ES2943573R1 - Proceso para la preparación de 21-(acetiloxi)-17-(1-oxopropoxi)-pregn-4-eno-3,20-diona - Google Patents

Proceso para la preparación de 21-(acetiloxi)-17-(1-oxopropoxi)-pregn-4-eno-3,20-diona Download PDF

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Publication number
ES2943573R1
ES2943573R1 ES202390019A ES202390019A ES2943573R1 ES 2943573 R1 ES2943573 R1 ES 2943573R1 ES 202390019 A ES202390019 A ES 202390019A ES 202390019 A ES202390019 A ES 202390019A ES 2943573 R1 ES2943573 R1 ES 2943573R1
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ES
Spain
Prior art keywords
pregn
oxopropoxy
acetyloxy
dione
ene
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
ES202390019A
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English (en)
Other versions
ES2943573A2 (es
ES2943573B2 (es
Inventor
Roberto Lenna
Claudio Delfrate
Davide Rigamonti
Silvia Genovese
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.)
Industriale Chimica SRL
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Industriale Chimica SRL
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Publication date
Application filed by Industriale Chimica SRL filed Critical Industriale Chimica SRL
Publication of ES2943573A2 publication Critical patent/ES2943573A2/es
Publication of ES2943573R1 publication Critical patent/ES2943573R1/es
Application granted granted Critical
Publication of ES2943573B2 publication Critical patent/ES2943573B2/es
Active legal-status Critical Current
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P33/00—Preparation of steroids
    • C12P33/005—Degradation of the lateral chains at position 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
    • C07J5/0053—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 not substituted in position 16
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/28—Antiandrogens
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
    • C07C317/04—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
    • C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
    • C07J7/0045—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa not substituted in position 16
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/008—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
    • C07J7/0085—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21 by an halogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Endocrinology (AREA)
  • Diabetes (AREA)
  • Epidemiology (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Dermatology (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Steroid Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
ES202390019A 2020-10-19 2021-02-05 Proceso para la preparación de 21-(acetiloxi)-17-(1-oxopropoxi)-pregn-4-eno-3,20-diona Active ES2943573B2 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IT202000024640 2020-10-19
IT202000032530 2020-12-28
PCT/IB2021/050953 WO2022084752A1 (en) 2020-10-19 2021-02-05 Process for the production of 21-(acetyloxy)-17-(propionyloxy)-pregn-4-ene-3,20-dione

Publications (3)

Publication Number Publication Date
ES2943573A2 ES2943573A2 (es) 2023-06-14
ES2943573R1 true ES2943573R1 (es) 2024-04-09
ES2943573B2 ES2943573B2 (es) 2024-11-29

Family

ID=74873782

Family Applications (1)

Application Number Title Priority Date Filing Date
ES202390019A Active ES2943573B2 (es) 2020-10-19 2021-02-05 Proceso para la preparación de 21-(acetiloxi)-17-(1-oxopropoxi)-pregn-4-eno-3,20-diona

Country Status (7)

Country Link
US (2) US20240018181A1 (es)
CN (2) CN120923569A (es)
CH (1) CH719319B1 (es)
DE (1) DE112021004932T5 (es)
ES (1) ES2943573B2 (es)
FR (1) FR3115284B1 (es)
WO (1) WO2022084752A1 (es)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT202300001929A1 (it) * 2023-02-07 2024-08-07 Farmabios Spa Cocristalli di cortexolone 17-propionato e metodi per la loro preparazione

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009019138A2 (en) * 2007-08-03 2009-02-12 Cosmo Spa Enzymatic process for obtaining 17 alpha-monoesters of cortexolone and/or its 9,11-dehydroderivatives
CN103421070A (zh) * 2013-08-30 2013-12-04 郑州大学 一种改进的孕甾烯类化合物c21-乙酰氧基化方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3147249A (en) 1961-06-13 1964-09-01 Vismara Francesco Spa 17alpha, 21-substituted methylenedioxy steroids and methods therefor
CH429716A (de) 1961-06-24 1967-02-15 Vismara Francesco Spa Verfahren zur Herstellung von 17a-Acyloxy-21-hydroxy-Steroiden
US3711602A (en) 1970-10-30 1973-01-16 Crown Zellerbach Corp Compositions for topical application for enhancing tissue penetration of physiologically active agents with dmso
CN101812108B (zh) * 2009-11-26 2012-05-23 天津金耀集团有限公司 丁酸氢化可的松的合成

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009019138A2 (en) * 2007-08-03 2009-02-12 Cosmo Spa Enzymatic process for obtaining 17 alpha-monoesters of cortexolone and/or its 9,11-dehydroderivatives
CN103421070A (zh) * 2013-08-30 2013-12-04 郑州大学 一种改进的孕甾烯类化合物c21-乙酰氧基化方法

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CLAUDEL, E. ET AL. An Efficient Hemisynthesis of 20- and 21-[13C]-Labeled Cortexolone: A Model for the Study of Skin Sensitization to Corticosteroids. Synthesis, 03/09/2009, Vol. 20, Páginas 3391-3398 (DOI: 10.1055/s-0029-1216986) resumen, figura 1, esquema 2 y 3. *
FERRABOSCHI, P. ET AL. Full spectroscopic characterization of two crystal pseudopolymorphic forms of the antiandrogen cortexolone 17 alpha-propionate for topic application. STEROIDS ELSEVIER SCIENCE PUBLISHERS, NEW YORK, NY, US. Jordan Craig, 17/09/2017, Vol. 128, Páginas 95-104 (DOI: 10.1016/j.steroids.2017.09.003) Ver resumen y sección 2.2 *
FERRABOSCHI, P. ET AL. Lipase-catalyzed preparation of corticosteroid 17alpha-esters endowed with antiandrogenic activity. Tetrahedron Letters, 23/05/2008, Vol. 49, Páginas 4610- 612 (DOI: 10.1016/j.tetlet.2008.05.086) Ver figura 1, esquema 1, conclusiones y punto 17. *
RYAKHOVSKAYA M. I. ET AL. Synthesis of the 21-acetate of substance S from 17.alpha.-hydroxyprogesterone. Pharmaceutical Chemistry Journal, 11/1990, Vol. 24, Páginas 839-842 (DOI: 10.1007/BF00768389) Ver esquema y sección experimental. *

Also Published As

Publication number Publication date
US20240018181A1 (en) 2024-01-18
CN116490512B (zh) 2025-09-16
CH719319B1 (it) 2024-08-15
ES2943573A2 (es) 2023-06-14
FR3115284B1 (fr) 2023-12-08
WO2022084752A1 (en) 2022-04-28
CN120923569A (zh) 2025-11-11
ES2943573B2 (es) 2024-11-29
FR3115284A1 (fr) 2022-04-22
DE112021004932T5 (de) 2023-08-10
CN116490512A (zh) 2023-07-25
US20260152524A1 (en) 2026-06-04

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