JP5776115B2 - (r)−および(s)−n−(3,4−ジフルオロ−2−(2−フルオロ−4−ヨードフェニルアミノ)−6−メトキシフェニル)−1−(2,3−ジヒドロキシプロピル)シクロプロパン−1−スルホンアミドの調製と、その保護された誘導体 - Google Patents
(r)−および(s)−n−(3,4−ジフルオロ−2−(2−フルオロ−4−ヨードフェニルアミノ)−6−メトキシフェニル)−1−(2,3−ジヒドロキシプロピル)シクロプロパン−1−スルホンアミドの調製と、その保護された誘導体 Download PDFInfo
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- JP5776115B2 JP5776115B2 JP2012520927A JP2012520927A JP5776115B2 JP 5776115 B2 JP5776115 B2 JP 5776115B2 JP 2012520927 A JP2012520927 A JP 2012520927A JP 2012520927 A JP2012520927 A JP 2012520927A JP 5776115 B2 JP5776115 B2 JP 5776115B2
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- dimethyl
- cyclopropane
- difluoro
- fluoro
- dioxolan
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- 0 *OC[C@@](CC1(CC1)S(Cl)(=O)=O)O*I Chemical compound *OC[C@@](CC1(CC1)S(Cl)(=O)=O)O*I 0.000 description 6
- AHQZBWSZFZAPEL-COBSHVIPSA-N BC(C)C[C@H]1OC(C)(C)OC1 Chemical compound BC(C)C[C@H]1OC(C)(C)OC1 AHQZBWSZFZAPEL-COBSHVIPSA-N 0.000 description 1
- CMRYKYXMZRPDCA-UHFFFAOYSA-O CC1(C)OC(CC(S(OC=O)[U])=C)CO1 Chemical compound CC1(C)OC(CC(S(OC=O)[U])=C)CO1 CMRYKYXMZRPDCA-UHFFFAOYSA-O 0.000 description 1
- GWCDONAKQDHZRM-UHFFFAOYSA-N CC1(C)OC(CC2(CC2)[S]([NH3+])(O)(=O)=O)CO1 Chemical compound CC1(C)OC(CC2(CC2)[S]([NH3+])(O)(=O)=O)CO1 GWCDONAKQDHZRM-UHFFFAOYSA-N 0.000 description 1
- ASSRLGKCFLQSDY-SSDOTTSWSA-N CC1(C)O[C@H](CC(Br)=C)CO1 Chemical compound CC1(C)O[C@H](CC(Br)=C)CO1 ASSRLGKCFLQSDY-SSDOTTSWSA-N 0.000 description 1
- RWHWQTPESNBQGS-DDWIOCJRSA-N CC1(C)O[C@H](CC(C[U])=C)CO1 Chemical compound CC1(C)O[C@H](CC(C[U])=C)CO1 RWHWQTPESNBQGS-DDWIOCJRSA-N 0.000 description 1
- XOOIQJCVRKUDIR-SSDOTTSWSA-N CC1(C)O[C@H](CC(I)=C)CO1 Chemical compound CC1(C)O[C@H](CC(I)=C)CO1 XOOIQJCVRKUDIR-SSDOTTSWSA-N 0.000 description 1
- RHSQCLAGWOZJOH-CYBMUJFWSA-N CC1(C)O[C@H](CC2(CC2)S(Nc(c(Nc(ccc(I)c2)c2F)c(c(F)c2)F)c2OC)(=O)=O)CO1 Chemical compound CC1(C)O[C@H](CC2(CC2)S(Nc(c(Nc(ccc(I)c2)c2F)c(c(F)c2)F)c2OC)(=O)=O)CO1 RHSQCLAGWOZJOH-CYBMUJFWSA-N 0.000 description 1
- PAMXNIQFMFAEGP-JAMMHHFISA-N CC1(O[C@@H](CC2(CC2)[S]([NH+]=C)(O)(=O)=O)CO1)I Chemical compound CC1(O[C@@H](CC2(CC2)[S]([NH+]=C)(O)(=O)=O)CO1)I PAMXNIQFMFAEGP-JAMMHHFISA-N 0.000 description 1
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Classifications
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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)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
R1は、Hまたはアルコール保護基であり;
R2は、Hまたはアルコール保護基である;または
R1とR2は、これらの基が結合する炭素原子と合わさって、環状1,2-ジオール保護基を形成する。
R1は、Hまたはアルコール保護基であり;
R2は、Hまたはアルコール保護基である;または
R1とR2は、これらの基が結合する炭素原子と合わさって、環状1,2-ジオール保護基を形成する。
R1は、Hまたはアルコール保護基であり;
R2は、Hまたはアルコール保護基である;または
R1とR2は、これらの基が結合する炭素原子と合わさって、環状1,2-ジオール保護基を形成する。
R1は、Hまたはアルコール保護基であり;
R2は、Hまたはアルコール保護基である;または
R1とR2は、これらの基が結合する炭素原子と合わさって、環状1,2-ジオール保護基を形成する。
この明細書で言及するあらゆる刊行物と特許出願は、個々の刊行物または特許出願が具体的かつ個別に参考として組み込まれていることが示されているかのようにして参考としてこの明細書に組み込まれている。
1H NMR (CDCl3, 300MHz):δ3.78〜3.86 (m, 1H)、3.71 (dd, 1H)、3.64 (dd, 1H)、2.52 (d, 1H)、2.36〜2.44 (m, 2H)、0.96 (s, 9H)、0.05 (s, 6H)。
1H NMR (CDCl3, 300MHz):δ6.11 (s, 1H)、5.85 (s, 1H)、3.98〜4.07 (m, 1H)、3.74 (dd, 1H)、3.54 (dd, 1H)、2.62 (d, 2H)、2.19 (bs, OH)、1.64 (bs, OH)。
1H NMR (CDCl3, 500MHz):δ3.91〜3.95 (m, 1H)、3.60 (dd, J=10, 5Hz, 1H)、3.47 (dd, J=10, 6Hz, 1H)、1.95 (dd, J=10, 4Hz, 1H)、1.28 (dd, J=10, 6Hz,1H)、0.99〜1.07 (m, 2H)、0.75〜0.90 (m, 2H)、0.89 (s, 18H)、0.12 (s, 3H)、0.08 (s, 3H)、0.04 (s, 6H)。
1H NMR (CDCl3, 500MHz):δ4.31〜4.37 (m, 1H)、4.16 (dd, J=10, 5Hz, 1H)、3.56 (dd, J=10, 8 Hz, 1H)、1.72〜1.80 (m, 2H)、1.35 (s, 6H)、1.04〜1.11 (m, 2H)、0.90〜0.94 (m, 1H)、0.73〜0.77 (m, 1H)。
m/z=255 [M+1]-
m/z=611 [M-1]-
1H NMR (CDCl3, 300MHz):δ3.78〜3.86 (m, 1H)、3.71 (dd, 1H)、3.64 (dd, 1H)、2.52 (d, 1H)、2.36〜2.44 (m, 2H)、0.96 (s, 9H)、0.05 (s, 6H)。
1H NMR (CDCl3, 300MHz):δ6.11 (s, 1H)、5.85 (s, 1H)、3.98〜4.07 (m, 1H)、3.74 (dd, 1H)、3.54 (dd, 1H)、2.62 (d, 2H)、2.19 (bs, OH)、1.64 (bs, OH)。
m/z=182 [M+1]-
1H NMR (500MHz, クロロホルム-d):δppm 1.34 (s, 3H)、1.39 (s, 3H)、2.52 (dd, J=14.49, 6.05Hz, 1H)、2.73 (dd, J=14.67, 6.60Hz, 1H)、3.60 (dd, J=8.16, 6.14Hz, 1H)、4.06 (dd, J=8.07, 6.05Hz, 1H)、4.34 (quin, J=6.28Hz, 1H)、5.78 (d, J=1.10Hz, 1H)、6.13 (d, J=1.10Hz, 1H)。
1H NMR (400MHz, CD3OD):δppm 0.39 (ddd, J=9.85, 6.71, 5.27Hz, 1H)、0.57〜0.76 (m, 2H), 0.76〜0.89 (m, 1H)、1.31 (s, 3H)、1.51 (dd, J=13.30, 2.76Hz, 1H)、1.57 (s, 3H)、1.94〜2.07 (m, 1H)、2.89 (dd, J=13.80, 8.03Hz, 1H)、3.07 (dd, J=13.80, 4.27Hz, 1H)、4.51〜4.62 (m, 1H)。
13C NMR (メタノール-d4)δppm 10.30、15.17、21.75、30.13、38.88、54.79、58.37、67.15、101.78。
Claims (8)
- 前記環状1,2-ジオール保護基が、5員の環状1,2-ジオール保護基である、請求項1又は2に記載の方法。
- 前記環状1,2-ジオール保護基が、2,2-ジメチル-1,3-ジオキソラン-4-イルである、請求項3に記載の方法。
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 |
---|---|
JP2013500242A JP2013500242A (ja) | 2013-01-07 |
JP5776115B2 true JP5776115B2 (ja) | 2015-09-09 |
Family
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Application Number | Title | Priority Date | Filing Date |
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JP2012520927A Expired - Fee Related JP5776115B2 (ja) | 2009-07-24 | 2010-07-10 | (r)−および(s)−n−(3,4−ジフルオロ−2−(2−フルオロ−4−ヨードフェニルアミノ)−6−メトキシフェニル)−1−(2,3−ジヒドロキシプロピル)シクロプロパン−1−スルホンアミドの調製と、その保護された誘導体 |
Country Status (32)
Country | Link |
---|---|
US (3) | US8513443B2 (ja) |
EP (1) | EP2462111B1 (ja) |
JP (1) | JP5776115B2 (ja) |
KR (1) | KR101763437B1 (ja) |
CN (2) | CN103848808B (ja) |
AR (1) | AR079183A1 (ja) |
AU (1) | AU2010275780B2 (ja) |
BR (1) | BR112012001592A2 (ja) |
CA (2) | CA2990097A1 (ja) |
CL (1) | CL2012000192A1 (ja) |
CO (1) | CO6491075A2 (ja) |
CR (1) | CR20120044A (ja) |
CU (1) | CU24113B1 (ja) |
DO (1) | DOP2012000017A (ja) |
EA (1) | EA023623B1 (ja) |
EC (1) | ECSP12011621A (ja) |
GT (1) | GT201200017A (ja) |
HK (2) | HK1171218A1 (ja) |
HN (1) | HN2012000142A (ja) |
IL (1) | IL217312A (ja) |
IN (1) | IN2012DN00696A (ja) |
MA (1) | MA33452B1 (ja) |
MX (2) | MX2012001063A (ja) |
MY (1) | MY160421A (ja) |
NZ (1) | NZ597738A (ja) |
PE (1) | PE20120573A1 (ja) |
PH (1) | PH12014500158A1 (ja) |
SG (1) | SG177535A1 (ja) |
TN (1) | TN2012000027A1 (ja) |
TW (1) | TWI524890B (ja) |
UY (1) | UY32800A (ja) |
WO (1) | WO2011009541A1 (ja) |
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 |
EP2714652B8 (en) * | 2011-05-27 | 2018-09-05 | Ardea Biosciences, Inc. | Chiral synthesis of n-{3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]-6-methoxyphenyl}-1-[2,3-dihydroxy-propyl]cyclopropanesulfonamides |
CN104011039A (zh) * | 2011-12-19 | 2014-08-27 | 住友化学株式会社 | 磺酸盐的制造方法 |
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 |
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US8101799B2 (en) * | 2005-07-21 | 2012-01-24 | Ardea Biosciences | Derivatives of N-(arylamino) sulfonamides as inhibitors of MEK |
SI1912636T1 (sl) * | 2005-07-21 | 2014-08-29 | Ardea Biosciences, Inc. | N-(arilamino)-sulfonamidni inhibitorji MEK |
WO2007121269A2 (en) * | 2006-04-11 | 2007-10-25 | Ardea Biosciences, Inc. | N-aryl-n'alkyl sulfamides as mek inhibitors |
JP5269762B2 (ja) | 2006-04-18 | 2013-08-21 | アーディア・バイオサイエンシーズ・インコーポレイテッド | Mek阻害剤としてのピリドンスルホンアミドおよびピリドンスルファミド |
JP5479337B2 (ja) * | 2007-07-30 | 2014-04-23 | アルディア バイオサイエンス,インク. | Mek阻害剤およびrafキナーゼ阻害剤の組み合わせ、ならびにその使用 |
AU2009236325A1 (en) * | 2008-04-14 | 2009-10-22 | 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 |
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- 2010-07-10 CA CA2768788A patent/CA2768788C/en not_active Expired - Fee Related
- 2010-07-10 US US13/386,519 patent/US8513443B2/en not_active Expired - Fee Related
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- 2010-07-10 CN CN201310670649.XA patent/CN103848808B/zh not_active Expired - Fee Related
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