AU2010275780B2 - Preparation of (R)- and (S)-N-(3, 4-difluoro-2-(2-fluoro-4-iodophenylamino)--6-methoxyphenyl) -1- (2, 3-dihydroxypropyl)cyclopropane-1-sulfonamide and protected derivatives thereof - Google Patents

Preparation of (R)- and (S)-N-(3, 4-difluoro-2-(2-fluoro-4-iodophenylamino)--6-methoxyphenyl) -1- (2, 3-dihydroxypropyl)cyclopropane-1-sulfonamide and protected derivatives thereof Download PDF

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Publication number
AU2010275780B2
AU2010275780B2 AU2010275780A AU2010275780A AU2010275780B2 AU 2010275780 B2 AU2010275780 B2 AU 2010275780B2 AU 2010275780 A AU2010275780 A AU 2010275780A AU 2010275780 A AU2010275780 A AU 2010275780A AU 2010275780 B2 AU2010275780 B2 AU 2010275780B2
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AU
Australia
Prior art keywords
cyclopropane
dimethyl
difluoro
fluoro
dioxolan
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Ceased
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AU2010275780A
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AU2010275780A1 (en
Inventor
Andreas Maderna
Jean-Michel Vernier
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Ardea Biociences Inc
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Ardea Biociences Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Indole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
AU2010275780A 2009-07-24 2010-07-10 Preparation of (R)- and (S)-N-(3, 4-difluoro-2-(2-fluoro-4-iodophenylamino)--6-methoxyphenyl) -1- (2, 3-dihydroxypropyl)cyclopropane-1-sulfonamide and protected derivatives thereof Ceased AU2010275780B2 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US22850109P 2009-07-24 2009-07-24
US22850909P 2009-07-24 2009-07-24
US61/228,501 2009-07-24
US61/228,509 2009-07-24
PCT/EP2010/004222 WO2011009541A1 (en) 2009-07-24 2010-07-10 Preparation of (r)- and (s)-n-(3, 4-difluoro-2-(2-fluoro-4-iodophenylamino)--6-methoxyphenyl) -1- (2, 3-dihydroxypropyl)cyclopropane-1-sulfonamide and protected derivatives thereof

Publications (2)

Publication Number Publication Date
AU2010275780A1 AU2010275780A1 (en) 2012-02-02
AU2010275780B2 true AU2010275780B2 (en) 2015-10-22

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AU2010275780A Ceased AU2010275780B2 (en) 2009-07-24 2010-07-10 Preparation of (R)- and (S)-N-(3, 4-difluoro-2-(2-fluoro-4-iodophenylamino)--6-methoxyphenyl) -1- (2, 3-dihydroxypropyl)cyclopropane-1-sulfonamide and protected derivatives thereof

Country Status (31)

Country Link
US (3) US8513443B2 (cg-RX-API-DMAC10.html)
EP (1) EP2462111B1 (cg-RX-API-DMAC10.html)
JP (1) JP5776115B2 (cg-RX-API-DMAC10.html)
KR (1) KR101763437B1 (cg-RX-API-DMAC10.html)
CN (2) CN103848808B (cg-RX-API-DMAC10.html)
AR (1) AR079183A1 (cg-RX-API-DMAC10.html)
AU (1) AU2010275780B2 (cg-RX-API-DMAC10.html)
BR (1) BR112012001592A2 (cg-RX-API-DMAC10.html)
CA (2) CA2768788C (cg-RX-API-DMAC10.html)
CL (1) CL2012000192A1 (cg-RX-API-DMAC10.html)
CO (1) CO6491075A2 (cg-RX-API-DMAC10.html)
CR (1) CR20120044A (cg-RX-API-DMAC10.html)
CU (1) CU24113B1 (cg-RX-API-DMAC10.html)
DO (1) DOP2012000017A (cg-RX-API-DMAC10.html)
EA (1) EA023623B1 (cg-RX-API-DMAC10.html)
EC (1) ECSP12011621A (cg-RX-API-DMAC10.html)
GT (1) GT201200017A (cg-RX-API-DMAC10.html)
HN (1) HN2012000142A (cg-RX-API-DMAC10.html)
IL (1) IL217312A (cg-RX-API-DMAC10.html)
IN (1) IN2012DN00696A (cg-RX-API-DMAC10.html)
MA (1) MA33452B1 (cg-RX-API-DMAC10.html)
MX (2) MX2012001063A (cg-RX-API-DMAC10.html)
MY (1) MY160421A (cg-RX-API-DMAC10.html)
NZ (1) NZ597738A (cg-RX-API-DMAC10.html)
PE (1) PE20120573A1 (cg-RX-API-DMAC10.html)
PH (1) PH12014500158B1 (cg-RX-API-DMAC10.html)
SG (1) SG177535A1 (cg-RX-API-DMAC10.html)
TN (1) TN2012000027A1 (cg-RX-API-DMAC10.html)
TW (1) TWI524890B (cg-RX-API-DMAC10.html)
UY (1) UY32800A (cg-RX-API-DMAC10.html)
WO (1) WO2011009541A1 (cg-RX-API-DMAC10.html)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI524890B (zh) * 2009-07-24 2016-03-11 亞德生化公司 （ｒ）－ｎ－（３，４－二氟－２－（２－氟－４－碘苯胺基）－６－甲氧基苯基）－１－（２，３－二羥丙基）環丙烷－１－磺醯胺及（ｓ）－ｎ－（３，４－二氟－２－（２－氟－４－碘苯胺基）－６－甲氧基苯基）－１－（２，３－二羥丙基）環丙烷－１－磺醯胺之製備
UA113850C2 (xx) * 2011-05-27 2017-03-27 Хіральний синтез n-{3,4-дифтор-2-$(2-фтор-4-йодфеніл)аміно]-6-метоксифеніл}-1-$2,3-дигідроксипропіл]циклопропансульфонамідів
EP2796455A4 (en) * 2011-12-19 2015-08-19 Sumitomo Chemical Co PROCESS FOR THE PREPARATION OF SULPHONATE
EP2848246A1 (en) 2013-09-13 2015-03-18 Bayer Pharma Aktiengesellschaft Pharmaceutical compositions containing refametinib

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007121269A2 (en) * 2006-04-11 2007-10-25 Ardea Biosciences, Inc. N-aryl-n'alkyl sulfamides as mek inhibitors
US20080058340A1 (en) * 2005-07-21 2008-03-06 Ardea Biosciences, Inc. Derivatives of n-(arylamino) sulfonamides as inhibitors of mek

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101495118B (zh) * 2005-07-21 2012-09-05 阿迪亚生命科学公司 Mek的n-(芳基氨基)磺酰胺抑制剂
AU2007237901B2 (en) * 2006-04-18 2012-07-05 Ardea Biosciences, Inc. Pyridone sulfonamides and pyridone sulfamides as MEK inhibitors
CA2694646C (en) * 2007-07-30 2017-09-05 Ardea Biosciences, Inc. Combinations of mek inhibitors and raf kinase inhibitors and uses thereof
CN102131771A (zh) * 2008-04-14 2011-07-20 阿迪生物科学公司 组合物及其制备和使用方法
TWI524890B (zh) * 2009-07-24 2016-03-11 亞德生化公司 （ｒ）－ｎ－（３，４－二氟－２－（２－氟－４－碘苯胺基）－６－甲氧基苯基）－１－（２，３－二羥丙基）環丙烷－１－磺醯胺及（ｓ）－ｎ－（３，４－二氟－２－（２－氟－４－碘苯胺基）－６－甲氧基苯基）－１－（２，３－二羥丙基）環丙烷－１－磺醯胺之製備

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080058340A1 (en) * 2005-07-21 2008-03-06 Ardea Biosciences, Inc. Derivatives of n-(arylamino) sulfonamides as inhibitors of mek
WO2007121269A2 (en) * 2006-04-11 2007-10-25 Ardea Biosciences, Inc. N-aryl-n'alkyl sulfamides as mek inhibitors

Also Published As

Publication number Publication date
EA201200175A1 (ru) 2012-12-28
CA2768788A1 (en) 2011-01-27
CO6491075A2 (es) 2012-07-31
MA33452B1 (fr) 2012-07-03
KR101763437B1 (ko) 2017-07-31
CL2012000192A1 (es) 2012-10-05
UY32800A (es) 2011-01-31
HN2012000142A (es) 2015-06-08
ECSP12011621A (es) 2012-02-29
CN102471246B (zh) 2015-08-26
IL217312A (en) 2017-02-28
JP5776115B2 (ja) 2015-09-09
US9296686B2 (en) 2016-03-29
TW201113017A (en) 2011-04-16
KR20120032536A (ko) 2012-04-05
PE20120573A1 (es) 2012-05-17
BR112012001592A2 (pt) 2016-03-08
PH12014500158A1 (en) 2015-09-07
MX2012001063A (es) 2012-03-26
US8513443B2 (en) 2013-08-20
AR079183A1 (es) 2012-01-04
CU24113B1 (es) 2015-08-27
IL217312A0 (en) 2012-02-29
AU2010275780A1 (en) 2012-02-02
CU20120014A7 (es) 2012-06-21
US20150274651A1 (en) 2015-10-01
US20130261320A1 (en) 2013-10-03
HK1198364A1 (zh) 2015-04-10
JP2013500242A (ja) 2013-01-07
CR20120044A (es) 2012-03-12
TN2012000027A1 (en) 2013-09-19
SG177535A1 (en) 2012-03-29
US8884058B2 (en) 2014-11-11
EA023623B1 (ru) 2016-06-30
CN103848808A (zh) 2014-06-11
CA2768788C (en) 2018-01-09
NZ597738A (en) 2014-03-28
CA2990097A1 (en) 2011-01-27
HK1171218A1 (en) 2013-03-22
DOP2012000017A (es) 2012-05-15
PH12014500158B1 (en) 2015-09-07
IN2012DN00696A (cg-RX-API-DMAC10.html) 2015-06-19
WO2011009541A1 (en) 2011-01-27
CN102471246A (zh) 2012-05-23
GT201200017A (es) 2013-12-19
MY160421A (en) 2017-03-15
US20120178946A1 (en) 2012-07-12
CN103848808B (zh) 2016-02-10
TWI524890B (zh) 2016-03-11
EP2462111B1 (en) 2016-03-30
EP2462111A1 (en) 2012-06-13
MX344965B (es) 2017-01-12

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