SU493963A3 - Способ получени азотнокислых эфиров 21-спиртов прегнанового р да - Google Patents

Способ получени азотнокислых эфиров 21-спиртов прегнанового р да

Info

Publication number: SU493963A3
Authority: SU; USSR - Soviet Union
Prior art keywords: mol; dione; product; mmk; chloroform
Prior art date: 1971-05-07

Application number

SU1783400A

Other languages

English (en)

Russian (ru)

Inventor

Боор Анна

Тот Иозеф

Гергеньи Каталин

Ковачич Мате

Сен Тамаш

Цизер Ева

Холли Шандор

Original Assignee

Рихтер Гедеон Ведьесети Дьяр Рт (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.)

1971-05-07

Filing date

1972-05-05

Publication date

1975-11-28

1972-05-05 Application filed by Рихтер Гедеон Ведьесети Дьяр Рт (Фирма) filed Critical Рихтер Гедеон Ведьесети Дьяр Рт (Фирма)

1975-11-28 Application granted granted Critical

1975-11-28 Publication of SU493963A3 publication Critical patent/SU493963A3/ru

Links

238000000034 method Methods 0.000 title description 9
150000002823 nitrates Chemical class 0.000 title description 2
150000003128 pregnanes Chemical class 0.000 title description 2
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 39
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 19
238000000354 decomposition reaction Methods 0.000 description 17
239000000203 mixture Substances 0.000 description 16
229910017604 nitric acid Inorganic materials 0.000 description 16
229910002651 NO3 Inorganic materials 0.000 description 15
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
238000004809 thin layer chromatography Methods 0.000 description 8
238000010521 absorption reaction Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000000155 melt Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000002118 epoxides Chemical class 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
-1 halide compounds Chemical class 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
150000003431 steroids Chemical class 0.000 description 2
YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 description 1
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
125000001153 fluoro group Chemical class F* 0.000 description 1
230000005484 gravity Effects 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
- C07J71/0015—Oxiranes at position 9(11)
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU1783400A 1971-05-07 1972-05-05 Способ получени азотнокислых эфиров 21-спиртов прегнанового р да SU493963A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HURI429A HU164115B (2)	1971-05-07	1971-05-07

Publications (1)

Publication Number	Publication Date
SU493963A3 true SU493963A3 (ru)	1975-11-28

Family

ID=11000864

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU1783400A SU493963A3 (ru)	1971-05-07	1972-05-05	Способ получени азотнокислых эфиров 21-спиртов прегнанового р да

Country Status (15)

Country	Link
JP (1)	JPS5330707B1 (2)
AT (1)	AT316767B (2)
AU (1)	AU469581B2 (2)
CA (1)	CA975755A (2)
CS (2)	CS171258B2 (2)
DD (1)	DD98668A5 (2)
DE (1)	DE2222491C3 (2)
ES (1)	ES402230A1 (2)
FR (1)	FR2143664A1 (2)
HU (1)	HU164115B (2)
NL (1)	NL7206134A (2)
PL (1)	PL75494B1 (2)
SE (2)	SE385590B (2)
SU (1)	SU493963A3 (2)
YU (1)	YU34701B (2)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5792758A (en) *	1995-12-08	1998-08-11	G. D. Searle & Co.	Steroid nitrite ester derivatives useful as anti-inflammatory drugs
US5707984A (en) *	1995-12-08	1998-01-13	G. D. Searle & Co.	Steroid nitrite/nitrate ester derivatives useful as anti-inflammatory drugs
US5824669A (en) *	1996-03-22	1998-10-20	Nitromed, Inc.	Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders
US5837698A (en) *	1996-05-02	1998-11-17	G. D. Searle & Co.	Steroid nitrite and nitrate ester derivatives useful as anti-inflammatory drugs
US5985862A (en) *	1996-05-02	1999-11-16	G.D. Searle & Co.	Pharmaceutical compositions having steroid nitrate ester derivatives useful as anti-inflammatory drugs
IT1285770B1 (it) *	1996-10-04	1998-06-18	Nicox Sa	Composti corticoidei
ITMI20020148A1 (it)	2002-01-29	2003-07-29	Nicox Sa	Nuovi corticosteroidi
BRPI0807078A2 (pt)	2007-02-05	2014-04-08	Nicox Sa	Composto, e, formulação farmacêutica
JP5780521B2 (ja)	2008-05-28	2015-09-16	リベラジェン・バイオファーマ・インコーポレイテッドＲｅｖｅｒａＧｅｎＢｉｏＰｈａｒｍａ，Ｉｎｃ．	疾患を治療するための、ＮＦ−κＢの非ホルモン性ステロイド調節因子
WO2011127048A2 (en)	2010-04-05	2011-10-13	Validus Biopharma	NON-HORMONAL STEROID MODULATORS OF NF-ĸB FOR TREATMENT OF DISEASE
US8716268B2 (en) *	2010-06-07	2014-05-06	Chao Liu	Nitrate esters of corticoid compounds useful as diuretics
WO2017004205A1 (en)	2015-06-29	2017-01-05	Reveragen Biopharma, Inc.	NON-HORMONAL STEROID MODULATORS OF NF-κB FOR TREATMENT OF DISEASE
US11382922B2 (en)	2019-03-07	2022-07-12	Reveragen Biopharma, Inc.	Aqueous oral pharmaceutical suspension compositions

1971
- 1971-05-07 HU HURI429A patent/HU164115B/hu unknown
1972
- 1972-04-20 AT AT345872A patent/AT316767B/de not_active IP Right Cessation
- 1972-04-22 ES ES402230A patent/ES402230A1/es not_active Expired
- 1972-04-26 YU YU1117/72A patent/YU34701B/xx unknown
- 1972-04-28 DD DD162651A patent/DD98668A5/xx unknown
- 1972-05-01 AU AU41722/72A patent/AU469581B2/en not_active Expired
- 1972-05-04 FR FR7215938A patent/FR2143664A1/fr active Granted
- 1972-05-04 JP JP4376772A patent/JPS5330707B1/ja active Pending
- 1972-05-05 CS CS3050A patent/CS171258B2/cs unknown
- 1972-05-05 PL PL15518272A patent/PL75494B1/pl unknown
- 1972-05-05 SE SE7205915A patent/SE385590B/xx unknown
- 1972-05-05 CA CA141,366A patent/CA975755A/en not_active Expired
- 1972-05-05 CS CS2266*[A patent/CS171259B2/cs unknown
- 1972-05-05 NL NL7206134A patent/NL7206134A/xx not_active Application Discontinuation
- 1972-05-05 SU SU1783400A patent/SU493963A3/ru active
- 1972-05-08 DE DE2222491A patent/DE2222491C3/de not_active Expired
1975
- 1975-03-21 SE SE7503290A patent/SE7503290L/xx unknown

Also Published As

Publication number	Publication date
DE2222491C3 (de)	1978-05-03
CA975755A (en)	1975-10-07
DE2222491B2 (de)	1977-09-29
SE385590B (sv)	1976-07-12
YU111772A (en)	1979-07-10
DD98668A5 (2)	1973-07-05
YU34701B (en)	1979-12-31
AU4172272A (en)	1973-11-08
FR2143664B1 (2)	1976-07-02
NL7206134A (2)	1972-11-09
CS171259B2 (2)	1976-10-29
SE7503290L (2)	1975-03-21
AT316767B (de)	1974-07-25
ES402230A1 (es)	1975-03-16
HU164115B (2)	1973-12-28
PL75494B1 (2)	1974-12-31
CS171258B2 (2)	1976-10-29
JPS5330707B1 (2)	1978-08-29
DE2222491A1 (de)	1972-11-16
AU469581B2 (en)	1976-02-19
FR2143664A1 (en)	1973-02-09

Publication	Publication Date	Title
SU493963A3 (ru)	1975-11-28	Способ получени азотнокислых эфиров 21-спиртов прегнанового р да
US4006172A (en)	1977-02-01	Process for 7-keto-Δ5 -steroids
US3993675A (en)	1976-11-23	Process for the preparation of 1α,25-dihydroxycholecalciferol
US3687944A (en)	1972-08-29	Process for the preparation of bufalin and related compounds
US2980699A (en)	1961-04-18	Dihydropyranocoumarin derivatives and process for their production
DK153483B (da)	1988-07-18	Fremgangsmaade til fremstilling af gamma-pyroner
US4334969A (en)	1982-06-15	Photochemical process for the synthesis of strobilurin
US3313809A (en)	1967-04-11	Steroido[21, 20-d]isoxazoles
SEKI et al.	1973	Synthesis of active forms of vitamin D. IV. Synthesis of 24, 25-and 25, 26-dihydroxycholesterols
DE2705876A1 (de)	1977-08-18	Steroid eckige klammer auf 16 alpha, 17-d eckige klammer zu isoxazolidine, verfahren zu ihrer herstellung, zwischenprodukte und arzneimittel
NL8104985A (nl)	1982-06-01	17-oxazolinosteroieden, werkwijze voor de bereiding daarvan, en toepassing daarvan voor de bereiding van corticosteroieden.
CN108047291B (zh)	2020-06-16	一种鱼腥草素杂合黄酮类化合物的合成方法
Suginome et al.	1969	Some Observations on Photolysis of Fused Cyclopentyl Nitrites
US3196161A (en)	1965-07-20	Process for preparing alkyl 3-alkyl-isoxazole-5-carboxylate
SU1498767A1 (ru)	1989-08-07	Способ получени ( @ ) 3 @ ,6,6,9 @ -тетраметилпергидронафто [2,1-в]фурана
US2854454A (en)	1958-09-30	Rescennamine
SU576958A3 (ru)	1977-10-15	Способ получени 15 ,16 метилен-4-прегненов
US3277125A (en)	1966-10-04	5beta, 6beta-methanoestrenes
KUO et al.	1982	New Methods and Reagents in Organic Synthesis. 20. 2-Mesitylenesulfonyl diazomethane: Synthesis and Application to the Arndt-Eistert Synthesis
SU526283A3 (ru)	1976-08-25	Способ получени соединений р да простагландинов
SU1533625A3 (ru)	1989-12-30	Способ получени (+)-(3S, 4R)-3,4,7,11-тетраметил-6,10-додекадиенал
SU1053746A3 (ru)	1983-11-07	Способ получени 4-тиа-или 4-сульфинил- @ производных
US3087944A (en)	1963-04-30	19-methyl-19-acyloxy strophanthidin derivatives
Rivett	1980	Preparation of 1, 1-Diphenyl-1-hydroxy-3-butanone
US3087926A (en)	1963-04-30	18-acyloxy-5-pregnen-3-ols, derivatives, and intermediates for their preparation