CH369450A - Verfahren zur Herstellung von 16a-Alkyl-11a,17a-dioxy-4-pregnen-3,20-dionen - Google Patents

Verfahren zur Herstellung von 16a-Alkyl-11a,17a-dioxy-4-pregnen-3,20-dionen

Info

Publication number: CH369450A
Authority: CH; Switzerland
Prior art keywords: pregnen; dione; alkyl; dioxy; oxidizing
Prior art date: 1957-11-22

Application number

CH6648658A

Other languages

German (de)

English (en)

Inventor

Joseph Mcaleer William

Henry Stoudt Thomas

Original Assignee

Merck & Co Inc

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.)

1957-11-22

Filing date

1958-11-22

Publication date

1963-05-31

1958-11-22 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1963-05-31 Publication of CH369450A publication Critical patent/CH369450A/de

Links

238000000034 method Methods 0.000 title claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
230000001590 oxidative effect Effects 0.000 claims description 10
241000221931 Hypomyces rosellus Species 0.000 claims description 9
229910052757 nitrogen Inorganic materials 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
238000004519 manufacturing process Methods 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
102000004190 Enzymes Human genes 0.000 claims description 2
108090000790 Enzymes Proteins 0.000 claims description 2
239000012736 aqueous medium Substances 0.000 claims description 2
241000555268 Dendroides Species 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
239000002609 medium Substances 0.000 description 15
230000004151 fermentation Effects 0.000 description 13
238000000855 fermentation Methods 0.000 description 12
230000003647 oxidation Effects 0.000 description 7
238000007254 oxidation reaction Methods 0.000 description 7
150000003431 steroids Chemical class 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
244000005700 microbiome Species 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
235000015097 nutrients Nutrition 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
-1 steroid compounds Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
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
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
241000364057 Peoria Species 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
238000007654 immersion Methods 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 description 1
102000004407 Lactalbumin Human genes 0.000 description 1
108090000942 Lactalbumin Proteins 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
238000005273 aeration Methods 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
230000001055 chewing effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000009655 industrial fermentation Methods 0.000 description 1
229910052742 iron Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000203 mixture Substances 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000011591 potassium Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000007659 semicarbazones Chemical class 0.000 description 1
239000011734 sodium Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000009423 ventilation Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C12P33/12—Acting on D ring
- C12P33/16—Acting at 17 position
- C12P33/18—Hydroxylating at 17 position
- 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
- C12P33/10—Hydroxylating at 11 position at 11 alpha-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)
Preparation Of Compounds By Using Micro-Organisms (AREA)

CH6648658A 1957-11-22 1958-11-22 Verfahren zur Herstellung von 16a-Alkyl-11a,17a-dioxy-4-pregnen-3,20-dionen CH369450A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US69806157A	1957-11-22	1957-11-22

Publications (1)

Publication Number	Publication Date
CH369450A true CH369450A (de)	1963-05-31

Family

ID=24803766

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6648658A CH369450A (de)	1957-11-22	1958-11-22	Verfahren zur Herstellung von 16a-Alkyl-11a,17a-dioxy-4-pregnen-3,20-dionen

Country Status (2)

Country	Link
CH (1)	CH369450A (da)
DK (1)	DK108138C (da)

1958
- 1958-11-21 DK DK423558A patent/DK108138C/da active
- 1958-11-22 CH CH6648658A patent/CH369450A/de unknown

Also Published As

Publication number	Publication date
DK108138C (da)	1967-09-18

Publication	Publication Date	Title
CH513845A (de)	1971-10-15	Verfahren zur Herstellung neuer Halogenpregnadiene
DE1768215C3 (de)	1975-12-18	Verfahren zur Herstellung von 1,4-Androstadien-3,17-dlon und 4-Androsten-3,17-dion durch mikrobiologischem Abbau
DE1154102B (de)	1963-09-12	Verfahren zur Herstellung therapeutisch wirksamer Steroidverbindungen
EP0054810B1 (de)	1986-07-30	Verfahren zur Herstellung von 3-Oxo-delta-1,4-steroiden
EP0014991B1 (de)	1983-01-19	Mikrobiologisches Verfahren zur Herstellung 7-alpha-hydroxylierter Steroide
DE3884777T2 (de)	1994-02-10	Verfahren zur Herstellung von Pregneno-Oxazolinen.
CH369450A (de)	1963-05-31	Verfahren zur Herstellung von 16a-Alkyl-11a,17a-dioxy-4-pregnen-3,20-dionen
EP0014971B1 (de)	1982-06-16	Verfahren zur Herstellung von 1-alpha-Hydroxydehydroepiandrosteron
DE1418394C3 (de)	1973-10-11	Verfahren zur Herstellung von Fluorverbindungen der Pregnanreihe
US2954326A (en)	1960-09-27	Steroid production with dactylium dendroides
DE962435C (de)	1957-04-25	Verfahren zur Einfuehrung von Sauerstoff in Steroide
WO1992005269A1 (de)	1992-04-02	VERFAHREN ZUR HERSTELLUNG VON β-CARBOLIN-DERIVATEN
DE1793750C3 (de)	1976-08-05	Verfahren zur Herstellung von Fluorverbindungen der Pregnanreihe
AT235476B (de)	1964-08-25	Verfahren zur Herstellung der neuen 11β,21-Dihydroxy-16α-alkyl-4,17(20)-pregnadien-3-one
DE1620628A1 (de)	1970-08-20	Verfahren zur Einfuehrung von Sauerstoff in den hetrozyklischen Ring von N-Acylderivaten in Polymethyleniminen und Azabicycloalkanen
EP0019162B1 (de)	1982-12-01	12-alpha-Hydroxysteroide und deren Herstellung
AT254407B (de)	1967-05-26	Herstellung von Retrosteroiden
DE1618848A1 (de)	1971-02-18	Verfahren zur Herstellung von 3-alpha,5-Cyclo-6ss,19-oxido-5alpha-androstan-17-on
DE1793248C3 (de)	1977-09-01	Verfahren zur Herstellung von Os tränen
DE1128854B (de)	1962-05-03	Verfahren zur Herstellung von 11-hydroxylierten Steroiden der Pregnanreihe
DE1001681B (de)	1957-01-31	Verfahren zur Herstellung von 21-Oxypregnanen
DE1295552B (de)	1969-05-22	Verfahren zur Herstellung von 3-oxygenierten 11ª‰-Hydroxy-1, 4-pregnadienen auf mikrobiologischem Wege
DE1027667B (de)	1958-04-10	Verfahren zur Herstellung polyoxigenierter Pregnane
DE1122949B (de)	1962-02-01	Verfahren zur Herstellung von 16ª‡-Methyl-11ª‡,17ª‡-dioxy-4-pregnen-3,20-dion
DE1005960B (de)	1957-04-11	Verfahren zur Herstellung von 17-Oxypregnanen