BE400505A - - Google Patents

Info

Publication number

BE400505A

BE400505A BE400505DA BE400505A BE 400505 A BE400505 A BE 400505A BE 400505D A BE400505D A BE 400505DA BE 400505 A BE400505 A BE 400505A

Authority

BE

Belgium

Prior art keywords

hormone

subjected

follicular

follicle

reduction

Prior art date

Links

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• Global Dossier
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• 239000005556 hormone Substances 0.000 claims description 7
• 229940088597 hormone Drugs 0.000 claims description 7
• 238000000034 method Methods 0.000 claims description 6
• DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims description 4
• VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical class OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 3
• 230000010933 acylation Effects 0.000 claims description 3
• 238000005917 acylation reaction Methods 0.000 claims description 3
• 230000002829 reductive effect Effects 0.000 claims description 3
• 230000001476 alcoholic effect Effects 0.000 claims description 2
• 238000005984 hydrogenation reaction Methods 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• 125000003118 aryl group Chemical group 0.000 claims 1
• 239000003795 chemical substances by application Substances 0.000 claims 1
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• 239000000047 product Substances 0.000 description 6
• 230000003325 follicular Effects 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 238000006243 chemical reaction Methods 0.000 description 3
• 239000007795 chemical reaction product Substances 0.000 description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
• 230000008018 melting Effects 0.000 description 3
• 238000006722 reduction reaction Methods 0.000 description 3
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
• UYIFTLBWAOGQBI-RRKYFUOXSA-N [(13s)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate Chemical compound C([C@]1(C2CCC1O)C)CC(C1=CC=3)C2CCC1=CC=3OC(=O)C1=CC=CC=C1 UYIFTLBWAOGQBI-RRKYFUOXSA-N 0.000 description 2
• 125000002252 acyl group Chemical group 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• APLGXMKUJWCEBP-UHFFFAOYSA-N 1-butoxy-4-[(4-methylphenyl)methoxy]benzene Chemical compound C1=CC(OCCCC)=CC=C1OCC1=CC=C(C)C=C1 APLGXMKUJWCEBP-UHFFFAOYSA-N 0.000 description 1
• CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
• 241000332699 Moneses Species 0.000 description 1
• 229910018487 Ni—Cr Inorganic materials 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
• 238000006254 arylation reaction Methods 0.000 description 1
• WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
• 238000006480 benzoylation reaction Methods 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 238000010531 catalytic reduction reaction Methods 0.000 description 1
• VNNRSPGTAMTISX-UHFFFAOYSA-N chromium nickel Chemical compound [Cr].[Ni] VNNRSPGTAMTISX-UHFFFAOYSA-N 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 125000002320 montanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 235000011121 sodium hydroxide Nutrition 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1