BE567365A - - Google Patents

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Publication number: BE567365A
Authority: BE; Belgium
Prior art keywords: steroid; methyl; cyclo; hydroxy; oxo
Prior art date

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English (en)

French (fr)

Publication of BE567365A publication Critical patent/BE567365A/fr

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JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 30
238000000034 method Methods 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 19
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 7
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims description 7
-1 methyl magnesium halide Chemical class 0.000 claims description 7
230000003647 oxidation Effects 0.000 claims description 7
238000007254 oxidation reaction Methods 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 5
230000017105 transposition Effects 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
239000003153 chemical reaction reagent Substances 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 claims description 2
125000002524 organometallic group Chemical group 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
150000003431 steroids Chemical class 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 1
SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 66
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 20
239000000243 solution Substances 0.000 description 19
230000008018 melting Effects 0.000 description 18
238000002844 melting Methods 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
229960000583 acetic acid Drugs 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
238000002425 crystallisation Methods 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
238000010992 reflux Methods 0.000 description 6
239000000543 intermediate Substances 0.000 description 5
238000005406 washing Methods 0.000 description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
235000019270 ammonium chloride Nutrition 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
239000011777 magnesium Substances 0.000 description 4
229910052749 magnesium Inorganic materials 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
125000004043 oxo group Chemical group O=* 0.000 description 3
RJQCTQMDJCNDGK-RKZZQTKVSA-N (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13,19-pentamethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-ol Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=C(C)C[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 RJQCTQMDJCNDGK-RKZZQTKVSA-N 0.000 description 2
RJQCTQMDJCNDGK-UHFFFAOYSA-N 6-Methyldiosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=C(C)CC3C2C2)C)C2OC11CCC(C)CO1 RJQCTQMDJCNDGK-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229940040526 anhydrous sodium acetate Drugs 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
235000011056 potassium acetate Nutrition 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000003270 steroid hormone Substances 0.000 description 2
XWCQCIXHSIXOAW-IJPPCXMXSA-N (5s,8s,9s,10r,13s,14s)-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one Chemical compound C([C@@H]1C(=O)C2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 XWCQCIXHSIXOAW-IJPPCXMXSA-N 0.000 description 1
QRHBXQAFGLVWFW-XZPFMNNQSA-N (8r,9s,10r,13s,14s,17s)-17-hydroxy-6,10,13-trimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C([C@@]12C)CC(=O)C=C1C(C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@H]21 QRHBXQAFGLVWFW-XZPFMNNQSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
CQSSFBCFANSXMM-HKFQWECPSA-N 3,5-cycloandrostane Chemical class C([C@H]1[C@@H]2CCC[C@]2(CC[C@@H]1[C@@]1(C)CC2)C)CC31C2C3 CQSSFBCFANSXMM-HKFQWECPSA-N 0.000 description 1
UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
DWCSNWXARWMZTG-UHFFFAOYSA-N Trigonegenin A Natural products CC1C(C2(CCC3C4(C)CCC(O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 DWCSNWXARWMZTG-UHFFFAOYSA-N 0.000 description 1
GMILDXZMQHJWRG-SAGKYWRTSA-N [(3s,8s,9s,10r,13s,14s,17s)-17-acetyl-6,10,13-trimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H](C(C)=O)CC[C@H]3[C@@H]1CC(C)=C1[C@]2(C)CC[C@H](OC(=O)C)C1 GMILDXZMQHJWRG-SAGKYWRTSA-N 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000003263 anabolic agent Substances 0.000 description 1
230000001195 anabolic effect Effects 0.000 description 1
239000003098 androgen Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
UGIARLNNAPRCPF-HUPPADNKSA-N cyclopregnol Chemical compound C([C@H]1[C@@H]2CC[C@@H]([C@]2(CC[C@@H]1[C@@]1(C)CC2)C)C(=O)C)[C@@H](O)[C@]31[C@@H]2C3 UGIARLNNAPRCPF-HUPPADNKSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
WQLVFSAGQJTQCK-VKROHFNGSA-N diosgenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 WQLVFSAGQJTQCK-VKROHFNGSA-N 0.000 description 1
WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229950008604 mestanolone Drugs 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000583 progesterone congener Substances 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
ZNVGYHOBTCWGTO-UHFFFAOYSA-N solutin Natural products Cc1cc(O)cc2OC(C)(O)C(=O)c12 ZNVGYHOBTCWGTO-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1

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Steroid Compounds (AREA)

BE567365D BE567365A (de)

Publications (1)

Publication Number	Publication Date
BE567365A true BE567365A (de)

Family

ID=187116

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Application Number	Title	Priority Date	Filing Date
BE567365D BE567365A (de)

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BE (1)	BE567365A (de)

0
- BE BE567365D patent/BE567365A/fr unknown

Publication	Publication Date	Title
US4425273A (en)	1984-01-10	Process for production of chenodeoxycholic acid
Banachowicz et al.	2019	Gram-scale carbasugar synthesis via intramolecular seleno-Michael/aldol reaction
FR2569408A1 (fr)	1986-02-28	Nouveaux steroides substitues en position 10 par un radical comportant une double ou triple liaison, leur procede de preparation, leur application comme medicaments, les compositions pharmaceutiques les renfermant
FR2530641A1 (fr)	1984-01-27	Procede d'introduction d'un atome de fluor dans un steroide et produit obtenu
BE567365A (de)
EP0101383B1 (de)	1986-11-12	14-Aminosteroidderivate, ihre therapeutische Anwendung und Verfahren zu ihrer Herstellung
EP0520879B1 (de)	1997-04-23	Neue 16-Methyl substituierte Steroidderivate von Pregna-1,4-dien-3,20-dion, ihre Herstellung, ihre Verwendung zur Herstellung von 16-Methylene-substituierte Steroide und neue Zwischenprodukten dafür
EP0058097B1 (de)	1984-07-25	Verfahren zur Herstellung von 17-alpha-Hydroxy-17beta-hydroxyacetyl-Steroiden und die erhaltenen entsprechenden Zwischenprodukte
JPH10507451A (ja)	1998-07-21	６−アザアンドロステノンの合成
PL118827B1 (en)	1981-10-31	Method of manufacture of tricyclicdiketone
EP0059146B1 (de)	1985-09-25	Arzneimittel, abgeleitet von 3-Hydroxy-dodecahydro-benz(e)inden-7-on, Produkte, abgeleitet von 3-Hydroxy-dodecahydro-benz(e)inden-7-on und Verfahren zu ihrer Herstellung
US3325481A (en)	1967-06-13	3-(optionally substituted)amino-estra-1, 3, 5(10), 8(9), 14-pentaen - 17 - ones and derivatives thereof
US2992243A (en)	1961-07-11	3-keto-17-hydroxy-compounds of etiocholane and androstane and method for their manufacture
JP2714392B2 (ja)	1998-02-16	ステロイド誘導体の製造法
JP2953665B2 (ja)	1999-09-27	ステロイド誘導体の製造方法
MC1121A1 (fr)	1977-08-12	Nouveaux d-homosteroides
BE564226A (de)
BE560182A (de)
JPH0153680B2 (de)	1989-11-15
BE563651A (de)
JPH02108696A (ja)	1990-04-20	１０−置換−４−エストレン化合物
BE491355A (de)
BE556145A (de)
JPS6352637B2 (de)	1988-10-19
BE563649A (de)

BE567365A - - Google Patents

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ID=187116

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