BE535452A - - Google Patents

Info

Publication number: BE535452A
Authority: BE; Belgium
Prior art keywords: derivatives; saturated; pregnane; oxo; hydroxy
Prior art date: 1954-02-05

Application number

Other languages

Priority date (The priority date 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 date listed.)

1954-02-05

Publication of BE535452A publication Critical patent/BE535452A/fr

Links

229920006395 saturated elastomer Polymers 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 14
-1 derivatives of 18,20 dihydroxy-3-oxo-pregnane Chemical class 0.000 claims description 9
238000000034 method Methods 0.000 claims description 8
125000004043 oxo group Chemical group O=* 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
QKLAQQPYBMSHRP-NBVNSWMFSA-N (8R,9S,10S,13R,14S,17S)-17-(1-hydroxyethyl)-13-(hydroxymethyl)-10-methyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol Chemical class OC1CC2CC[C@@H]3[C@H](CC[C@@]4([C@H](CC[C@H]43)C(C)O)CO)[C@]2(CC1)C QKLAQQPYBMSHRP-NBVNSWMFSA-N 0.000 claims description 2
150000001720 carbohydrates Chemical class 0.000 claims 2
235000014633 carbohydrates Nutrition 0.000 claims 2
MSZGDMFMUIATIC-ZGZMCMJOSA-N (8r,9s,10s,13s,14s,17s)-17-ethyl-10-methyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene-13-carbaldehyde Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C=O)CC2 MSZGDMFMUIATIC-ZGZMCMJOSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
108090000790 Enzymes Proteins 0.000 description 8
102000004190 Enzymes Human genes 0.000 description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
229910052760 oxygen Inorganic materials 0.000 description 7
239000001301 oxygen Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
150000003431 steroids Chemical class 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
244000005700 microbiome Species 0.000 description 6
239000000047 product Substances 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000000155 melt Substances 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
150000003128 pregnanes Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
241000186361 Actinobacteria <class> Species 0.000 description 2
PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 2
PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 2
241000228212 Aspergillus Species 0.000 description 2
241000235555 Cunninghamella Species 0.000 description 2
241000223208 Curvularia Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
241000233866 Fungi Species 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
241000235388 Mucorales Species 0.000 description 2
241000228143 Penicillium Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
241001655322 Streptomycetales Species 0.000 description 2
229960002478 aldosterone Drugs 0.000 description 2
239000002036 chloroform fraction Substances 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000008103 glucose Substances 0.000 description 2
230000002906 microbiologic effect Effects 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
150000007970 thio esters Chemical class 0.000 description 2
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-pregnane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-NUNROCCHSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
210000001557 animal structure Anatomy 0.000 description 1
URAPFRVSOJQECJ-UHFFFAOYSA-N benzene chromium Chemical compound [Cr].C1=CC=CC=C1 URAPFRVSOJQECJ-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
229960004544 cortisone Drugs 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000002032 methanolic fraction Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000005445 natural material Substances 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000008961 swelling Effects 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P33/00—Preparation of steroids
- C12P33/06—Hydroxylating
- C12P33/08—Hydroxylating at 11 position

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Zoology (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
Microbiology (AREA)
General Chemical & Material Sciences (AREA)
Biotechnology (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

BE535452D 1954-02-05 BE535452A (xx)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1161328X		1954-02-05

Publications (1)

Publication Number	Publication Date
BE535452A true BE535452A (xx)

Family

ID=4560711

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE535452D BE535452A (xx)	1954-02-05

Country Status (3)

Country	Link
BE (1)	BE535452A (xx)
FR (1)	FR1161328A (xx)
NL (1)	NL99566C (xx)

0
- NL NL99566D patent/NL99566C/xx active
- BE BE535452D patent/BE535452A/fr unknown
1955
- 1955-01-31 FR FR1161328D patent/FR1161328A/fr not_active Expired

Also Published As

Publication number	Publication date
NL99566C (xx)
FR1161328A (fr)	1958-08-26

Publication	Publication Date	Title
CA1266466A (fr)	1990-03-06	Procede de preparation de steroides substitues en position 10
Ohloff et al.	1983	Structural and configurational dependence of the sensory process in steroids
FR2771105A1 (fr)	1999-05-21	Utilisation du fusarium monoliforme pour la preparation des derives 7alpha-hydroxyles de la dehydroepiandrosterone et de la pregnenolone
BE535452A (xx)
Laskin et al.	1964	Microbial hydroxylation of estrone and estradiol in the 6β-, 7α-, and 15α-positions
Eppstein et al.	1953	Microbiological Transformations of Steroids. VII. Preparation of 11α-Hydroxypregnane-3, 20-dione and 11α-Hydroxyallopregnane-3, 20-dione1
EHRENSTEIN et al.	1956	Investigations on Steroids. XXVI. Synthesis of 19-Hydroxy-▵ 4-androstene-3, 17-dione1, 2
EP0231234B1 (fr)	1990-07-04	Procede d'hydroxylation par voie microbiologique de la quinine, de la quinidine, et de derives
Tan	1977	Synthesis and properties of two new steroid hydroperoxides: An alternative pathway for the formation of 6β-hydroxyprogesterone
CA1220195A (en)	1987-04-07	METHOD OF PREPARING 11.beta., 17.alpha., 20, 21-TETRAHYDROXY STEROIDS AND CORRESPONDING 11.beta., 17.alpha., 21- TRIHYDROXY-20-OXO STEROIDS
US3880895A (en)	1975-04-29	Hydroxylation of d-13-alkyl-17{60 -ethynyl-hydroxygon-4-en-3-one and derivatures thereof
BE546636A (xx)
BE531289A (xx)
Zohri et al.	1999	Progesterone transformations by three species of Humicola
BE551726A (xx)
US3116220A (en)	1963-12-31	Process for the 9alpha-hydroxylation of steroids with ascochyta
Boar et al.	1982	A mild and efficient degradation of ring A of steroids
FR2510138A1 (fr)	1983-01-28	Procede de production du 9-hydroxy-3-oxo-4,17 (20)-pregnadiene-20-carboxaldehyde par fermentation et produit obtenu
BE550906A (xx)
BE564914A (xx)
BE537353A (xx)
US3395079A (en)	1968-07-30	Process for the microbiological side chain degradation of 9beta, 10alpha-pregnane-20-ones
DE1027664B (de)	1958-04-10	Verfahren zur Herstellung polyoxigenierter Dehydrosteroide
BE540478A (xx)
US3063989A (en)	1962-11-13	2beta-hydroxy-9 alpha-halo-11-oxygenated pregnenes