MA65191B1 - Procédé industriel de préparation de l'ester 6(nitrooxy)-,(1s,2e)-3-[(1r,2r,3s,5r)-2-[(2z)-7-(éthylamino)-7-oxo-2-heptène-1-yl]3,5-dihydroxycyclopentyl]-1-(2-phényléthyl)-2-propène-1-yl de l'acide hexanoïque et produit de haute pureté - Google Patents

Procédé industriel de préparation de l'ester 6(nitrooxy)-,(1s,2e)-3-[(1r,2r,3s,5r)-2-[(2z)-7-(éthylamino)-7-oxo-2-heptène-1-yl]3,5-dihydroxycyclopentyl]-1-(2-phényléthyl)-2-propène-1-yl de l'acide hexanoïque et produit de haute pureté

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Publication number
MA65191B1
MA65191B1 MA65191A MA65191A MA65191B1 MA 65191 B1 MA65191 B1 MA 65191B1 MA 65191 A MA65191 A MA 65191A MA 65191 A MA65191 A MA 65191A MA 65191 B1 MA65191 B1 MA 65191B1
Authority
MA
Morocco
Prior art keywords
nitrooxy
high purity
hexanoic acid
dihydroxycyclopentyl
ethylamino
Prior art date
Application number
MA65191A
Other languages
English (en)
Inventor
Szabolcs Kovács
Andrea SÁNTÁNÉ CSUTOR
Irén HORTOBÁGYI
Judit PÓTI
Gael Ronsin
Nicoletta Almirante
Original Assignee
Nicox S.A.
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
Application filed by Nicox S.A. filed Critical Nicox S.A.
Publication of MA65191B1 publication Critical patent/MA65191B1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • 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
    • A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
    • A61K31/5575—Eicosanoids, e.g. leukotrienes or prostaglandins having a cyclopentane, e.g. prostaglandin E2, prostaglandin F2-alpha
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/22—Separation; Purification; Stabilisation; Use of additives
    • C07C231/24—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
    • C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
    • C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
    • 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
    • C07B2200/07—Optical isomers
    • 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
    • C07B2200/09—Geometrical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Ophthalmology & Optometry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne un procédé de préparation de l'acide hexanoïque, 6-(nitrooxy)-, (1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(éthylamino)-7-oxo-2-hepten-1-yl]-3,5-dihydroxycyclopentyl]-1-(2-phényléthyl)-2-propen-1-yl ester <img file="imga0001.tif" frnum="0001" he="62" id="ia01" img-content="chem" img-format="tif" inline="no" orientation="portrait" pgnum="0001" wi="69"/><h3>Conformément à la présente invention, un composé de qualité pharmaceutique (I) peut être préparé efficacement par une étape de préparation de réactions en un seul pot qui comprend l'estérification du 15-OH bimatoprost par couplage du phénylboronate de bimatoprost avec l'acide 6-(nitrooxy)hexanoïque et l'élimination du groupe protecteur d'ester de boronate, suivie d'une étape de purification efficace.</h3><h3>L'invention concerne également un composé de haute pureté (I) sensiblement exempt de l'impureté 15-(6-chlorohexanoyl) ester de bimatoprost et des formulations pharmaceutiques ophtalmiques contenant le composé de haute pureté.</h3>
MA65191A 2022-07-07 2022-07-07 Procédé industriel de préparation de l'ester 6(nitrooxy)-,(1s,2e)-3-[(1r,2r,3s,5r)-2-[(2z)-7-(éthylamino)-7-oxo-2-heptène-1-yl]3,5-dihydroxycyclopentyl]-1-(2-phényléthyl)-2-propène-1-yl de l'acide hexanoïque et produit de haute pureté MA65191B1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP22290046.6A EP4303211B1 (fr) 2022-07-07 2022-07-07 Procédé industriel de préparation de l'ester 6(nitrooxy)-,(1s,2e)-3-[(1r,2r,3s,5r)-2-[(2z)-7-(éthylamino)-7-oxo-2-heptène-1-yl]3,5-dihydroxycyclopentyl]-1-(2-phényléthyl)-2-propène-1-yl de l'acide hexanoïque et produit de haute pureté

Publications (1)

Publication Number Publication Date
MA65191B1 true MA65191B1 (fr) 2024-10-31

Family

ID=82850340

Family Applications (2)

Application Number Title Priority Date Filing Date
MA71652A MA71652A (fr) 2022-07-07 2022-07-07 Procédé industriel pour la préparation d'acide hexanoique, 6-(nitrooxy)-, (1s,2e)-3-(1r,2r,3s,5r)-2- (2z)-7-(éthylamino)-7-oxo-2-hepten-1-yl)
MA65191A MA65191B1 (fr) 2022-07-07 2022-07-07 Procédé industriel de préparation de l'ester 6(nitrooxy)-,(1s,2e)-3-[(1r,2r,3s,5r)-2-[(2z)-7-(éthylamino)-7-oxo-2-heptène-1-yl]3,5-dihydroxycyclopentyl]-1-(2-phényléthyl)-2-propène-1-yl de l'acide hexanoïque et produit de haute pureté

Family Applications Before (1)

Application Number Title Priority Date Filing Date
MA71652A MA71652A (fr) 2022-07-07 2022-07-07 Procédé industriel pour la préparation d'acide hexanoique, 6-(nitrooxy)-, (1s,2e)-3-(1r,2r,3s,5r)-2- (2z)-7-(éthylamino)-7-oxo-2-hepten-1-yl)

Country Status (23)

Country Link
US (2) US20250320182A1 (fr)
EP (3) EP4303211B1 (fr)
JP (2) JP2024012261A (fr)
KR (1) KR20250034143A (fr)
CN (2) CN119522211A (fr)
AR (1) AR129847A1 (fr)
AU (1) AU2023303861A1 (fr)
CA (1) CA3261164A1 (fr)
DK (1) DK4303211T3 (fr)
ES (1) ES2992696T3 (fr)
FI (1) FI4303211T3 (fr)
HR (1) HRP20241504T1 (fr)
HU (1) HUE069026T2 (fr)
LT (1) LT4303211T (fr)
MA (2) MA71652A (fr)
MX (1) MX2025000209A (fr)
PL (1) PL4303211T3 (fr)
PT (1) PT4303211T (fr)
RS (1) RS66198B1 (fr)
SI (1) SI4303211T1 (fr)
SM (1) SMT202400481T1 (fr)
TW (1) TW202408995A (fr)
WO (1) WO2024008844A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3772511B1 (fr) * 2019-08-05 2023-11-08 Nicox S.A. Procédé de préparation d'un analogue de prostaglandine de don d'oxyde nitrique

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR076731A1 (es) 2008-05-09 2011-07-06 Pfizer Prostamidas donadoras de oxido nitrico, uso de los mismos y composiciones farmaceuticas
ES2923623T3 (es) * 2018-02-21 2022-09-29 Nicox Sa Procedimiento para la preparación de un análogo de prostaglandina donante de óxido nítrico
EP3772511B1 (fr) * 2019-08-05 2023-11-08 Nicox S.A. Procédé de préparation d'un analogue de prostaglandine de don d'oxyde nitrique
HUE071098T2 (hu) * 2021-02-03 2025-08-28 Nicox Sa Eljárás nitrogén-monoxidot donáló prosztaglandin analóg elõállítására

Also Published As

Publication number Publication date
HRP20241504T1 (hr) 2025-01-03
CN117362210A (zh) 2024-01-09
LT4303211T (lt) 2024-11-25
EP4303211A1 (fr) 2024-01-10
US20250320182A1 (en) 2025-10-16
CN119522211A (zh) 2025-02-25
DK4303211T3 (da) 2024-10-07
WO2024008844A1 (fr) 2024-01-11
EP4410294A3 (fr) 2024-11-06
PL4303211T3 (pl) 2024-12-16
ES2992696T3 (en) 2024-12-17
FI4303211T3 (fi) 2024-11-21
EP4303211B1 (fr) 2024-08-21
AU2023303861A1 (en) 2025-02-20
TW202408995A (zh) 2024-03-01
EP4410294A2 (fr) 2024-08-07
US20240018096A1 (en) 2024-01-18
KR20250034143A (ko) 2025-03-10
AR129847A1 (es) 2024-10-02
RS66198B1 (sr) 2024-12-31
SI4303211T1 (sl) 2025-01-31
EP4551553A1 (fr) 2025-05-14
CA3261164A1 (fr) 2024-01-11
MX2025000209A (es) 2025-02-10
MA71652A (fr) 2025-05-30
SMT202400481T1 (it) 2025-01-14
PT4303211T (pt) 2024-11-18
HUE069026T2 (hu) 2025-02-28
JP2025523301A (ja) 2025-07-18
JP2024012261A (ja) 2024-01-30

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