DE1793649A1 - Verfahren zur Herstellung von 7alpha-Methyl-gona-4,9-dienen - Google Patents
Verfahren zur Herstellung von 7alpha-Methyl-gona-4,9-dienenInfo
- Publication number
- DE1793649A1 DE1793649A1 DE19661793649 DE1793649A DE1793649A1 DE 1793649 A1 DE1793649 A1 DE 1793649A1 DE 19661793649 DE19661793649 DE 19661793649 DE 1793649 A DE1793649 A DE 1793649A DE 1793649 A1 DE1793649 A1 DE 1793649A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- acid
- gona
- ketal
- denotes
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 230000008569 process Effects 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 7alpha-methyl-gona-4,9-dienes Chemical class 0.000 title description 5
- 239000002253 acid Substances 0.000 claims description 8
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
- 150000008046 alkali metal hydrides Chemical group 0.000 claims description 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000003826 tablet Substances 0.000 description 5
- 206010067572 Oestrogenic effect Diseases 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000001076 estrogenic effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000001195 anabolic effect Effects 0.000 description 2
- 230000001548 androgenic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CJRNSAVENUDGNX-PEYYIBSZSA-N (8s,13s,14r)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1C[C@@H]2CCC[C@H]2[C@@H]2CCC3=CC(=O)CCC3=C21 CJRNSAVENUDGNX-PEYYIBSZSA-N 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 201000009273 Endometriosis Diseases 0.000 description 1
- 206010027295 Menometrorrhagia Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 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
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 208000037063 Thinness Diseases 0.000 description 1
- 206010046798 Uterine leiomyoma Diseases 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 206010003549 asthenia Diseases 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 210000004392 genitalia Anatomy 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 201000010260 leiomyoma Diseases 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D5/00—Rigid or semi-rigid containers of polygonal cross-section, e.g. boxes, cartons or trays, formed by folding or erecting one or more blanks made of paper
- B65D5/42—Details of containers or of foldable or erectable container blanks
- B65D5/72—Contents-dispensing means
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR40659A FR5913M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-12-02 | 1965-12-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1793649A1 true DE1793649A1 (de) | 1972-02-03 |
Family
ID=8594147
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593337 Withdrawn DE1593337A1 (de) | 1965-12-02 | 1966-11-24 | Verfahren zur Herstellung von 7alpha-Methoyl-gona-4,9-dienen |
| DE19661793649 Pending DE1793649A1 (de) | 1965-12-02 | 1966-11-24 | Verfahren zur Herstellung von 7alpha-Methyl-gona-4,9-dienen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593337 Withdrawn DE1593337A1 (de) | 1965-12-02 | 1966-11-24 | Verfahren zur Herstellung von 7alpha-Methoyl-gona-4,9-dienen |
Country Status (13)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2054527B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1969-07-28 | 1973-06-08 | Roussel Uclaf | |
| FR2054525B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1969-07-28 | 1973-01-12 | Roussel Uclaf | |
| GB8513723D0 (en) * | 1985-05-31 | 1985-07-03 | Erba Farmitalia | 11-beta substituted steroids |
| US4698429A (en) * | 1985-12-03 | 1987-10-06 | Henkel Corporation | Alkylated 8-hydroxyquinoline derivatives via a diels-alder cycloaddition to 5,7-diallyl or 7-allyl substituents thereon |
| EP1846434B1 (en) * | 2005-02-04 | 2009-03-25 | Government of the United States of America, Represented by the Secretary, Department of Health and Human Services | NANDROLONE 17ß-CARBONATES |
-
1965
- 1965-12-02 FR FR40659A patent/FR5913M/fr not_active Expired
-
1966
- 1966-11-24 DE DE19661593337 patent/DE1593337A1/de not_active Withdrawn
- 1966-11-24 DE DE19661793649 patent/DE1793649A1/de active Pending
- 1966-11-28 BE BE690368D patent/BE690368A/xx unknown
- 1966-11-29 CH CH1703166A patent/CH480318A/fr not_active IP Right Cessation
- 1966-11-30 SE SE01475/69A patent/SE336333B/xx unknown
- 1966-11-30 IL IL26986A patent/IL26986A/en unknown
- 1966-11-30 SE SE16418/66A patent/SE319768B/xx unknown
- 1966-11-30 IL IL35698A patent/IL35698A/xx unknown
- 1966-12-01 ES ES0334021A patent/ES334021A1/es not_active Expired
- 1966-12-01 DK DK621666AA patent/DK121759B/da unknown
- 1966-12-02 BR BR185068/66A patent/BR6685068D0/pt unknown
- 1966-12-02 NL NL6617047.A patent/NL160568C/xx not_active IP Right Cessation
- 1966-12-02 GB GB13853/68A patent/GB1135690A/en not_active Expired
- 1966-12-02 AT AT1117666A patent/AT333446B/de not_active IP Right Cessation
- 1966-12-02 GB GB54091/66A patent/GB1135689A/en not_active Expired
-
1969
- 1969-07-07 US US839711A patent/US3637771A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE1593337A1 (de) | 1970-07-23 |
| BE690368A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-05-29 |
| DK121759B (da) | 1971-11-29 |
| BR6685068D0 (pt) | 1973-11-13 |
| CH480318A (fr) | 1969-10-31 |
| GB1135690A (en) | 1968-12-04 |
| GB1135689A (en) | 1968-12-04 |
| ES334021A1 (es) | 1967-11-01 |
| IL35698A (en) | 1971-07-28 |
| IL26986A (en) | 1971-04-28 |
| FR5913M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-04-01 |
| AT333446B (de) | 1976-11-25 |
| SE336333B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-07-05 |
| NL6617047A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-06-05 |
| US3637771A (en) | 1972-01-25 |
| SE319768B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-01-26 |
| NL160568C (nl) | 1979-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1618830C3 (de) | In 3-und 17-Stellung sauerstoffhaltige 11 beta-OB-13beta-C-gona-1,3,5(10)-triene und Verfahren zu ihrer Herstellung | |
| DE2107835A1 (de) | Neues Pregnanderivat und Verfahren zu dessen Herstellung | |
| DE1793649A1 (de) | Verfahren zur Herstellung von 7alpha-Methyl-gona-4,9-dienen | |
| DE1468905C3 (de) | Verfahren zur Herstellung von 3 beta, 6 beta-Dihydroxy-(bzw. Diacyloxy> Delta hoch 5(10) -19-nor-Steroiden und einige dieser Verbindungen | |
| US3649621A (en) | Novel 3-cyclopentyl ethers of 13-alkylgon-poly-enes | |
| DE1518666A1 (de) | Verfahren zur Herstellung von 13,14-Seco-steroiden | |
| AT251772B (de) | Verfahren zur Herstellung eines neuen Äthinylderivates des 8-iso-Östrons | |
| DE1793608B1 (de) | 17alpha-Alkyl-,-Alkenyl- oder -Alkinyl-13ss-alkylgon-4-oder-5(10)-en-17ss-ol-3-one | |
| DE1643010A1 (de) | Verfahren zur Herstellung von 17alpha-Alkinyl-17ss-alkanoyloxy-Steroiden der Andostran- und Oestranreihe | |
| DE1793608C (de) | 17alpha-Alkyl-, -Alkenyl- oder -Alkinyl-13beta-alkylgon-4- oder -5(10)-en-17betaol-3-one. Ausscheidung aus: 1468604 | |
| DE1593337C (de) | Verfahren zur Herstellung von 3 Oxo 7 alpha Methyl gona 4,9 dienen | |
| DE1808425C (de) | 3 Oxo 17beta hydroxy 17 alpha (but 2 myl> 13 beta C tief 1 bis C tief 3 alkyl gona 4,9,11 tnene | |
| DE1228257B (de) | Verfahren zur Herstellung von 8-Iso-17alpha-aethinyl-oestradiol sowie von 3-AEthern u3-Estern bzw. 3, 17-Diestern desselben | |
| DE1543842C3 (de) | 3-Oxo-2-oxa-4,9,l 1-gonatriene, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE2110117C3 (de) | Verfahren zur Herstellung von 6-Keto-Δ↑1↑.3.5(10)-steroiden und 3,17β-Dihydroxy-17α -äthinyl-1,3,5(10)-östratrien-6-on | |
| DE1518829C3 (de) | Einfach oder mehrfach ungesättigte 3-Cyanmethylen-20-oxo-pregnanderivate und Verfahren zu ihrer Herstellung | |
| AT269380B (de) | Verfahren zur Herstellung neuer 7α-Methylöstratrienderivate | |
| DE2748250A1 (de) | Neue 17-spirosultinderivate, die entsprechenden gamma-hydroxysaeuren, verfahren zu deren herstellung und pharmazeutische zusammensetzungen | |
| DE2118995A1 (de) | Neue oestrogen hochwirksame Steroide und ein Verfahren zu deren Herstellung | |
| DE1179548B (de) | Verfahren zur Herstellung von 21-Bromsteroiden | |
| AT275054B (de) | Verfahren zur Herstellung von neuen 9β,10α-Steroiden | |
| CH513838A (de) | Verfahren zur Herstellung von 17a-Propadiensteroiden | |
| DE1177147B (de) | Verfahren zur Herstellung von 3-Enolaethern von 6-Formyl-3-oxo-?-steroiden | |
| DE1199263B (de) | Verfahren zur Herstellung von 17-(2-Alkenyl)-bzw. 17-(2-Alkinyl)-oestra-1, 3, 5(10)-trien-3, 17beta-diolen sowie von deren Estern | |
| DE1593337B (de) | Verfahren zur Herstellung von 3 Oxo 7 alpha Methyl gona 4,9 dienen |