ES2184628A1 - Procedimiento estereoselectivo para la produccion de 6 -fluorpregnanos e intermedios. - Google Patents

Procedimiento estereoselectivo para la produccion de 6 -fluorpregnanos e intermedios.

Info

Publication number
ES2184628A1
ES2184628A1 ES200101754A ES200101754A ES2184628A1 ES 2184628 A1 ES2184628 A1 ES 2184628A1 ES 200101754 A ES200101754 A ES 200101754A ES 200101754 A ES200101754 A ES 200101754A ES 2184628 A1 ES2184628 A1 ES 2184628A1
Authority
ES
Spain
Prior art keywords
alkyl
fluoropregnanes
6alpha
intermediaries
producing
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
ES200101754A
Other languages
English (en)
Other versions
ES2184628B1 (es
Inventor
Garrido Jose Vicente Murillo
Guisasola Luis Octavio Silva
Juarez Jorge Martin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Raga Consultores SL
Original Assignee
Raga Consultores SL
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.)
Filing date
Publication date
Priority to ES200101754A priority Critical patent/ES2184628B1/es
Application filed by Raga Consultores SL filed Critical Raga Consultores SL
Priority to AU2002355187A priority patent/AU2002355187A1/en
Priority to JP2003515540A priority patent/JP2004538294A/ja
Priority to DE60215193T priority patent/DE60215193T2/de
Priority to PCT/ES2002/000372 priority patent/WO2003010181A1/es
Priority to AT02751191T priority patent/ATE341561T1/de
Priority to CA002455229A priority patent/CA2455229A1/en
Priority to EP02751191A priority patent/EP1422235B1/en
Priority to ES02751191T priority patent/ES2274065T3/es
Publication of ES2184628A1 publication Critical patent/ES2184628A1/es
Priority to US10/764,915 priority patent/US20040181055A1/en
Application granted granted Critical
Publication of ES2184628B1 publication Critical patent/ES2184628B1/es
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

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)
  • Compositions Of Oxide Ceramics (AREA)
  • Glass Compositions (AREA)

Abstract

Procedimiento estereoselectivo para la producción de 6{al} fluorpregnanos e intermedios. 6{al} fluorpregnanos (I), donde la línea de puntos entre las posiciones 1 y 2 representa un enlace sencillo o doble; R{sub,1} es OH, OCOR{sub,2}, X, SO{sub,3}R {sub,3}, o un grupo (R{sub,7})(R{sub,8})(R{sub,9})SiO-, donde X es halógeno, R{sub,2} y R{sub,3} 3 son alquilo C{sub,1-6} ó fenilo opcionalmente sustituido por alquilo C{sub,1-4}, y R{sub,7}, R{sub,8} y R{sub,9}, iguales o diferentes, son alquilo C{sub,1-6} o fenilo opcionalmente sustituido por alquilo C{sub,1- 4}, pueden obtenerse mediante un procedimiento de elevada estereoseletividad que comprende hacer reaccionar un 3- (trisustituido)sililoxi-pregna-3,5-dieno (IV) con un agente de fluoración seleccionado entre N-fluorosulfonimidas y N- fluorosulfonamidas. Los 6{al} fluorpregnanos (I) son intermedios para la síntesis de esteroides útiles como agentes antiinflamatorios y antiasmáticos.
ES200101754A 2001-07-26 2001-07-26 Procedimiento estereoselectivo para la produccion de 6alfa-fluorpregnanos intermedios. Expired - Fee Related ES2184628B1 (es)

Priority Applications (10)

Application Number Priority Date Filing Date Title
ES200101754A ES2184628B1 (es) 2001-07-26 2001-07-26 Procedimiento estereoselectivo para la produccion de 6alfa-fluorpregnanos intermedios.
ES02751191T ES2274065T3 (es) 2001-07-26 2002-07-24 Procedimiento estereoselectivo para la produccion de 6alfa-fluorpregnados e intermedios.
DE60215193T DE60215193T2 (de) 2001-07-26 2002-07-24 Stereoselektives verfahren zur herstellung von 6alpha-fluorpregnanen und zwischenprodukten
PCT/ES2002/000372 WO2003010181A1 (es) 2001-07-26 2002-07-24 PROCEDIMIENTO ESTEREOSELECTIVO PARA LA PRODUCCIÓN DE 6α-FLUORPREGNANOS E INTERMEDIOS
AT02751191T ATE341561T1 (de) 2001-07-26 2002-07-24 Stereoselektives verfahren zur herstellung von 6alpha-fluorpregnanen und zwischenprodukten
CA002455229A CA2455229A1 (en) 2001-07-26 2002-07-24 Stereoselective method of producing 6.alpha.-fluoropregnanes and intermediaries
AU2002355187A AU2002355187A1 (en) 2001-07-26 2002-07-24 Stereoselective method of producing 6alpha-fluoropregnanes and intermediaries
JP2003515540A JP2004538294A (ja) 2001-07-26 2002-07-24 ６α−フルオロプレグナンの立体選択的製造方法および中間体
EP02751191A EP1422235B1 (en) 2001-07-26 2002-07-24 Stereoselective method of producing 6alpha-fluoropregnanes and intermediaries
US10/764,915 US20040181055A1 (en) 2001-07-26 2004-01-26 Stereoselective process for the production of 6alpha-fluorpregnanes and intermediates

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES200101754A ES2184628B1 (es) 2001-07-26 2001-07-26 Procedimiento estereoselectivo para la produccion de 6alfa-fluorpregnanos intermedios.

Publications (2)

Publication Number Publication Date
ES2184628A1 true ES2184628A1 (es) 2003-04-01
ES2184628B1 ES2184628B1 (es) 2005-02-01

Family

ID=8498522

Family Applications (2)

Application Number Title Priority Date Filing Date
ES200101754A Expired - Fee Related ES2184628B1 (es) 2001-07-26 2001-07-26 Procedimiento estereoselectivo para la produccion de 6alfa-fluorpregnanos intermedios.
ES02751191T Expired - Lifetime ES2274065T3 (es) 2001-07-26 2002-07-24 Procedimiento estereoselectivo para la produccion de 6alfa-fluorpregnados e intermedios.

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES02751191T Expired - Lifetime ES2274065T3 (es) 2001-07-26 2002-07-24 Procedimiento estereoselectivo para la produccion de 6alfa-fluorpregnados e intermedios.

Country Status (9)

Country Link
US (1) US20040181055A1 (es)
EP (1) EP1422235B1 (es)
JP (1) JP2004538294A (es)
AT (1) ATE341561T1 (es)
AU (1) AU2002355187A1 (es)
CA (1) CA2455229A1 (es)
DE (1) DE60215193T2 (es)
ES (2) ES2184628B1 (es)
WO (1) WO2003010181A1 (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3656385A1 (en) 2008-05-28 2020-05-27 ReveraGen BioPharma, Inc. Non-hormonal steroid modulators of nf-kb for treatment of disease
WO2011127048A2 (en) 2010-04-05 2011-10-13 Validus Biopharma NON-HORMONAL STEROID MODULATORS OF NF-ĸB FOR TREATMENT OF DISEASE
US10799514B2 (en) 2015-06-29 2020-10-13 Reveragen Biopharma, Inc. Non-hormonal steroid modulators of NF-kappa beta for treatment of disease
US11382922B2 (en) 2019-03-07 2022-07-12 Reveragen Biopharma, Inc. Aqueous oral pharmaceutical suspension compositions

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2002495A1 (fr) * 1968-02-23 1969-10-17 Hoffmann La Roche Ethers silyliques de steroides et procede pour leur preparation
US4036831A (en) * 1975-10-28 1977-07-19 Steroid Development Company Establishment Trimethyl siloxane steroid intermediates
US5086190A (en) * 1989-05-12 1992-02-04 Allied-Signal Inc. Method of fluorinating by using N-fluoropyridinium pyridine heptafluorodiborate
ES2091100T3 (es) * 1993-02-05 1996-10-16 Roussel Uclaf Nuevo procedimiento de preparacion de esteroides 6alfa,9alfa-difluorados y nuevos productos intermedios obtenidos.

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2838499A (en) * 1957-11-29 1958-06-10 Upjohn Co 6-fluoro steroids and process
US3499016A (en) * 1958-08-04 1970-03-03 Upjohn Co 6alpha-fluoro-16alpha-methyl derivatives of the pregnane series
NL245860A (es) * 1958-11-28
US3014938A (en) * 1959-09-07 1961-12-26 Syntex Sa Preparation of 16, 21-diacetate derivative of cyclopentanophenanthrene compounds
US3506650A (en) * 1966-11-18 1970-04-14 Warner Lambert Pharmaceutical 1alpha-alkoxy-delta**4-3-keto pregnenes,3-enol ether thereof and process for their preparation
US4188322A (en) * 1978-04-28 1980-02-12 Blasinachim S.P.A. Process for the preparation of 6-halo-pregnanes
DE3640709A1 (de) * 1986-11-28 1988-06-09 Schering Ag Verfahren zur herstellung von 6(alpha),9(alpha)-difluor-11ss,17(alpha)-dihydroxy-16(alpha)-methyl-4-pregnen-3,20-dion und dessen derivate
IT1319663B1 (it) * 2000-11-17 2003-10-23 Farmabios Srl Processo per la preparazione di fluoro-steroidi.

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2002495A1 (fr) * 1968-02-23 1969-10-17 Hoffmann La Roche Ethers silyliques de steroides et procede pour leur preparation
US4036831A (en) * 1975-10-28 1977-07-19 Steroid Development Company Establishment Trimethyl siloxane steroid intermediates
US5086190A (en) * 1989-05-12 1992-02-04 Allied-Signal Inc. Method of fluorinating by using N-fluoropyridinium pyridine heptafluorodiborate
ES2091100T3 (es) * 1993-02-05 1996-10-16 Roussel Uclaf Nuevo procedimiento de preparacion de esteroides 6alfa,9alfa-difluorados y nuevos productos intermedios obtenidos.

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
E. DIFFERDING et al. "N-Fluorobenzenesulfonimide: A practical reagent for Electrophilic Fluorinations", Synlett, 1991, pßginas 187-189. *
M.G. THOMAS et al. "The Synthesis of A- and B-ring Fluorinated analogues of Cholesterol", J. Chem. Soc. Perkin Trans., 1999, Vol. 21, pßginas 3191-3198. *
P.A. PROCOPIOU et al. "An Extremely Powerful Acylation Reaction of Alcohols with Anhydrides Catalyzed by Trimethylsilyl Trifluoromethanesulfonate", J. Org. Chem., 1998, Vol. 63, Nö 7, páginas 2342-2347. *
S.D. TAYLOR et al. "Recent Advances in Electrophilic Fluorination", Tetrahedron, 1999, Vol. 55, pßginas 12431-12477. *

Also Published As

Publication number Publication date
JP2004538294A (ja) 2004-12-24
CA2455229A1 (en) 2003-02-06
DE60215193T2 (de) 2007-08-23
EP1422235A1 (en) 2004-05-26
AU2002355187A1 (en) 2003-02-17
ES2274065T3 (es) 2007-05-16
EP1422235B1 (en) 2006-10-04
DE60215193D1 (de) 2006-11-16
WO2003010181A8 (es) 2003-04-24
ES2184628B1 (es) 2005-02-01
WO2003010181A1 (es) 2003-02-06
US20040181055A1 (en) 2004-09-16
ATE341561T1 (de) 2006-10-15

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