DE2633559A1 - Verfahren zur herstellung von prostaglandinen - Google Patents
Verfahren zur herstellung von prostaglandinenInfo
- Publication number
- DE2633559A1 DE2633559A1 DE19762633559 DE2633559A DE2633559A1 DE 2633559 A1 DE2633559 A1 DE 2633559A1 DE 19762633559 DE19762633559 DE 19762633559 DE 2633559 A DE2633559 A DE 2633559A DE 2633559 A1 DE2633559 A1 DE 2633559A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- prostaglandin
- tetrahydropyran
- phenoxymethyl
- stands
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- -1 alkyl radical Chemical class 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 15
- 150000003180 prostaglandins Chemical class 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- 230000002997 prostaglandinlike Effects 0.000 claims description 4
- CPVNCBJFUQQXSU-UHFFFAOYSA-N 5-triphenylphosphaniumylpentanoate Chemical class C1(=CC=CC=C1)[P+](CCCCC(=O)[O-])(C1=CC=CC=C1)C1=CC=CC=C1 CPVNCBJFUQQXSU-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims description 3
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000004714 phosphonium salts Chemical class 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 claims description 2
- BZLZKLMROPIZSR-UHFFFAOYSA-N triphenylsilicon Chemical compound C1=CC=CC=C1[Si](C=1C=CC=CC=1)C1=CC=CC=C1 BZLZKLMROPIZSR-UHFFFAOYSA-N 0.000 claims 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- 150000001649 bromium compounds Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000005046 Chlorosilane Substances 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002596 lactones Chemical group 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000011916 stereoselective reduction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 2
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
- MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KIGXMYYGQYMICF-UHFFFAOYSA-N Diphenylphosphine Acid Chemical compound C=1C=CC=CC=1P(=O)(CCCCC(=O)O)C1=CC=CC=C1 KIGXMYYGQYMICF-UHFFFAOYSA-N 0.000 description 1
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical class [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3192875A GB1524574A (en) | 1975-07-30 | 1975-07-30 | Process for the manufacture of prostaglandins |
| GB3343375 | 1975-08-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2633559A1 true DE2633559A1 (de) | 1977-02-17 |
Family
ID=26261137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762633559 Withdrawn DE2633559A1 (de) | 1975-07-30 | 1976-07-26 | Verfahren zur herstellung von prostaglandinen |
Country Status (16)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025149165A1 (en) * | 2024-01-12 | 2025-07-17 | Intervet International B.V. | A PROCESS FOR PURIFICATION OF INTERMEDIATES OF PROSTAGLANDIN F2Αα COMPOUNDS AND ITS USE IN THE PREPARATION OF PROSTAGLANDIN F2α COMPOUNDS |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4052446A (en) * | 1973-08-06 | 1977-10-04 | Hoffmann-La Roche Inc. | 11,16-substituted prostaglandins |
-
1976
- 1976-06-29 IN IN1153/CAL/76A patent/IN143632B/en unknown
- 1976-07-01 AU AU15481/76A patent/AU509048B2/en not_active Expired
- 1976-07-01 PT PT65303A patent/PT65303B/pt unknown
- 1976-07-06 CA CA256,385A patent/CA1089452A/en not_active Expired
- 1976-07-16 DK DK322976A patent/DK322976A/da not_active Application Discontinuation
- 1976-07-21 FI FI762096A patent/FI762096A7/fi not_active Application Discontinuation
- 1976-07-26 DE DE19762633559 patent/DE2633559A1/de not_active Withdrawn
- 1976-07-28 EG EG76462A patent/EG12287A/xx active
- 1976-07-28 AT AT554076A patent/AT356300B/de not_active IP Right Cessation
- 1976-07-29 FR FR7623197A patent/FR2319630A1/fr active Granted
- 1976-07-29 CH CH972376A patent/CH621774A5/de not_active IP Right Cessation
- 1976-07-29 YU YU01874/76A patent/YU187476A/xx unknown
- 1976-07-29 SE SE7608567A patent/SE7608567L/xx unknown
- 1976-07-29 DD DD194122A patent/DD127111A5/xx unknown
- 1976-07-29 NO NO762641A patent/NO146908C/no unknown
- 1976-07-30 JP JP51091187A patent/JPS5227749A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025149165A1 (en) * | 2024-01-12 | 2025-07-17 | Intervet International B.V. | A PROCESS FOR PURIFICATION OF INTERMEDIATES OF PROSTAGLANDIN F2Αα COMPOUNDS AND ITS USE IN THE PREPARATION OF PROSTAGLANDIN F2α COMPOUNDS |
Also Published As
| Publication number | Publication date |
|---|---|
| NO762641L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-02-01 |
| EG12287A (en) | 1978-12-31 |
| ATA554076A (de) | 1979-09-15 |
| YU187476A (en) | 1982-02-28 |
| AT356300B (de) | 1980-04-25 |
| FR2319630A1 (fr) | 1977-02-25 |
| PT65303A (en) | 1976-08-01 |
| DD127111A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-09-07 |
| FR2319630B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-04-10 |
| NO146908C (no) | 1982-12-29 |
| CH621774A5 (en) | 1981-02-27 |
| AU1548176A (en) | 1978-01-05 |
| PT65303B (en) | 1978-01-05 |
| CA1089452A (en) | 1980-11-11 |
| JPS5227749A (en) | 1977-03-02 |
| DK322976A (da) | 1977-01-31 |
| NO146908B (no) | 1982-09-20 |
| AU509048B2 (en) | 1980-04-17 |
| SE7608567L (sv) | 1977-01-31 |
| IN143632B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-01-07 |
| FI762096A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-01-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3153460C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2900352C2 (de) | Carbacyclinderivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| DE68908440T2 (de) | Synthese von Trichostatin. | |
| DE68909166T2 (de) | Verfahren zur Herstellung von in 5-Stellung substituierten 3-Furaldehyden. | |
| EP0107806B1 (de) | Verfahren zur Herstellung von optisch aktiven Hydrochinonderivaten sowie von d-alpha-Tocopherol | |
| DE2539116C2 (de) | ω-Nor-cycloalkyl-13,14-dehydro-prostaglandine, Verfahren zu ihrer Herstellung sowie sie enthaltende pharmazeutische Mittel | |
| DE2633559A1 (de) | Verfahren zur herstellung von prostaglandinen | |
| DE68910774T2 (de) | Cyclopentanheptencarbonsäurederivate und Verfahren zu ihrer Herstellung. | |
| DE2610503C2 (de) | Optisch aktive 13,14-Dehydro-11- desoxy-prostaglandine, Verfahren zu ihrer Herstellung und sie enthaltendes pharmazeutisches Mittel | |
| DE60024353T2 (de) | Verfahren zur Herstellung Antiosteoporicagenz | |
| DE2626288C2 (de) | Verfahren zur Herstellung von Prostaglandinzwischenprodukten durch stereoselektive Reduktion | |
| DE2540869A1 (de) | Verfahren zur herstellung von 3 alpha, 5alpha-cyclo-6beta-alkoxy-25- hydroxycholesterin | |
| EP0766660A1 (de) | Cyclohexanon-derivate, verfahren zu deren herstellung und zwischenprodukte des verfahrens | |
| DE19735575A1 (de) | Neue (C13-C15)-Fragmente, Verfahren zur Herstellung und ihre Verwendung zur Synthese von Epothilon und Epothilonderivaten | |
| DE3234253A1 (de) | (11r)-11-desoxy-11-alkyl-6-oxo-pg-artige verbindungen | |
| DE3142733A1 (de) | Verfahren zur herstellung von carbacyclin-zwischenprodukten | |
| DE19735574A1 (de) | Neue [C1(Carboxa)-C6]-Fragmente, Verfahren zu ihrer Herstellung und ihre Verwendung zur Synthese von Epothilon und Epothilonderivaten | |
| DE69527684T2 (de) | Herstellung von 3-oxy-5-oxo-6-Heptensäurederivaten | |
| DE2654668A1 (de) | Verfahren zur herstellung von verbindungen des prostaglandintyps und nach diesem verfahren erhaltene produkte | |
| KR800001263B1 (ko) | 프로스타글란딘류의 제법 | |
| CH659472A5 (de) | Epoxycarbacyclinderivate, ihre herstellung und verwendung. | |
| DE2543732A1 (de) | Derivate des 3alpha,5alpha-cyclo- 6beta-alkoxy-25-hydroxycholesterins und 3alpha,5alpha-cyclo-6beta-alkoxycholest- 22t-en-24,25-oxids, verfahren zur herstellung derselben und von zwischenprodukten fuer hydroxyliertes vitamin d tief 2 und d tief 3 | |
| CH617650A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2536754A1 (de) | Prostansaeurederivate | |
| DE2703471A1 (de) | Zwischenprodukte zur herstellung, von prostaglandinen und prostaglandinanaloga und verfahren zu deren herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |