HRP20140339T1 - Sinteza bortezomiba - Google Patents

Sinteza bortezomiba Download PDF

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Publication number
HRP20140339T1
HRP20140339T1 HRP20140339TT HRP20140339T HRP20140339T1 HR P20140339 T1 HRP20140339 T1 HR P20140339T1 HR P20140339T T HRP20140339T T HR P20140339TT HR P20140339 T HRP20140339 T HR P20140339T HR P20140339 T1 HRP20140339 T1 HR P20140339T1
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HR
Croatia
Prior art keywords
formula
compound
organoboric
image
iii
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HRP20140339TT
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English (en)
Inventor
I. Fraser Pickersgill
John Bishop
Vince Ammoscato
Stephen Munk
Young Lo
Fang-Ting Chiu
Vithalanand R. Kulkarni
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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=HRP20140339(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 HRP20140339T1 publication Critical patent/HRP20140339T1/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
    • 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
    • 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
    • C07F5/04—Esters of boric acids
    • 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)
  • General Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (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)
  • Transplantation (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • AIDS & HIV (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Claims (8)

1. Postupak velikih razmjera za formiranje spoja formule (XIV): [image] ili njegovog anhidrida organoborne kiseline, koji sadrži korake: (aa) spajanja spojaformule (XVIII): [image] ili njegove kisele adicijske soli, sa spojem formule (XIX): [image] u kojem: P1je zaštitna grupa za amino grupu koja se može odvojiti; i X je OH ili odlazeća grupa; da se formira spojformule (XX): [image] gdje P1je kao što je definiran u prethodnom tekstu, pri čemu navedeni korak spajanja (aa) sadrži korake: (i) spajanja spoja formule (XVIII) sa spojem formule (XIX) gde X je OH u prisutnosti2-(1H-benzotriazol-1-il)-1,1,3,3-tetrametiluronij tetrafluoroborata (TBTU) i tercijarnog amina u diklorometanu; (ii) izvođenja izmjene otapala da se diklorometan zamijeni etil acetatom; i (iii) izvođenja ispiranja vodom etil acetatneotopine; (bb) uklanjanja zaštitne grupe P1da se formira spoj formule (XXI): [image] ili njegova kisela adicijska sol, pri čemu navedeni korak uklanjanja (bb) zaštitne grupe sadrži korake: (i) tretmana spoja formule (XX) sa HCl u etil acetatu; (ii) dodavanja heptanau reakcijsku smjesu; i (iii) izolacije putem kristalizacije spojaformule (XXI) kao njegove HCl adicijske soli; (cc) spajanja spoja formule (XXI) sa reagensom formule (XXII) [image] gdje X je OH ili dolazeća grupa, da bi formira spoj formule (XXIII): [image] pri čemu navedeni korak spajanja (cc) sadrži korake: (i) spajanja spoja formule (XXI) sa 2-pirazinkarboksilnom kiselinom u prisustvu TBTU i tercijarnog amina u diklorometanu; (ii) izvođenja izmjene otapala da se dilklorometan zamijeni etil acetatom; i (iii) izvođenja ispiranja vodom etil acetatneotopne; i (dd) deprotekcije grupe organoborne kiseline da se formira spoj formule (XIV) ili njegov anhidrid organoborne kiseline, pri čemu navedeni korak deprotekcije (dd) sadrži korake: (i) osiguravanje dvofazne smjese koja sadrži spoj formule (XXIII), organski akceptor organoborne kiseline, niži alkanol, C5-8ugljovodičnootapalo i vodenuotopinu mineralne kiseline; (ii) mješanja dvofazne smjese da se dobijespoj formule (XIV); (iii) odvajanja slojeva otapala; i (iv) ekstrakcije spojaformule (XIV), ili njegovog anhidrida organoborne kiseline, u organskootapalo.
2. Postupak prema patentnom zahtjevu 1, naznačen time što P1je terc-butoksikarbonil.
3. Postupak prema patentnom zahtjevu 1 ili 2, naznačen time što je etil acetatni otopina iz koraka (aa)(iii) sušen azeotropno i zatim tretiran plinovitimHCl.
4. Postupak prema patentnom zahtjevu 1, naznačen time što korak (dd)(iii) sadrži korake: (1) odvajanja slojeva otapala; (2) podešavanja vodenog sloja do bazne pH vrijednosti; (3) ispiranja vodenog sloja organskim otapalom; i (4) podešavanja vodenog sloja do pH vrijednosti manje od 8.
5. Postupak prema patentnom zahtjevu 4, naznačen time što je u koraku (dd)(iii)(4), vodeni sloj podešen do pH vrijednosti manje od 6.
6. Postupak prema patentnom zahtjevu 4, naznačen time što je u koraku (dd)(iv), spoj formule (XIV), ili njegov anhidrid organoborne kiseline, ekstrahiran u diklorometanu, otapalo je izmijenjeno u etil acetat i spoj formule (XIV) ili njegov anhidrid organoborne kiseline, su kristalizirani dodavanjem heksana ili heptana.
7. Postupak prema patentnom zahtjevu 6, naznačen time što dodavanje heksana ili heptana rezultira u kristalizaciji cikličnog trimernog anhidrida organoborne kiseline formule (XXIV): [image]
8. Postupak prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time što se u postupku koristi 5 molovanajmanje jednog početnog materijala.
HRP20140339TT 2004-03-30 2014-04-08 Sinteza bortezomiba HRP20140339T1 (hr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US55753504P 2004-03-30 2004-03-30

Publications (1)

Publication Number Publication Date
HRP20140339T1 true HRP20140339T1 (hr) 2014-05-09

Family

ID=34968044

Family Applications (4)

Application Number Title Priority Date Filing Date
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
HR20110846T HRP20110846T1 (hr) 2004-03-30 2011-11-14 Sinteza spojeva estera organoborne kiseline i organoborne kiseline
HRP20140339TT HRP20140339T1 (hr) 2004-03-30 2014-04-08 Sinteza bortezomiba

Family Applications Before (3)

Application Number Title Priority Date Filing Date
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
HR20110846T HRP20110846T1 (hr) 2004-03-30 2011-11-14 Sinteza spojeva estera organoborne kiseline i organoborne kiseline

Country Status (41)

Country Link
US (14) US7714159B2 (hr)
EP (5) EP2377868A1 (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) CA2560886C (hr)
CL (2) CL2010000350A1 (hr)
CR (1) CR8653A (hr)
CY (3) CY1112053T1 (hr)
DK (4) DK4008721T3 (hr)
DO (1) DOP2011000293A (hr)
EA (1) EA012927B1 (hr)
EC (1) ECSP066960A (hr)
ES (4) ES2371652T3 (hr)
FI (1) FI4008721T3 (hr)
HK (4) HK1100004A1 (hr)
HR (4) HRP20240307T3 (hr)
HU (1) 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) NZ586824A (hr)
PE (3) PE20060162A1 (hr)
PL (4) PL1756121T3 (hr)
PT (4) PT1756121E (hr)
RS (4) RS62738B1 (hr)
SG (5) SG182998A1 (hr)
SI (4) SI2377869T1 (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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