NO128766B - - Google Patents
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- Publication number
- NO128766B NO128766B NO03088/68A NO308868A NO128766B NO 128766 B NO128766 B NO 128766B NO 03088/68 A NO03088/68 A NO 03088/68A NO 308868 A NO308868 A NO 308868A NO 128766 B NO128766 B NO 128766B
- Authority
- NO
- Norway
- Prior art keywords
- dichloro
- hydroxy
- solution
- group
- diene
- Prior art date
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)
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 |
|---|---|---|---|
| NO03088/68A NO128766B (da) | 1967-08-07 | 1968-08-06 | |
| NO03087/68A NO128765B (da) | 1967-08-07 | 1968-08-06 |
Family Applications After (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) | AT285832B (da) |
| BE (2) | BE719050A (da) |
| CH (10) | CH544074A (da) |
| DE (1) | DE1793063A1 (da) |
| DK (2) | DK122606B (da) |
| ES (2) | ES356957A1 (da) |
| FI (2) | FI45321C (da) |
| FR (4) | FR8417M (da) |
| GB (2) | GB1217530A (da) |
| IE (2) | IE32344B1 (da) |
| IL (2) | IL30491A (da) |
| MY (1) | MY7100216A (da) |
| NL (2) | NL6811217A (da) |
| NO (2) | NO128766B (da) |
| SE (2) | SE351632B (da) |
| YU (2) | YU185768A (da) |
-
1968
- 1968-07-17 CH CH418971A patent/CH544074A/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 CH418771A patent/CH544073A/de not_active IP Right Cessation
- 1968-07-17 CH CH419071A patent/CH541550A/de not_active IP Right Cessation
- 1968-07-17 CH CH1070668A patent/CH555329A/xx not_active IP Right Cessation
- 1968-07-17 CH CH418871A patent/CH544072A/de not_active IP Right Cessation
- 1968-07-17 CH CH419271A patent/CH544076A/de not_active IP Right Cessation
- 1968-07-17 CH CH419171A patent/CH544081A/de not_active IP Right Cessation
- 1968-07-17 CH CH418671A patent/CH544075A/de not_active IP Right Cessation
- 1968-07-30 DE DE19681793063 patent/DE1793063A1/de active Pending
- 1968-08-05 YU YU01857/68A patent/YU185768A/xx unknown
- 1968-08-05 AT AT760368A patent/AT285832B/de not_active IP Right Cessation
- 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 AT AT760468A patent/AT285833B/de not_active IP Right Cessation
- 1968-08-05 IL IL6830491A patent/IL30491A/en unknown
- 1968-08-05 IL IL30492A patent/IL30492A/xx unknown
- 1968-08-05 YU YU1858/68A patent/YU33190B/xx unknown
- 1968-08-05 BE BE719049D patent/BE719049A/xx unknown
- 1968-08-05 AT AT888169A patent/AT290030B/de not_active IP Right Cessation
- 1968-08-06 FR FR162043A patent/FR8417M/fr not_active Expired
- 1968-08-06 FR FR1588547D patent/FR1588547A/fr 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 JP JP43055307A patent/JPS5021474B1/ja active Pending
- 1968-08-06 NO NO03088/68A patent/NO128766B/no unknown
- 1968-08-06 FR FR1588548D patent/FR1588548A/fr not_active Expired
- 1968-08-06 ES ES356957A patent/ES356957A1/es not_active Expired
- 1968-08-06 GB GB37509/68A patent/GB1217530A/en not_active Expired
- 1968-08-06 IE IE949/68A patent/IE32344B1/xx unknown
- 1968-08-06 NO NO03087/68A patent/NO128765B/no unknown
- 1968-08-06 IE IE950/68A patent/IE32397B1/xx unknown
- 1968-08-06 GB GB37510/68A patent/GB1215752A/en not_active Expired
- 1968-08-06 DK DK379168AA patent/DK126187B/da unknown
- 1968-08-06 ES ES356956A patent/ES356956A1/es not_active Expired
- 1968-08-07 NL NL6811217A patent/NL6811217A/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 FI FI682233A patent/FI45321C/fi active
- 1968-08-07 SE SE10631/68A patent/SE351633B/xx unknown
- 1968-08-07 FI FI682234A patent/FI45322C/fi active
- 1968-08-07 NL NL6811218A patent/NL6811218A/xx unknown
-
1971
- 1971-12-30 MY MY216/71A patent/MY7100216A/xx unknown
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