CO6491075A2 - Preparacion de (r) y (s)- n-(3,4-difluoro-2-(2-fluoro-4-yodofenilamino)-6-metoxifenil)-1-(2,3-dihidroxipropil) ciclopropan-1-sulfonamida y derivados protegidos de los mismos - Google Patents

Preparacion de (r) y (s)- n-(3,4-difluoro-2-(2-fluoro-4-yodofenilamino)-6-metoxifenil)-1-(2,3-dihidroxipropil) ciclopropan-1-sulfonamida y derivados protegidos de los mismos

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Publication number
CO6491075A2
CO6491075A2 CO12010431A CO12010431A CO6491075A2 CO 6491075 A2 CO6491075 A2 CO 6491075A2 CO 12010431 A CO12010431 A CO 12010431A CO 12010431 A CO12010431 A CO 12010431A CO 6491075 A2 CO6491075 A2 CO 6491075A2
Authority
CO
Colombia
Prior art keywords
difluoro
fluoro
sulfonamide
preparation
iodofenilamino
Prior art date
Application number
CO12010431A
Other languages
English (en)
Inventor
Andreas Maderna
Jean-Michel Vernier
Original Assignee
Ardea Biosciences 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=CO6491075(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Ardea Biosciences Inc filed Critical Ardea Biosciences Inc
Publication of CO6491075A2 publication Critical patent/CO6491075A2/es

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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)

Abstract

La presente invención revela procedimientos para la preparación de (R)-N-(3,4-difluoro-2-(2-fluoro-4-yodofenilamino)-6-metoxifenil)-1-(2,3-dihidroxipropil) ciclopropan-1-sulfonamida y (S)-N-(3,4-difluoro-2-(2-fluoro-4-yodofenilamino)-6-metoxifenil)-1-(2,3-dihidroxipropil) ciclopropan-1-sulfonamida que comprenden poner en contacto un compuesto de fórmula (I-a) o (I-b), respectivamente, con un ácido, una base o un nucleófilo, o exponer dichos compuesto de fórmula (I-a) o (I-b) a luz UV. También se revelan procedimientos para obtener los compuestos de fórmula (I-a) o (I-b) que comprende poner en contacto 5,6-difluoro-N l -(2-fluoro-4-yodofenil)-3-metoxibencen-1,2-diamina con un compuesto de fórmula (II-a) o (II-b), respectivamente. Asimismo, la presente invención se relaciona con los compuestos: cloruro de (R)-1-((2,2- dimetil- 1,3-dioxolan-4-il)metil)ciclopropan-1-sulfonilo, cloruro de (S)-1-((2,2-dimetil-1,3-dioxolan-4-il)metil)ciclopropan-1-sulfonilo, cloruro de (R)-3-(2,2-dimetil-1,3-dioxolan-4-il)prop-1-en-2-sulfonilo y cloruro de (S)-3-(2,2-dimetil-1,3-dioxolan-4-il)prop-1-en-2-sulfonilo.
CO12010431A 2009-07-24 2012-01-24 Preparacion de (r) y (s)- n-(3,4-difluoro-2-(2-fluoro-4-yodofenilamino)-6-metoxifenil)-1-(2,3-dihidroxipropil) ciclopropan-1-sulfonamida y derivados protegidos de los mismos CO6491075A2 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US22850909P 2009-07-24 2009-07-24
US22850109P 2009-07-24 2009-07-24

Publications (1)

Publication Number Publication Date
CO6491075A2 true CO6491075A2 (es) 2012-07-31

Family

ID=42830488

Family Applications (1)

Application Number Title Priority Date Filing Date
CO12010431A CO6491075A2 (es) 2009-07-24 2012-01-24 Preparacion de (r) y (s)- n-(3,4-difluoro-2-(2-fluoro-4-yodofenilamino)-6-metoxifenil)-1-(2,3-dihidroxipropil) ciclopropan-1-sulfonamida y derivados protegidos de los mismos

Country Status (32)

Country Link
US (3) US8513443B2 (es)
EP (1) EP2462111B1 (es)
JP (1) JP5776115B2 (es)
KR (1) KR101763437B1 (es)
CN (2) CN103848808B (es)
AR (1) AR079183A1 (es)
AU (1) AU2010275780B2 (es)
BR (1) BR112012001592A2 (es)
CA (2) CA2990097A1 (es)
CL (1) CL2012000192A1 (es)
CO (1) CO6491075A2 (es)
CR (1) CR20120044A (es)
CU (1) CU24113B1 (es)
DO (1) DOP2012000017A (es)
EA (1) EA023623B1 (es)
EC (1) ECSP12011621A (es)
GT (1) GT201200017A (es)
HK (2) HK1171218A1 (es)
HN (1) HN2012000142A (es)
IL (1) IL217312A (es)
IN (1) IN2012DN00696A (es)
MA (1) MA33452B1 (es)
MX (2) MX2012001063A (es)
MY (1) MY160421A (es)
NZ (1) NZ597738A (es)
PE (1) PE20120573A1 (es)
PH (1) PH12014500158A1 (es)
SG (1) SG177535A1 (es)
TN (1) TN2012000027A1 (es)
TW (1) TWI524890B (es)
UY (1) UY32800A (es)
WO (1) WO2011009541A1 (es)

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
MY186875A (en) * 2011-05-27 2021-08-26 Bayer Ip Gmbh Chiral synthesis of n-{3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]-6-methoxyphenyl}-1-[2,3-dihydroxy-propyl]cyclopropanesulfonamides
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

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8101799B2 (en) * 2005-07-21 2012-01-24 Ardea Biosciences Derivatives of N-(arylamino) sulfonamides as inhibitors of MEK
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
US7842836B2 (en) 2006-04-11 2010-11-30 Ardea Biosciences N-aryl-N'alkyl sulfamides as MEK inhibitors
CN101454004B (zh) 2006-04-18 2013-12-04 阿迪亚生命科学公司 作为mek抑制剂的吡啶酮磺酰胺类和吡啶酮硫酰胺类
UA99731C2 (ru) * 2007-07-30 2012-09-25 Ардеа Биосайенсис, Инк Кристаллические полиморфные формы n-(ариламино)сульфонамидов как ингибиторы мэк, композиция (варианты) и применение
JP2011518786A (ja) * 2008-04-14 2011-06-30 アルデア バイオサイエンシズ，インコーポレイティド 調製及び使用のための組成物及び方法
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

Also Published As

Publication number Publication date
UY32800A (es) 2011-01-31
AU2010275780B2 (en) 2015-10-22
TWI524890B (zh) 2016-03-11
KR101763437B1 (ko) 2017-07-31
CA2768788C (en) 2018-01-09
CU20120014A7 (es) 2012-06-21
CN103848808B (zh) 2016-02-10
PH12014500158B1 (en) 2015-09-07
ECSP12011621A (es) 2012-02-29
US20150274651A1 (en) 2015-10-01
JP2013500242A (ja) 2013-01-07
SG177535A1 (en) 2012-03-29
IL217312A0 (en) 2012-02-29
US9296686B2 (en) 2016-03-29
KR20120032536A (ko) 2012-04-05
CU24113B1 (es) 2015-08-27
EA023623B1 (ru) 2016-06-30
JP5776115B2 (ja) 2015-09-09
US8513443B2 (en) 2013-08-20
CN103848808A (zh) 2014-06-11
CN102471246B (zh) 2015-08-26
IL217312A (en) 2017-02-28
AR079183A1 (es) 2012-01-04
EA201200175A1 (ru) 2012-12-28
PH12014500158A1 (en) 2015-09-07
CN102471246A (zh) 2012-05-23
HK1198364A1 (zh) 2015-04-10
HK1171218A1 (en) 2013-03-22
MX344965B (es) 2017-01-12
MX2012001063A (es) 2012-03-26
GT201200017A (es) 2013-12-19
MY160421A (en) 2017-03-15
CA2768788A1 (en) 2011-01-27
HN2012000142A (es) 2015-06-08
EP2462111B1 (en) 2016-03-30
WO2011009541A1 (en) 2011-01-27
TW201113017A (en) 2011-04-16
US8884058B2 (en) 2014-11-11
CL2012000192A1 (es) 2012-10-05
AU2010275780A1 (en) 2012-02-02
US20120178946A1 (en) 2012-07-12
NZ597738A (en) 2014-03-28
BR112012001592A2 (pt) 2016-03-08
US20130261320A1 (en) 2013-10-03
CA2990097A1 (en) 2011-01-27
DOP2012000017A (es) 2012-05-15
IN2012DN00696A (es) 2015-06-19
TN2012000027A1 (en) 2013-09-19
PE20120573A1 (es) 2012-05-17
MA33452B1 (fr) 2012-07-03
CR20120044A (es) 2012-03-12
EP2462111A1 (en) 2012-06-13

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