NZ782816B2 - Synthesis method of furoimidazopyridine compound, crystal form of furoimidazopyridine compound, and crystal form of salt thereof - Google Patents

Synthesis method of furoimidazopyridine compound, crystal form of furoimidazopyridine compound, and crystal form of salt thereof

Info

Publication number
NZ782816B2
NZ782816B2 NZ782816A NZ78281620A NZ782816B2 NZ 782816 B2 NZ782816 B2 NZ 782816B2 NZ 782816 A NZ782816 A NZ 782816A NZ 78281620 A NZ78281620 A NZ 78281620A NZ 782816 B2 NZ782816 B2 NZ 782816B2
Authority
NZ
New Zealand
Prior art keywords
compound
crystal form
furoimidazopyridine
crystal
formula
Prior art date
Application number
NZ782816A
Other versions
NZ782816A (en
Inventor
Congxin Liang
Haihui Liu
Laibao Wang
Original Assignee
Hangzhou Highlightll Pharmaceutical Co Ltd
Filing date
Publication date
Application filed by Hangzhou Highlightll Pharmaceutical Co Ltd filed Critical Hangzhou Highlightll Pharmaceutical Co Ltd
Priority claimed from PCT/CN2020/088121 external-priority patent/WO2020244348A1/en
Publication of NZ782816A publication Critical patent/NZ782816A/en
Publication of NZ782816B2 publication Critical patent/NZ782816B2/en

Links

Classifications

    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—Ortho-condensed systems
    • C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom

Abstract

Provided is a method for synthesizing a compound 2-[(2R,5S)-5-[2-[(R)-1-hydroxyethyl]furo[3,2-b]imidazo[4,5-d]pyridin-1-yl]tetrahydropyran-2-yl]acetonitrile as a selective JAK1/TYK2 kinase inhibitor. The compound is prepared by nucleophilic substitution, palladium on carbon reduction, and cyclization reaction using 7-chloro-6-nitrofuro[3,2-b]pyridine as a starting material. The synthesis method has mild reaction conditions, high product yield, and high purity, and is suitable for industrial production. Further provided are a crystal form of the compound, crystal forma of its salts, and their preparation methods. The crystal form of the compound and the crystal forms of its salts have good physical and chemical properties and are suitable for drug development.

Claims (1)

Claims
1. A method for preparing a compound of formula I, wherein the synthesis route of the method is as follows: N N O Cl V O N O HN Pd/C O O O N O H2N O O N N III II O N OH N the method comprises the following steps: step 1: adding ethanol, a compound of formula IV, a compound of formula V and DIPEA to a reaction container, starting stirring; g to raise the temperature to 65 - 90 ?, maintaining the ature and stirring overnight; ating the reaction and lowering the temperature of the system to 15 - 30 ?; adding water to the system dropwise and then stirring; filtering and washing the filter cake; drying the filter cake to obtain a compound of formula III; 1005223803 step 2: adding tetrahydrofuran (THF), the compound of formula III obtained in step 1 and palladium on carbon to a reaction container; purging the system with nitrogen and then hydrogen; ining the temperature between 20 - 35 ? and stirring for 16 -
NZ782816A 2020-04-30 Synthesis method of furoimidazopyridine compound, crystal form of furoimidazopyridine compound, and crystal form of salt thereof NZ782816B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201910490418 2019-06-06
PCT/CN2020/088121 WO2020244348A1 (en) 2019-06-06 2020-04-30 Synthesis method of furoimidazopyridine compound, crystal form of furoimidazopyridine compound, and crystal form of salt thereof

Publications (2)

Publication Number Publication Date
NZ782816A NZ782816A (en) 2025-02-28
NZ782816B2 true NZ782816B2 (en) 2025-06-04

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