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HRP20212002T1 - Sinteza estera i spojeva borove kiseline - Google Patents

Sinteza estera i spojeva borove kiseline Download PDF

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Publication number
HRP20212002T1
HRP20212002T1 HRP20212002TT HRP20212002T HRP20212002T1 HR P20212002 T1 HRP20212002 T1 HR P20212002T1 HR P20212002T T HRP20212002T T HR P20212002TT HR P20212002 T HRP20212002 T HR P20212002T HR P20212002 T1 HRP20212002 T1 HR P20212002T1
Authority
HR
Croatia
Prior art keywords
compound
formula
acid
xiv
boric
Prior art date
Application number
HRP20212002TT
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English (en)
Inventor
Fraser I. Pickersgill
John Bishop
Young Lo
Fang-Ting Chui
Vithalanand R. Kulkarni
Original Assignee
Millennium Pharmaceuticals, Inc.
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=34968044&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=HRP20212002(T1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Millennium Pharmaceuticals, Inc. filed Critical Millennium Pharmaceuticals, Inc.
Publication of HRP20212002T1 publication Critical patent/HRP20212002T1/hr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/04—Esters of boric acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • 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
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
    • 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

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Virology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • AIDS & HIV (AREA)
  • Transplantation (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Claims (7)

1. Postupak za formiranje anhidrida borove kiseline spoja formule (XIV): [image] koji sadrži korake: (A) spajanja adicione soli trifluoroctene kiseline spoja formule (XVIII): [image] sa spojem formule (XIXa): [image] pri čemu, grupa -C(O)X je aktivirani ester generiran in situ dovođenjem u kontakt N-(2-pirazinkarbonil)-L-fenilalanina sa dicikloheksilkarbodiimidom i N-hidroksisukcinimidom, pri čemu, grupa C(O)-X je O-(N-hidroksisukcinimid)ester, da se formira spoj formule (XXIII): [image] i (B) uklanjanja zaštite sa ostatka borove kiseline da bi se formirao anhidrid borove kiseline spoja formule (XIV); pri čemu korak spajanja (A) sadrži: (i) osiguravanje otopine (1R)-(S)-pinandiol 1-amonij trifluoroacetat-3-metilbutan-1-boronata i N-hidroksisukcinimida, nakon čega slijedi dodavanje dicikloheksilkarbodiimida da bi se formirala suspenzija; (ii) osiguravanje otopine N-(2-pirazinkarbonil)-L-fenilalanina i dodavanje N-metilmorfolina u njega; (iii) dodavanje otopine dobivene iz koraka (ii) u suspenziju dobivenu iz koraka (i) i izborno podešavanje dobivene suspenzije do pH 7 dodavanjem N-metilmorfolina; i pri čemu korak spajanja (A)(i) sadrži osiguravanje otopine (1R)-(S)-pinandiol 1-amonij trifluoroacetat-3-metilbutan-1-boronata i N-hidroksisukcinimida u DMF, nakon čega slijedi dodavanje dicikloheksilkarbodiimida da bi se formirala suspenzija; i/ili korak spajanja (A)(ii) obuhvaća osiguravanje otopine N-(2-pirazinkarbonil)-L-fenilalanina u DMF i dodavanje N-metilmorfolina u to.
2. Postupak prema bilo kojem prethodnom zahtjevu, naznačen time što se korak uklanjanja zaštite sa borove kiseline (B) izvodi u prisustvu akceptora organske borove kiseline (izborno 2-metilpropanborove kiseline), nižeg alkanola (izborno metanola), C5-8 ugljikovodičnog otapala (izborno heksana) i vodene mineralne kiseline (izborno HCl).
3. Postupak prema zahtjevu 2, naznačen time što se korak uklanjanja zaštite sa borove kiseline (B) izvodi u prisustvu 2-metilpropanborove kiseline, metanola, heksana i HCl.
4. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što korak uklanjanja zaštite sa borove kiseline (B) sadrži korake: (i) osiguravanje dvofazne mješavine koja sadrži spoj formule (XXIII), akceptor organske borove kiseline, niži alkanol, C5-8 ugljikovodično otapalo i vodenu mineralnu kiselinu; (ii) miješanja dvofazne mješavine da bi se dobilo spoj formule (XIV) na temperaturi od 15 do 25°C; (iii) odvajanja slojeva otapala; i (iv) ekstrakciju anhidrida borove kiseline spoja formule (XIV) u organsko otapalo.
5. Postupak prema zahtjevu 4, naznačen time što korak (B)(iii) sadrži korake: (1) odvajanja slojeva otapala; (2) podešavanja vodenog sloja do baznog pH; (3) ispiranja vodenog sloja organskim otapalom; i (4) podešavanja vodenog sloja do pH manjeg od 8.
6. Postupak prema zahtjevu 5, naznačen time što se u koraku (B)(iii)(4), vodeni sloj podešava do pH manjeg od 6.
7. Postupak prema zahtjevu 4, naznačen time što se u koraku (B)(iv), anhidrid borove kiseline spoja formule (XIV) ekstrahira u etil acetat, i anhidrid borove kiseline spoja formule (XIV) se istaloži dodavanjem terc-butilmetil etera.
HRP20212002TT 2004-03-30 2005-03-24 Sinteza estera i spojeva borove kiseline HRP20212002T1 (hr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US55753504P 2004-03-30 2004-03-30
EP18172486.5A EP3385267B1 (en) 2004-03-30 2005-03-24 Synthesis of boronic ester and acid compounds

Publications (1)

Publication Number Publication Date
HRP20212002T1 true HRP20212002T1 (hr) 2022-04-01

Family

ID=34968044

Family Applications (4)

Application Number Title Priority Date Filing Date
HR20110846T HRP20110846T1 (hr) 2004-03-30 2005-03-24 Sinteza spojeva estera organoborne kiseline i organoborne kiseline
HRP20240307TT HRP20240307T3 (hr) 2004-03-30 2005-03-24 Sinteza spojeva estera borne kiseline i kiseline
HRP20212002TT HRP20212002T1 (hr) 2004-03-30 2005-03-24 Sinteza estera i spojeva borove kiseline
HRP20140339TT HRP20140339T1 (hr) 2004-03-30 2014-04-08 Sinteza bortezomiba

Family Applications Before (2)

Application Number Title Priority Date Filing Date
HR20110846T HRP20110846T1 (hr) 2004-03-30 2005-03-24 Sinteza spojeva estera organoborne kiseline i organoborne kiseline
HRP20240307TT HRP20240307T3 (hr) 2004-03-30 2005-03-24 Sinteza spojeva estera borne kiseline i kiseline

Family Applications After (1)

Application Number Title Priority Date Filing Date
HRP20140339TT HRP20140339T1 (hr) 2004-03-30 2014-04-08 Sinteza bortezomiba

Country Status (41)

Country Link
US (14) US7714159B2 (hr)
EP (5) EP3385267B1 (hr)
JP (4) JP4558039B2 (hr)
KR (1) KR100939598B1 (hr)
CN (5) CN107474062A (hr)
AR (3) AR049374A1 (hr)
AT (1) ATE521612T1 (hr)
AU (1) AU2005230930B2 (hr)
BR (1) BRPI0509587A (hr)
CA (4) CA2853272A1 (hr)
CL (2) CL2010000350A1 (hr)
CR (1) CR8653A (hr)
CY (3) CY1112053T1 (hr)
DK (4) DK1756121T3 (hr)
DO (1) DOP2011000293A (hr)
EA (1) EA012927B1 (hr)
EC (1) ECSP066960A (hr)
ES (4) ES2974758T3 (hr)
FI (1) FI4008721T3 (hr)
HK (1) HK1246300A1 (hr)
HR (4) HRP20110846T1 (hr)
HU (2) HUE056859T2 (hr)
IL (3) IL178250A (hr)
LT (2) LT3385267T (hr)
ME (1) ME01975B (hr)
MX (1) MX367324B (hr)
MY (1) MY145427A (hr)
NL (3) NL1028639C2 (hr)
NO (4) NO338905B1 (hr)
NZ (3) NZ550522A (hr)
PE (3) PE20060162A1 (hr)
PL (4) PL4008721T3 (hr)
PT (4) PT1756121E (hr)
RS (4) RS65253B1 (hr)
SG (5) SG151322A1 (hr)
SI (4) SI1756121T1 (hr)
TW (1) TWI386212B (hr)
UA (1) UA90108C2 (hr)
UY (3) UY28830A1 (hr)
WO (1) WO2005097809A2 (hr)
ZA (1) ZA200608689B (hr)

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