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

206010033616 Pancreatic disease Diseases 0.000 claims description 9
239000004480 active ingredient Substances 0.000 claims description 4
150000001875 compounds Chemical class 0.000 description 57
-1 3-propylcyclopentyl Chemical group 0.000 description 53
239000000203 mixture Substances 0.000 description 32
239000000243 solution Substances 0.000 description 28
125000000217 alkyl group Chemical group 0.000 description 27
229910052799 carbon Inorganic materials 0.000 description 21
125000004432 carbon atoms Chemical group C* 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
150000004702 methyl esters Chemical class 0.000 description 15
239000011780 sodium chloride Substances 0.000 description 15
125000001424 substituent group Chemical group 0.000 description 14
SESFRYSPDFLNCH-UHFFFAOYSA-N Benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 13
239000012043 crude product Substances 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 11
150000003839 salts Chemical class 0.000 description 11
230000002194 synthesizing Effects 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
230000000694 effects Effects 0.000 description 9
125000004043 oxo group Chemical group O=* 0.000 description 9
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239000003795 chemical substances by application Substances 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
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
229910052731 fluorine Inorganic materials 0.000 description 7
239000011737 fluorine Substances 0.000 description 7
YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
125000005843 halogen group Chemical group 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
VYTZWRCSPHQSFX-GBNDHIKLSA-N (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one Chemical compound O1C(=O)C[C@@H]2[C@@H](CO)[C@H](O)C[C@@H]21 VYTZWRCSPHQSFX-GBNDHIKLSA-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
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QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
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125000004104 aryloxy group Chemical group 0.000 description 4
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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
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