CH408910A - Verfahren zur Herstellung von Polyhydrophenanthrenverbindungen - Google Patents

Verfahren zur Herstellung von Polyhydrophenanthrenverbindungen

Info

Publication number: CH408910A
Authority: CH; Switzerland
Prior art keywords: compound; formula; ether; solution; phenanthrene
Prior art date: 1961-05-15

Application number

CH481662A

Other languages

German (de)

English (en)

Inventor

Wolf Goldberg Moses

Mischa Jampolsky Lester

Montclair Upper

Wightman Kierstead Richard

Original Assignee

Hoffmann La Roche

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.)

1961-05-15

Filing date

1962-04-19

Publication date

1966-03-15

1962-04-19 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1966-03-15 Publication of CH408910A publication Critical patent/CH408910A/de

Links

150000001875 compounds Chemical class 0.000 title claims description 24
238000000034 method Methods 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 7
229910052744 lithium Inorganic materials 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 5
229910052987 metal hydride Inorganic materials 0.000 claims description 3
150000004681 metal hydrides Chemical class 0.000 claims description 3
QTWYUOSZMIWHJV-UHFFFAOYSA-N phenanthrene-2-carboxylic acid Chemical compound C1=CC=C2C3=CC=C(C(=O)O)C=C3C=CC2=C1 QTWYUOSZMIWHJV-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
150000003138 primary alcohols Chemical class 0.000 claims description 2
239000007858 starting material Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
239000000243 solution Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 4
239000012259 ether extract Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
-1 lithium aluminum hydride Chemical compound 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
230000002054 antogonadotrophic effect Effects 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 2
IKIUSKNQHYCDKO-UHFFFAOYSA-N (7-methoxy-1,2,3,4,4a,5,8,9,10,10a-decahydrophenanthren-2-yl)methanol Chemical compound OCC1CC2CCC=3CC(=CCC3C2CC1)OC IKIUSKNQHYCDKO-UHFFFAOYSA-N 0.000 description 1
BJDOJWBENBROCK-UHFFFAOYSA-N (7-methoxy-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-yl)methanol Chemical compound COC1=CC=C2C3CCC(CO)CC3CCC2=C1 BJDOJWBENBROCK-UHFFFAOYSA-N 0.000 description 1
HTMJMVLSHPCPSE-UHFFFAOYSA-N 1,2,3,4,4a,4b,5,6,7,8-decahydrophenanthrene Chemical compound C1CCCC2C(CCCC3)C3=CC=C21 HTMJMVLSHPCPSE-UHFFFAOYSA-N 0.000 description 1
PJDWNSYGMXODTB-UHFFFAOYSA-N 1,2,3,4,4a,4b,5,6-octahydrophenanthrene Chemical class C1=CCCC2C(CCCC3)C3=CC=C21 PJDWNSYGMXODTB-UHFFFAOYSA-N 0.000 description 1
NQAAHYYWBSZFKZ-UHFFFAOYSA-N 1,2,3,4,4a,5,8,9,10,10a-decahydrophenanthrene Chemical compound C1CCCC2C=3CC=CCC=3CCC12 NQAAHYYWBSZFKZ-UHFFFAOYSA-N 0.000 description 1
KFGROPZLGDSAPK-UHFFFAOYSA-N 1,2,3,4,4a,9,10,10a-octahydrophenanthrene Chemical compound C1=CC=C2C3CCCCC3CCC2=C1 KFGROPZLGDSAPK-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
XLKNGQGPDDGZAB-UHFFFAOYSA-N 1-(7-methoxy-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-yl)ethanone Chemical compound C(C)(=O)C1CC2CCC3=CC(=CC=C3C2CC1)OC XLKNGQGPDDGZAB-UHFFFAOYSA-N 0.000 description 1
VSFMPONNBHWBME-UHFFFAOYSA-N 1-(7-methoxy-1,2,3,4,9,10-hexahydrophenanthren-2-yl)ethanone Chemical compound C1C(C(C)=O)CCC2=C1CCC1=CC(OC)=CC=C12 VSFMPONNBHWBME-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
230000001195 anabolic effect Effects 0.000 description 1
230000001548 androgenic effect Effects 0.000 description 1
230000002280 anti-androgenic effect Effects 0.000 description 1
230000003388 anti-hormonal effect Effects 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
230000001076 estrogenic effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
230000003054 hormonal effect Effects 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000000871 hypocholesterolemic effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/32—Unsaturated compounds containing hydroxy or O-metal groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/37—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings
- C07C35/42—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings derived from the phenanthrene skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/20—Preparation of ethers by reactions not forming ether-oxygen bonds by hydrogenation of carbon-to-carbon double or triple bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/29—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with halogen-containing compounds which may be formed in situ
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pyrrole Compounds (AREA)

CH481662A 1961-05-15 1962-04-19 Verfahren zur Herstellung von Polyhydrophenanthrenverbindungen CH408910A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US10988261A	1961-05-15	1961-05-15

Publications (1)

Publication Number	Publication Date
CH408910A true CH408910A (de)	1966-03-15

Family

ID=22330073

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH481662A CH408910A (de)	1961-05-15	1962-04-19	Verfahren zur Herstellung von Polyhydrophenanthrenverbindungen

Country Status (7)

Country	Link
BE (1)	BE617616A (fr)
CH (1)	CH408910A (fr)
DE (2)	DE1518983A1 (fr)
DK (3)	DK103073C (fr)
ES (1)	ES277295A1 (fr)
FR (1)	FR2110M (fr)
GB (1)	GB969083A (fr)

1962
- 1962-04-19 CH CH481662A patent/CH408910A/de unknown
- 1962-04-21 DE DE19621518983 patent/DE1518983A1/de active Pending
- 1962-04-24 DE DE19621443986 patent/DE1443986A1/de active Pending
- 1962-05-12 ES ES277295A patent/ES277295A1/es not_active Expired
- 1962-05-14 GB GB18413/62A patent/GB969083A/en not_active Expired
- 1962-05-14 BE BE617616A patent/BE617616A/fr unknown
- 1962-05-15 DK DK218562AA patent/DK103073C/da active
- 1962-05-15 DK DK219663AA patent/DK104457C/da active
- 1962-05-15 DK DK219563AA patent/DK103183C/da active
- 1962-07-17 FR FR904140A patent/FR2110M/fr not_active Expired

Also Published As

Publication number	Publication date
DE1443986A1 (de)	1969-03-20
FR2110M (fr)	1963-10-28
DK103183C (da)	1965-11-29
ES277295A1 (es)	1962-10-16
DK104457C (da)	1966-05-23
DE1518983A1 (de)	1969-08-21
DK103073C (da)	1965-11-15
BE617616A (fr)	1962-11-14
GB969083A (en)	1964-09-09

Publication	Publication Date	Title
CH408910A (de)	1966-03-15	Verfahren zur Herstellung von Polyhydrophenanthrenverbindungen
AT233558B (de)	1964-05-11	Verfahren zur Herstellung von neuen Polyhydrophenanthrenverbindungen
DE2132315C3 (de)	1975-02-06	Verfahren zur Herstellung der 1 beta, 11 alpha-Dimethyl-1,2,3,4,10 alpha, 11hexahydro-9 beta-hydroxyfluoren-1 alpha, 9alpha-dicarbonsäure aus Abietinsäure
DE1027663B (de)	1958-04-10	Verfahren zur Herstellung von in 12-Stellung unsubstituierten 11-Oxy-oder 11-Acyloxysteroiden
AT248622B (de)	1966-08-10	Verfahren zur Herstellung neuer 2-Cyano-3-oxo-steroide
DE825686C (de)	1951-12-20	Verfahren zur UEberfuehrung von í¸-20-Cyanpregnenen mit einer oder mehreren kerngebundenen Hydroxylgruppen in 17 alpha-Oxy-20-ketopregnane
DE1264441B (de)	1968-03-28	Verfahren zur Herstellung von 17alpha-AEthinyl-delta 5(10-19-nor-androsten-17beta-ol-3-on und 17alpha-AEthynil-19-nor-testosteron sowie dessen Estern
AT231083B (de)	1964-01-10	Verfahren zur Herstellung eines neuen 16 α-Methyl-17α-hydroxy-20-ketons der Allopregnanreihe
AT232998B (de)	1964-04-10	Verfahren zur Herstellung von neuen Polyhydrophenanthrenverbindungen
CH227069A (de)	1943-05-15	Verfahren zur Herstellung einer Cyclopentano-dimethyl-polyhydrophenanthren-carbonsäure.
AT215089B (de)	1961-05-10	Verfahren zur Herstellung von 6-Hydroxy-3:5-cyclopregnan-20-on
AT224119B (de)	1962-11-12	Verfahren zur Isomerisierung von basisch substituierten tricyclischen Verbindungen
AT230367B (de)	1963-12-10	Verfahren zur Herstellung von neuen Octahydrophenanthrencarbonsäuren
AT160482B (de)	1941-06-25	Verfahren zur Darstellung von Pregnen-(5)-ol-(3)-on-(20) oder dessen Stereoisomeren bzw. deren Derivaten.
AT273387B (de)	1969-08-11	Verfahren zur Herstellung von neuen Cholesterinderivaten sowie von deren Säureadditionssalzen
AT241706B (de)	1965-08-10	Verfahren zur Herstellung von 18, 20-Laktonen der Pregnanreihe
AT219204B (de)	1962-01-10	Verfahren zur Herstellung von 3-Alkoxy-19-nor-δ<2,5(10)> -androstadien-17-on
AT253704B (de)	1967-04-25	Verfahren zur Herstellung des neuen 7α-Methyl-16α-hydroxy-östrons und seines 3, 16-Diacetates
US2563846A (en)	1951-08-14	Cyclopentanoperhydrophenanthrene compounds
AT250581B (de)	1966-11-25	Verfahren zur Herstellung von 2α-Methylandrostan-Derivaten
AT299169B (de)	1972-06-12	Verfahren zur Herstellung der neuen α-[p-(1-Cyclohexenyl)-phenyl]-propionsäure
DE1593385C (de)	1973-07-26	Verfahren zur Herstellung von 18 Oxoverbindungen der 5alpha oder 5beta D Homoandrostanreihe bzw von 3 Methoxy 20 oxo 19 nor 1,3,5(10) pregnatrien 18 al 20 athylenketal Ausscheidung aus 1260466
AT233184B (de)	1964-04-25	Verfahren zur Herstellung von 3-Oxo-Δ<1,4>-steroiden
DE1050765B (de)	1959-02-19	Verfahren zur Herstellung von Testan-3a-ol-ll-on und seinen Estern
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