GB935701A - 17-desoxy steroids and methods of preparing the same - Google Patents
17-desoxy steroids and methods of preparing the sameInfo
- Publication number
- GB935701A GB935701A GB24394/60A GB2439460A GB935701A GB 935701 A GB935701 A GB 935701A GB 24394/60 A GB24394/60 A GB 24394/60A GB 2439460 A GB2439460 A GB 2439460A GB 935701 A GB935701 A GB 935701A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- hydrogen
- griseus
- product
- alkanoyl
- 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
- 238000000034 method Methods 0.000 title abstract 3
- 241000015473 Schizothorax griseus Species 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- SUPOKHOQAKXOHJ-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical class C1CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 SUPOKHOQAKXOHJ-BYZMTCBYSA-N 0.000 abstract 3
- 241000187747 Streptomyces Species 0.000 abstract 3
- -1 alkanoyl radicals Chemical class 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 244000005700 microbiome Species 0.000 abstract 3
- QQCBOIWDENXRLP-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-3h-cyclopenta[a]phenanthrene Chemical compound C1CC2=CCC=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 QQCBOIWDENXRLP-BYZMTCBYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 abstract 2
- 150000003431 steroids Chemical class 0.000 abstract 2
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 abstract 1
- 241000223600 Alternaria Species 0.000 abstract 1
- 241000193830 Bacillus <bacterium> Species 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- 241000222199 Colletotrichum Species 0.000 abstract 1
- 241000186216 Corynebacterium Species 0.000 abstract 1
- 241000723247 Cylindrocarpon Species 0.000 abstract 1
- 241000555695 Didymella Species 0.000 abstract 1
- 241000223218 Fusarium Species 0.000 abstract 1
- 241000187708 Micromonospora Species 0.000 abstract 1
- 241000218939 Micromonospora purpureochromogenes Species 0.000 abstract 1
- 241000187654 Nocardia Species 0.000 abstract 1
- 241000190509 Ophiobolus Species 0.000 abstract 1
- 241000586779 Protaminobacter Species 0.000 abstract 1
- 241000958254 Streptomyces argenteolus Species 0.000 abstract 1
- 241000958217 Streptomyces fimicarius Species 0.000 abstract 1
- 241000187435 Streptomyces griseolus Species 0.000 abstract 1
- 241000187395 Streptomyces microflavus Species 0.000 abstract 1
- 241000813867 Streptomyces roseochromogenus Species 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000013048 microbiological method Methods 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 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
- C12P33/02—Dehydrogenating; Dehydroxylating
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- 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
-
- 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
- C12P33/14—Hydroxylating at 16 position
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (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)
Abstract
The invention comprises 16a -hydroxylated steroids of the general formula <FORM:0935701/IV(a)/1> wherein R and R1 represent hydrogen atoms or alkanoyl radicals containing 1 to 6 carbon atoms, R11 represents <FORM:0935701/IV(a)/2> or =O, X represents a hydrogen or halogen atom, and X1 represents a fluorine atom or a methyl radical; a process for the preparation of 16a -hydroxylated-3-keto-4-pregnenes by treating 3-keto-D 4-pregnenes in which the C16 is saturated and unsubstituted with a fermenting microorganism of the genus Streptomyces, particularly S. griseus, S. griseus var. vilascens, S. aureus, S. purpeochromogenus, S. fimicarius, S. olivaceous, S. argenteolus, S. roseochromogenus, S. griseolus, S. microflavus, S. lipmonii, S. griseus var. castaneous, and S. griseus var. violascens; and a process for the preparation of 16a -hydroxylated steroids of the general formula <FORM:0935701/IV(a)/3> wherein R, R1, R11 and X have the above significance, X1 represents a hydrogen or fluorine atom or the methyl radical, and -C1-C2- represents a -CH2-CH2- or -CH=CH- radical, by treating the corresponding 16-unsubstituted 4-pregnene or 1,4-pregnadiene with fermenting microorganisms of the genus Streptomyces to introduce the 16a -hydroxy radical and, if desired, dehydrogenating a 4-pregnene product to form a 1,4-pregnadiene product, for example by a microbiological method using microorganisms such as Protaminobacter, Streptomyces, Bacillus, Nocardia, Myobacterium, Bacterium, Corynebacterium, Fusarium, Cylindrocarpon, Micromonospora, Alternaria, Ophiobolus, Septomyxa, Didymella, and Colletotrichum, or by means of selenium dioxide, and, if desired, alkanoylating the product to convert R and R1 from hydrogen to the alkanoyl radical or saponifying to convert R and R1 from the alkanoyl radical to hydrogen. Reference has been directed by the Comptroller to Specification 824,351.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82769759A | 1959-07-17 | 1959-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB935701A true GB935701A (en) | 1963-09-04 |
Family
ID=25249903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24394/60A Expired GB935701A (en) | 1959-07-17 | 1960-07-13 | 17-desoxy steroids and methods of preparing the same |
Country Status (2)
| Country | Link |
|---|---|
| FR (2) | FR38M (en) |
| GB (1) | GB935701A (en) |
-
1960
- 1960-07-13 GB GB24394/60A patent/GB935701A/en not_active Expired
- 1960-07-15 FR FR833006A patent/FR38M/en not_active Expired
- 1960-07-15 FR FR833014A patent/FR1375659A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR38M (en) | 1960-11-28 |
| FR1375659A (en) | 1964-10-23 |
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