BE526313A - - Google Patents

Info

Publication number: BE526313A
Authority: BE; Belgium
Prior art keywords: compound; steroid; sep; organism; curvularia
Prior art date: 1953-04-21

Application number

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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.)

1953-04-21

Publication of BE526313A publication Critical patent/BE526313A/fr

Links

150000001875 compounds Chemical class 0.000 claims description 60
238000000034 method Methods 0.000 claims description 45
-1 steroid compound Chemical class 0.000 claims description 24
244000005700 microbiome Species 0.000 claims description 23
150000003431 steroids Chemical class 0.000 claims description 22
241000223208 Curvularia Species 0.000 claims description 11
241000223211 Curvularia lunata Species 0.000 claims description 10
230000001706 oxygenating effect Effects 0.000 claims description 9
238000005805 hydroxylation reaction Methods 0.000 claims description 7
235000015097 nutrients Nutrition 0.000 claims description 7
241001330709 Cochliobolus pallescens Species 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 claims description 4
ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 claims description 4
229940119740 deoxycorticosterone Drugs 0.000 claims description 4
OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 claims description 3
230000001054 cortical effect Effects 0.000 claims description 3
OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 claims description 3
239000007900 aqueous suspension Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
230000003637 steroidlike Effects 0.000 claims 1
239000000203 mixture Substances 0.000 description 40
239000000047 product Substances 0.000 description 35
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
239000000463 material Substances 0.000 description 22
238000000855 fermentation Methods 0.000 description 14
230000004151 fermentation Effects 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
239000002609 medium Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
239000000284 extract Substances 0.000 description 6
238000006213 oxygenation reaction Methods 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
238000000926 separation method Methods 0.000 description 5
239000007858 starting material Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000004688 heptahydrates Chemical class 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003463 adsorbent Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
229940088598 enzyme Drugs 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
WHBHBVVOGNECLV-OBQKJFGGSA-N 11-deoxycortisol Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 WHBHBVVOGNECLV-OBQKJFGGSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
208000031968 Cadaver Diseases 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 2
241000233866 Fungi Species 0.000 description 2
229920002527 Glycogen Polymers 0.000 description 2
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 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
241000235388 Mucorales Species 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
241000364057 Peoria Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
229930182558 Sterol Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
239000008272 agar Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000003925 fat Substances 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
229940096919 glycogen Drugs 0.000 description 2
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
238000004816 paper chromatography Methods 0.000 description 2
239000000049 pigment Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000011160 research Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000012265 solid product Substances 0.000 description 2
241000894007 species Species 0.000 description 2
150000003432 sterols Chemical class 0.000 description 2
235000003702 sterols Nutrition 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
238000012360 testing method Methods 0.000 description 2
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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
WHBHBVVOGNECLV-UHFFFAOYSA-N 11-deoxy-17-hydroxy-corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 WHBHBVVOGNECLV-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-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
240000005695 Crotalaria pallida var. obovata Species 0.000 description 1
241000235555 Cunninghamella Species 0.000 description 1
241001531392 Curvularia brachyspora Species 0.000 description 1
241001558166 Curvularia sp. Species 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
241000187438 Streptomyces fradiae Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
238000005273 aeration Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
238000002306 biochemical method Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
229960004544 cortisone Drugs 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000012258 culturing Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
229940079919 digestives enzyme preparation Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229960000890 hydrocortisone Drugs 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
230000000050 nutritive effect Effects 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229940072033 potash Drugs 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
238000004382 potting Methods 0.000 description 1
230000000644 propagated effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000004445 quantitative analysis Methods 0.000 description 1
229940054283 quartermaster Drugs 0.000 description 1
201000003068 rheumatic fever Diseases 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000012137 tryptone Substances 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)
Steroid Compounds (AREA)

BE526313D 1953-04-21 BE526313A (xx)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US1164173XA	1953-04-21	1953-04-21
US322066XA	1953-04-21	1953-04-21

Publications (1)

Publication Number	Publication Date
BE526313A true BE526313A (xx)

Family

ID=34914733

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE526313D BE526313A (xx)	1953-04-21

Country Status (2)

Country	Link
BE (1)	BE526313A (xx)
FR (1)	FR1164173A (xx)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2018309A1 (en) *	1968-09-18	1970-05-29	Squibb & Sons Inc	Anti-androgenic 11-beta, 17 alpha-dihydroxy-a-nor- - progesterone and its esters
EP0042451B1 (de) *	1980-06-21	1983-06-22	Schering Aktiengesellschaft	Verfahren zur Herstellung von 11-beta-Hydroxysteroiden

0
- BE BE526313D patent/BE526313A/fr unknown
1953
- 1953-12-15 FR FR1164173D patent/FR1164173A/fr not_active Expired

Also Published As

Publication number	Publication date
FR1164173A (fr)	1958-10-07

Publication	Publication Date	Title
US2658023A (en)	1953-11-03	Oxygenation of steroids
FR2462417A1 (fr)	1981-02-13	Nouveaux derives de la monacoline k, leur procede de preparation et leur application en therapeutique
EP0231234B1 (fr)	1990-07-04	Procede d'hydroxylation par voie microbiologique de la quinine, de la quinidine, et de derives
BE526313A (xx)
JP2663294B2 (ja)	1997-10-15	ビタミンｄ類の製造方法
CH322066A (fr)	1957-05-31	Procédé de préparation de stéroïdes 11B-hydroxylés
FR2557455A1 (fr)	1985-07-05	Antibiotique nouveau 81-484 antitumeur et sa production
FR2468646A1 (fr)	1981-05-08	Production de l'acide d(-)-b-hydroxyisobutyrique par fermentation de l'acide isobutyrique et/ou methacrylique
JPH07123997A (ja)	1995-05-16	ステロイド類の２５位水酸化物の生物学的製造法
BE865589A (fr)	1978-10-02	Antibiotiques et leur preparation
CH323467A (fr)	1957-07-31	Procédé de préparation de stéroïdes 11B-hydroxylés
US2875134A (en)	1959-02-24	11 beta hydroxylation of steroids by epicoccum
US2876170A (en)	1959-03-03	Oxygenation of steroids in the 11beta position by spondylocladium
FR2524886A1 (xx)	1983-10-14
FR2479260A1 (fr)	1981-10-02	Procede de separation et de recuperation de la coproporphyrine et de l'uroporphyrine d'un bouillon de culture
JPS5953033B2 (ja)	1984-12-22	微生物培養法
BE538327A (xx)
JPS6244915B2 (xx)	1987-09-24
BE884518A (fr)	1981-01-28	Nouveaux derives de la monacoline k, leur procede de preparation et leur application en therapeutique
BE553590A (xx)
CH344999A (fr)	1960-03-15	Procédé de déshydrogénation d'un 3-céto-stéroïde non saturé en position 4(5)
FR2626006A1 (fr)	1989-07-21	Procede de synthese de mononitrates de glyceryle par bioconversion de la nitroglycerine
CH398885A (fr)	1966-03-15	Procédé de préparation d'un antibiotique
BE575588A (xx)	1959-08-11
JPH02119786A (ja)	1990-05-07	Ｌ―カルニチンの製造法