JP2013500242A - (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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- JP2013500242A JP2013500242A JP2012520927A JP2012520927A JP2013500242A JP 2013500242 A JP2013500242 A JP 2013500242A JP 2012520927 A JP2012520927 A JP 2012520927A JP 2012520927 A JP2012520927 A JP 2012520927A JP 2013500242 A JP2013500242 A JP 2013500242A
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- cyclopropane
- dimethyl
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- dioxolan
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- 0 CC1(C)O[C@@](CC2(*NC3(C[C@]4OC(C)(C)OC4)CC3)CC2)CO1 Chemical compound CC1(C)O[C@@](CC2(*NC3(C[C@]4OC(C)(C)OC4)CC3)CC2)CO1 0.000 description 3
- FRPCAHHPHLTDDV-ZETCQYMHSA-N CC1(C)O[C@@H](CC(S(Cl)(=O)=O)=C)CO1 Chemical compound CC1(C)O[C@@H](CC(S(Cl)(=O)=O)=C)CO1 FRPCAHHPHLTDDV-ZETCQYMHSA-N 0.000 description 1
- XZKWFWOCXKFYCF-ZETCQYMHSA-N CC1(C)O[C@@H](CC2(CC2)S(Cl)(=O)=O)CO1 Chemical compound CC1(C)O[C@@H](CC2(CC2)S(Cl)(=O)=O)CO1 XZKWFWOCXKFYCF-ZETCQYMHSA-N 0.000 description 1
- FRPCAHHPHLTDDV-SSDOTTSWSA-N CC1(C)O[C@H](CC(S(Cl)(=O)=O)=C)CO1 Chemical compound CC1(C)O[C@H](CC(S(Cl)(=O)=O)=C)CO1 FRPCAHHPHLTDDV-SSDOTTSWSA-N 0.000 description 1
- UOFAGKYEGBTZCZ-UHFFFAOYSA-N COc(cc(c(F)c12)F)c1NC(c1ccccc1)N2c(ccc(I)c1)c1F Chemical compound COc(cc(c(F)c12)F)c1NC(c1ccccc1)N2c(ccc(I)c1)c1F UOFAGKYEGBTZCZ-UHFFFAOYSA-N 0.000 description 1
- FFXPFPGDIKMCEA-UHFFFAOYSA-O COc(cc(c(F)c1N(c2ccccc2)c(ccc(I)c2)c2F)F)c1[NH3+] Chemical compound COc(cc(c(F)c1N(c2ccccc2)c(ccc(I)c2)c2F)F)c1[NH3+] FFXPFPGDIKMCEA-UHFFFAOYSA-O 0.000 description 1
- YPFLLTAFCYQUGO-UHFFFAOYSA-N COc(cc(c(F)c1N2c(ccc(I)c3)c3F)F)c1NC2=O Chemical compound COc(cc(c(F)c1N2c(ccc(I)c3)c3F)F)c1NC2=O YPFLLTAFCYQUGO-UHFFFAOYSA-N 0.000 description 1
- RMBTUHCPHHKBJX-UHFFFAOYSA-N COc(cc(c(F)c1Nc(ccc(I)c2)c2F)F)c1Nc1ccccc1 Chemical compound COc(cc(c(F)c1Nc(ccc(I)c2)c2F)F)c1Nc1ccccc1 RMBTUHCPHHKBJX-UHFFFAOYSA-N 0.000 description 1
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- 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
- 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
- C07D317/26—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)
Abstract
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 (11)
- R1とR2が、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、請求項1〜4のいずれか1項に記載の方法。
- 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5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6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 |
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Publication Number | Publication Date |
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JP2013500242A true JP2013500242A (ja) | 2013-01-07 |
JP5776115B2 JP5776115B2 (ja) | 2015-09-09 |
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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 |
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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 |
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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 |
KR101939682B1 (ko) * | 2011-05-27 | 2019-01-17 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | N-{3,4-디플루오로-2-〔(2-플루오로-4-요오도페닐)아미노〕-6-메톡시페닐}-1-[2,3-디하이드록시프로필]사이클로프로판설폰아미드의 키랄 합성 |
EP2796455A4 (en) * | 2011-12-19 | 2015-08-19 | Sumitomo Chemical Co | PROCESS FOR PRODUCING SULFONATE |
EP2848246A1 (en) | 2013-09-13 | 2015-03-18 | Bayer Pharma Aktiengesellschaft | Pharmaceutical compositions containing refametinib |
Citations (2)
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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 |
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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 |
CA2649122C (en) | 2006-04-18 | 2015-06-30 | 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 |
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 |
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Patent Citations (2)
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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 |
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