JP2011513467A5 - - Google Patents
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- Publication number
- JP2011513467A5 JP2011513467A5 JP2010550194A JP2010550194A JP2011513467A5 JP 2011513467 A5 JP2011513467 A5 JP 2011513467A5 JP 2010550194 A JP2010550194 A JP 2010550194A JP 2010550194 A JP2010550194 A JP 2010550194A JP 2011513467 A5 JP2011513467 A5 JP 2011513467A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- compound
- alkoxy
- group
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 22
- -1 1-4C-alkyl Inorganic materials 0.000 claims description 18
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 8
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 238000013329 compounding Methods 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical group CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 0 CC(c(c(C)c1*)c(*)[n]1S(*)(=O)=O)=C(*)C(Cl)=O Chemical compound CC(c(c(C)c1*)c(*)[n]1S(*)(=O)=O)=C(*)C(Cl)=O 0.000 description 7
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08004567.7 | 2008-03-12 | ||
| EP08004567A EP2100878A1 (en) | 2008-03-12 | 2008-03-12 | Novel method for the production of sulphonylpyrroles as HDAC inhibitors |
| PCT/EP2009/052870 WO2009112529A1 (en) | 2008-03-12 | 2009-03-11 | Novel method for the production of sulphonylpyrroles as hdac inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011513467A JP2011513467A (ja) | 2011-04-28 |
| JP2011513467A5 true JP2011513467A5 (https=) | 2014-01-23 |
| JP5530939B2 JP5530939B2 (ja) | 2014-06-25 |
Family
ID=39639400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010550194A Active JP5530939B2 (ja) | 2008-03-12 | 2009-03-11 | Ｈｄａｃ阻害剤としてのスルホニルピロールの新規製造法 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US8785659B2 (https=) |
| EP (2) | EP2100878A1 (https=) |
| JP (1) | JP5530939B2 (https=) |
| KR (1) | KR101571915B1 (https=) |
| CN (1) | CN101970404B (https=) |
| AT (1) | ATE519739T1 (https=) |
| AU (1) | AU2009224623C1 (https=) |
| BR (1) | BRPI0909752B8 (https=) |
| CA (1) | CA2719074C (https=) |
| CY (1) | CY1111994T1 (https=) |
| DK (1) | DK2265580T3 (https=) |
| EA (1) | EA017929B1 (https=) |
| ES (1) | ES2370592T3 (https=) |
| IL (1) | IL207995A (https=) |
| MX (1) | MX2010010015A (https=) |
| NZ (1) | NZ587824A (https=) |
| PL (1) | PL2265580T3 (https=) |
| PT (1) | PT2265580E (https=) |
| SI (1) | SI2265580T1 (https=) |
| UA (1) | UA102091C2 (https=) |
| WO (1) | WO2009112529A1 (https=) |
| ZA (1) | ZA201006422B (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2100882A1 (en) * | 2008-03-12 | 2009-09-16 | 4Sc Ag | (E) -N -(2-Amino-phenyl) -3-{1-[4-(1-methyl-1H-pyrazol-4-yl)- benzenesulfonyl]-1H-pyrrol-3-yl} -acrylamide salts |
| WO2017178577A1 (en) | 2016-04-14 | 2017-10-19 | 4Sc Ag | Medical application of resminostat in asian patients |
| TW201912183A (zh) | 2017-08-31 | 2019-04-01 | 德商４Ｓｃ製藥公司 | Hdac抑制劑與抗代謝藥劑組合用於癌症治療 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4960787A (en) | 1989-02-06 | 1990-10-02 | Ciba-Geigy Corporation | Certain pyrrolyl-substituted hydroxamic acid derivatives |
| KR100236806B1 (ko) | 1991-12-10 | 2000-01-15 | 시오노 요시히코 | 방향족 설폰아미드계 하이드록삼산 유도체 |
| CA2223154A1 (en) | 1995-06-02 | 1996-12-05 | G.D. Searle & Co. | Heterocyclo substituted hydroxamic acid derivatives as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
| HRP20130810T1 (en) | 2004-03-11 | 2013-09-30 | 4Sc Ag | Sulphonylpyrroles as hdac inhibitors |
| PT1861365E (pt) * | 2005-03-15 | 2009-09-22 | 4Sc Ag | N-sulfonilpirroles e a sua utilização como inibidores de histona-desacetilase |
| BRPI0617167B8 (pt) | 2005-09-21 | 2021-05-25 | Nycomed Gmbh | sulfonilpirróis como inibidores de hdac's, seu uso, composição farmacêutica e combinação |
| CN101287706A (zh) | 2005-09-21 | 2008-10-15 | 尼科梅德有限责任公司 | 作为组蛋白脱乙酰基酶抑制剂的磺酰基吡咯盐酸盐 |
-
2008
- 2008-03-12 EP EP08004567A patent/EP2100878A1/en not_active Ceased
-
2009
- 2009-03-11 AT AT09721108T patent/ATE519739T1/de active
- 2009-03-11 BR BRPI0909752A patent/BRPI0909752B8/pt active IP Right Grant
- 2009-03-11 NZ NZ587824A patent/NZ587824A/en unknown
- 2009-03-11 EP EP09721108A patent/EP2265580B1/en active Active
- 2009-03-11 PT PT09721108T patent/PT2265580E/pt unknown
- 2009-03-11 ES ES09721108T patent/ES2370592T3/es active Active
- 2009-03-11 MX MX2010010015A patent/MX2010010015A/es active IP Right Grant
- 2009-03-11 CA CA2719074A patent/CA2719074C/en active Active
- 2009-03-11 JP JP2010550194A patent/JP5530939B2/ja active Active
- 2009-03-11 KR KR1020107020293A patent/KR101571915B1/ko active Active
- 2009-03-11 CN CN2009801082773A patent/CN101970404B/zh active Active
- 2009-03-11 SI SI200930103T patent/SI2265580T1/sl unknown
- 2009-03-11 PL PL09721108T patent/PL2265580T3/pl unknown
- 2009-03-11 DK DK09721108.0T patent/DK2265580T3/da active
- 2009-03-11 US US12/921,928 patent/US8785659B2/en active Active
- 2009-03-11 UA UAA201011865A patent/UA102091C2/ru unknown
- 2009-03-11 AU AU2009224623A patent/AU2009224623C1/en active Active
- 2009-03-11 WO PCT/EP2009/052870 patent/WO2009112529A1/en not_active Ceased
- 2009-03-11 EA EA201001270A patent/EA017929B1/ru not_active IP Right Cessation
-
2010
- 2010-09-05 IL IL207995A patent/IL207995A/en active IP Right Grant
- 2010-09-07 ZA ZA2010/06422A patent/ZA201006422B/en unknown
-
2011
- 2011-11-03 CY CY20111101060T patent/CY1111994T1/el unknown
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