NO128766B - - Google Patents

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Publication number: NO128766B
Authority: NO; Norway
Prior art keywords: dichloro; hydroxy; solution; group; diene
Prior art date: 1967-08-07

Application number

NO03088/68A

Other languages

English (en)

Norwegian (no)

Inventor

R Kierstead

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.)

1967-08-07

Filing date

1968-08-06

Publication date

1974-01-07

1968-08-06 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1974-01-07 Publication of NO128766B publication Critical patent/NO128766B/no

Links

125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
125000004423 acyloxy group Chemical group 0.000 claims description 5
238000000034 method Methods 0.000 claims description 4
150000003431 steroids Chemical class 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000000468 ketone group Chemical group 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000002904 solvent Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
-1 acetyloxy, butyroyloxy Chemical group 0.000 description 3
238000010828 elution Methods 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000012043 crude product Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 1
GRUSAVIQVPDITA-CDBBBHKJSA-N [(8R,9S,10R,13S,14S,17R)-17-acetyl-4,6-dichloro-10,13-dimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound ClC1=C2C(=C[C@H]3[C@@H]4CC([C@](C(C)=O)([C@]4(CC[C@@H]3[C@]2(CCC1=O)C)C)OC(C)=O)=C)Cl GRUSAVIQVPDITA-CDBBBHKJSA-N 0.000 description 1
ZTXJZSCFNCDIQL-JOOCFJGPSA-N [(8r,9s,10r,13s,14s,16r,17r)-17-acetyl-4,6-dichloro-10,13,16-trimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1=C(Cl)C2=C(Cl)C(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(C)=O)(OC(C)=O)[C@@]1(C)CC2 ZTXJZSCFNCDIQL-JOOCFJGPSA-N 0.000 description 1
JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
238000011888 autopsy Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000002357 endometrial effect Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
239000000262 estrogen Substances 0.000 description 1
229940011871 estrogen Drugs 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
239000006260 foam Substances 0.000 description 1
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000583 progesterone congener Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)

NO03088/68A 1967-08-07 1968-08-06 NO128766B (da)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US65860267A	1967-08-07	1967-08-07

Publications (1)

Publication Number	Publication Date
NO128766B true NO128766B (da)	1974-01-07

Family

ID=24641922

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO03087/68A NO128765B (da)	1967-08-07	1968-08-06
NO03088/68A NO128766B (da)	1967-08-07	1968-08-06

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
NO03087/68A NO128765B (da)	1967-08-07	1968-08-06

Country Status (17)

Country	Link
JP (2)	JPS5021474B1 (da)
AT (4)	AT290030B (da)
BE (2)	BE719050A (da)
CH (10)	CH544074A (da)
DE (1)	DE1793063A1 (da)
DK (2)	DK122606B (da)
ES (2)	ES356957A1 (da)
FI (2)	FI45322C (da)
FR (4)	FR8417M (da)
GB (2)	GB1215752A (da)
IE (2)	IE32397B1 (da)
IL (2)	IL30492A (da)
MY (1)	MY7100216A (da)
NL (2)	NL6811218A (da)
NO (2)	NO128765B (da)
SE (2)	SE351633B (da)
YU (2)	YU33190B (da)

1968
- 1968-07-17 CH CH418971A patent/CH544074A/de not_active IP Right Cessation
- 1968-07-17 CH CH418871A patent/CH544072A/de not_active IP Right Cessation
- 1968-07-17 CH CH418671A patent/CH544075A/de not_active IP Right Cessation
- 1968-07-17 CH CH418571A patent/CH541549A/de not_active IP Right Cessation
- 1968-07-17 CH CH1070568A patent/CH565198A5/xx not_active IP Right Cessation
- 1968-07-17 CH CH1070668A patent/CH555329A/xx not_active IP Right Cessation
- 1968-07-17 CH CH419071A patent/CH541550A/de not_active IP Right Cessation
- 1968-07-17 CH CH419271A patent/CH544076A/de not_active IP Right Cessation
- 1968-07-17 CH CH418771A patent/CH544073A/de not_active IP Right Cessation
- 1968-07-17 CH CH419171A patent/CH544081A/de not_active IP Right Cessation
- 1968-07-30 DE DE19681793063 patent/DE1793063A1/de active Pending
- 1968-08-05 AT AT888169A patent/AT290030B/de not_active IP Right Cessation
- 1968-08-05 YU YU1858/68A patent/YU33190B/xx unknown
- 1968-08-05 BE BE719050D patent/BE719050A/xx unknown
- 1968-08-05 AT AT08882/69A patent/AT290031B/de not_active IP Right Cessation
- 1968-08-05 YU YU01857/68A patent/YU185768A/xx unknown
- 1968-08-05 IL IL30492A patent/IL30492A/xx unknown
- 1968-08-05 IL IL6830491A patent/IL30491A/en unknown
- 1968-08-05 AT AT760468A patent/AT285833B/de not_active IP Right Cessation
- 1968-08-05 BE BE719049D patent/BE719049A/xx unknown
- 1968-08-05 AT AT760368A patent/AT285832B/de not_active IP Right Cessation
- 1968-08-06 NO NO03087/68A patent/NO128765B/no unknown
- 1968-08-06 FR FR162043A patent/FR8417M/fr not_active Expired
- 1968-08-06 ES ES356957A patent/ES356957A1/es not_active Expired
- 1968-08-06 FR FR162042A patent/FR7921M/fr not_active Expired
- 1968-08-06 DK DK379268AA patent/DK122606B/da unknown
- 1968-08-06 IE IE950/68A patent/IE32397B1/xx unknown
- 1968-08-06 FR FR1588547D patent/FR1588547A/fr not_active Expired
- 1968-08-06 GB GB37510/68A patent/GB1215752A/en not_active Expired
- 1968-08-06 DK DK379168AA patent/DK126187B/da unknown
- 1968-08-06 JP JP43055307A patent/JPS5021474B1/ja active Pending
- 1968-08-06 GB GB37509/68A patent/GB1217530A/en not_active Expired
- 1968-08-06 NO NO03088/68A patent/NO128766B/no unknown
- 1968-08-06 ES ES356956A patent/ES356956A1/es not_active Expired
- 1968-08-06 IE IE949/68A patent/IE32344B1/xx unknown
- 1968-08-06 FR FR1588548D patent/FR1588548A/fr not_active Expired
- 1968-08-07 FI FI682234A patent/FI45322C/fi active
- 1968-08-07 NL NL6811218A patent/NL6811218A/xx unknown
- 1968-08-07 SE SE10631/68A patent/SE351633B/xx unknown
- 1968-08-07 SE SE10630/68A patent/SE351632B/xx unknown
- 1968-08-07 JP JP43055539A patent/JPS5010859B1/ja active Pending
- 1968-08-07 NL NL6811217A patent/NL6811217A/xx unknown
- 1968-08-07 FI FI682233A patent/FI45321C/fi active
1971
- 1971-12-30 MY MY216/71A patent/MY7100216A/xx unknown

Also Published As

Publication number	Publication date
CH565198A5 (da)	1975-08-15
CH555329A (de)	1974-10-31
IL30491A (en)	1973-06-29
JPS5010859B1 (da)	1975-04-24
ES356956A1 (es)	1970-02-16
DK122606B (da)	1972-03-20
AT285833B (de)	1970-11-10
CH544076A (de)	1973-12-28
BE719050A (da)	1969-02-05
JPS5021474B1 (da)	1975-07-23
IL30491A0 (en)	1968-10-24
DE1793064B2 (de)	1977-01-20
FR1588548A (da)	1970-04-17
IL30492A (en)	1973-03-30
BE719049A (da)	1969-02-05
FI45322B (da)	1972-01-31
FR1588547A (da)	1970-04-17
AT290031B (de)	1971-03-15
ES356957A1 (es)	1970-02-16
DK126187B (da)	1973-06-18
IE32397B1 (en)	1973-07-25
IL30492A0 (en)	1968-10-24
CH544075A (de)	1973-12-28
IE32397L (en)	1969-02-07
CH544081A (de)	1973-12-28
GB1217530A (en)	1970-12-31
SE351633B (da)	1972-12-04
CH544074A (de)	1973-12-28
IE32344B1 (en)	1973-06-27
FR8417M (da)	1971-06-10
YU185768A (en)	1975-08-31
NL6811217A (da)	1969-02-11
DE1793064A1 (de)	1971-12-16
FR7921M (da)	1970-05-19
CH544072A (de)	1973-12-28
YU185868A (en)	1975-12-31
MY7100216A (en)	1971-12-31
IE32344L (en)	1969-02-07
YU33190B (en)	1976-06-30
CH541550A (de)	1973-10-31
AT290030B (de)	1971-05-10
DE1793063A1 (de)	1971-07-08
CH541549A (de)	1973-10-31
FI45321B (da)	1972-01-31
FI45321C (fi)	1972-05-10
NL6811218A (da)	1969-02-11
FI45322C (fi)	1972-05-10
AT285832B (de)	1970-11-10
GB1215752A (en)	1970-12-16
CH544073A (de)	1973-12-28
SE351632B (da)	1972-12-04
NO128765B (da)	1974-01-07

Publication	Publication Date	Title
US2843608A (en)	1958-07-15	4-estrene-3, 17-diol, esters and 17-alkyl derivatives
CH533094A (de)	1973-01-31	Verfahren zur Herstellung neuer Steroide
US3262949A (en)	1966-07-26	7-methyl androstane compounds
NO128152B (da)	1973-10-08
US3170919A (en)	1965-02-23	A-nor derivatives of the pregnane series and intermediates in the production thereof
US3453267A (en)	1969-07-01	Novel process for the preparation of 3-oxo-delta**4,9,11-trienic steroids
NO164677B (no)	1990-07-23	Fremgangsmaate for selektiv opprettelse av en fluidsperre.
US2774776A (en)	1956-12-18	Dihalosteroids
US4102884A (en)	1978-07-25	14 β-Hydroxy 3-deoxycardenolides
US3438975A (en)	1969-04-15	15alpha,16alpha-methylene pregnanes and 19-nor-pregnanes
US3207753A (en)	1965-09-21	Ring a aromatic 9beta-estratrienes and -19-norpregnatrienes
US2855413A (en)	1958-10-07	16-haloestradiol esters and ethers
US3032552A (en)	1962-05-01	1-methyl steroids of the androstane series
US3527778A (en)	1970-09-08	3,17 - bisoxygenated 11betamethyl - 19 - norpregn - 4 - en - 20 - ones and derivatives thereof
US2705719A (en)	1955-04-05	Preparation of aromatic steroids and intermediates therefor
US3193563A (en)	1965-07-06	Process for the preparation of steroidal ethers and thioethers
HU177452B (en)	1981-10-28	Process for preparing new d-homo-steroids
US3127428A (en)	1964-03-31	Process for converting a 3-keto-delta-steroid to the corresponding 3-keto delta-compound
US3627757A (en)	1971-12-14	6-alkanoylthio-4-en-3-oxo steroids and process for production thereof
US3166551A (en)	1965-01-19	Process for the preparation of 3-oxo-delta4-6-methyl steroids
US3374228A (en)	1968-03-19	14beta-estra-1, 3, 5(10)-trienes
US2888468A (en)	1959-05-26	Process for the production of delta5-3-keto and delta4-3-keto steroids
US3383385A (en)	1968-05-14	Process for the preparation of steroid derivatives of the pregnane series
US3080381A (en)	1963-03-05	Optionally 6-methylated and optionally 17-alkanoyloxygenated 2-oxapregnane-3, 20-diones, a-homo compounds corresponding, and 4, 5-dehydro and 4, 5; 6, 7-bisdehydro derivatives thereof
US3845040A (en)	1974-10-29	Protection of steroid carbonyl group by enolisation