 GUVQJTNFUXKYJL-UHFFFAOYSA-N 0.000 description 1
IUJPFLUHZSYFBX-UHFFFAOYSA-N methyl 3-[(1-methylcyclohex-3-ene-1-carbonyl)amino]-4-oxopentanoate Chemical compound COC(=O)CC(C(C)=O)NC(=O)C1(C)CCC=CC1 IUJPFLUHZSYFBX-UHFFFAOYSA-N 0.000 description 1
HQSOCCCPYUKDMY-UHFFFAOYSA-N methyl 3-[(1-methylcyclohexanecarbonyl)amino]-4-oxopentanoate Chemical compound COC(=O)CC(C(C)=O)NC(=O)C1(C)CCCCC1 HQSOCCCPYUKDMY-UHFFFAOYSA-N 0.000 description 1
LTPSOSDFJPQNSV-UHFFFAOYSA-N methyl 3-oxo-2-(3-phenylprop-2-enoylamino)nonanoate Chemical compound CCCCCCC(=O)C(C(=O)OC)NC(=O)C=CC1=CC=CC=C1 LTPSOSDFJPQNSV-UHFFFAOYSA-N 0.000 description 1
LPAVPXHNVJWUHA-UHFFFAOYSA-N methyl 4-methyl-3-oxo-2-(3-phenylprop-2-enoylamino)pentanoate Chemical compound COC(=O)C(C(=O)C(C)C)NC(=O)C=CC1=CC=CC=C1 LPAVPXHNVJWUHA-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-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
125000004344 phenylpropyl group Chemical group 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000004044 response Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
125000005504 styryl group Chemical group 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
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229940124597 therapeutic agent Drugs 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

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- 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
- C07D263/36—One oxygen atom
- C07D263/40—One oxygen atom attached in position 4

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
General Chemical & Material Sciences (AREA)
Emergency Medicine (AREA)
Hematology (AREA)
Obesity (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Endocrinology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO832146A 1982-06-15 1983-06-14 Fremgangsmaate ved fremstilling av oxazoleddiksyrederivater NO832146L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP57103544A JPS58219169A (ja)	1982-06-15	1982-06-15	オキサゾ−ル酢酸誘導体

Publications (1)

Publication Number	Publication Date
NO832146L true NO832146L (no)	1983-12-16

Family

ID=14356777

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO832146A NO832146L (no)	1982-06-15	1983-06-14	Fremgangsmaate ved fremstilling av oxazoleddiksyrederivater

Country Status (15)

Country	Link
US (1)	US4602027A (es)
EP (1)	EP0096890B1 (es)
JP (1)	JPS58219169A (es)
KR (1)	KR840005116A (es)
AU (1)	AU1565783A (es)
CA (1)	CA1195986A (es)
DE (1)	DE3374685D1 (es)
DK (1)	DK272083A (es)
ES (2)	ES523152A0 (es)
FI (1)	FI832036L (es)
GR (1)	GR78290B (es)
HU (1)	HU189296B (es)
NO (1)	NO832146L (es)
PT (1)	PT76871B (es)
ZA (1)	ZA834307B (es)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8531608D0 (en) *	1985-12-23	1986-02-05	Beecham Group Plc	Treatment
US5239080A (en) *	1989-02-08	1993-08-24	Takeda Chemical Industries, Ltd.	Oxazole compounds and their use as antidiabetic and bone-reduction inhibitory agents
EP0409418A1 (en) *	1989-07-20	1991-01-23	Imperial Chemical Industries Plc	Heterocyclic tertiary alcohols
EP0440183A1 (en) *	1990-02-01	1991-08-07	Takeda Chemical Industries, Ltd.	Oxazole compounds, their production and use
ES2245660T3 (es) *	1990-11-30	2006-01-16	Otsuka Pharmaceutical Co., Ltd.	Derivados de azol y su utilizacion como inhibidores de los radicales superoxidos.
CA2118706A1 (en) *	1992-07-13	1994-01-20	Saizo Shibata	Novel thiazolidinedione compounds and use thereof
MY128323A (en)	1996-09-30	2007-01-31	Otsuka Pharma Co Ltd	Thiazole derivatives for inhibition of cytokine production and of cell adhesion
DE69914557T2 (de)	1998-03-30	2005-01-05	Japan Tobacco Inc.	Verfahren zur herstellung einer isooxazolidindion-verbindung
EP1214303A1 (en) *	1999-08-31	2002-06-19	Merck & Co., Inc.	Heterocyclic compounds and methods of use thereof
KR100459917B1 (ko) *	2001-12-14	2004-12-03	(주)바이오뉴트리젠	페놀릭산 유도체 및 이를 포함하는 혈중 지질 농도 관련질환의 예방 및 치료용 조성물

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3401120A (en) *	1965-10-23	1968-09-10	Gaf Corp	Corrosion inhibitors
FI53314C (fi) *	1967-06-14	1978-04-10	Wyeth John & Brother Ltd	Foerfarande foer framstaellning av farmaceutiskt anvaendbar 2-(fenyleller p-klorfenyl) oxazol-4-yl (aettiksyra -acetatsalt eller -acetamid)
GB1245087A (en) *	1967-10-26	1971-09-02	Wyeth John & Brother Ltd	Heterocyclic compounds
US3578671A (en) *	1967-11-06	1971-05-11	Wyeth John & Brother Ltd	Oxazoles
AR208400A1 (es) *	1974-03-13	1976-12-27	Yoshitomi Pharmaceutical	Un metodo para producir nuevos acidos 5-alcoxi-4-oxazolalcanoicos 2-substituidos y sus esteres
JPS57188587A (en) *	1981-05-15	1982-11-19	Tanabe Seiyaku Co Ltd	Thienyloxazolylacetic acid derivative and its preparation

1982
- 1982-06-15 JP JP57103544A patent/JPS58219169A/ja active Granted
1983
- 1983-06-06 US US06/501,012 patent/US4602027A/en not_active Expired - Fee Related
- 1983-06-07 CA CA000429900A patent/CA1195986A/en not_active Expired
- 1983-06-07 FI FI832036A patent/FI832036L/fi not_active Application Discontinuation
- 1983-06-09 AU AU15657/83A patent/AU1565783A/en not_active Abandoned
- 1983-06-10 ES ES523152A patent/ES523152A0/es active Granted
- 1983-06-13 ZA ZA834307A patent/ZA834307B/xx unknown
- 1983-06-13 GR GR71647A patent/GR78290B/el unknown
- 1983-06-14 EP EP83105829A patent/EP0096890B1/en not_active Expired
- 1983-06-14 DE DE8383105829T patent/DE3374685D1/de not_active Expired
- 1983-06-14 NO NO832146A patent/NO832146L/no unknown
- 1983-06-14 DK DK272083A patent/DK272083A/da not_active Application Discontinuation
- 1983-06-14 PT PT76871A patent/PT76871B/pt unknown
- 1983-06-15 KR KR1019830002662A patent/KR840005116A/ko not_active Application Discontinuation
- 1983-06-15 HU HU832135A patent/HU189296B/hu unknown
1984
- 1984-11-16 ES ES538030A patent/ES8600751A1/es not_active Expired

Also Published As

Publication number	Publication date
CA1195986A (en)	1985-10-29
EP0096890B1 (en)	1987-11-25
US4602027A (en)	1986-07-22
PT76871A (en)	1983-07-01
PT76871B (en)	1986-01-27
ES8503676A1 (es)	1985-04-01
ES523152A0 (es)	1985-04-01
JPH044312B2 (es)	1992-01-27
KR840005116A (ko)	1984-11-03
HU189296B (en)	1986-06-30
FI832036A0 (fi)	1983-06-07
AU1565783A (en)	1983-12-22
ES538030A0 (es)	1985-11-01
EP0096890A3 (en)	1984-11-14
DK272083A (da)	1983-12-16
DE3374685D1 (en)	1988-01-07
GR78290B (es)	1984-09-26
EP0096890A2 (en)	1983-12-28
DK272083D0 (da)	1983-06-14
FI832036L (fi)	1983-12-16
ZA834307B (en)	1984-03-28
ES8600751A1 (es)	1985-11-01
JPS58219169A (ja)	1983-12-20

Publication	Publication Date	Title
US3647858A (en)	1972-03-07	Process for preparing 1-benzylidene-3-indenyl acetic acids
KR840002434B1 (ko)	1984-12-27	이미다졸 유도체의 제조방법
US20030225158A1 (en)	2003-12-04	Compounds that modulate PPAR activity and methods for their preparation
CA2620662C (fr)	2015-10-06	Derives de pyrrolopyridine et leurs utilisations comme modulateurs des recepteurs ppar
US20070099991A1 (en)	2007-05-03	Selective rxr ligands
NO154346B (no)	1986-05-26	Analogifremgangsmaate for fremstilling av terapeutisk aktive ftalazin-4-yl-eddiksyrederivater.
NO312100B1 (no)	2002-03-18	Nytt tiazolidindion-2-derivat, fremgangsmåter for dets fremstilling, mellomproduktforbindelser, samt farmasöytiskepreparater som inneholder det
FR2787789A1 (fr)	2000-06-30	Benzopyranes et benzoxepines utilisables dans le traitement de dyslipidemies, de l'atherosclerose et du diabete, compositions pharmaceutiques les contenant et procedes de preparations
NO832146L (no)	1983-12-16	Fremgangsmaate ved fremstilling av oxazoleddiksyrederivater
US5866596A (en)	1999-02-02	3,4-diaryloxazolone derivatives, their methods of preparation and their uses in therapeutics
IL98908A (en)	1995-03-30	History of acetamide, their preparation and the pharmaceutical preparations containing them
NO162556B (no)	1989-10-09	Analogifremgangsmaate for fremstilling av terapeutisk aktive pyridylfenyl- og difenylforbindelser.
KR20040068996A (ko)	2004-08-02	ＰＰＡＲα활성화에 반응하는 질병의 치료에 유용한α－페닐티오카르복시산 및＄Ｇ（ａ）－페닐옥시－카르복시산의 유도체
US4596816A (en)	1986-06-24	4-aryl oxazoles
DK160760B (da)	1991-04-15	Analogifremgangsmaade til fremstilling af n-naphthoylglycinderivater
EP0078241A2 (de)	1983-05-04	Furane
HU191167B (en)	1987-01-28	Process for preparing 2-hydroxymethyl-1,4-dihydro-pyridine-3-carboxylic acid lactones and pharmaceutical compositions containing thereof
DK159110B (da)	1990-09-03	4h-benzo(4,5)cyclohepta(1,2-b)thiophenderivater, fremgangsmaade til fremstilling deraf samt farmaceutiske praeparater indeholdende derivaterne
IE43101B1 (en)	1980-12-17	Process for the preparation of an oxadiazole compound
NO154493B (no)	1986-06-23	Analogifremgangsmaate for fremstilling av nye, terapeutisk aktive 1-substituerte-3-cycloalkyl-sulfonyl-pyrrolidin-2,5-dion-derivater.
AU597513B2 (en)	1990-05-31	Process for preparing haloalkyl thiazoles and haloalkyl thiazoles prepared thereby
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