JP2515442C

JP2515442C -

Info

Publication number: JP2515442C
Authority: JP; Japan
Prior art keywords: keto; group; ester; dihydro; methyl
Prior art date: 1998-04-02
Legal status : Expired - Lifetime

Application number

Other languages

English (en)

Japanese (ja)

Original Assignee

株式会社上野製薬応用研究所

Publication date

1998-04-02

Links

208000016222 Pancreatic disease Diseases 0.000 claims description 9
239000004480 active ingredient Substances 0.000 claims description 4
-1 3-propylcyclopentyl Chemical group 0.000 description 64
150000001875 compounds Chemical class 0.000 description 56
239000000203 mixture Substances 0.000 description 32
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 28
125000000217 alkyl group Chemical group 0.000 description 27
229910052799 carbon Inorganic materials 0.000 description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
150000004702 methyl esters Chemical class 0.000 description 15
125000001424 substituent group Chemical group 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000012043 crude product Substances 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 11
125000004432 carbon atom Chemical group C* 0.000 description 11
238000000034 method Methods 0.000 description 11
150000003839 salts Chemical class 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
150000001721 carbon Chemical group 0.000 description 9
125000004043 oxo group Chemical group O=* 0.000 description 9
RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 8
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
229910052736 halogen Inorganic materials 0.000 description 8
150000002367 halogens Chemical class 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
229910052731 fluorine Inorganic materials 0.000 description 7
239000011737 fluorine Substances 0.000 description 7
125000005843 halogen group Chemical group 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
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BXSCNNADPQDDOK-HYPYWDQKSA-N (3ar,4r,5r,6as)-4-[(e)-4,4-difluoro-5-oxooct-2-enyl]-5-(oxan-2-yloxy)-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one Chemical compound O([C@H]1[C@@H]([C@H]2CC(=O)O[C@H]2C1)C/C=C/C(F)(F)C(=O)CCC)C1CCCCO1 BXSCNNADPQDDOK-HYPYWDQKSA-N 0.000 description 6
QWYQDJDKFHFXFU-UHFFFAOYSA-N (5-fluoro-6-methoxy-6-oxohexyl) benzoate Chemical compound COC(=O)C(F)CCCCOC(=O)C1=CC=CC=C1 QWYQDJDKFHFXFU-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CZEBTZMIQZVUSE-UHFFFAOYSA-N [6-cyano-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]boronic acid Chemical compound C1=C(C#N)C=C2N(C(=O)OC(C)(C)C)C(B(O)O)=CC2=C1 CZEBTZMIQZVUSE-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
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201000003229 acute pancreatitis Diseases 0.000 description 5
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239000000460 chlorine Substances 0.000 description 5
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125000003545 alkoxy group Chemical group 0.000 description 4
125000004104 aryloxy group Chemical group 0.000 description 4
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238000007796 conventional method Methods 0.000 description 4
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239000003701 inert diluent Substances 0.000 description 4
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WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
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230000001154 acute effect Effects 0.000 description 3
150000001338 aliphatic hydrocarbons Chemical group 0.000 description 3
125000005907 alkyl ester group Chemical group 0.000 description 3
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ZHIUGKWQJHAHTQ-UHFFFAOYSA-N (6-methoxy-6-oxohexyl) benzoate Chemical compound COC(=O)CCCCCOC(=O)C1=CC=CC=C1 ZHIUGKWQJHAHTQ-UHFFFAOYSA-N 0.000 description 2
ZGTJZBPSILKDAB-UHFFFAOYSA-N (6-oxo-6-phenylmethoxyhexyl) benzoate Chemical compound C=1C=CC=CC=1COC(=O)CCCCCOC(=O)C1=CC=CC=C1 ZGTJZBPSILKDAB-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
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208000000668 Chronic Pancreatitis Diseases 0.000 description 2
239000012027 Collins reagent Substances 0.000 description 2
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
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QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 2
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238000005160 1H NMR spectroscopy Methods 0.000 description 1
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