NZ597738A - 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 thereofInfo
- Publication number
- NZ597738A NZ597738A NZ597738A NZ59773810A NZ597738A NZ 597738 A NZ597738 A NZ 597738A NZ 597738 A NZ597738 A NZ 597738A NZ 59773810 A NZ59773810 A NZ 59773810A NZ 597738 A NZ597738 A NZ 597738A
- Authority
- NZ
- New Zealand
- Prior art keywords
- formula
- cyclopropane
- difluoro
- fluoro
- iodophenylamino
- Prior art date
Links
- RDSACQWTXKSHJT-NSHDSACASA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)-6-methoxyphenyl]-1-[(2s)-2,3-dihydroxypropyl]cyclopropane-1-sulfonamide Chemical compound C1CC1(C[C@H](O)CO)S(=O)(=O)NC=1C(OC)=CC(F)=C(F)C=1NC1=CC=C(I)C=C1F RDSACQWTXKSHJT-NSHDSACASA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- XZKWFWOCXKFYCF-ZETCQYMHSA-N 1-[[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]cyclopropane-1-sulfonyl chloride Chemical compound O1C(C)(C)OC[C@@H]1CC1(S(Cl)(=O)=O)CC1 XZKWFWOCXKFYCF-ZETCQYMHSA-N 0.000 abstract 1
- HZMCKCFNDFZVCM-UHFFFAOYSA-N 3,4-difluoro-2-n-(2-fluoro-4-iodophenyl)-6-methoxybenzene-1,2-diamine Chemical compound COC1=CC(F)=C(F)C(NC=2C(=CC(I)=CC=2)F)=C1N HZMCKCFNDFZVCM-UHFFFAOYSA-N 0.000 abstract 1
- FRPCAHHPHLTDDV-ZETCQYMHSA-N 3-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-1-ene-2-sulfonyl chloride Chemical compound CC1(C)OC[C@H](CC(=C)S(Cl)(=O)=O)O1 FRPCAHHPHLTDDV-ZETCQYMHSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000012038 nucleophile Substances 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
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)
- 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22850109P | 2009-07-24 | 2009-07-24 | |
| US22850909P | 2009-07-24 | 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 (1)
| Publication Number | Publication Date |
|---|---|
| NZ597738A true NZ597738A (en) | 2014-03-28 |
Family
ID=42830488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ597738A NZ597738A (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 (https=) |
| EP (1) | EP2462111B1 (https=) |
| JP (1) | JP5776115B2 (https=) |
| KR (1) | KR101763437B1 (https=) |
| CN (2) | CN103848808B (https=) |
| AR (1) | AR079183A1 (https=) |
| AU (1) | AU2010275780B2 (https=) |
| BR (1) | BR112012001592A2 (https=) |
| CA (2) | CA2990097A1 (https=) |
| CL (1) | CL2012000192A1 (https=) |
| CO (1) | CO6491075A2 (https=) |
| CR (1) | CR20120044A (https=) |
| CU (1) | CU24113B1 (https=) |
| DO (1) | DOP2012000017A (https=) |
| EA (1) | EA023623B1 (https=) |
| EC (1) | ECSP12011621A (https=) |
| GT (1) | GT201200017A (https=) |
| HN (1) | HN2012000142A (https=) |
| IL (1) | IL217312A (https=) |
| IN (1) | IN2012DN00696A (https=) |
| MA (1) | MA33452B1 (https=) |
| MX (2) | MX2012001063A (https=) |
| MY (1) | MY160421A (https=) |
| NZ (1) | NZ597738A (https=) |
| PE (1) | PE20120573A1 (https=) |
| PH (1) | PH12014500158B1 (https=) |
| SG (1) | SG177535A1 (https=) |
| TN (1) | TN2012000027A1 (https=) |
| TW (1) | TWI524890B (https=) |
| UY (1) | UY32800A (https=) |
| WO (1) | WO2011009541A1 (https=) |
Families Citing this family (4)
| 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 |
| PH12013502446A1 (en) * | 2011-05-27 | 2014-01-20 | 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1912636T1 (sl) * | 2005-07-21 | 2014-08-29 | Ardea Biosciences, Inc. | N-(arilamino)-sulfonamidni inhibitorji MEK |
| US8101799B2 (en) * | 2005-07-21 | 2012-01-24 | Ardea Biosciences | Derivatives of N-(arylamino) sulfonamides as inhibitors of MEK |
| US7842836B2 (en) | 2006-04-11 | 2010-11-30 | Ardea Biosciences | N-aryl-N'alkyl sulfamides as MEK inhibitors |
| MX2008013097A (es) | 2006-04-18 | 2008-10-27 | Ardea Biosciences Inc | Piridona sulfonamidas y piridona sulfamidas como inhibidores de metiletilcetona. |
| UA99731C2 (ru) * | 2007-07-30 | 2012-09-25 | Ардеа Биосайенсис, Инк | Кристаллические полиморфные формы n-(ариламино)сульфонамидов как ингибиторы мэк, композиция (варианты) и применение |
| 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 |
-
2010
- 2010-07-09 TW TW099122740A patent/TWI524890B/zh not_active IP Right Cessation
- 2010-07-10 MY MYPI2012000099A patent/MY160421A/en unknown
- 2010-07-10 CU CUP2012000014A patent/CU24113B1/es active IP Right Grant
- 2010-07-10 EP EP10734043.2A patent/EP2462111B1/en active Active
- 2010-07-10 CA CA2990097A patent/CA2990097A1/en not_active Abandoned
- 2010-07-10 BR BR112012001592A patent/BR112012001592A2/pt not_active Application Discontinuation
- 2010-07-10 IN IN696DEN2012 patent/IN2012DN00696A/en unknown
- 2010-07-10 JP JP2012520927A patent/JP5776115B2/ja not_active Expired - Fee Related
- 2010-07-10 NZ NZ597738A patent/NZ597738A/en not_active IP Right Cessation
- 2010-07-10 US US13/386,519 patent/US8513443B2/en not_active Expired - Fee Related
- 2010-07-10 EA EA201200175A patent/EA023623B1/ru not_active IP Right Cessation
- 2010-07-10 SG SG2012000964A patent/SG177535A1/en unknown
- 2010-07-10 CN CN201310670649.XA patent/CN103848808B/zh not_active Expired - Fee Related
- 2010-07-10 CA CA2768788A patent/CA2768788C/en not_active Expired - Fee Related
- 2010-07-10 MA MA34562A patent/MA33452B1/fr unknown
- 2010-07-10 KR KR1020127001737A patent/KR101763437B1/ko not_active Expired - Fee Related
- 2010-07-10 MX MX2012001063A patent/MX2012001063A/es active IP Right Grant
- 2010-07-10 PE PE2012000092A patent/PE20120573A1/es not_active Application Discontinuation
- 2010-07-10 CN CN201080031572.6A patent/CN102471246B/zh not_active Expired - Fee Related
- 2010-07-10 WO PCT/EP2010/004222 patent/WO2011009541A1/en not_active Ceased
- 2010-07-10 AU AU2010275780A patent/AU2010275780B2/en not_active Ceased
- 2010-07-22 UY UY0001032800A patent/UY32800A/es not_active Application Discontinuation
- 2010-07-23 AR ARP100102678A patent/AR079183A1/es unknown
-
2012
- 2012-01-01 IL IL217312A patent/IL217312A/en not_active IP Right Cessation
- 2012-01-19 TN TNP2012000027A patent/TN2012000027A1/en unknown
- 2012-01-23 CR CR20120044A patent/CR20120044A/es unknown
- 2012-01-24 CL CL2012000192A patent/CL2012000192A1/es unknown
- 2012-01-24 CO CO12010431A patent/CO6491075A2/es active IP Right Grant
- 2012-01-24 DO DO2012000017A patent/DOP2012000017A/es unknown
- 2012-01-24 MX MX2014000732A patent/MX344965B/es unknown
- 2012-01-24 GT GT201200017A patent/GT201200017A/es unknown
- 2012-01-24 EC EC2012011621A patent/ECSP12011621A/es unknown
- 2012-01-24 HN HN2012000142A patent/HN2012000142A/es unknown
-
2013
- 2013-04-23 US US13/868,621 patent/US8884058B2/en not_active Expired - Fee Related
-
2014
- 2014-01-16 PH PH12014500158A patent/PH12014500158B1/en unknown
- 2014-08-25 US US14/467,424 patent/US9296686B2/en not_active Expired - Fee Related
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