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

Info

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
Authority
AU
Australia
Prior art keywords
cyclopropane
dimethyl
difluoro
fluoro
dioxolan
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
AU2010275780A
Other languages
English (en)
Other versions
AU2010275780A1 (en
Inventor
Andreas Maderna
Jean-Michel Vernier
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.)
Ardea Biociences Inc
Original Assignee
Ardea Biociences 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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=42830488&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AU2010275780(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Ardea Biociences Inc filed Critical Ardea Biociences Inc
Publication of AU2010275780A1 publication Critical patent/AU2010275780A1/en
Application granted granted Critical
Publication of AU2010275780B2 publication Critical patent/AU2010275780B2/en
Ceased legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (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
US61/228,509 2009-07-24
US61/228,501 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

Family

ID=42830488

Family Applications (1)

Application Number Title Priority Date Filing Date
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 (enExample)
EP (1) EP2462111B1 (enExample)
JP (1) JP5776115B2 (enExample)
KR (1) KR101763437B1 (enExample)
CN (2) CN103848808B (enExample)
AR (1) AR079183A1 (enExample)
AU (1) AU2010275780B2 (enExample)
BR (1) BR112012001592A2 (enExample)
CA (2) CA2768788C (enExample)
CL (1) CL2012000192A1 (enExample)
CO (1) CO6491075A2 (enExample)
CR (1) CR20120044A (enExample)
CU (1) CU24113B1 (enExample)
DO (1) DOP2012000017A (enExample)
EA (1) EA023623B1 (enExample)
EC (1) ECSP12011621A (enExample)
GT (1) GT201200017A (enExample)
HN (1) HN2012000142A (enExample)
IL (1) IL217312A (enExample)
IN (1) IN2012DN00696A (enExample)
MA (1) MA33452B1 (enExample)
MX (2) MX2012001063A (enExample)
MY (1) MY160421A (enExample)
NZ (1) NZ597738A (enExample)
PE (1) PE20120573A1 (enExample)
PH (1) PH12014500158B1 (enExample)
SG (1) SG177535A1 (enExample)
TN (1) TN2012000027A1 (enExample)
TW (1) TWI524890B (enExample)
UY (1) UY32800A (enExample)
WO (1) WO2011009541A1 (enExample)

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
JPWO2013094546A1 (ja) * 2011-12-19 2015-04-27 住友化学株式会社 スルホン酸塩の製造方法
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
ES2354182T3 (es) * 2006-04-18 2011-03-10 Ardea Biosciences, Inc. Piridona sulfonamidas y piridona sulfamidas como inhibidores de mek.
CA2924418A1 (en) * 2007-07-30 2009-02-05 Jean-Michel Vernier Derivatives of n-(arylamino) sulfonamides including polymorphs as inhibitors of mek as well as compositions, methods of use and methods for preparing the same
US8808742B2 (en) * 2008-04-14 2014-08-19 Ardea Biosciences, Inc. Compositions and methods for preparing and using same
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
IL217312A0 (en) 2012-02-29
CA2990097A1 (en) 2011-01-27
CU20120014A7 (es) 2012-06-21
CN102471246A (zh) 2012-05-23
JP5776115B2 (ja) 2015-09-09
CR20120044A (es) 2012-03-12
CN102471246B (zh) 2015-08-26
US20120178946A1 (en) 2012-07-12
UY32800A (es) 2011-01-31
PH12014500158A1 (en) 2015-09-07
CA2768788C (en) 2018-01-09
HK1198364A1 (zh) 2015-04-10
CL2012000192A1 (es) 2012-10-05
MA33452B1 (fr) 2012-07-03
US8513443B2 (en) 2013-08-20
CU24113B1 (es) 2015-08-27
GT201200017A (es) 2013-12-19
US9296686B2 (en) 2016-03-29
TW201113017A (en) 2011-04-16
EA023623B1 (ru) 2016-06-30
HN2012000142A (es) 2015-06-08
EP2462111A1 (en) 2012-06-13
NZ597738A (en) 2014-03-28
AR079183A1 (es) 2012-01-04
AU2010275780A1 (en) 2012-02-02
SG177535A1 (en) 2012-03-29
WO2011009541A1 (en) 2011-01-27
HK1171218A1 (en) 2013-03-22
IN2012DN00696A (enExample) 2015-06-19
ECSP12011621A (es) 2012-02-29
CO6491075A2 (es) 2012-07-31
US8884058B2 (en) 2014-11-11
MY160421A (en) 2017-03-15
CN103848808B (zh) 2016-02-10
PH12014500158B1 (en) 2015-09-07
TWI524890B (zh) 2016-03-11
PE20120573A1 (es) 2012-05-17
MX344965B (es) 2017-01-12
MX2012001063A (es) 2012-03-26
EA201200175A1 (ru) 2012-12-28
CA2768788A1 (en) 2011-01-27
DOP2012000017A (es) 2012-05-15
CN103848808A (zh) 2014-06-11
BR112012001592A2 (pt) 2016-03-08
US20130261320A1 (en) 2013-10-03
EP2462111B1 (en) 2016-03-30
KR20120032536A (ko) 2012-04-05
US20150274651A1 (en) 2015-10-01
JP2013500242A (ja) 2013-01-07
KR101763437B1 (ko) 2017-07-31
TN2012000027A1 (en) 2013-09-19
IL217312A (en) 2017-02-28

Similar Documents

Publication Publication Date Title
AU2010275780A1 (en) 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
EP3686208B1 (en) Intermediates for preparing halichondrin compounds and preparation method therefor
CA2837162C (en) Chiral synthesis of n-{3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]-6-methoxyphenyl}-1-[2,3-dihydroxy-propyl]cyclopropanesulfonamides
HK1171218B (en) 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
HK1198364B (en) Midbody of mek enzyme inhibitor
Maegawa et al. Selective Deprotection of Methylene Acetal and MOM ether in the presence of Ketal-type Protective Groups: Remarkable Effect of TBSOTf
JP5698128B2 (ja) ジヒドロキシヘキセン酸エステル及びその製造方法
ES2703518T3 (es) Proceso mejorado para la preparación de derivados de ácido 2-(7-metilbenzo[d][1,3]dioxol-4-il 6-(sustituido))acético 2-sustituido
Makaev et al. Synthesis of (±)-5-methylidene-4-oxocyclopent-2-en-1-ylacetic acid ethanolamide
김현수 Asymmetric Total Synthesis of (+)-(3E)-Pinnatifidenyne and Studies Toward the Syntheses of trans-Rhodophytin and (-)-(3Z)-Venustinene
JPH03127760A (ja) イソカルバサイクリン類の製造法
EP2311841A1 (en) Method for obtaining zaragozic acid and derivatives thereof
RO131617B1 (ro) Intermediari aldehidici ( -lactonici de tip corey protejaţi ca acetali sau tioacetali ciclici
JPS61277642A (ja) シクロペンテンアルコ−ル類およびその製造法

Legal Events

Date Code Title Description
FGA Letters patent sealed or granted (standard patent)
MK14 Patent ceased section 143(a) (annual fees not paid) or expired