CH515227A - Verfahren zur Herstellung von 21-Fluor- 4,6-pregnadienen - Google Patents

Verfahren zur Herstellung von 21-Fluor- 4,6-pregnadienen

Info

Publication number: CH515227A
Authority: CH; Switzerland
Prior art keywords: methylene; fluoro; dione; chloro; pregnadiene
Prior art date: 1966-08-11

Application number

CH1100967A

Other languages

German (de)

English (en)

Inventor

Rudolf Dr Wiechert

Friedmund Dr Neumann

Henry Dr Laurent

Original Assignee

Schering Ag

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.)

1966-08-11

Filing date

1967-08-04

Publication date

1971-11-15

1967-08-04 Application filed by Schering Ag filed Critical Schering Ag

1967-08-04 Priority to CH903971A priority Critical patent/CH524590A/de

1971-11-15 Publication of CH515227A publication Critical patent/CH515227A/de

Links

238000004519 manufacturing process Methods 0.000 title 1
239000002253 acid Substances 0.000 claims abstract description 7
229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
239000000460 chlorine Chemical group 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
230000003152 gestagenic effect Effects 0.000 abstract description 5
206010001928 Amenorrhoea Diseases 0.000 abstract description 4
230000002280 anti-androgenic effect Effects 0.000 abstract description 4
150000001875 compounds Chemical class 0.000 abstract description 4
201000009273 Endometriosis Diseases 0.000 abstract description 2
208000030270 breast disease Diseases 0.000 abstract description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
238000003556 assay Methods 0.000 abstract 1
230000002175 menstrual effect Effects 0.000 abstract 1
210000004291 uterus Anatomy 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 3
239000000292 calcium oxide Substances 0.000 description 3
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
201000000736 Amenorrhea Diseases 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
231100000540 amenorrhea Toxicity 0.000 description 2
239000000051 antiandrogen Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
210000002307 prostate Anatomy 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
210000001625 seminal vesicle Anatomy 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229960001712 testosterone propionate Drugs 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
201000010653 vesiculitis Diseases 0.000 description 2
LGTNVTBMTQCJMS-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,3,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1=CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 LGTNVTBMTQCJMS-BYZMTCBYSA-N 0.000 description 1
OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
ASZZHBXPMOVHCU-UHFFFAOYSA-N 3,9-diazaspiro[5.5]undecane-2,4-dione Chemical compound C1C(=O)NC(=O)CC11CCNCC1 ASZZHBXPMOVHCU-UHFFFAOYSA-N 0.000 description 1
208000019255 Menstrual disease Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical group 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 1
241000700159 Rattus Species 0.000 description 1
238000003436 Schotten-Baumann reaction Methods 0.000 description 1
239000004133 Sodium thiosulphate Substances 0.000 description 1
206010063146 Uterine hypoplasia Diseases 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
239000004330 calcium propionate Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000001816 cooling Methods 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000000583 progesterone congener Substances 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000005303 weighing 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
- A61K31/573—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 substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone

Landscapes

Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)

CH1100967A 1966-08-11 1967-08-04 Verfahren zur Herstellung von 21-Fluor- 4,6-pregnadienen CH515227A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH903971A CH524590A (de)	1966-08-11	1967-08-04	Verfahren zur Herstellung von 21-Fluor- 4,6-pregnadienen

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DESC039385		1966-08-11
DESC040710		1967-05-13

Publications (1)

Publication Number	Publication Date
CH515227A true CH515227A (de)	1971-11-15

Family

ID=25993399

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1100967A CH515227A (de)	1966-08-11	1967-08-04	Verfahren zur Herstellung von 21-Fluor- 4,6-pregnadienen

Country Status (12)

Country	Link
BE (1)	BE702583A (no)
CH (1)	CH515227A (no)
DE (2)	DE1593515C3 (no)
DK (1)	DK117227B (no)
ES (1)	ES343859A1 (no)
FI (1)	FI45172C (no)
FR (1)	FR1561096A (no)
GB (1)	GB1196476A (no)
IL (1)	IL28465A (no)
NL (1)	NL152267B (no)
NO (1)	NO126525B (no)
SE (1)	SE320067B (no)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19908762A1 (de) *	1999-02-18	2000-08-31	Jenapharm Gmbh	Verwendung von Dienogest in hoher Dosierung

1966
- 1966-08-11 DE DE19661593515 patent/DE1593515C3/de not_active Expired
1967
- 1967-05-13 DE DE19671643021 patent/DE1643021A1/de active Pending
- 1967-06-28 SE SE9525/67*A patent/SE320067B/xx unknown
- 1967-07-11 FI FI191467A patent/FI45172C/fi active
- 1967-08-01 GB GB3531267A patent/GB1196476A/en not_active Expired
- 1967-08-02 DK DK394967A patent/DK117227B/da unknown
- 1967-08-04 CH CH1100967A patent/CH515227A/de not_active IP Right Cessation
- 1967-08-05 ES ES343859A patent/ES343859A1/es not_active Expired
- 1967-08-07 IL IL2846567A patent/IL28465A/en unknown
- 1967-08-10 NL NL6711020A patent/NL152267B/xx unknown
- 1967-08-10 FR FR1561096D patent/FR1561096A/fr not_active Expired
- 1967-08-10 NO NO16932167A patent/NO126525B/no unknown
- 1967-08-11 BE BE702583D patent/BE702583A/xx unknown

Also Published As

Publication number	Publication date
DK117227B (da)	1970-03-31
NO126525B (no)	1973-02-19
SE320067B (no)	1970-02-02
NL152267B (nl)	1977-02-15
DE1643021A1 (de)	1971-03-11
DE1593515A1 (de)	1970-08-13
GB1196476A (en)	1970-06-24
NL6711020A (no)	1968-02-12
FI45172B (no)	1971-12-31
DE1593515B2 (de)	1975-01-09
IL28465A (en)	1972-01-27
BE702583A (no)	1968-02-12
ES343859A1 (es)	1968-10-01
FI45172C (fi)	1972-04-10
DE1593515C3 (de)	1975-08-14
FR1561096A (no)	1969-03-28

Legal Events

Date	Code	Title	Description
1980-05-14	PL	Patent ceased

Publication	Publication Date	Title
CH635594A5 (de)	1983-04-15	Verfahren zur herstellung von neuen gona-4,9(10)-dienen.
CH515227A (de)	1971-11-15	Verfahren zur Herstellung von 21-Fluor- 4,6-pregnadienen
CH496683A (de)	1970-09-30	Verfahren zur Herstellung neuer D-Homosteroide
AT274260B (de)	1969-09-10	Verfahren zur Herstellung von neuen 21-Fluor-Δ<4,6>-pregnadienen
DE1468632C (de)	1971-04-15	öalpha Acetylthio 4 en 3 on steroide und Verfahren zu deren Herstellung
CH524590A (de)	1972-06-30	Verfahren zur Herstellung von 21-Fluor- 4,6-pregnadienen
AT224277B (de)	1962-11-12	Verfahren zur Herstellung von neuen 16-Methylen-17α-acetoxy-progesteron-derivaten
DE1618977C (de)	1973-03-01	Nitroostratnene und Verfahren zu deren Herstellung
DE1668685C3 (de)	1975-04-24	17-Hydroxy- und 17-Acyloxy-6 beta, 7 beta-epoxy-1 alpha, 2 alpha-methylen-4-pregnen-3,20-dione, Verfahren zu deren Herstellung sowie diese enthaltende Mittel
DE1813083B2 (de)	1974-02-07	11 beta-Methyl-19-norpregn-4-en 3,20-dione, Verfahren zu ihrer Herstellung sowie diese enthaltendes Mittel
CH553759A (de)	1974-09-13	Verfahren zur herstellung von neuen 4-chlor-1,2(alpha)-methylen-(delta)4,6-pregnadien-17(alpha)-ol-3,20-dion oder dessen 17estern.
DE1922126C3 (de)	1978-05-03	6,17-Dichlor-A4'6 -pregnadiene, Verfahren zu deren Herstellung, diese enthaltende Arzneimittel sowie
AT233177B (de)	1964-04-25	Verfahren zur Herstellung des neuen 6α-Methyl-17 α-hydroxyprogesterons und seiner Ester
AT240540B (de)	1965-06-10	Verfahren zur Herstellung von 4-Chlor-Δ<4>-3-ketosteroidverbindungen
AT235477B (de)	1964-08-25	Verfahren zur Herstellung von neuen, mit einem Isoxazolring kondensierten Steroidverbindungen
CH493506A (de)	1970-07-15	Verfahren zur Herstellung von neuen Nitroöstratrienen
DE1543282C3 (de)	1976-01-22	9beta, lOalpha-Steroide, Verfahren zur Herstellung dieser Verbindungen und pharmazeutische Präparate, welche diese Verbindungen als Wirkstoffe enthalten
DE1299635B (de)	1969-07-24	In 3-Stellung unsubstituierte ª€ -19-nor-Androstene und ein Verfahren zu deren Herstellung
DE1177147B (de)	1964-09-03	Verfahren zur Herstellung von 3-Enolaethern von 6-Formyl-3-oxo-?-steroiden
CH493507A (de)	1970-07-15	Verfahren zur Herstellung von 1B-Methyl-2,3a-methylen-steroiden
DE1468632B1 (de)	1970-08-27	6alpha-Acetylthio-4-en-3-on-steroide und Verfahren zu deren Herstellung
DE1195746B (de)	1965-07-01	Verfahren zur Herstellung von gegebenenfalls S-alkylierten oder S-acylierten 7alpha-Mercapto-delta 1,4-3-keto-steroiden
DE1768673B1 (de)	1971-10-14	6alpha,9alpha-Difluorprednisolon-17,21-diester
DE1119267B (de)	1961-12-14	Verfahren zur Herstellung von gonadenhemmenden Derivaten des 17-epi-Oestriols
DE1113453B (de)	1961-09-07	Verfahren zur Herstellung von Substitutionsprodukten von Reichsteins-Substanz-S bzw.von deren 21-Acylaten