CH374656A - Verfahren zur Herstellung von 6-Fluor-3-oxo- 1,4-steroiden - Google Patents

Verfahren zur Herstellung von 6-Fluor-3-oxo- 1,4-steroiden

Info

Publication number: CH374656A
Authority: CH; Switzerland
Prior art keywords: fluoro; oxo; benzoquinone; steroids; dichloro
Prior art date: 1959-12-29

Application number

CH1450860A

Other languages

German (de)

English (en)

Inventor

Neville Kirk David

Petrow Vladimir

Original Assignee

British Drug Houses Ltd

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.)

1959-12-29

Filing date

1960-12-28

Publication date

1964-01-31

1959-12-29 Priority claimed from GB4408059A external-priority patent/GB893584A/en

1960-12-28 Application filed by British Drug Houses Ltd filed Critical British Drug Houses Ltd

1964-01-31 Publication of CH374656A publication Critical patent/CH374656A/de

Links

238000000034 method Methods 0.000 title claims description 19
238000002360 preparation method Methods 0.000 title description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 23
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
239000012442 inert solvent Substances 0.000 claims description 6
DNXUGBMARDFRGG-UHFFFAOYSA-N 3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile Chemical compound O=C1C=CC(=O)C(C#N)=C1C#N DNXUGBMARDFRGG-UHFFFAOYSA-N 0.000 claims description 5
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 claims description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
150000003128 pregnanes Chemical class 0.000 claims description 4
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 2
125000003963 dichloro group Chemical group Cl* 0.000 claims description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
229940090181 propyl acetate Drugs 0.000 claims description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
RTYZBEVXCFLZPK-ADDDSGAWSA-N (6S,8S,9S,10R,13S,14S,17S)-17-acetyl-6-fluoro-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound F[C@H]1C[C@H]2[C@@H]3CC[C@H](C(C)=O)[C@]3(CC[C@@H]2[C@]2(C=CC(C=C12)=O)C)C RTYZBEVXCFLZPK-ADDDSGAWSA-N 0.000 description 2
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-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
238000009835 boiling Methods 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
229960005205 prednisolone Drugs 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000003431 steroids Chemical class 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
AQZMINLSVARCSL-UHFFFAOYSA-N 4-chloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile Chemical compound ClC1=CC(=O)C(C#N)=C(C#N)C1=O AQZMINLSVARCSL-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000010410 layer Substances 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
239000000583 progesterone congener Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1

Classifications

- 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
- 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
- C07J75/00—Processes for the preparation of steroids in general

Landscapes

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

CH1450860A 1959-12-29 1960-12-28 Verfahren zur Herstellung von 6-Fluor-3-oxo- 1,4-steroiden CH374656A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB4408059A GB893584A (en)	1959-12-29	1959-12-29	2-fluoro and 6-fluoro-í~-steroids
GB4423159		1959-12-30

Publications (1)

Publication Number	Publication Date
CH374656A true CH374656A (de)	1964-01-31

Family

ID=26265321

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1450860A CH374656A (de)	1959-12-29	1960-12-28	Verfahren zur Herstellung von 6-Fluor-3-oxo- 1,4-steroiden

Country Status (2)

Country	Link
BE (1)	BE598669R (fr)
CH (1)	CH374656A (fr)

1960
- 1960-12-28 CH CH1450860A patent/CH374656A/de unknown
- 1960-12-29 BE BE598669A patent/BE598669R/fr active

Also Published As

Publication number	Publication date
BE598669R (fr)	1961-06-29

Publication	Publication Date	Title
DE2301317C2 (de)	1983-11-03	Alkylierte 3,20-Diketo-&Delta;&uarr;4&uarr;-steroide der Pregnanreihe und Verfahren zu deren Herstellung
DE1468035A1 (de)	1968-12-12	Verfahren zur Herstellung von 19-Alkylsteroiden
DE1468410A1 (de)	1969-11-20	Verfahren zur Herstellung von 16-Methylensteroiden
DE1618871C3 (de)	1974-02-21	Verfahren zur Herstellung eines Steroidketonderivates. Ausscheidung aus: 1468988
CH374656A (de)	1964-01-31	Verfahren zur Herstellung von 6-Fluor-3-oxo- 1,4-steroiden
DE1793633C3 (de)	1973-10-04	Verfahren zur Herstellung von Gona 4(5),9(10)dien3 onen Ausscheidung aus 1468642
DE1493163C3 (de)	1974-04-11	nalpha-Äthinyl-ie-methyl-Delta hoch 4-östren-3 beta-17 betadiole, Verfahren zu deren Herstellung sowie diese enthaltende Mittel
AT233184B (de)	1964-04-25	Verfahren zur Herstellung von 3-Oxo-Δ<1,4>-steroiden
AT233175B (de)	1964-04-25	Verfahren zur Herstellung von 3-Oxo-Δ<1,4>- und 3-Oxo-Δ<1,4,6>-steroiden
AT228410B (de)	1963-07-10	Verfahren zur Herstellung neuer 6-Methyl-3-oxo-4, 6-dien-steroide
DE1643028C3 (de)	1975-01-09	Neue 1,2 alpha -Methylensteroide, Verfahren zu ihrer Herstellung, sowie diese enthaltende Mittel
AT233177B (de)	1964-04-25	Verfahren zur Herstellung des neuen 6α-Methyl-17 α-hydroxyprogesterons und seiner Ester
DE1468988C (de)	1972-07-06	nalpha-Chloräthinyl-lSbeta-äthyl-4-oder-5( 10)- gonen-3 -ketone.'
DE1468642C (de)	1971-10-28	Gona-4(5), 9(10>dien-3-one
AT274256B (de)	1969-09-10	Verfahren zur Herstellung von 3-Oxo-4,9,11-triensteroiden
DE1102144B (de)	1961-03-16	Verfahren zur Herstellung von 3-Oxo-?-6-methyl- und 3-Oxo-?-6-methylsteroiden
DE2110140A1 (de)	1971-09-16	Verfahren zur Herstellung von Steroiden der Pregnanreihe
DE1793775A1 (de)	1974-07-04	Verfahren zur herstellung von cyclopentanophenanthrenderivaten
DE1250433B (de)	1967-09-21	Verfahren zur Herstellung von Zl2 4-Steroiden der Androstan- 19-Norandrostan Pregnan oder 19 Norpregnanreihe
DE1215147B (de)	1966-04-28	Verfahren zur Herstellung von 19-Norsteroiden der Androstanreihe
DE1227901B (de)	1966-11-03	Verfahren zur Herstellung von 3-Desoxysteroiden der Androstanreihe
DE1152103B (de)	1963-08-01	Verfahren zur Herstellung von 1-Methyl-?-androsten-17ª‰-ol-3-onen
DE1070632B (de)	1959-12-10	Verfahren zur Herstellung von 2-AIkyl- und 2-Aralkyliderivaten von 17ec-niedrig-Alikyl-z!4-androsten-17/?ol-3-onen und 17a-nied'rig-Alkyl-androstan- (bzw.-testan) -17^-01-3-onen
DE1136331B (de)	1962-09-13	Verfahren zur Herstellung von 4-Chlor- bzw. 4-Brom í¸-3-Ketonen der Androstan- oder Pregnanreihe
DE3241833A1 (de)	1984-05-17	Verfahren zur trennung von 4 androsten-3,17-dion und 1,4-androstadien-3,17-dion