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NZ775526B2 - Benzoxazepin oxazolidinone compounds and methods of use - Google Patents
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NZ775526B2 - Benzoxazepin oxazolidinone compounds and methods of use - Google Patents

Benzoxazepin oxazolidinone compounds and methods of use Download PDF

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Publication number
NZ775526B2
NZ775526B2 NZ775526A NZ77552616A NZ775526B2 NZ 775526 B2 NZ775526 B2 NZ 775526B2 NZ 775526 A NZ775526 A NZ 775526A NZ 77552616 A NZ77552616 A NZ 77552616A NZ 775526 B2 NZ775526 B2 NZ 775526B2
Authority
NZ
New Zealand
Prior art keywords
compound
copper catalyst
methods
pi3k
pharmaceutically acceptable
Prior art date
Application number
NZ775526A
Other versions
NZ775526A (en
Inventor
Marie Gabrielle Braun
Richard Elliott
Emily Hanan
Robert Andrew Heald
Calum Macleod
Steven T Staben
Original Assignee
F Hoffmann La Roche Ag
Filing date
Publication date
Application filed by F Hoffmann La Roche Ag filed Critical F Hoffmann La Roche Ag
Publication of NZ775526A publication Critical patent/NZ775526A/en
Publication of NZ775526B2 publication Critical patent/NZ775526B2/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B43/00—Formation or introduction of functional groups containing nitrogen
    • C07B43/06—Formation or introduction of functional groups containing nitrogen of amide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D267/02—Seven-membered rings
    • C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems

Abstract

Described herein are benzoxazepin oxazolidinone compounds with phosphoinositide- 3 kinase (PI3K) modulation activity or function having the Formula (I) structure: or stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, and with the substituents and structural features described herein. Also described are pharmaceutical compositions and medicaments that include the Formula I compounds, as well as methods of using such PI3K modulators, alone and in combination with other therapeutic agents, for treating diseases or conditions that are mediated or dependent upon PI3K dysregulation.

Claims (12)

1. A process for the preparation of compound 8, having the structure: H N O 5 8 or stereoisomers, geometric isomers, tautomers, and pharmaceutically acceptable salts thereof, wherein: R is selected from -CH , -CH CH , cyclopropyl, and cyclobutyl; 3 2 3 R is selected from -CH , -CHF , -CH F, and -CF ; 3 2 2 3 10 comprising reacting compound 7, having the structure: with H NCH(R )CO H and a copper catalyst, followed by ammonium chloride, and HATU (1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate) to form 8. 15
2. The process of claim 1 wherein the copper catalyst to form 8 is CuI.
3. The process of claim 1 wherein R is -CH .
4. The process of claim 1 wherein R is -CHF .
5. The process of claim 1 wherein compound 8 has the structure: or a pharmaceutically acceptable salt thereof.
6. The process of claim 1 wherein compound 7 is prepared by a process comprising reacting compound 6, having the structure: 5 6 with a 4-substituted oxazolidinone having the structure: and a copper catalyst to form 7.
7. The process of claim 6 wherein the 4-substituted oxazolidinone is (S) 10 difluoromethyloxazolidinone.
8. The process of claim 6 wherein the copper catalyst to form 7 is selected from CuI and Cu(OAc) .
9. The process of claim 6 further comprising reacting compound 6 with trans-N,N'-dimethyl-1,2-cyclohexane diamine. 15
10. An intermediate compound of .
11. The process of any one of claims 1-9, substantially as herein described with reference to any example thereof and with or without reference to the accompanying drawings.
12. The intermediate compound of claim 10, substantially as herein described with 5 reference to any example thereof and with or without reference to the accompanying drawings. 2.70 A i
NZ775526A 2016-07-01 Benzoxazepin oxazolidinone compounds and methods of use NZ775526B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201562188029P 2015-07-02 2015-07-02
NZ736222A NZ736222B2 (en) 2016-07-01 Benzoxazepin oxazolidinone compounds and methods of use

Publications (2)

Publication Number Publication Date
NZ775526A NZ775526A (en) 2024-05-31
NZ775526B2 true NZ775526B2 (en) 2024-09-03

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