JP2005519932A5 - - Google Patents
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- JP2005519932A5 JP2005519932A5 JP2003567878A JP2003567878A JP2005519932A5 JP 2005519932 A5 JP2005519932 A5 JP 2005519932A5 JP 2003567878 A JP2003567878 A JP 2003567878A JP 2003567878 A JP2003567878 A JP 2003567878A JP 2005519932 A5 JP2005519932 A5 JP 2005519932A5
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- Prior art keywords
- optionally substituted
- alkyl
- groups
- cycloalkyl
- halogen
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000011780 sodium chloride Substances 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 150000002829 nitrogen Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- KKYABQBFGDZVNQ-UHFFFAOYSA-N Losmapimod Chemical compound CC1=C(F)C=C(C(=O)NC2CC2)C=C1C1=CC=C(C(=O)NCC(C)(C)C)C=N1 KKYABQBFGDZVNQ-UHFFFAOYSA-N 0.000 claims 2
- 102100000918 MAPK14 Human genes 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000005842 heteroatoms Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000001404 mediated Effects 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 102000004127 Cytokines Human genes 0.000 claims 1
- 108090000695 Cytokines Proteins 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 0 CC(*)(C=C(C=C=C)N=C1)C=C1C(N(C)*)=O Chemical compound CC(*)(C=C(C=C=C)N=C1)C=C1C(N(C)*)=O 0.000 description 4
- RMEDXVIWDFLGES-UHFFFAOYSA-N COC(c(cc1)cnc1Cl)=O Chemical compound COC(c(cc1)cnc1Cl)=O RMEDXVIWDFLGES-UHFFFAOYSA-N 0.000 description 1
Claims (14)
- 下記式(I)の化合物またはその製薬上許容される塩もしくは溶媒和物。
R1は、水素、C1-6アルコキシ、ハロゲンおよびヒドロキシから選択される3個以下の基によって置換されていても良いC1-6アルキル、C2-6アルケニル、1以上のC1-6アルキル基によって置換されていても良いC3-7シクロアルキル、R5およびR6から選択される3個以下の基によって置換されていても良いフェニル、ならびにR5およびR6から選択される3個以下の基によって置換されていても良いヘテロアリールから選択され;
R2は、水素、C1-6アルキルおよび1以上のC1-6アルキル基によって置換されていても良い-(CH2)q-C3-7シクロアルキルから選択され;
あるいは(CH2)mR1およびR2が、それらが結合している窒素原子と一体となって、3個以下のC1-6アルキル基によって置換されていても良い4〜6員の複素環を形成しており;
R3は、クロロまたはメチルであり;
R4は、基-NH-CO-R7または-CO-NH-(CH2)q-R8であり;
R5は、C1-6アルキル、C1-6アルコキシ、1以上のC1-6アルキル基によって置換されていても良い-(CH2)q-C3-7シクロアルキル、-CONR9R10、-NHCOR10、-SO2NHR9、-(CH2)sNHSO2R10、ハロゲン、CN、OH、-(CH2)sNR11R12およびトリフルオロメチルから選択され;
R6は、C1-6アルキル、C1-6アルコキシ、ハロゲン、トリフルオロメチルおよび-(CH2)sNR11R12から選択され;
R7は、水素、C1-6アルキル、1以上のC1-6アルキル基によって置換されていても良い-(CH2)q-C3-7シクロアルキル、トリフルオロメチル、R13および/またはR14によって置換されていても良い-(CH2)rヘテロアリール、ならびにR13および/またはR14によって置換されていても良い-(CH2)rフェニルから選択され;
R8は、水素、C1-6アルキル、1以上のC1-6アルキル基によって置換されていても良いC3-7シクロアルキル、CONHR9、R13および/またはR14によって置換されていても良いフェニル、ならびにR13および/またはR14によって置換されていても良いヘテロアリールから選択され;
R9およびR10はそれぞれ独立に、水素およびC1-6アルキルから選択され;
あるいはR9とR10が、それらが結合している窒素原子と一体となって、酸素、硫黄およびN-R15から選択される1個の更なるヘテロ原子を有していても良い5〜6員の複素環を形成しており、前記環は2個以下のC1-6アルキル基によって置換されていても良く;
R11は、水素、C1-6アルキルおよび1以上のC1-6アルキル基によって置換されていても良い-(CH2)q-C3-7シクロアルキルから選択され;
R12は、水素およびC1-6アルキルから選択され;
あるいはR11とR12が、それらが結合している窒素原子と一体となって、酸素、硫黄およびN-R15から選択される1個の更なるヘテロ原子を有していても良い5員もしくは6員の複素環を形成しており;
R13は、C1-6アルキル、C1-6アルコキシ、1以上のC1-6アルキル基によって置換されていても良い-(CH2)q-C3-7シクロアルキル、-CONR9R10、-NHCOR10、ハロゲン、CN、-(CH2)sNR11R12、トリフルオロメチル、1以上のR14基によって置換されていても良いフェニルおよび1以上のR14基によって置換されていても良いヘテロアリールから選択され;
R14は、C1-6アルキル、C1-6アルコキシ、ハロゲン、トリフルオロメチルおよび-NR11R12から選択され;
R15は、水素およびメチルから選択され;
XおよびYはそれぞれ独立に、水素、メチルおよびハロゲンから選択され;
Zはハロゲンであり;
mは0、1、2、3および4から選択され、得られる炭素鎖の各炭素原子はC1-6アルキルおよびハロゲンから独立に選択される2個以下の基によって置換されていても良く;
nは、0、1および2から選択され;
qは、0、1および2から選択され;
rは、0および1から選択され;
sは、0、1、2および3から選択される。] - R1が、C1-6アルキル、C2-6アルケニル、1以上のC1-6アルキル基によって置換されていても良いC3-7シクロアルキル、R5およびR6から選択される3個以下の置換基によって置換されていても良いフェニル、R5およびR6から選択される3個以下の置換基によって置換されていても良いヘテロアリールから選択される請求項1に記載の化合物。
- R2が水素である請求項1または請求項2に記載の化合物。
- R3がメチルである請求項1〜3のいずれかに記載の化合物。
- Xがフッ素である請求項1〜4のいずれかに記載の化合物。
- R7が、C1-6アルキル、-(CH2)q-C3-7シクロアルキル、トリフルオロメチル、R13および/またはR14によって置換されていても良い-(CH2)rヘテロアリール、ならびにC1-6アルキル、C1-6アルコキシ、-(CH2)q-C3-7シクロアルキル、-CONR9R10、-NHCOR10、ハロゲン、CN、トリフルオロメチル、1以上のR14基によって置換されていても良いフェニルおよび/または1以上のR14基によって置換されていても良いヘテロアリールによって置換されていても良い-(CH2)rフェニルから選択される請求項1〜5のいずれかに記載の化合物。
- R8が、C3-7シクロアルキル、CONHR9、R13および/またはR14によって置換されていても良いヘテロアリール、ならびにC1-6アルキル、C1-6アルコキシ、-(CH2)q-C3-7シクロアルキル、-CONR9R10、-NHCOR10、ハロゲン、CN、トリフルオロメチル、1以上のR14基によって置換されていても良いフェニルおよび/または1以上のR14基によって置換されていても良いヘテロアリールによって置換されていても良いフェニルから選択される請求項1〜6のいずれかに記載の化合物。
- 実施例1〜123のいずれかで定義される請求項1に記載の化合物。
- 6-(5-シクロプロピルカルバモイル-3-フルオロ-2-メチル-フェニル)-N-(2,2-ジメチルプロピル)-ニコチンアミドである請求項1に記載の化合物またはその製薬上許容される塩もしくは溶媒和物。
- 6-(5-シクロプロピルカルバモイル-3-フルオロ-2-メチル-フェニル)-N-(2,2-ジメチルプロピル)-ニコチンアミドである請求項1に記載の化合物。
- 1以上の製薬上許容される担体、希釈剤または賦形剤との混合で請求項1〜10のいずれかに記載の化合物またはその製薬上許容される塩もしくは溶媒和物を含む医薬組成物。
- 治療において使用するための請求項1〜10のいずれかに記載の化合物またはその製薬上許容される塩もしくは溶媒和物。
- p38キナーゼ活性が介在するまたはp38キナーゼの活性によって産生されるサイトカイン類が介在する状態または疾患状態の治療において使用するための医薬の製造における請求項1〜10のいずれかに記載の化合物またはその製薬上許容される塩もしくは溶媒和物。
- 請求項1〜10のいずれかに記載の化合物またはその製薬上許容される塩もしくは溶媒和物を製造する方法において、
(a)下記式(II)の化合物:
(b)下記式(VIII)の化合物:
(c)上記で定義される式(II)の化合物を下記式(IX)の化合物:
を有する方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0203301.7A GB0203301D0 (en) | 2002-02-12 | 2002-02-12 | Novel compounds |
GB0225385A GB0225385D0 (en) | 2002-10-31 | 2002-10-31 | Novel compounds |
PCT/GB2003/000554 WO2003068747A1 (en) | 2002-02-12 | 2003-02-10 | Nicotinamide derivates useful as p38 inhibitors |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010005100A Division JP2010111699A (ja) | 2002-02-12 | 2010-01-13 | p38阻害薬として有用なニコチンアミド誘導体 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2005519932A JP2005519932A (ja) | 2005-07-07 |
JP2005519932A5 true JP2005519932A5 (ja) | 2006-02-02 |
JP4472349B2 JP4472349B2 (ja) | 2010-06-02 |
Family
ID=27736200
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003567878A Expired - Lifetime JP4472349B2 (ja) | 2002-02-12 | 2003-02-10 | p38阻害薬として有用なニコチンアミド誘導体 |
JP2010005100A Pending JP2010111699A (ja) | 2002-02-12 | 2010-01-13 | p38阻害薬として有用なニコチンアミド誘導体 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010005100A Pending JP2010111699A (ja) | 2002-02-12 | 2010-01-13 | p38阻害薬として有用なニコチンアミド誘導体 |
Country Status (26)
Country | Link |
---|---|
US (5) | US7125898B2 (ja) |
EP (3) | EP1474395B1 (ja) |
JP (2) | JP4472349B2 (ja) |
KR (1) | KR101058292B1 (ja) |
CN (1) | CN100369898C (ja) |
AT (2) | ATE375980T1 (ja) |
AU (1) | AU2003207298B2 (ja) |
BR (1) | BRPI0307351B8 (ja) |
CA (1) | CA2474192C (ja) |
CO (1) | CO5611147A2 (ja) |
CY (2) | CY1107117T1 (ja) |
DE (2) | DE60334651D1 (ja) |
DK (2) | DK1474395T3 (ja) |
ES (2) | ES2295553T3 (ja) |
HK (2) | HK1113056A1 (ja) |
IL (1) | IL163090A (ja) |
IS (1) | IS2520B (ja) |
MX (1) | MXPA04007838A (ja) |
NO (1) | NO327418B1 (ja) |
NZ (1) | NZ533865A (ja) |
PL (1) | PL212910B1 (ja) |
PT (2) | PT1474395E (ja) |
RU (1) | RU2309951C2 (ja) |
SI (2) | SI1864975T1 (ja) |
WO (1) | WO2003068747A1 (ja) |
ZA (1) | ZA200405602B (ja) |
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- 2003-02-10 EP EP07117575A patent/EP1864975B1/en not_active Expired - Lifetime
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- 2003-02-10 SI SI200331042T patent/SI1474395T1/sl unknown
- 2003-02-10 EP EP10180693A patent/EP2258687B1/en not_active Expired - Lifetime
- 2003-02-10 MX MXPA04007838A patent/MXPA04007838A/es active IP Right Grant
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2004
- 2004-06-28 IS IS7337A patent/IS2520B/is unknown
- 2004-07-14 ZA ZA2004/05602A patent/ZA200405602B/en unknown
- 2004-07-19 IL IL163090A patent/IL163090A/en not_active IP Right Cessation
- 2004-07-26 NO NO20043176A patent/NO327418B1/no not_active IP Right Cessation
- 2004-08-12 CO CO04078826A patent/CO5611147A2/es active IP Right Grant
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2005
- 2005-04-29 HK HK08103321.6A patent/HK1113056A1/xx not_active IP Right Cessation
- 2005-04-29 HK HK05103699A patent/HK1070896A1/xx not_active IP Right Cessation
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2006
- 2006-08-07 US US11/462,851 patent/US7709506B2/en active Active
- 2006-08-07 US US11/462,858 patent/US7514456B2/en active Active
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2007
- 2007-12-28 CY CY20071101642T patent/CY1107117T1/el unknown
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2010
- 2010-01-13 JP JP2010005100A patent/JP2010111699A/ja active Pending
- 2010-02-26 US US12/713,448 patent/US8575204B2/en not_active Expired - Lifetime
- 2010-02-26 US US12/713,433 patent/US8252818B2/en not_active Expired - Lifetime
- 2010-12-08 CY CY20101101128T patent/CY1111083T1/el unknown
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