CH380114A - Verfahren zur Herstellung eines Acylthio-hydroxy-steroids - Google Patents

Verfahren zur Herstellung eines Acylthio-hydroxy-steroids

Info

Publication number: CH380114A
Authority: CH; Switzerland
Prior art keywords: epoxy; steroid; acylthio; hydroxy; acid
Prior art date: 1959-07-27

Application number

CH854460A

Other languages

German (de)

English (en)

Inventor

Komeno Taichiro

Original Assignee

Shionogi & 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.)

1959-07-27

Filing date

1960-07-26

Publication date

1964-07-31

1960-07-26 Application filed by Shionogi & Co filed Critical Shionogi & Co

1964-07-31 Publication of CH380114A publication Critical patent/CH380114A/de

Links

238000000034 method Methods 0.000 title claims description 15
238000004519 manufacturing process Methods 0.000 title claims description 4
150000003431 steroids Chemical class 0.000 claims description 19
239000004593 Epoxy Substances 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 12
125000005035 acylthio group Chemical group 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000003700 epoxy group Chemical group 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
229960003387 progesterone Drugs 0.000 description 2
239000000186 progesterone Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
FPHIYNDIWHMUMI-CYPDMGDPSA-N (1S,2R,7R,9S,11S,12S,15S,16S)-15-acetyl-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-5-one Chemical compound O1[C@]23[C@@H]1C[C@H]1[C@@H]4CC[C@H](C(C)=O)[C@]4(CC[C@@H]1[C@]3(CCC(C2)=O)C)C FPHIYNDIWHMUMI-CYPDMGDPSA-N 0.000 description 1
QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 description 1
206010006187 Breast cancer Diseases 0.000 description 1
208000026310 Breast neoplasm Diseases 0.000 description 1
206010054834 Hypergonadism Diseases 0.000 description 1
208000017657 Menopausal disease Diseases 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
208000007913 Pituitary Neoplasms Diseases 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
QSHQKIURKJITMZ-BRPMRXRMSA-N cholane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCC)[C@@]1(C)CC2 QSHQKIURKJITMZ-BRPMRXRMSA-N 0.000 description 1
XIIAYQZJNBULGD-LDHZKLTISA-N cholestane Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 XIIAYQZJNBULGD-LDHZKLTISA-N 0.000 description 1
239000003433 contraceptive agent Substances 0.000 description 1
229940124558 contraceptive agent Drugs 0.000 description 1
239000012043 crude product Substances 0.000 description 1
DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000001456 gonadotroph Effects 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
230000016087 ovulation Effects 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
230000001817 pituitary effect Effects 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 description 1
230000002028 premature Effects 0.000 description 1
230000001072 progestational effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
LUNRRBVBDCOROT-ACXQXYJUSA-N s-[2-[(8s,9s,10r,13s,14s,17s)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] ethanethioate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)CSC(=O)C)[C@@]1(C)CC2 LUNRRBVBDCOROT-ACXQXYJUSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F03—MACHINES OR ENGINES FOR LIQUIDS; WIND, SPRING, OR WEIGHT MOTORS; PRODUCING MECHANICAL POWER OR A REACTIVE PROPULSIVE THRUST, NOT OTHERWISE PROVIDED FOR
- F03H—PRODUCING A REACTIVE PROPULSIVE THRUST, NOT OTHERWISE PROVIDED FOR
- F03H1/00—Using plasma to produce a reactive propulsive thrust
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05H—PLASMA TECHNIQUE; PRODUCTION OF ACCELERATED ELECTRICALLY-CHARGED PARTICLES OR OF NEUTRONS; PRODUCTION OR ACCELERATION OF NEUTRAL MOLECULAR OR ATOMIC BEAMS
- H05H1/00—Generating plasma; Handling plasma
- H05H1/24—Generating plasma
- H05H1/48—Generating plasma using an arc
- H05H1/50—Generating plasma using an arc and using applied magnetic fields, e.g. for focusing or rotating the arc
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05H—PLASMA TECHNIQUE; PRODUCTION OF ACCELERATED ELECTRICALLY-CHARGED PARTICLES OR OF NEUTRONS; PRODUCTION OR ACCELERATION OF NEUTRAL MOLECULAR OR ATOMIC BEAMS
- H05H1/00—Generating plasma; Handling plasma
- H05H1/24—Generating plasma
- H05H1/26—Plasma torches
- H05H1/32—Plasma torches using an arc
- H05H1/34—Details, e.g. electrodes, nozzles
- H05H1/40—Details, e.g. electrodes, nozzles using applied magnetic fields, e.g. for focusing or rotating the arc

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Physics & Mathematics (AREA)
Combustion & Propulsion (AREA)
Plasma & Fusion (AREA)
Mechanical Engineering (AREA)
General Engineering & Computer Science (AREA)
Spectroscopy & Molecular Physics (AREA)
Steroid Compounds (AREA)

CH854460A 1959-07-27 1960-07-26 Verfahren zur Herstellung eines Acylthio-hydroxy-steroids CH380114A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2427359		1959-07-27

Publications (1)

Publication Number	Publication Date
CH380114A true CH380114A (de)	1964-07-31

Family

ID=12133589

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH854460A CH380114A (de)	1959-07-27	1960-07-26	Verfahren zur Herstellung eines Acylthio-hydroxy-steroids

Country Status (4)

Country	Link
CH (1)	CH380114A (fr)
DE (1)	DE1164403B (fr)
FR (1)	FR135M (fr)
GB (1)	GB907522A (fr)

1960
- 1960-07-22 GB GB25662/60A patent/GB907522A/en not_active Expired
- 1960-07-25 DE DES69588A patent/DE1164403B/de active Pending
- 1960-07-26 CH CH854460A patent/CH380114A/de unknown
- 1960-07-27 FR FR834180A patent/FR135M/fr active Active

Also Published As

Publication number	Publication date
GB907522A (en)	1962-10-03
FR135M (fr)	1961-02-06
DE1164403B (de)	1964-03-05

Publication	Publication Date	Title
DE1468950A1 (de)	1972-06-15	Neues Verfahren zur Herstellung von 3-Oxo-4,9,11-triensteroiden
DE1468302A1 (de)	1969-05-29	6-Substituierte 3 beta,17 alpha-Diacyloxy-4,6-pregnadien-20-one sowie Verfahren zu ihrer Herstellung
CH380114A (de)	1964-07-31	Verfahren zur Herstellung eines Acylthio-hydroxy-steroids
CH494216A (de)	1970-07-31	Verfahren zur Herstellung von in 3-Stellung einer verätherte Hydroxygruppe tragenden 6-Aminomethyl- 3,5-steroiden
DE1468985A1 (de)	1969-08-07	17alpha-Alkyl-,17alpha-Alkenyl- und 17alpha-Alkinyl-4,5-epoxy-19-norandrostan-17beta-diole und deren Carbonsaeureester sowie Verfahren zur Herstellung dieser Verbindungen
DE1947221A1 (de)	1970-04-16	3-Aza-19-hydroxy-3,19-cyclo-A-homosteroide und ein Verfahren zu deren Herstellung
DE825686C (de)	1951-12-20	Verfahren zur UEberfuehrung von í¸-20-Cyanpregnenen mit einer oder mehreren kerngebundenen Hydroxylgruppen in 17 alpha-Oxy-20-ketopregnane
AT226383B (de)	1963-03-11	Verfahren zur Herstellung von neuen Steroidverbindungen
AT232658B (de)	1964-03-25	Verfahren zur Herstellung von neuen in 1- und 4-Stellung ungesättigten Steroiden
AT257849B (de)	1967-10-25	Verfahren zur Herstellung von neuen 20-Oxo-21-hydroxy-16, 21-methano-Δ<21>-steroiden
DE1568971C3 (de)	1974-03-14	Steroidoxazoline und Verfahren zu ihrer Herstellung
AT220764B (de)	1962-04-10	Verfahren zur Herstellung von neuen 3-Oxo-Δ<1,4>-6-methyl- und 3-Oxo-Δ<1,4,6>-6-methylsteroiden
DE1079040B (de)	1960-04-07	Verfahren zur Herstellung stark androgen und anabol wirksamer ?-ungesaettigter 3, 17-Diole der Androstan-bzw. 19-Norandrostanreihe
AT232654B (de)	1964-03-25	Verfahren zur Herstellung von 16α-Methyl-17α-hydroxy-20-ketonen der Allopregnan-Reihe
CH561230A5 (en)	1975-04-30	6,8-Pentaenes - has oestrogenic activity
DE1443546C (de)	1971-01-07	Verfahren zur Herstellung von 6 Methyl Delta hoch 14 steroiden der Pregnanreihe
DE959189C (de)	1957-02-28	Verfahren zur Herstellung von 17ª‰-Acyloxy-20-keto-allopregnanen und -pregnenen
DE965238C (de)	1957-06-06	Verfahren zur Herstellung von in 11(12)-Stellung ungesaettigten Pregnanen
DE1041042B (de)	1958-10-16	Verfahren zur Herstellung von in 4-Stellung substituierten Steroiden
DE1267219B (de)	1968-05-02	Verfahren zur Abtrennung von 17alpha-AEthinyl-19-nor-delta 4-androsten-17beta-ol-3-on
DE1593064A1 (de)	1970-07-30	Verfahren zur Herstellung von 16-Methyl-4-pregnen-3-ss-o1-20-onen
CH380113A (de)	1964-07-31	Verfahren zur Herstellung von 16-Methylen-17a-hydroxy-steroiden
DE1159947B (de)	1963-12-27	Verfahren zur Herstellung von 9ª‡-Fluor-11ª‰, 17ª‡, 21-trihydroxy-3, 20-diketo-í¸-pregnadien oder 9ª‡-Fluor-17ª‡, 21-dihydroxy-3, 11, 20-triketo-í¸-pregnadien bzw. 21-Estern derselben
DE1174778B (de)	1964-07-30	Verfahren zur Herstellung von 3, 4-Dimethyl-?-oestratrien-1, 17ª‰-diol
CH325299A (de)	1957-10-31	Verfahren zur Herstellung von Steroidverbindungen