WO2014158952A1 - Hydrochloride salts of an antibiotic compound - Google Patents

Hydrochloride salts of an antibiotic compound Download PDF

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Publication number
WO2014158952A1
WO2014158952A1 PCT/US2014/021064 US2014021064W WO2014158952A1 WO 2014158952 A1 WO2014158952 A1 WO 2014158952A1 US 2014021064 W US2014021064 W US 2014021064W WO 2014158952 A1 WO2014158952 A1 WO 2014158952A1
Authority
WO
WIPO (PCT)
Prior art keywords
amino
compound
formula
pharmaceutical composition
glycine
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US2014/021064
Other languages
English (en)
French (fr)
Inventor
Weijiang Zhang
Ronnie Cheung
Dimitar Filipov
Jack Green
Junning Lee
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Innoviva Inc
Original Assignee
Theravance Inc
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
Priority to HRP20171188TT priority Critical patent/HRP20171188T1/hr
Priority to JP2016500713A priority patent/JP6482523B2/ja
Priority to MDA20150101A priority patent/MD4599C1/ro
Priority to AU2014241481A priority patent/AU2014241481B9/en
Priority to SM20170369T priority patent/SMT201700369T1/it
Priority to DK14717248.0T priority patent/DK2968446T3/en
Priority to ES14717248.0T priority patent/ES2633964T3/es
Priority to HK16102557.3A priority patent/HK1214524B/en
Priority to CA2902720A priority patent/CA2902720A1/en
Priority to SG11201507235YA priority patent/SG11201507235YA/en
Priority to UAA201509921A priority patent/UA115086C2/uk
Priority to EA201591697A priority patent/EA027282B1/ru
Priority to MEP-2017-133A priority patent/ME02854B/me
Priority to LTEP14717248.0T priority patent/LT2968446T/lt
Priority to MX2015012170A priority patent/MX361984B/es
Priority to SI201430302T priority patent/SI2968446T1/sl
Application filed by Theravance Inc filed Critical Theravance Inc
Priority to KR1020157027597A priority patent/KR20150126659A/ko
Priority to EP14717248.0A priority patent/EP2968446B1/en
Priority to RS20170621A priority patent/RS56141B1/sr
Priority to BR112015022716A priority patent/BR112015022716A2/pt
Priority to CN201480013969.0A priority patent/CN105120883B/zh
Publication of WO2014158952A1 publication Critical patent/WO2014158952A1/en
Priority to IL240663A priority patent/IL240663A0/en
Priority to ZA2015/06748A priority patent/ZA201506748B/en
Priority to PH12015502060A priority patent/PH12015502060A1/en
Anticipated expiration legal-status Critical
Priority to CY20171100810T priority patent/CY1119316T1/el
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
    • A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/14—Peptides containing saccharide radicals; Derivatives thereof, e.g. bleomycin, phleomycin, muramylpeptides or vancomycin
    • 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
    • A61P31/04—Antibacterial agents
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
    • C07K9/006—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure
    • C07K9/008—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure directly attached to a hetero atom of the saccharide radical, e.g. actaplanin, avoparcin, ristomycin, vancomycin

Definitions

  • any reference to the molar ratio of the compound to hydrochloric acid will be understood to refer to the molar ratio of the components in the form of the acid addition salts.
  • this reaction is conducted by contacting vancomycin or a salt thereof, with about 1 to about 1.1 molar equivalents of a peptide coupling reagent in a diluent, such as DMF, DMSO, or a mixture thereof.
  • a diluent such as DMF, DMSO, or a mixture thereof.
  • This reaction is typically conducted at a temperature in the range of from about -10 °C to about 10 °C for about 10 minutes to about 60 minutes or until the reaction is substantially complete.
  • a solution of about 0.9 to about 1.1 molar equivalents of compound A or a salt thereof in a diluent, such as DMF, DMSO or a mixture thereof, is then added to the activated vancomycin derivative.
  • Vancomycin is also known in the art.
  • vancomycin hydrochloride is commercially-available from Sigma-Aldrich (St. Louis, MO 63103) and from Haorui Pharma-Chem Inc. (Irvine, CA 92618).
  • the compound of formula I When administered in a physiologically-acceptable aqueous carrier, the compound of formula I is typically administered intravenously to the patient over a period of about 0.5 h to about 2 h, such as for about 1 h.
  • Test samples were assayed for 26-[[[3-[[(Z)-[l-(2-amino-5-chloro-4-thiazolyl)-2- [[(6R,7R)-2-carboxy-8-oxo-3-(pyridiniomethyl)-5-thia-l-azabicyclo[4.2.0]-oct-2-en-7- yl]amino]-2-oxoethylidene]amino]oxy]propyl]amino]carbonyl]-26-decarboxyvancomycin and its degradation products using an HPLC system with a photodiode array detector (Agilent 1 100 or 1200 HPLC System; Agilent Technologies Inc., Santa Clara, CA 95051) controlled with chromatography data software (Empower Software, Waters Corporation, Milford, MA 01757). All solvents were HPLC grade and were purchased from
  • the mixture was allowed to stand for 1 h and then the lower aqueous layer was separated and discarded.
  • the organic layer was concentrated under vacuum to a volume of about 500 mL.
  • Acetonitrile (1.0 L) was added and the mixture was concentrated under vacuum. This was repeated by again adding acetonitrile (1.0 L) and concentrating the mixture under vacuum to a volume of about 600 mL.
  • the mixture was then filtered through diatomaceous earth (Celite). Triethylamine (350 mL, 2508 mmol) was added and the mixture was cooled to 0 °C at which time a precipitate formed.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Immunology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
PCT/US2014/021064 2013-03-13 2014-03-06 Hydrochloride salts of an antibiotic compound Ceased WO2014158952A1 (en)

Priority Applications (25)

Application Number Priority Date Filing Date Title
MX2015012170A MX361984B (es) 2013-03-13 2014-03-06 Sales clorhidrato de un compuesto antibiótico.
MDA20150101A MD4599C1 (ro) 2013-03-13 2014-03-06 Săruri de hidroclorură a unui compus antibiotic
AU2014241481A AU2014241481B9 (en) 2013-03-13 2014-03-06 Hydrochloride salts of an antibiotic compound
SM20170369T SMT201700369T1 (it) 2013-03-13 2014-03-06 Sali di idrocloruro di un composto antibiotico
DK14717248.0T DK2968446T3 (en) 2013-03-13 2014-03-06 HCL-Salts of an antibiotic compound
ES14717248.0T ES2633964T3 (es) 2013-03-13 2014-03-06 Sales de clorhidrato de un compuesto antibiótico
HK16102557.3A HK1214524B (en) 2013-03-13 2014-03-06 Hydrochloride salts of an antibiotic compound
CA2902720A CA2902720A1 (en) 2013-03-13 2014-03-06 Hydrochloride salts of an antibiotic compound
SG11201507235YA SG11201507235YA (en) 2013-03-13 2014-03-06 Hydrochloride salts of an antibiotic compound
UAA201509921A UA115086C2 (uk) 2013-03-13 2014-03-06 Гідрохлоридні солі антибіотичної сполуки
EA201591697A EA027282B1 (ru) 2013-03-13 2014-03-06 Гидрохлоридные соли антибиотического соединения
MEP-2017-133A ME02854B (me) 2013-03-13 2014-03-06 Hidrohloridne soli antibiotskog jedinjenja
LTEP14717248.0T LT2968446T (lt) 2013-03-13 2014-03-06 Antibiotinių junginių hidrochlorido druskos
HRP20171188TT HRP20171188T1 (hr) 2013-03-13 2014-03-06 Hidrokloridne soli antibiotskog spoja
RS20170621A RS56141B1 (sr) 2013-03-13 2014-03-06 Hidrohloridne soli antibiotskog jedinjenja
SI201430302T SI2968446T1 (sl) 2013-03-13 2014-03-06 Hidrokloridne soli antibiotične spojine
KR1020157027597A KR20150126659A (ko) 2013-03-13 2014-03-06 항생제 화합물의 히드로클로리드 염
EP14717248.0A EP2968446B1 (en) 2013-03-13 2014-03-06 Hydrochloride salts of an antibiotic compound
JP2016500713A JP6482523B2 (ja) 2013-03-13 2014-03-06 抗生物質化合物の塩酸塩
BR112015022716A BR112015022716A2 (pt) 2013-03-13 2014-03-06 sais de cloridrato de um composto antibiótico
CN201480013969.0A CN105120883B (zh) 2013-03-13 2014-03-06 抗生素化合物的盐酸盐
IL240663A IL240663A0 (en) 2013-03-13 2015-08-18 Hydrochloride salts of an antibiotic compound
ZA2015/06748A ZA201506748B (en) 2013-03-13 2015-09-11 Hydrochloride salts of an antibiotic compound
PH12015502060A PH12015502060A1 (en) 2013-03-13 2015-09-11 Hydrochloride salts of an antibiotic compound
CY20171100810T CY1119316T1 (el) 2013-03-13 2017-07-28 Υδροχλωρικα αλατα μιας αντιβιοτικης ενωσης

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361779065P 2013-03-13 2013-03-13
US61/779,065 2013-03-13

Publications (1)

Publication Number Publication Date
WO2014158952A1 true WO2014158952A1 (en) 2014-10-02

Family

ID=50483481

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2014/021064 Ceased WO2014158952A1 (en) 2013-03-13 2014-03-06 Hydrochloride salts of an antibiotic compound

Country Status (32)

Country Link
US (1) US9161990B2 (enExample)
EP (1) EP2968446B1 (enExample)
JP (3) JP6482523B2 (enExample)
KR (1) KR20150126659A (enExample)
CN (1) CN105120883B (enExample)
AR (1) AR095044A1 (enExample)
AU (1) AU2014241481B9 (enExample)
BR (1) BR112015022716A2 (enExample)
CA (1) CA2902720A1 (enExample)
CY (1) CY1119316T1 (enExample)
DK (1) DK2968446T3 (enExample)
EA (1) EA027282B1 (enExample)
ES (1) ES2633964T3 (enExample)
GE (1) GEP20186874B (enExample)
HR (1) HRP20171188T1 (enExample)
HU (1) HUE033738T2 (enExample)
IL (1) IL240663A0 (enExample)
LT (1) LT2968446T (enExample)
MD (1) MD4599C1 (enExample)
ME (1) ME02854B (enExample)
MX (1) MX361984B (enExample)
PH (1) PH12015502060A1 (enExample)
PL (1) PL2968446T3 (enExample)
PT (1) PT2968446T (enExample)
RS (1) RS56141B1 (enExample)
SG (1) SG11201507235YA (enExample)
SI (1) SI2968446T1 (enExample)
SM (1) SMT201700369T1 (enExample)
TW (1) TWI608845B (enExample)
UA (1) UA115086C2 (enExample)
WO (1) WO2014158952A1 (enExample)
ZA (1) ZA201506748B (enExample)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2980537A1 (en) * 2015-03-24 2016-09-29 Elevance Renewable Sciences, Inc. Polyol esters of metathesized fatty acids and uses thereof

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Also Published As

Publication number Publication date
TWI608845B (zh) 2017-12-21
AU2014241481B2 (en) 2018-02-01
DK2968446T3 (en) 2017-08-28
GEP20186874B (en) 2018-06-25
EP2968446A1 (en) 2016-01-20
IL240663A0 (en) 2015-10-29
ZA201506748B (en) 2017-08-30
AR095044A1 (es) 2015-09-16
MD4599C1 (ro) 2019-06-30
CN105120883A (zh) 2015-12-02
ME02854B (me) 2018-04-20
CA2902720A1 (en) 2014-10-02
MD4599B1 (ro) 2018-11-30
AU2014241481A1 (en) 2015-10-01
MX2015012170A (es) 2015-11-30
MD20150101A2 (ro) 2016-02-29
EA027282B1 (ru) 2017-07-31
TW201444572A (zh) 2014-12-01
JP2018177817A (ja) 2018-11-15
JP6482523B2 (ja) 2019-03-13
AU2014241481B9 (en) 2018-02-15
MX361984B (es) 2018-12-19
LT2968446T (lt) 2017-07-25
UA115086C2 (uk) 2017-09-11
PT2968446T (pt) 2017-07-27
SMT201700369T1 (it) 2017-09-07
HK1214524A1 (en) 2016-07-29
HRP20171188T1 (hr) 2017-10-06
PH12015502060A1 (en) 2016-01-25
US9161990B2 (en) 2015-10-20
SG11201507235YA (en) 2015-10-29
SI2968446T1 (sl) 2017-08-31
JP2016513642A (ja) 2016-05-16
HUE033738T2 (hu) 2018-01-29
KR20150126659A (ko) 2015-11-12
CY1119316T1 (el) 2018-02-14
PL2968446T3 (pl) 2017-11-30
US20140274877A1 (en) 2014-09-18
CN105120883B (zh) 2017-11-17
JP2017082016A (ja) 2017-05-18
EA201591697A1 (ru) 2016-02-29
RS56141B1 (sr) 2017-10-31
EP2968446B1 (en) 2017-05-03
ES2633964T3 (es) 2017-09-26
BR112015022716A2 (pt) 2017-07-18

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