BG61608B1 - Метод за получаване на будезонид - Google Patents

Метод за получаване на будезонид Download PDF

Info

Publication number: BG61608B1
Authority: BG; Bulgaria
Prior art keywords: reaction; budesonide; water; diene; methanol
Prior art date: 1989-10-02

Application number

BG96166A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG96166A (bg

Inventor

Robert G. Hofstraat

Petrus H. Raijmakers

Pieter Vrijhof

Original Assignee

Ab Astra

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.)

1989-10-02

Filing date

1992-04-01

Publication date

1998-01-30

1992-04-01 Application filed by Ab Astra filed Critical Ab Astra

1993-12-24 Publication of BG96166A publication Critical patent/BG96166A/bg

1998-01-30 Publication of BG61608B1 publication Critical patent/BG61608B1/bg

Links

238000000034 method Methods 0.000 title claims abstract description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 18
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 9
239000003054 catalyst Substances 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 13
229960004436 budesonide Drugs 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
239000012043 crude product Substances 0.000 claims description 5
239000004215 Carbon black (E152) Substances 0.000 claims description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
239000013078 crystal Substances 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
150000002430 hydrocarbons Chemical class 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 3
-1 ligroin Chemical class 0.000 claims description 2
239000000203 mixture Substances 0.000 claims description 2
DPWQJNOCSXEZDU-VRYCVARASA-N (8r,9s,10r,13s,14s,17r)-17-hydroxy-10,13-dimethyl-17-(2,2,2-trihydroxyacetyl)-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)C(=O)C(O)(O)O)[C@@H]4[C@@H]3CCC2=C1 DPWQJNOCSXEZDU-VRYCVARASA-N 0.000 claims 1
238000009472 formulation Methods 0.000 claims 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract description 6
239000000047 product Substances 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
238000000746 purification Methods 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
SEKYBDYVXDAYPY-ILNISADRSA-N (8s,9s,10r,11s,13s,14s,16r,17s)-11,16,17-trihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 SEKYBDYVXDAYPY-ILNISADRSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
WVHWKXMIXGTSLT-RSMQETDKSA-N CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=C(O)C(=O)C(O)=C(O)[C@]4(C)[C@H]3CC[C@]12C Chemical compound CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=C(O)C(=O)C(O)=C(O)[C@]4(C)[C@H]3CC[C@]12C WVHWKXMIXGTSLT-RSMQETDKSA-N 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000001273 butane Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
230000035515 penetration Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
229920006395 saturated elastomer Polymers 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
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17
- 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
- C07J5/0046—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 substituted in position 17 alfa
- C07J5/0061—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 substituted in position 17 alfa substituted in position 16
- C07J5/0092—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 substituted in position 17 alfa substituted in position 16 by an OH group free esterified or etherified

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Paper (AREA)
Load-Bearing And Curtain Walls (AREA)

BG96166A 1989-10-02 1992-04-01 Метод за получаване на будезонид BG61608B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE8903219A SE8903219D0 (sv)	1989-10-02	1989-10-02	Process for the manufacture of budesonide
PCT/SE1990/000619 WO1991004984A1 (en)	1989-10-02	1990-09-27	Process for the manufacture of budesonide

Publications (2)

Publication Number	Publication Date
BG96166A BG96166A (bg)	1993-12-24
BG61608B1 true BG61608B1 (bg)	1998-01-30

Family

ID=20377019

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG96166A BG61608B1 (bg)	1989-10-02	1992-04-01	Метод за получаване на будезонид

Country Status (25)

Country	Link
US (1)	US5556964A (uk)
EP (1)	EP0494942B1 (uk)
JP (1)	JP2965352B2 (uk)
KR (1)	KR0160527B1 (uk)
AT (1)	ATE130310T1 (uk)
AU (1)	AU632864B2 (uk)
BG (1)	BG61608B1 (uk)
BR (1)	BR9007700A (uk)
CA (1)	CA2065861C (uk)
CY (1)	CY2084B1 (uk)
DE (1)	DE69023664T2 (uk)
DK (1)	DK0494942T3 (uk)
ES (1)	ES2079491T3 (uk)
FI (1)	FI103204B (uk)
HK (1)	HK52097A (uk)
HU (1)	HU212576B (uk)
LT (1)	LT3697B (uk)
LV (1)	LV10283B (uk)
NO (1)	NO178827C (uk)
RO (1)	RO110947B1 (uk)
RU (1)	RU2048472C1 (uk)
SE (1)	SE8903219D0 (uk)
SG (1)	SG43344A1 (uk)
UA (1)	UA26860C2 (uk)
WO (1)	WO1991004984A1 (uk)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6028190A (en)	1994-02-01	2000-02-22	The Regents Of The University Of California	Probes labeled with energy transfer coupled dyes
US6166024A (en)	1995-03-30	2000-12-26	Mayo Foundation For Medical Education And Research	Use of topical azathioprine and thioguanine to treat colorectal adenomas
IT1291288B1 (it)	1997-04-30	1999-01-07	Farmabios Srl	Processo per la preparazione di 16,17 acetali di derivati pregnanici con controllo della distribuzione epimerica al c-22.
SE9704186D0 (sv) *	1997-11-14	1997-11-14	Astra Ab	New composition of matter
US6266556B1 (en)	1998-04-27	2001-07-24	Beth Israel Deaconess Medical Center, Inc.	Method and apparatus for recording an electroencephalogram during transcranial magnetic stimulation
FR2782823B1 (fr)	1998-09-01	2000-11-17	Neopost Ind	Procede d'impression thermique
US6234167B1 (en)	1998-10-14	2001-05-22	Chrysalis Technologies, Incorporated	Aerosol generator and methods of making and using an aerosol generator
MY136453A (en)	2000-04-27	2008-10-31	Philip Morris Usa Inc	"improved method and apparatus for generating an aerosol"
US6883516B2 (en)	2000-04-27	2005-04-26	Chrysalis Technologies Incorporated	Method for generating an aerosol with a predetermined and/or substantially monodispersed particle size distribution
US6681998B2 (en)	2000-12-22	2004-01-27	Chrysalis Technologies Incorporated	Aerosol generator having inductive heater and method of use thereof
US7077130B2 (en)	2000-12-22	2006-07-18	Chrysalis Technologies Incorporated	Disposable inhaler system
US6799572B2 (en)	2000-12-22	2004-10-05	Chrysalis Technologies Incorporated	Disposable aerosol generator system and methods for administering the aerosol
US6491233B2 (en)	2000-12-22	2002-12-10	Chrysalis Technologies Incorporated	Vapor driven aerosol generator and method of use thereof
US6701921B2 (en)	2000-12-22	2004-03-09	Chrysalis Technologies Incorporated	Aerosol generator having heater in multilayered composite and method of use thereof
US6501052B2 (en)	2000-12-22	2002-12-31	Chrysalis Technologies Incorporated	Aerosol generator having multiple heating zones and methods of use thereof
US20030055026A1 (en) *	2001-04-17	2003-03-20	Dey L.P.	Formoterol/steroid bronchodilating compositions and methods of use thereof
US6640050B2 (en)	2001-09-21	2003-10-28	Chrysalis Technologies Incorporated	Fluid vaporizing device having controlled temperature profile heater/capillary tube
US6568390B2 (en)	2001-09-21	2003-05-27	Chrysalis Technologies Incorporated	Dual capillary fluid vaporizing device
US6681769B2 (en)	2001-12-06	2004-01-27	Crysalis Technologies Incorporated	Aerosol generator having a multiple path heater arrangement and method of use thereof
US6804458B2 (en)	2001-12-06	2004-10-12	Chrysalis Technologies Incorporated	Aerosol generator having heater arranged to vaporize fluid in fluid passage between bonded layers of laminate
US6701922B2 (en)	2001-12-20	2004-03-09	Chrysalis Technologies Incorporated	Mouthpiece entrainment airflow control for aerosol generators
TWI359675B (en)	2003-07-10	2012-03-11	Dey L P	Bronchodilating β-agonist compositions
US7367334B2 (en)	2003-08-27	2008-05-06	Philip Morris Usa Inc.	Fluid vaporizing device having controlled temperature profile heater/capillary tube
US20070020299A1 (en) *	2003-12-31	2007-01-25	Pipkin James D	Inhalant formulation containing sulfoalkyl ether cyclodextrin and corticosteroid
US20070020298A1 (en) *	2003-12-31	2007-01-25	Pipkin James D	Inhalant formulation containing sulfoalkyl ether gamma-cyclodextrin and corticosteroid
US20070020196A1 (en) *	2003-12-31	2007-01-25	Pipkin James D	Inhalant formulation containing sulfoalkyl ether cyclodextrin and corticosteroid prepared from a unit dose suspension
ATE446581T1 (de) *	2004-03-12	2009-11-15	Trinity College Dublin	Magnetoresistives medium
US20070185066A1 (en) *	2005-12-20	2007-08-09	Verus Pharmaceuticals, Inc.	Systems and methods for the delivery of corticosteroids
US20070249572A1 (en) *	2005-12-20	2007-10-25	Verus Pharmaceuticals, Inc.	Systems and methods for the delivery of corticosteroids
US20070160542A1 (en) *	2005-12-20	2007-07-12	Verus Pharmaceuticals, Inc.	Methods and systems for the delivery of corticosteroids having an enhanced pharmacokinetic profile
US20070197486A1 (en) *	2005-12-20	2007-08-23	Verus Pharmaceuticals, Inc.	Methods and systems for the delivery of corticosteroids
JP2009526858A (ja) *	2006-02-15	2009-07-23	ティカレーケメデルアーベー	コルチコステロイド溶液を製造する方法
US12370352B2 (en)	2007-06-28	2025-07-29	Cydex Pharmaceuticals, Inc.	Nasal and ophthalmic delivery of aqueous corticosteroid solutions
CN102060906B (zh) *	2010-12-23	2013-01-16	鲁南贝特制药有限公司	一种r布地奈德的制备方法
WO2016120891A1 (en)	2015-01-30	2016-08-04	Coral Drugs Pvt. Ltd.	Novel process for preparation of glucocorticoid steroids

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3197469A (en) *	1958-08-06	1965-07-27	Pharmaceutical Res Products In	16, 17-acetals and ketals of 6-halo-16, 17-dihydroxy steroids of the pregnane seriesand intermediates therefor
US3077471A (en) *	1961-08-04	1963-02-12	Olin Mathieson	Steroids of the 19-norpregnane series
SE378109B (uk) *	1972-05-19	1975-08-18	Bofors Ab
SE8008524L (sv) *	1980-12-04	1982-06-05	Draco Ab	4-pregnen-derivat, ett forfarande for deras framstellning, beredning och metod for behandling av inflammatoriska tillstand
IT1196142B (it) *	1984-06-11	1988-11-10	Sicor Spa	Procedimento per la preparazione di 16,17-acetali di derivati pregnanici e nuovi composti ottenuti
SE8604059D0 (sv) *	1986-09-25	1986-09-25	Astra Pharma Prod	A method of controlling the epimeric distribution in the preparation of 16,17-acetals of pregnane derivatives

1989
- 1989-10-02 SE SE8903219A patent/SE8903219D0/xx unknown
1990
- 1990-09-27 BR BR909007700A patent/BR9007700A/pt not_active IP Right Cessation
- 1990-09-27 ES ES90915222T patent/ES2079491T3/es not_active Expired - Lifetime
- 1990-09-27 EP EP90915222A patent/EP0494942B1/en not_active Expired - Lifetime
- 1990-09-27 CA CA002065861A patent/CA2065861C/en not_active Expired - Lifetime
- 1990-09-27 JP JP2514161A patent/JP2965352B2/ja not_active Expired - Lifetime
- 1990-09-27 RO RO92-200446A patent/RO110947B1/ro unknown
- 1990-09-27 KR KR1019920700728A patent/KR0160527B1/ko not_active Expired - Lifetime
- 1990-09-27 UA UA94010159A patent/UA26860C2/uk unknown
- 1990-09-27 WO PCT/SE1990/000619 patent/WO1991004984A1/en not_active Ceased
- 1990-09-27 DK DK90915222.5T patent/DK0494942T3/da active
- 1990-09-27 AU AU65309/90A patent/AU632864B2/en not_active Expired
- 1990-09-27 RU SU905011922A patent/RU2048472C1/ru active
- 1990-09-27 HU HU9201064A patent/HU212576B/hu unknown
- 1990-09-27 AT AT90915222T patent/ATE130310T1/de not_active IP Right Cessation
- 1990-09-27 DE DE69023664T patent/DE69023664T2/de not_active Expired - Lifetime
- 1990-11-27 SG SG1996008769A patent/SG43344A1/en unknown
1992
- 1992-03-30 NO NO921233A patent/NO178827C/no not_active IP Right Cessation
- 1992-04-01 BG BG96166A patent/BG61608B1/bg unknown
- 1992-04-01 FI FI921426A patent/FI103204B/fi active
1993
- 1993-06-30 LV LVP-93-858A patent/LV10283B/xx unknown
- 1993-12-30 LT LTIP1729A patent/LT3697B/lt not_active IP Right Cessation
1994
- 1994-12-16 US US08/357,773 patent/US5556964A/en not_active Expired - Lifetime
1997
- 1997-04-24 HK HK52097A patent/HK52097A/en not_active IP Right Cessation
1998
- 1998-10-16 CY CY9802084A patent/CY2084B1/xx unknown

Also Published As

Publication number	Publication date
AU6530990A (en)	1991-04-28
EP0494942B1 (en)	1995-11-15
FI921426L (fi)	1992-04-01
AU632864B2 (en)	1993-01-14
WO1991004984A1 (en)	1991-04-18
DE69023664T2 (de)	1996-05-02
JPH05500669A (ja)	1993-02-12
HU9201064D0 (en)	1992-06-29
CA2065861C (en)	2001-06-05
LV10283A (lv)	1994-10-20
ES2079491T3 (es)	1996-01-16
DE69023664D1 (de)	1995-12-21
HU212576B (en)	1996-08-29
LT3697B (en)	1996-02-26
SG43344A1 (en)	1997-10-17
RU2048472C1 (ru)	1995-11-20
FI103204B1 (fi)	1999-05-14
LTIP1729A (en)	1995-07-25
KR0160527B1 (ko)	1998-11-16
HUT60281A (en)	1992-08-28
EP0494942A1 (en)	1992-07-22
SE8903219D0 (sv)	1989-10-02
CA2065861A1 (en)	1991-04-03
LV10283B (en)	1995-04-20
JP2965352B2 (ja)	1999-10-18
ATE130310T1 (de)	1995-12-15
NO921233L (no)	1992-03-30
HK52097A (en)	1997-05-02
FI921426A0 (fi)	1992-04-01
BG96166A (bg)	1993-12-24
NO921233D0 (no)	1992-03-30
US5556964A (en)	1996-09-17
FI103204B (fi)	1999-05-14
NO178827C (no)	1996-06-12
RO110947B1 (ro)	1996-05-30
DK0494942T3 (da)	1996-03-11
NO178827B (no)	1996-03-04
UA26860C2 (uk)	1999-12-29
BR9007700A (pt)	1992-08-11
CY2084B1 (en)	1998-10-16

Publication	Publication Date	Title
BG61608B1 (bg)	1998-01-30	Метод за получаване на будезонид
CA1310009C (en)	1992-11-10	Ester prodrugs of steroids
CA1159049A (en)	1983-12-20	Process for the preparation of 6-halo-pregnanes
DE2715863A1 (de)	1977-11-03	Verfahren zur herstellung von steroidcarbonsaeuren und ihren estern
SU890979A3 (ru)	1981-12-15	Способ получени кортикоидов
CH645110A5 (de)	1984-09-14	Racemische oder optisch aktive oxyaminoeburnane sowie verfahren zu ihrer herstellung.
EP0576330B1 (fr)	1995-09-27	Nouveau procédé de préparation d'un composé stéroide delta 9(11)
DD251356A5 (de)	1987-11-11	Verfahren zur herstellung von 17a-ethilnyl-17beta-hydroxy-18-methyl-4,15-estradien-3-on und die neuen ausgangsverbindungen fuer dieses verfahren
SU453833A3 (uk)	1974-12-15
US2873284A (en)	1959-02-10	N, n-dialkyl acylamide solvate of 1, 4-pregnadiene-17alpha, 21-diol-3, 11, 20-trione-21-acylate and process of preparing such
JPS581000A (ja)	1983-01-06	４α，５α−エポキシ−３，２０−ジオキソプレグナン−２α，１６α−ジカルボニトリル，その製造法およびそれを含む製薬学的組成物
SU330627A1 (ru)		Способ получения нитростероидов
ITMI982196A1 (it)	2000-04-13	Processo stereoselettivo per la preparazione di budesonide nella forma di epimero 22-r.
CH634081A5 (en)	1983-01-14	Process for the preparation of novel androstadiene-17beta-carboxylic acid esters
SU1711675A3 (ru)	1992-02-07	Способ получени 22 /R, S/-11 @ , 21 - дигидрокси-16 @ , 17-бутилиденбисоксипрегна - 1,4-диен-3,20-диона
US4058551A (en)	1977-11-15	Substituted phenyl esters of PGA2
SU483830A3 (ru)	1975-09-05	Способ получени 7-ациламиноцефалоспоринов
SU406349A1 (ru)		Виблиотекл
US3673179A (en)	1972-06-27	C-21 lower alkylsulfinyl esters of certain 21-hydroxycorticosteroids
CH613711A5 (en)	1979-10-15	Process for the preparation of 9,11beta-dihalo-(16alpha, 17-b)-1,4-dioxane steroids
DE2309030A1 (de)	1973-09-13	Neue pregnan-21-aldehyde und deren derivate und ein verfahren zu deren herstellung
Suc	1983	21-chloro-21-deoxy Derivatives SABURO Suc-A1,*'” SANYA AK/\BosHi,“and Sumo IKEGAMlb
JPS5948823B2 (ja)	1984-11-29	Ｐｇｄ↓２のエステル及び製法
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