CH500962A - Verfahren zur Herstellung neuer 3,5-Cyclo-steroide - Google Patents

Verfahren zur Herstellung neuer 3,5-Cyclo-steroide

Info

Publication number: CH500962A
Authority: CH; Switzerland
Prior art keywords: cyclo; hydroxy; reagent; formula; added
Prior art date: 1962-04-28

Application number

CH420167A

Other languages

German (de)

English (en)

Inventor

Takasaki Rinji

Sakai Kiyoshi

Hayashi Ryozo

Morisawa Yasuhiro

Hashimoto Teruo

Nakazawa Tadamasa

Original Assignee

Sankyo Co

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.)

1962-04-28

Filing date

1963-04-26

Publication date

1970-12-31

1963-04-26 Application filed by Sankyo Co filed Critical Sankyo Co

1970-12-31 Publication of CH500962A publication Critical patent/CH500962A/de

Links

125000000217 alkyl group Chemical group 0.000 claims abstract description 3
239000007800 oxidant agent Substances 0.000 claims description 9
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000004043 oxo group Chemical group O=* 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
239000000543 intermediate Substances 0.000 abstract description 4
150000003431 steroids Chemical class 0.000 abstract description 2
125000001931 aliphatic group Chemical group 0.000 abstract 2
125000003710 aryl alkyl group Chemical group 0.000 abstract 2
125000000304 alkynyl group Chemical group 0.000 abstract 1
230000001195 anabolic effect Effects 0.000 abstract 1
229940088597 hormone Drugs 0.000 abstract 1
239000005556 hormone Substances 0.000 abstract 1
230000001568 sexual effect Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000003153 chemical reaction reagent Substances 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
238000003756 stirring Methods 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000010410 layer Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000000284 extract Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000013078 crystal Substances 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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 compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000002024 ethyl acetate extract Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000155 melt Substances 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000004593 Epoxy Substances 0.000 description 1
PNZVFASWDSMJER-UHFFFAOYSA-N acetic acid;lead Chemical compound [Pb].CC(O)=O PNZVFASWDSMJER-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
-1 steroid compound Chemical class 0.000 description 1
238000005292 vacuum distillation 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
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/567—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in position 17 alpha, e.g. mestranol, norethandrolone
- 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
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- 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
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/566—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol having an oxo group in position 17, e.g. estrone
- 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
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- 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
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- A61K31/5685—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone having an oxo group in position 17, e.g. androsterone
- 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
- 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
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
- 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
- C07J75/00—Processes for the preparation of steroids in general

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (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)
Organic Chemistry (AREA)
Steroid Compounds (AREA)

CH420167A 1962-04-28 1963-04-26 Verfahren zur Herstellung neuer 3,5-Cyclo-steroide CH500962A (de)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
JP1717962		1962-04-28
JP1718262		1962-04-28
JP1717862		1962-04-28
JP2774762		1962-07-06
JP375763		1963-01-26
JP375663		1963-01-26

Publications (1)

Publication Number	Publication Date
CH500962A true CH500962A (de)	1970-12-31

Family

ID=27547794

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH420167A CH500962A (de)	1962-04-28	1963-04-26	Verfahren zur Herstellung neuer 3,5-Cyclo-steroide

Country Status (4)

Country	Link
CH (1)	CH500962A (da)
DE (1)	DE1468637A1 (da)
DK (1)	DK111748B (da)
SE (1)	SE317372B (da)

1963
- 1963-04-26 CH CH420167A patent/CH500962A/de not_active IP Right Cessation
- 1963-04-27 DE DE19631468637 patent/DE1468637A1/de active Pending
- 1963-04-27 DK DK197363A patent/DK111748B/da unknown
- 1963-04-29 SE SE468563A patent/SE317372B/xx unknown

Also Published As

Publication number	Publication date
DE1468637A1 (de)	1969-01-02
SE317372B (da)	1969-11-17
DK111748B (da)	1968-10-07

Legal Events

Date	Code	Title	Description
1974-11-29	PL	Patent ceased

Publication	Publication Date	Title
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AT224275B (de)	1962-11-12	Verfahren zur Herstellung neuer Steroidverbindungen
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DE914973C (de)	1954-07-12	Verfahren zur Herstellung von substituierten threo-konfigurierten ª‡-Halogen-ª‰-oxy-acylamino-aethanen
AT228804B (de)	1963-08-12	Verfahren zur Herstellung von Thionothiolphosphorsäureestern
DE964677C (de)	1957-05-29	Verfahren zur Herstellung von Allopregnanen
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DE948974C (de)	1956-09-13	Verfahren zur Herstellung von cyclischen 4-Halogenpregnan-3, 20-dion-3, 20-diketalen
AT249048B (de)	1966-08-25	Verfahren zur Herstellung von neuen Benzimidazolonderivaten
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AT217994B (de)	1961-11-10	Verfahren zur Herstellung von neuen Derivaten von Polyhydroxyalkoholen
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DE1298523B (de)	1969-07-03	Verfahren zur Herstellung substituierter Dibenzo-[a,d] Cycloheptanverbindungen
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