SU525432A3 - Способ получени 21-ацетокси-6 -фтор-4-прегнен3,20-дионов - Google Patents

Способ получени 21-ацетокси-6 -фтор-4-прегнен3,20-дионов

Info

Publication number: SU525432A3
Authority: SU; USSR - Soviet Union
Prior art keywords: acetoxy; fluoro; water; pregnen; acetone
Prior art date: 1972-05-02

Application number

SU1917216A

Other languages

English (en)

Russian (ru)

Inventor

Данута Ксенжны Чеслава

Скибиньска Мария

Вайхт Иосиф

Ушицка-Горава Тереса

Яворска Романа

Смолиньска Ядвига

Стшелецка Тереса

Original Assignee

Институт Пржемыслу Фармацевтичнэго Варшава (Инопредприятие)

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.)

1972-05-02

Filing date

1973-04-28

Publication date

1976-08-15

1973-04-28 Application filed by Институт Пржемыслу Фармацевтичнэго Варшава (Инопредприятие) filed Critical Институт Пржемыслу Фармацевтичнэго Варшава (Инопредприятие)

1976-08-15 Application granted granted Critical

1976-08-15 Publication of SU525432A3 publication Critical patent/SU525432A3/ru

Links

-1 21-acetoxy-6-fluoro-4-pregnen Chemical compound 0.000 title description 9
238000000034 method Methods 0.000 title description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
239000000203 mixture Substances 0.000 description 12
239000002244 precipitate Substances 0.000 description 10
229960000583 acetic acid Drugs 0.000 description 9
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
229910052731 fluorine Inorganic materials 0.000 description 6
239000011737 fluorine Substances 0.000 description 6
230000003647 oxidation Effects 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
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
239000007864 aqueous solution Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
229940117975 chromium trioxide Drugs 0.000 description 4
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 4
239000007800 oxidant agent Substances 0.000 description 4
235000011056 potassium acetate Nutrition 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000005457 ice water Substances 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
239000000047 product Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000003810 Jones reagent Substances 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000000538 analytical sample Substances 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
229910000039 hydrogen halide Inorganic materials 0.000 description 2
239000012433 hydrogen halide Substances 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RSRDWHPVTMQUGZ-OZIWPBGVSA-N 1-[(8r,9s,10s,13s,14s,17s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RSRDWHPVTMQUGZ-OZIWPBGVSA-N 0.000 description 1
ORNBQBCIOKFOEO-OZIWPBGVSA-N 1-[(8s,9s,10r,13s,14s,17s)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1C=C2CC(O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 ORNBQBCIOKFOEO-OZIWPBGVSA-N 0.000 description 1
AURFZBICLPNKBZ-YZRLXODZSA-N 3alpha-hydroxy-5beta-pregnan-20-one Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 AURFZBICLPNKBZ-YZRLXODZSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
101000587820 Homo sapiens Selenide, water dikinase 1 Proteins 0.000 description 1
101000701815 Homo sapiens Spermidine synthase Proteins 0.000 description 1
102100030413 Spermidine synthase Human genes 0.000 description 1
UUPQBRISSXULLA-LZELGGJRSA-N [2-[(6s,8s,9s,10r,13s,14s,17s)-6-fluoro-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical class C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)COC(=O)C)[C@@]2(C)CC1 UUPQBRISSXULLA-LZELGGJRSA-N 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000001309 chloro group Chemical class Cl* 0.000 description 1
239000012043 crude product Substances 0.000 description 1
LNZMEOLVTKHUAS-UHFFFAOYSA-N cyclohexane;dichloromethane Chemical compound ClCCl.C1CCCCC1 LNZMEOLVTKHUAS-UHFFFAOYSA-N 0.000 description 1
238000007269 dehydrobromination reaction Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

Landscapes

Steroid Compounds (AREA)

SU1917216A 1972-05-02 1973-04-28 Способ получени 21-ацетокси-6 -фтор-4-прегнен3,20-дионов SU525432A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PL15507872A PL78903B1 (cs)	1972-05-02	1972-05-02

Publications (1)

Publication Number	Publication Date
SU525432A3 true SU525432A3 (ru)	1976-08-15

Family

ID=19958396

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU1917216A SU525432A3 (ru)	1972-05-02	1973-04-28	Способ получени 21-ацетокси-6 -фтор-4-прегнен3,20-дионов

Country Status (5)

Country	Link
DD (1)	DD104077A5 (cs)
HU (1)	HU166425B (cs)
PL (1)	PL78903B1 (cs)
RO (1)	RO71432A (cs)
SU (1)	SU525432A3 (cs)

1972
- 1972-05-02 PL PL15507872A patent/PL78903B1/xx unknown
1973
- 1973-04-27 DD DD17049373A patent/DD104077A5/xx unknown
- 1973-04-28 RO RO7374647A patent/RO71432A/ro unknown
- 1973-04-28 SU SU1917216A patent/SU525432A3/ru active
- 1973-05-02 HU HUII000145 patent/HU166425B/hu unknown

Also Published As

Publication number	Publication date
PL78903B1 (cs)	1975-06-30
HU166425B (cs)	1975-03-28
DD104077A5 (cs)	1974-02-20
RO71432A (ro)	1982-05-10

Publication	Publication Date	Title
NO132558B (cs)	1975-08-18
US3313809A (en)	1967-04-11	Steroido[21, 20-d]isoxazoles
SU525432A3 (ru)	1976-08-15	Способ получени 21-ацетокси-6 -фтор-4-прегнен3,20-дионов
US2786857A (en)	1957-03-26	Process for producing 17-hydroxy-desoxycorticosterone
US2951074A (en)	1960-08-30	C14 cortical steroids and methods of preparing same
SU440830A1 (cs)	1974-08-25
US2615902A (en)	1952-10-28	Chemical compounds and processes for preparing the same
US3133940A (en)	1964-05-19	Process for the separation of delta-1, 4-3-keto steroid compounds from mixtures thereof with other 3-keto steroids
US2716125A (en)	1955-08-23	3(beta)-acetoxy-16(delta-acetoxyisocaprooxy)-allopregnanedione-11, 20
US2750381A (en)	1956-06-12	Steroid alkali-metal enolates
US2783254A (en)	1957-02-26	Process for the manufacture of 17alpha-hydroxycorticosterone and intermediates obtained thereby
US2740782A (en)	1956-04-03	Steroids
US2548922A (en)	1951-04-17	Process for preparation of steroidal hydroxy ketones
Oliveto et al.	1956	11-Oxygenated Steroids. XIV. New Syntheses of Corticosterone1
Turner et al.	1952	Steroids Derived from Bile Acids. XIX. Barbier—Wieland Degradation in the 11-Keto Series1
US2982774A (en)	1961-05-02	21-aldehydes of 9alpha-fluoro-steroids and derivatives thereof
US3136758A (en)	1964-06-09	Delta16-20-keto-pregnene derivatives and their preparation
KR860000587B1 (ko)	1986-05-17	소염진통 작용을 갖는 살리실산 유도체의 제조방법
US3190895A (en)	1965-06-22	Substituted androstan-16alpha-ylacetic acids
US3281431A (en)	1966-10-25	17-oxygenated-2-thia-5alpha-androstanes and derivatives thereof
US3178408A (en)	1965-04-13	Aminosteroid compounds and process for their manufacture
US3152119A (en)	1964-10-06	16-substituted-3, 20-diketo pregnenes and esters thereof
US2749338A (en)	1956-06-05	Isoallospirostanes
PL98296B1 (pl)	1978-04-29	Sposob otrzymywania estrow acetoksymetylowych cefalosporyn
US2691013A (en)	1954-10-05	Bromosteroids