SU689621A3 - Способ получени -гомостероидов - Google Patents

Способ получени -гомостероидов

Info

Publication number: SU689621A3
Authority: SU; USSR - Soviet Union
Prior art keywords: carboxylic acid; oxo; hydroxy; spectrum; diene
Prior art date: 1975-04-03

Application number

SU762339139A

Other languages

English (en)

Russian (ru)

Inventor

Алиг Лео

Фюрст Андор

Мюллер Марсель

Керб Ульрих

Вихерт Рудольф

Кизлих Клаус

Никольсон Роберт

Original Assignee

Ф.Хоффманн-Ля Рош И Ко Аг (Фирма)

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.)

1975-04-03

Filing date

1976-04-01

Publication date

1979-09-30

1976-04-01 Application filed by Ф.Хоффманн-Ля Рош И Ко Аг (Фирма) filed Critical Ф.Хоффманн-Ля Рош И Ко Аг (Фирма)

1979-09-30 Application granted granted Critical

1979-09-30 Publication of SU689621A3 publication Critical patent/SU689621A3/ru

Links

238000000034 method Methods 0.000 title description 4
150000000795 D-homosteroids Chemical class 0.000 title description 2
238000002211 ultraviolet spectrum Methods 0.000 description 50
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
150000004702 methyl esters Chemical class 0.000 description 15
-1 acyl hydride Chemical class 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 10
239000002253 acid Substances 0.000 description 7
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
241000790917 Dioxys <bee> Species 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
241000546339 Trioxys Species 0.000 description 5
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
235000002639 sodium chloride Nutrition 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
230000010933 acylation Effects 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-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
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
PJGJQVRXEUVAFT-UHFFFAOYSA-N chloroiodomethane Chemical compound ClCI PJGJQVRXEUVAFT-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000006260 foam Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
229940096017 silver fluoride Drugs 0.000 description 2
REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
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
YAQLSKVCTLCIIE-UHFFFAOYSA-N 2-bromobutyric acid Chemical compound CCC(Br)C(O)=O YAQLSKVCTLCIIE-UHFFFAOYSA-N 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
229940008406 diethyl sulfate Drugs 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000005429 oxyalkyl group Chemical group 0.000 description 1
239000000047 product Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms

Landscapes

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

SU762339139A 1975-04-03 1976-04-01 Способ получени -гомостероидов SU689621A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH422475A CH620455A5 (en)	1975-04-03	1975-04-03	Process for the preparation of D-homosteroids

Publications (1)

Publication Number	Publication Date
SU689621A3 true SU689621A3 (ru)	1979-09-30

Family

ID=4272112

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU762339139A SU689621A3 (ru)	1975-04-03	1976-04-01	Способ получени -гомостероидов

Country Status (5)

Country	Link
AT (1)	AT357701B (de)
BE (1)	BE840346A (de)
CH (2)	CH620455A5 (de)
SU (1)	SU689621A3 (de)
ZA (1)	ZA761970B (de)

1975
- 1975-04-03 CH CH422475A patent/CH620455A5/de not_active IP Right Cessation
1976
- 1976-04-01 ZA ZA761970A patent/ZA761970B/xx unknown
- 1976-04-01 SU SU762339139A patent/SU689621A3/ru active
- 1976-04-02 AT AT239476A patent/AT357701B/de not_active IP Right Cessation
- 1976-04-02 BE BE165816A patent/BE840346A/xx not_active IP Right Cessation
1979
- 1979-03-27 CH CH282879A patent/CH620456A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
CH620455A5 (en)	1980-11-28
CH620456A5 (en)	1980-11-28
ATA239476A (de)	1979-12-15
AT357701B (de)	1980-07-25
ZA761970B (en)	1977-03-30
BE840346A (fr)	1976-10-04

Publication	Publication Date	Title
NO137321B (no)	1977-10-31	Analogifremgangsm}te for fremstilling av terapeutisk aktive 3-okso-17alfa-acyloksyandrost-4-en-17beta-karboksylsyreestere
GB1578243A (en)	1980-11-05	Androstadiene - 17 - carboxylic acids and their esters
CH620452A5 (de)	1980-11-28
US4119625A (en)	1978-10-10	Process for the manufacture of steroid carboxylic acids and the esters thereof
NO760607L (de)	1976-08-31
SU689621A3 (ru)	1979-09-30	Способ получени -гомостероидов
US3313809A (en)	1967-04-11	Steroido[21, 20-d]isoxazoles
SU676170A3 (ru)	1979-07-25	Способ получени 7-оксиэстрадиолов
SU1440351A3 (ru)	1988-11-23	Способ получени производных прегнана
SU440830A1 (de)	1974-08-25
GOTO et al.	1980	Synthesis of monosulfates of cholic acid derivatives
US3639392A (en)	1972-02-01	Cardioactive oxido-bufatrienolides
US2800489A (en)	1957-07-23	11-trifluoroacetoxy steroids and process
US3764615A (en)	1973-10-09	Process for the preparation of pregnane derivatives
KOMATSUBARA	1954	The Synthesis of Stero-bile Acid. IX. The Synthesis of 3 (α)• 7 (α)• 12 (α)-Trihydroxycoprostanic Acid
US3030391A (en)	1962-04-17	12-alkoxy-11-oxygenated pregnanes
US3271390A (en)	1966-09-06	Sulfurenic acid and derivatives thereof
US2263785A (en)	1941-11-25	Hydroxy-ketones of pregnane series
NO127190B (de)	1973-05-21
US2744110A (en)	1956-05-01	3-ethylene mercaptole derivatives of progesterone
US3094521A (en)	1963-06-18	Alkanoylthio and pyrazolo androstane derivatives
US4044022A (en)	1977-08-23	15-Oxasteroids
US3094522A (en)	1963-06-18	Alkanoylthio and pyrazolo androstane derivatives
US2897214A (en)	1959-07-28	3-hydroxy-11-keto-delta22-ergostene and esters thereof
US4076944A (en)	1978-02-28	3β,14β-Dihydroxy-14,17-seco-D-bisnorandrostan-17-oic acid derivatives