JPH0140020B2 - - Google Patents
Info
- Publication number
- JPH0140020B2 JPH0140020B2 JP3819083A JP3819083A JPH0140020B2 JP H0140020 B2 JPH0140020 B2 JP H0140020B2 JP 3819083 A JP3819083 A JP 3819083A JP 3819083 A JP3819083 A JP 3819083A JP H0140020 B2 JPH0140020 B2 JP H0140020B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydroxy
- cyclopentenone
- formula
- hydroxyalkyl
- Prior art date
- 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.)
- Expired
Links
- -1 t-butyldimethylsilyloxy group Chemical group 0.000 claims description 99
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 125000001931 aliphatic group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical class O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 claims description 16
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
- 150000002642 lithium compounds Chemical class 0.000 claims description 9
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- DHNDDRBMUVFQIZ-UHFFFAOYSA-N 4-hydroxycyclopent-2-en-1-one Chemical class OC1CC(=O)C=C1 DHNDDRBMUVFQIZ-UHFFFAOYSA-N 0.000 claims description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- WOPKYMRPOKFYNI-UHFFFAOYSA-N 2-hydroxycyclopent-2-en-1-one Chemical class OC1=CCCC1=O WOPKYMRPOKFYNI-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 34
- 239000000243 solution Substances 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000012156 elution solvent Substances 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 238000010898 silica gel chromatography Methods 0.000 description 12
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- 230000003595 spectral effect Effects 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 238000000605 extraction Methods 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- OLJUSJRMJIWJIA-UHFFFAOYSA-N 4-butyl-5-(1-hydroxybutyl)cyclopent-2-en-1-one Chemical compound CCCCC1C=CC(=O)C1C(O)CCC OLJUSJRMJIWJIA-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 230000001093 anti-cancer Effects 0.000 description 5
- 150000003180 prostaglandins Chemical class 0.000 description 5
- BGKHCLZFGPIKKU-UHFFFAOYSA-N (13E,15S)-15-hydroxy-9-oxo-prosta-10,13-dienoic acid Natural products CCCCCC(O)C=CC1C=CC(=O)C1CCCCCCC(O)=O BGKHCLZFGPIKKU-UHFFFAOYSA-N 0.000 description 4
- JKUJIPQUSIYNLA-UHFFFAOYSA-N 3-butyl-4-[tert-butyl(dimethyl)silyl]oxy-2-(1-hydroxybutyl)cyclopentan-1-one Chemical compound CCCCC1C(O[Si](C)(C)C(C)(C)C)CC(=O)C1C(O)CCC JKUJIPQUSIYNLA-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000002246 antineoplastic agent Substances 0.000 description 4
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- VJVQQNSGTRYVLF-UHFFFAOYSA-N methyl 7-[2-butyl-3-[tert-butyl(dimethyl)silyl]oxy-5-oxocyclopentyl]-7-hydroxyheptanoate Chemical compound CCCCC1C(O[Si](C)(C)C(C)(C)C)CC(=O)C1C(O)CCCCCC(=O)OC VJVQQNSGTRYVLF-UHFFFAOYSA-N 0.000 description 4
- QZFRHCARENNNID-UHFFFAOYSA-N methyl 7-[4-tert-butyl-5-[3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-3,3-dimethyl-2-oxo-1-silyloxycyclopentyl]-7-hydroxyheptanoate Chemical compound C(C)(C)(C)C1C(C(C(C1(C)C)=O)(C(CCCCCC(=O)OC)O)O[SiH3])C=CC(CCCCC)O[Si](C)(C)C(C)(C)C QZFRHCARENNNID-UHFFFAOYSA-N 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- DAPZSGCXUJECAI-UHFFFAOYSA-N 4-[tert-butyl(dimethyl)silyl]oxycyclopent-2-en-1-one Chemical compound CC(C)(C)[Si](C)(C)OC1CC(=O)C=C1 DAPZSGCXUJECAI-UHFFFAOYSA-N 0.000 description 3
- UHHKNFFYHYIGIQ-UHFFFAOYSA-N 5-(1-hydroxybutyl)-4-prop-2-enylcyclopent-2-en-1-one Chemical compound CCCC(O)C1C(CC=C)C=CC1=O UHHKNFFYHYIGIQ-UHFFFAOYSA-N 0.000 description 3
- AVQKLRMRZOEQNT-UHFFFAOYSA-N 7-(2-butyl-5-oxocyclopent-3-en-1-yl)-7-hydroxyheptanoic acid Chemical compound CCCCC1C=CC(=O)C1C(O)CCCCCC(O)=O AVQKLRMRZOEQNT-UHFFFAOYSA-N 0.000 description 3
- JQHKMMGJFTULSH-UHFFFAOYSA-N 7-(2-decyl-5-oxocyclopent-3-en-1-yl)-7-hydroxyheptanoic acid Chemical compound CCCCCCCCCCC1C=CC(=O)C1C(O)CCCCCC(O)=O JQHKMMGJFTULSH-UHFFFAOYSA-N 0.000 description 3
- HPQUNWBIJRFAMB-UHFFFAOYSA-N 7-[2-(3-cyclohexyl-3-hydroxyprop-1-enyl)-5-oxocyclopent-3-en-1-yl]-7-hydroxyhept-5-ynoic acid Chemical compound C1CCCCC1C(O)C=CC1C=CC(=O)C1C(O)C#CCCCC(O)=O HPQUNWBIJRFAMB-UHFFFAOYSA-N 0.000 description 3
- YFWHYZQFODIVEE-UHFFFAOYSA-N 7-[2-(3-cyclohexylprop-1-enyl)-5-oxocyclopent-3-en-1-yl]-7-hydroxyheptanoic acid Chemical compound C1=CC(=O)C(C(CCCCCC(O)=O)O)C1C=CCC1CCCCC1 YFWHYZQFODIVEE-UHFFFAOYSA-N 0.000 description 3
- SWTCRCDRKWFQDC-UHFFFAOYSA-N 7-hydroxy-7-(2-octyl-5-oxocyclopent-3-en-1-yl)heptanoic acid Chemical compound CCCCCCCCC1C=CC(=O)C1C(O)CCCCCC(O)=O SWTCRCDRKWFQDC-UHFFFAOYSA-N 0.000 description 3
- YEWYZPZASGQGBN-UHFFFAOYSA-N 7-hydroxy-7-[2-(3-hydroxy-4-methylnon-1-enyl)-5-oxocyclopent-3-en-1-yl]hept-5-ynoic acid Chemical compound CCCCCC(C)C(O)C=CC1C=CC(=O)C1C(O)C#CCCCC(O)=O YEWYZPZASGQGBN-UHFFFAOYSA-N 0.000 description 3
- DWYGZTMEYUWDKI-UHFFFAOYSA-N 7-hydroxy-7-[2-(3-hydroxyoct-1-enyl)-5-oxocyclopent-3-en-1-yl]hept-2-enoic acid Chemical compound CCCCCC(O)C=CC1C=CC(=O)C1C(O)CCCC=CC(O)=O DWYGZTMEYUWDKI-UHFFFAOYSA-N 0.000 description 3
- RHKACQUGNDBDSR-UHFFFAOYSA-N 7-hydroxy-7-[2-(3-hydroxyoct-1-enyl)-5-oxocyclopent-3-en-1-yl]hept-4-enoic acid Chemical compound CCCCCC(O)C=CC1C=CC(=O)C1C(O)CC=CCCC(O)=O RHKACQUGNDBDSR-UHFFFAOYSA-N 0.000 description 3
- CPTMAXSIYIDUIE-UHFFFAOYSA-N 7-hydroxy-7-[2-(3-hydroxyoct-1-enyl)-5-oxocyclopent-3-en-1-yl]hept-5-enoic acid Chemical compound CCCCCC(O)C=CC1C=CC(=O)C1C(O)C=CCCCC(O)=O CPTMAXSIYIDUIE-UHFFFAOYSA-N 0.000 description 3
- GFINAQJCDZEJFB-UHFFFAOYSA-N 7-hydroxy-7-[2-(3-hydroxyoct-1-enyl)-5-oxocyclopent-3-en-1-yl]heptanoic acid Chemical compound CCCCCC(O)C=CC1C=CC(=O)C1C(O)CCCCCC(O)=O GFINAQJCDZEJFB-UHFFFAOYSA-N 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- TWJVNKMWXNTSAP-UHFFFAOYSA-N azanium;hydroxide;hydrochloride Chemical class [NH4+].O.[Cl-] TWJVNKMWXNTSAP-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001734 carboxylic acid salts Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 3
- 239000012024 dehydrating agents Substances 0.000 description 3
- 238000010931 ester hydrolysis Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- KDHIOWQSFJTRQG-UHFFFAOYSA-N methyl 7-(5-oxocyclopenten-1-yl)heptanoate Chemical compound COC(=O)CCCCCCC1=CCCC1=O KDHIOWQSFJTRQG-UHFFFAOYSA-N 0.000 description 3
- UNBGBUBQNGUMFD-UHFFFAOYSA-N methyl 7-[2-(3-cyclopentyl-3-hydroxyprop-1-enyl)-5-oxocyclopent-3-en-1-yl]-7-hydroxyhept-5-ynoate Chemical compound C1=CC(=O)C(C(O)C#CCCCC(=O)OC)C1C=CC(O)C1CCCC1 UNBGBUBQNGUMFD-UHFFFAOYSA-N 0.000 description 3
- OGZCRSPZIQAPJY-UHFFFAOYSA-N methyl 7-[2-[3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-5-oxocyclopent-3-en-1-yl]-7-hydroxyheptanoate Chemical compound CCCCCC(O[Si](C)(C)C(C)(C)C)C=CC1C=CC(=O)C1C(O)CCCCCC(=O)OC OGZCRSPZIQAPJY-UHFFFAOYSA-N 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- LUTDLYPHDVQSHT-UHFFFAOYSA-N 2-hydroxycyclopentan-1-one Chemical class OC1CCCC1=O LUTDLYPHDVQSHT-UHFFFAOYSA-N 0.000 description 2
- NKTDTMONXHODTI-UHFFFAOYSA-N 2-pentyne Chemical compound CCC#CC NKTDTMONXHODTI-UHFFFAOYSA-N 0.000 description 2
- DCSDFCDVBHVMCT-UHFFFAOYSA-N 4-[tert-butyl(dimethyl)silyl]cyclopent-2-en-1-one Chemical compound CC(C)(C)[Si](C)(C)C1CC(=O)C=C1 DCSDFCDVBHVMCT-UHFFFAOYSA-N 0.000 description 2
- SAURQQIRASEKMS-UHFFFAOYSA-N 4-[tert-butyl(dimethyl)silyl]oxy-2-(1-hydroxybutyl)-3-prop-2-enylcyclopentan-1-one Chemical compound CCCC(O)C1C(CC=C)C(O[Si](C)(C)C(C)(C)C)CC1=O SAURQQIRASEKMS-UHFFFAOYSA-N 0.000 description 2
- YMEPTVVGYQYXDX-UHFFFAOYSA-N 4-butyl-5-(1-hydroxy-2,2-dimethylpropyl)cyclopent-2-en-1-one Chemical compound CCCCC1C=CC(=O)C1C(O)C(C)(C)C YMEPTVVGYQYXDX-UHFFFAOYSA-N 0.000 description 2
- CIVITAXPIGHANW-UHFFFAOYSA-N 4-butyl-5-(1-hydroxy-3-phenylprop-2-enyl)cyclopent-2-en-1-one Chemical compound CCCCC1C=CC(=O)C1C(O)C=CC1=CC=CC=C1 CIVITAXPIGHANW-UHFFFAOYSA-N 0.000 description 2
- JIRJBIVRXSKVKL-UHFFFAOYSA-N 5-(1-hydroxybutyl)-4-oct-1-enylcyclopent-2-en-1-one Chemical compound CCCCCCC=CC1C=CC(=O)C1C(O)CCC JIRJBIVRXSKVKL-UHFFFAOYSA-N 0.000 description 2
- HZNOMIKAIREVMV-UHFFFAOYSA-N 5-(1-hydroxybutyl)-4-octylcyclopent-2-en-1-one Chemical compound CCCCCCCCC1C=CC(=O)C1C(O)CCC HZNOMIKAIREVMV-UHFFFAOYSA-N 0.000 description 2
- SANYQZZQRPKUEQ-UHFFFAOYSA-N 6-hydroxy-6-(2-oct-1-enyl-5-oxocyclopent-3-en-1-yl)hexanoic acid Chemical compound CCCCCCC=CC1C=CC(=O)C1C(O)CCCCC(O)=O SANYQZZQRPKUEQ-UHFFFAOYSA-N 0.000 description 2
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- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 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
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
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- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
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- XHRBVPBLXFVPKJ-UHFFFAOYSA-N methyl 7-[2-[3-[tert-butyl(dimethyl)silyl]oxy-5-methylnon-1-enyl]-5-oxocyclopent-3-en-1-yl]-7-hydroxyhept-2-enoate Chemical compound CCCCC(C)CC(O[Si](C)(C)C(C)(C)C)C=CC1C=CC(=O)C1C(O)CCCC=CC(=O)OC XHRBVPBLXFVPKJ-UHFFFAOYSA-N 0.000 description 1
- JBERMBPXCIROIT-UHFFFAOYSA-N methyl 7-hydroxy-7-[2-(3-hydroxyoct-1-enyl)-5-oxocyclopent-3-en-1-yl]heptanoate Chemical compound CCCCCC(O)C=CC1C=CC(=O)C1C(O)CCCCCC(=O)OC JBERMBPXCIROIT-UHFFFAOYSA-N 0.000 description 1
- NJVFYRBRYZXABC-UHFFFAOYSA-N methyl 7-oxoheptanoate Chemical compound COC(=O)CCCCCC=O NJVFYRBRYZXABC-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
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- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
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- 150000002895 organic esters Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 230000003836 peripheral circulation Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- MYHXHCUNDDAEOZ-FOSBLDSVSA-N prostaglandin A2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O MYHXHCUNDDAEOZ-FOSBLDSVSA-N 0.000 description 1
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 1
- 230000002997 prostaglandinlike Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 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
- 210000002966 serum Anatomy 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical compound [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- LTLQAJZGKYDIDX-UHFFFAOYSA-N tert-butyl-(1-iodooct-1-en-3-yloxy)-dimethylsilane Chemical compound CCCCCC(C=CI)O[Si](C)(C)C(C)(C)C LTLQAJZGKYDIDX-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- DSKYTPNZLCVELA-UHFFFAOYSA-N trihexyl phosphite Chemical compound CCCCCCOP(OCCCCCC)OCCCCCC DSKYTPNZLCVELA-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 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
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3819083A JPS59164747A (ja) | 1983-03-10 | 1983-03-10 | ５―（１―ヒドロキシアルキル）―２―シクロペンテノン誘導体およびその製造法 |
| DE8383305650T DE3375914D1 (en) | 1982-10-07 | 1983-09-22 | Novel 5-membered cyclic compounds, process for the production thereof, and pharmaceutical use thereof |
| EP83305650A EP0106576B1 (en) | 1982-10-07 | 1983-09-22 | Novel 5-membered cyclic compounds, process for the production thereof, and pharmaceutical use thereof |
| US06/823,146 US4766147A (en) | 1982-10-07 | 1986-01-29 | Novel 5-membered cyclic compounds, process for production thereof, and pharmaceutical use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3819083A JPS59164747A (ja) | 1983-03-10 | 1983-03-10 | ５―（１―ヒドロキシアルキル）―２―シクロペンテノン誘導体およびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59164747A JPS59164747A (ja) | 1984-09-17 |
| JPH0140020B2 true JPH0140020B2 (enrdf_load_stackoverflow) | 1989-08-24 |
Family
ID=12518443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3819083A Granted JPS59164747A (ja) | 1982-10-07 | 1983-03-10 | ５―（１―ヒドロキシアルキル）―２―シクロペンテノン誘導体およびその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59164747A (enrdf_load_stackoverflow) |
-
1983
- 1983-03-10 JP JP3819083A patent/JPS59164747A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59164747A (ja) | 1984-09-17 |
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