NO863077L - Fremgangsmaate til mikrobiell hydroksylering av forskolin og dens derivater ved neurospora crassa. - Google Patents

Fremgangsmaate til mikrobiell hydroksylering av forskolin og dens derivater ved neurospora crassa.

Info

Publication number: NO863077L
Authority: NO; Norway
Prior art keywords: forskolin; neurospora crassa; atcc; means hydrogen; derivatives
Prior art date: 1985-07-31

Application number

NO863077A

Other languages

English (en)

Norwegian (no)

Other versions

NO863077D0 (no

Inventor

Werner Aretz

Dirk Boettger

Klaus Sauber

Original Assignee

Hoechst Ag

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.)

1985-07-31

Filing date

1986-07-30

Publication date

1987-02-02

1986-07-30 Application filed by Hoechst Ag filed Critical Hoechst Ag

1986-07-30 Publication of NO863077D0 publication Critical patent/NO863077D0/no

1987-02-02 Publication of NO863077L publication Critical patent/NO863077L/no

Links

238000000034 method Methods 0.000 title claims description 15
241000221961 Neurospora crassa Species 0.000 title claims description 6
230000033444 hydroxylation Effects 0.000 title claims description 5
238000005805 hydroxylation reaction Methods 0.000 title claims description 5
230000000813 microbial effect Effects 0.000 title claims description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
235000015097 nutrients Nutrition 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
238000000605 extraction Methods 0.000 claims description 3
238000000855 fermentation Methods 0.000 claims description 3
230000004151 fermentation Effects 0.000 claims description 3
239000000706 filtrate Substances 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
150000003505 terpenes Chemical class 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
238000004587 chromatography analysis Methods 0.000 claims description 2
238000002425 crystallisation Methods 0.000 claims description 2
230000008025 crystallization Effects 0.000 claims description 2
244000005700 microbiome Species 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
230000003647 oxidation Effects 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
239000000758 substrate Substances 0.000 claims description 2
239000007788 liquid Substances 0.000 claims 1
OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 45
SUZLHDUTVMZSEV-UHFFFAOYSA-N Deoxycoleonol Natural products C12C(=O)CC(C)(C=C)OC2(C)C(OC(=O)C)C(O)C2C1(C)C(O)CCC2(C)C SUZLHDUTVMZSEV-UHFFFAOYSA-N 0.000 description 22
OHCQJHSOBUTRHG-UHFFFAOYSA-N colforsin Natural products OC12C(=O)CC(C)(C=C)OC1(C)C(OC(=O)C)C(O)C1C2(C)C(O)CCC1(C)C OHCQJHSOBUTRHG-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
230000036983 biotransformation Effects 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
ZKZMDXUDDJYAIB-MLITWPTNSA-N 1,9-dideoxyforskolin Chemical compound O=C([C@@H]12)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)C1[C@]2(C)CCCC1(C)C ZKZMDXUDDJYAIB-MLITWPTNSA-N 0.000 description 5
239000000126 substance Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
PXYAFNGUEZPJBI-OAUGPMCWSA-N [(3r,4ar,5s,6s,6as,10as,10bs)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)CCCC1(C)C PXYAFNGUEZPJBI-OAUGPMCWSA-N 0.000 description 4
230000008878 coupling Effects 0.000 description 4
238000010168 coupling process Methods 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000131459 Plectranthus barbatus Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
WPDITXOBNLYZHH-UHFFFAOYSA-N desacetylforskolin Natural products O1C(C)(C=C)CC(=O)C2(O)C3(C)C(O)CCC(C)(C)C3C(O)C(O)C21C WPDITXOBNLYZHH-UHFFFAOYSA-N 0.000 description 3
238000001514 detection method Methods 0.000 description 3
ZKZMDXUDDJYAIB-UHFFFAOYSA-N dideoxy-forskolin Natural products C12C(=O)CC(C)(C=C)OC2(C)C(OC(=O)C)C(O)C2C1(C)CCCC2(C)C ZKZMDXUDDJYAIB-UHFFFAOYSA-N 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
150000004160 forskolin derivatives Chemical class 0.000 description 3
239000002609 medium Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
SUZLHDUTVMZSEV-WESICCPUSA-N (3R,4aR,5S,6S,6aS,10S,10aS,10bS)-3-ethenyl-6,10-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxododecahydro-1H-benzo[f]chromen-5-yl acetate Chemical compound O=C([C@@H]12)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C SUZLHDUTVMZSEV-WESICCPUSA-N 0.000 description 2
WDJJFDJQYGLZPA-CGPDBNODSA-N (3R,4aS,5S,6S,6aS,10S,10aS,10bR)-3-ethenyl-5,6,10-trihydroxy-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydrobenzo[f]chromen-1-one Chemical compound O1[C@@](C)(C=C)CC(=O)[C@@H]2[C@@]3(C)[C@@H](O)CCC(C)(C)[C@@H]3[C@H](O)[C@H](O)[C@]21C WDJJFDJQYGLZPA-CGPDBNODSA-N 0.000 description 2
ZKZMDXUDDJYAIB-SUCLLAFCSA-N 1,9-dideoxyforskolin Natural products O=C([C@@H]12)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)CCCC1(C)C ZKZMDXUDDJYAIB-SUCLLAFCSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
SBMKZIAQTQIEHN-NRADYMPXSA-N Coleonol C Natural products [H][C@@]12[C@H](OC(C)=O)[C@@H](O)[C@@]3(C)O[C@@](C)(CC(=O)[C@]3(O)[C@@]1(C)[C@@H](C)CCC2(C)C)C=C SBMKZIAQTQIEHN-NRADYMPXSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
208000010412 Glaucoma Diseases 0.000 description 2
206010019280 Heart failures Diseases 0.000 description 2
206010020751 Hypersensitivity Diseases 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
CLOQVZCSBYBUPB-VDCUXWMXSA-N [(3r,4ar,5s,6s,10s,10ar,10bs)-3-ethenyl-5,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-6-yl] acetate Chemical compound O[C@H]([C@@]12C)CCC(C)(C)C1[C@H](OC(=O)C)[C@H](O)[C@]1(C)[C@]2(O)C(=O)C[C@](C)(C=C)O1 CLOQVZCSBYBUPB-VDCUXWMXSA-N 0.000 description 2
230000007815 allergy Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000000284 extract Substances 0.000 description 2
230000002538 fungal effect Effects 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000011573 trace mineral Substances 0.000 description 2
235000013619 trace mineral Nutrition 0.000 description 2
230000009466 transformation Effects 0.000 description 2
WPDITXOBNLYZHH-KAACEJSMSA-N (3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-5,6,10,10b-tetrahydroxy-3,4a,7,7,10a-pentamethyl-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-1-one Chemical compound O1[C@@](C)(C=C)CC(=O)[C@]2(O)[C@@]3(C)[C@@H](O)CCC(C)(C)[C@@H]3[C@H](O)[C@H](O)[C@]21C WPDITXOBNLYZHH-KAACEJSMSA-N 0.000 description 1
CTIHYOZNWNAKHD-UHFFFAOYSA-N 4-methoxybenzaldehyde;sulfuric acid Chemical compound OS(O)(=O)=O.COC1=CC=C(C=O)C=C1 CTIHYOZNWNAKHD-UHFFFAOYSA-N 0.000 description 1
208000014181 Bronchial disease Diseases 0.000 description 1
206010006482 Bronchospasm Diseases 0.000 description 1
235000005320 Coleus barbatus Nutrition 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
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 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
241000221960 Neurospora Species 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
230000007885 bronchoconstriction Effects 0.000 description 1
230000003491 cAMP production Effects 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229940041514 candida albicans extract Drugs 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
229930004069 diterpene Natural products 0.000 description 1
125000000567 diterpene group Chemical group 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000001727 glucose Nutrition 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000009630 liquid culture Methods 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
230000035764 nutrition Effects 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000000844 transformation Methods 0.000 description 1
230000007306 turnover Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
- 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein

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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)

NO863077A 1985-07-31 1986-07-30 Fremgangsmaate til mikrobiell hydroksylering av forskolin og dens derivater ved neurospora crassa. NO863077L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853527336 DE3527336A1 (de)	1985-07-31	1985-07-31	Verfahren zur mikrobiellen hydroxylierung von forskolin und seinen derivaten durch neurospora crassa

Publications (2)

Publication Number	Publication Date
NO863077D0 NO863077D0 (no)	1986-07-30
NO863077L true NO863077L (no)	1987-02-02

Family

ID=6277208

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO863077A NO863077L (no)	1985-07-31	1986-07-30	Fremgangsmaate til mikrobiell hydroksylering av forskolin og dens derivater ved neurospora crassa.

Country Status (12)

Country	Link
EP (1)	EP0212293A2 (fr)
JP (1)	JPS6232892A (fr)
KR (1)	KR870001313A (fr)
AU (1)	AU6068486A (fr)
DE (1)	DE3527336A1 (fr)
DK (1)	DK361886A (fr)
FI (1)	FI863102A7 (fr)
GR (1)	GR862016B (fr)
IL (1)	IL79558A0 (fr)
NO (1)	NO863077L (fr)
PT (1)	PT83100B (fr)
ZA (1)	ZA865690B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4740522A (en) *	1986-08-28	1988-04-26	Hoechst-Roussel Pharmaceuticals Inc.	Oxolabdanes useful as pharmaceuticals for reducing intraocular pressure
US5247097A (en) *	1986-08-28	1993-09-21	Hoechst-Roussel Pharmaceuticals Incorporated	Oxolabdanes
US6200665B1 (en)	1998-06-08	2001-03-13	Asahi Glass Company Ltd.	Stepped glass sheet

1985
- 1985-07-31 DE DE19853527336 patent/DE3527336A1/de not_active Withdrawn
1986
- 1986-07-22 EP EP86110026A patent/EP0212293A2/fr not_active Withdrawn
- 1986-07-29 FI FI863102A patent/FI863102A7/fi not_active Application Discontinuation
- 1986-07-29 KR KR1019860006207A patent/KR870001313A/ko not_active Withdrawn
- 1986-07-29 IL IL79558A patent/IL79558A0/xx unknown
- 1986-07-30 ZA ZA865690A patent/ZA865690B/xx unknown
- 1986-07-30 AU AU60684/86A patent/AU6068486A/en not_active Abandoned
- 1986-07-30 JP JP61177866A patent/JPS6232892A/ja active Pending
- 1986-07-30 GR GR862016A patent/GR862016B/el unknown
- 1986-07-30 PT PT83100A patent/PT83100B/pt unknown
- 1986-07-30 NO NO863077A patent/NO863077L/no unknown
- 1986-07-30 DK DK361886A patent/DK361886A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
DE3527336A1 (de)	1987-02-05
GR862016B (en)	1986-12-23
ZA865690B (en)	1987-03-25
IL79558A0 (en)	1986-10-31
DK361886A (da)	1987-02-01
PT83100B (de)	1988-08-26
NO863077D0 (no)	1986-07-30
PT83100A (de)	1986-08-01
FI863102A0 (fi)	1986-07-29
DK361886D0 (da)	1986-07-30
JPS6232892A (ja)	1987-02-12
AU6068486A (en)	1987-02-05
KR870001313A (ko)	1987-03-13
EP0212293A2 (fr)	1987-03-04
FI863102A7 (fi)	1987-02-01

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NO863077L (no)	1987-02-02	Fremgangsmaate til mikrobiell hydroksylering av forskolin og dens derivater ved neurospora crassa.
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US4086141A (en)	1978-04-25	Process for the fermentation production of ergoline derivatives
US4992570A (en)	1991-02-12	UCN-1028A and UCN-1028C and process for the production thereof
US5510501A (en)	1996-04-23	Saintopin derivatives
US4753959A (en)	1988-06-28	Antibiotic lactone compound
US3198809A (en)	1965-08-03	Microbiological reduction process and steroid products produced thereby
EP0083019A2 (fr)	1983-07-06	Procédé d'obtention de glycosides anthracycliques optiquement actifs, les 4-désoxy-aclacinomycines A et B, et leurs préparations pharmaceutiques
MXPA05014202A (es)	2006-07-03	Procedimiento microbiano para la hidrolisis y oxidacion de esteres esteroideos de androst-5-eno y preg-5-eno.
US4803275A (en)	1989-02-07	2-oxo-5-methyl-6-[4-heptene]-2H-pyrano[3,2-c]pyridine
ASAI et al.	1959	MICROBIOLOGICAL HYDROXYLATION OF STEROID IX. HYDROXYLATION OF STEROID BY SYNCEPHALASTRUM RACEMOSUM.(2)
Wong et al.	1999	Microbial hydroxylation of (Z)-2-benzylidene-1-azabicyclo [2.2. 2] octan-3-one
US3775433A (en)	1973-11-27	Antimicrobial metabolite s491beta and s491ypsilon and chemical derivatives
US3829447A (en)	1974-08-13	(-)-9-oxo-5(s)-hydroxy decanoic acid lactone
US3732268A (en)	1973-05-08	Microbiological preparation of optically active 9-oxo-5(s)-hydroxy-decanoic acid and the lactone thereof
CA1171869A (fr)	1984-07-31	Tylactone