JP2003525279A5 - - Google Patents
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- JP2003525279A5 JP2003525279A5 JP2001563498A JP2001563498A JP2003525279A5 JP 2003525279 A5 JP2003525279 A5 JP 2003525279A5 JP 2001563498 A JP2001563498 A JP 2001563498A JP 2001563498 A JP2001563498 A JP 2001563498A JP 2003525279 A5 JP2003525279 A5 JP 2003525279A5
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- alkyl
- substituted
- amino
- ureido
- carbamoyl
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- 125000000217 alkyl group Chemical group 0.000 claims 67
- -1 amino, phenyl Chemical group 0.000 claims 43
- 229910052757 nitrogen Inorganic materials 0.000 claims 22
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 150000002148 esters Chemical class 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 239000011780 sodium chloride Substances 0.000 claims 14
- 150000003230 pyrimidines Chemical class 0.000 claims 13
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 10
- 125000000304 alkynyl group Chemical group 0.000 claims 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 10
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000003282 alkyl amino group Chemical group 0.000 claims 6
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 5
- 125000005236 alkanoylamino group Chemical group 0.000 claims 5
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- PIEMJWXGWDBCMN-UHFFFAOYSA-N 2-[4-[(4-anilino-5-bromopyrimidin-2-yl)amino]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1NC1=NC=C(Br)C(NC=2C=CC=CC=2)=N1 PIEMJWXGWDBCMN-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- WOWFEFJKHWCYLY-UHFFFAOYSA-N 4-N-[5-bromo-4-(6-methylpyridin-2-yl)pyrimidin-2-yl]-1-N-(2-piperidin-1-ylethyl)benzene-1,4-diamine Chemical compound CC1=CC=CC(C=2C(=CN=C(NC=3C=CC(NCCN4CCCCC4)=CC=3)N=2)Br)=N1 WOWFEFJKHWCYLY-UHFFFAOYSA-N 0.000 claims 1
- DUPNQUDKGLFCEW-UHFFFAOYSA-N 5-bromo-2-N-[4-(1-methylpiperidin-4-yl)oxyphenyl]-4-N-phenylpyrimidine-2,4-diamine Chemical compound C1CN(C)CCC1OC(C=C1)=CC=C1NC1=NC=C(Br)C(NC=2C=CC=CC=2)=N1 DUPNQUDKGLFCEW-UHFFFAOYSA-N 0.000 claims 1
- FLYWDADPUYSEFG-UHFFFAOYSA-N 5-bromo-2-N-[4-[2-(dimethylamino)ethoxy]phenyl]-4-N-phenylpyrimidine-2,4-diamine Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC=C(Br)C(NC=2C=CC=CC=2)=N1 FLYWDADPUYSEFG-UHFFFAOYSA-N 0.000 claims 1
- VGDBUSCPHQFLTB-UHFFFAOYSA-N 5-bromo-4-N-phenyl-2-N-[4-[2-(propan-2-ylamino)ethylamino]phenyl]pyrimidine-2,4-diamine Chemical compound C1=CC(NCCNC(C)C)=CC=C1NC1=NC=C(Br)C(NC=2C=CC=CC=2)=N1 VGDBUSCPHQFLTB-UHFFFAOYSA-N 0.000 claims 1
- 206010059512 Apoptosis Diseases 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 230000001093 anti-cancer Effects 0.000 claims 1
- 230000006907 apoptotic process Effects 0.000 claims 1
- 125000005418 aryl aryl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001743 benzylic group Chemical group 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000022131 cell cycle Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 230000036571 hydration Effects 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 230000005012 migration Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 230000001225 therapeutic Effects 0.000 claims 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 1
Claims (14)
- 式(I)
Gは、−O−または−NR2−であり;
R2は、水素、C1−6アルキル、C3−6アルケニルおよびC3−6アルキニルより選択され;ここにおいて、該C1−6アルキル、C3−6アルケニルおよびC3−6アルキニルは、Rcより選択される1個またはそれより多い基で置換されていてよく;
R1は、水素、ハロ、ヒドロキシ、ニトロ、アミノ、N−(C1−3アルキル)アミノ、N,N−ジ−(C1−3アルキル)アミノ、シアノ、トリフルオロメチル、トリクロロメチル、C1−3アルキル[ハロ、シアノ、アミノ、N−(C1−3アルキル)アミノ、N,N−ジ−(C1−3アルキル)アミノ、ヒドロキシおよびトリフルオロメチルより独立して選択される1個または2個の置換基で置換されていてよい]、C3−5アルケニル[3個までのハロ置換基または1個のトリフルオロメチル置換基で置換されていてよい]、C3−5アルキニル、C1−3アルコキシ、メルカプト、C1−3アルキルスルファニル、カルボキシおよびC1−3アルコキシカルボニルより選択され;
Q1は、ハロ、メルカプト、ニトロ、ホルミル、ホルムアミド、カルボキシ、シアノ、アミノ、ウレイド、カルバモイル、スルファモイル、C1−4アルキル、C2−4アルケニル、C2−4アルキニル[ここにおいて、該C1−4アルキル、C2−4アルケニルおよびC2−4アルキニルは、Rdより選択される1個またはそれより多い基で置換されていてよい]、C1−4アルカノイル、C1−4アルコキシカルボニル、複素環式基、C1−4アルキルS(O)a(式中、aは0〜2である)[ヒドロキシで置換されていてよい]、N’−(C1−4アルキル)ウレイド、N’,N’−ジ−(C1−4アルキル)ウレイド、N’−(C1−4アルキル)−N−(C1−4アルキル)ウレイド、N’,N’−ジ−(C1−4アルキル)−N−(C1−4アルキル)ウレイド、N−C1−4アルキルアミノ、N,N−ジ−(C1−4アルキル)アミノ、N−(C1−4アルキル)スルファモイル、N,N−ジ−(C1−4アルキル)スルファモイル、N−C1−4アルキルカルバモイル、N,N−ジ−(C1−4アルキル)カルバモイルおよびC1−4アルカノイルアミノより独立して選択される1〜4個の置換基で環炭素上に置換されていてよく;そして更に独立して、または上の置換基に加えて、
Q1は、アリール、C3−8シクロアルキルおよび複素環式基より独立して選択される1〜2個の置換基で置換されていてもよく;ここにおいて、該アリール、C3−8シクロアルキルまたは複素環式基は、Reより選択される1個またはそれより多い基で環炭素上に置換されていてもよく;そしてここにおいて、該複素環式基が−NH−部分を含有する場合、その窒素は、Rfより選択される基で置換されていてもよく;
Q2は、ハロ、ヒドロキシ、メルカプト、ニトロ、ホルミル、ホルムアミド、カルボキシ、シアノ、アミノ、ウレイド、カルバモイル、スルファモイル、C1−4アルキル、C2−4アルケニル、C2−4アルキニル、C1−4アルコキシ[ここにおいて、該C1−4アルキル、C2−4アルケニル、C2−4アルキニルおよびC1−4アルコキシは、Rgより選択される1個またはそれより多い基で置換されていてよい]、C1−4アルカノイル、C1−4アルコキシカルボニル、複素環式基、C1−4アルキルS(O)a(式中、aは0〜2である)[ヒドロキシで置換されていてよい]、N’−(C1−4アルキル)ウレイド、N’,N’−ジ−(C1−4アルキル)ウレイド、N’−(C1−4アルキル)−N−(C1−4アルキル)ウレイド、N’,N’−ジ−(C1−4アルキル)−N−(C1−4アルキル)ウレイド、N−C1−4アルキルアミノ、N,N−ジ−(C1−4アルキル)アミノ、N−(C1−4アルキル)スルファモイル、N,N−ジ−(C1−4アルキル)スルファモイル、N−C1−4アルキルカルバモイル、N,N−ジ−(C1−4アルキル)カルバモイル、C2−4アルケニルオキシ、C2−4アルキニルオキシ、C1−4アルカノイルアミノより独立して選択される1〜4個の置換基で環炭素上に置換されていてよく;そして更に独立して、または上の置換基に加えて、
Q2は、アリール、C3−8シクロアルキルまたは複素環式基より独立して選択される1〜2個の置換基で置換されていてもよく;ここにおいて、該アリール、C3−8シクロアルキルまたは複素環式基は、Rhより選択される1個またはそれより多い基で環炭素上に置換されていてもよく;そしてここにおいて、該複素環式基が−NH−部分を含有する場合、その窒素は、Riより選択される基で置換されていてもよく;
Rc、RdおよびRgは、独立して、ヒドロキシ、ハロ、アミノ、シアノ、ホルミル、ホルムアミド、カルボキシ、ニトロ、メルカプト、カルバモイル、スルファモイル、N−C1−4アルキルアミノ、N,N−ジ−(C1−4アルキル)アミノ、C1−4アルカノイル、C1−4アルカノイルオキシ、C1−4アルコキシ、C1−4アルコキシカルボニル、N−C1−4アルキルカルバモイル、N,N−ジ−(C1−4アルキル)カルバモイル、C1−4アルカノイルアミノ、C1−4アルキルS(O)a(式中、aは0〜2である)、C1−4アルキルスルホニルアミノ、N−(C1−4アルキル)スルファモイル、N−(C1−4アルキル)2スルファモイル、N−(C1−4アルキル)カルバモイル、N−(C1−4アルキル)2カルバモイル、フェニル、フェニルチオ、フェノキシ、C3−8シクロアルキルおよび複素環式基より選択され;ここにおいて、該フェニル、フェニルチオ、フェノキシ、C3−8シクロアルキルまたは複素環式基は、Rjより選択される1個またはそれより多い基で環炭素上に置換されていてもよく;そしてここにおいて、該複素環式基が−NH−部分を含有する場合、その窒素は、Rkより選択される基で置換されていてもよく;
Ra、Re、RhおよびRjは、独立して、ヒドロキシ、ハロ、アミノ、シアノ、ホルミル、ホルムアミド、カルボキシ、ニトロ、メルカプト、カルバモイル、スルファモイル、C1−4アルキル[ハロ、シアノ、アミノ、N−C1−4アルキルアミノ、N,N−ジ−(C1−4アルキル)アミノまたはヒドロキシより選択される1個またはそれより多い基で置換されていてよい]、C2−4アルケニル[ハロより選択される1個またはそれより多い基で置換されていてよい]、C2−4アルキニル、N−C1−4アルキルアミノ、N,N−ジ−(C1−4アルキル)アミノ、C1−4アルカノイル、C1−4アルカノイルオキシ、C1−4アルコキシ[ハロより選択される1個またはそれより多い基で置換されていてよい]、C1−4アルコキシカルボニル、N−C1−4アルキルカルバモイル、N,N−ジ−(C1−4アルキル)カルバモイル、C1−4アルカノイルアミノ、C1−4アルキルS(O)a(式中、aは0〜2である)、C1−4アルキルスルホニルアミノ、N−(C1−4アルキル)スルファモイル、N−(C1−4アルキル)2スルファモイル、フェニル、C3−8シクロアルキルおよび複素環式基より選択され;そして
Rb、Rf、RiおよびRkは、独立して、C1−4アルキル、C1−4アルカノイル、C1−4アルキルスルホニル、カルバモイル、N−(C1−4アルキル)カルバモイル、N,N−(C1−4アルキル)カルバモイル、ベンジル、ベンジルオキシカルボニル、ベンゾイルおよびフェニルスルホニルより選択される)
を有するピリミジン誘導体;またはその薬学的に許容しうる塩または in vivo 加水分解性エステル。 - Q1がフェニルである請求項1に記載のピリミジン誘導体、またはその薬学的に許容しうる塩または in vivo 加水分解性エステル。
- Q2がフェニルまたはピリジルである請求項1または2のどちらかに記載のピリミジン誘導体、またはその薬学的に許容しうる塩または in vivo 加水分解性エステル。
- Q1およびQ2の一方またはQ1およびQ2の両方が、ジメチルアミノ、4−メチルピペラジノ、アミノメチル、2−ヒドロキシエトキシメチル、スクシンイミド−1−イルメチル、2−ピロリジン−1−イルエチル、2−アミノエチル、ピペリド−4−イルオキシ、1−メチルピペリド−4−イルオキシ、1−メチルピペリド−3−イルオキシ、カルボキシメトキシ、1−メチルピペリド−2−イルメトキシ、1−メチルピペリド−3−イルメトキシ、ピペリド−4−イルメトキシ、4−イソプロピルピペラジノカルボニルメトキシ、2−フタルイミド−1−イルエトキシ、2−モルホリノエトキシ、2−ジメチルアミノエトキシ、2−ジエチルアミノエトキシ、2−(4−メチルピペラジノ)エトキシ、2−イミダゾール−1−イルエトキシ、2−ピロリジン−1−イルエトキシ、2−アミノエチニル、2−ジメチルアミノエチニル、2−メチルアミノエチニル、2−(3−ヒドロキシキヌクリジン−3−イル)エチニル、2−モルホリノエトキシメチル、2−ジエチルアミノエトキシメチル、2−ピロリジン−1−イルエトキシメチル、2−(4−メチルピペラジノ)エトキシメチル、2−ジエチルアミノエトキシカルボニル、2−ピペリジノエチルアミノまたは2−イソプロピルアミノエチルアミノより選択される1個の置換基で環炭素上に置換されている請求項1〜3のいずれか1項に記載のピリミジン誘導体、またはその薬学的に許容しうる塩または in vivo 加水分解性エステル。
- Q1が、−NH−に相対してパラ位またはメタ位に置換されている請求項1〜4のいずれか1項に記載のピリミジン誘導体、またはその薬学的に許容しうる塩または in vivo 加水分解性エステル。
- Gが−NH−である請求項1〜5のいずれか1項に記載のピリミジン誘導体、またはその薬学的に許容しうる塩または in vivo 加水分解性エステル。
- R1が、水素、クロロまたはブロモである請求項1〜6のいずれか1項に記載のピリミジン誘導体、またはその薬学的に許容しうる塩または in vivo 加水分解性エステル。
- Q2が、置換されていない、またはフルオロ、ブロモ、メチル、メトキシおよびシアノより選択される1個の基で置換されている請求項1〜7のいずれか1項に記載のピリミジン誘導体、またはその薬学的に許容しうる塩または in vivo 加水分解性エステル。
- 4−アニリノ−5−ブロモ−2−[4−(2−ジメチルアミノエトキシ)アニリノ]ピリミジン;
4−アニリノ−5−ブロモ−2−[4−(カルボキシメトキシ)アニリノ]ピリミジン;
4−アニリノ−5−ブロモ−2−[4−(1−メチルピペリド−4−イルオキシ)アニリノ]ピリミジン;
4−(6−メチルピリド−2−イル)−5−ブロモ−2−[4−(2−ピペリド−1−イルエチルアミノ)アニリノ]ピリミジン;
4−アニリノ−5−ブロモ−2−[4−(2−イソプロピルアミノエチルアミノ)アニリノ]ピリミジン;または
4−アニリノ−5−ブロモ−2−[4−(3−メチルアミノ−1−プロピニル)アニリノ]ピリミジン
より選択される請求項1〜8のいずれか1項に記載のピリミジン誘導体、またはその薬学的に許容しうる塩または in vivo 加水分解性エステル。 - 請求項1〜9のいずれか1項に記載のピリミジン誘導体を製造する方法であって、
(a)Gが−NR2−である式(I)の化合物について、式(II)
を有するピリミジンと、式(III)
を有する化合物とを反応させること;
(b)式(IV)
を有するピリミジンと、式(V)
より選択され、その後、必要ならば、
(i)式(I)の化合物を式(I)の別の化合物に変換し;
(ii)保護基を全て除去し;
(iii)薬学的に許容しうる塩または in vivo 加水分解性エステルを形成する方法。 - 請求項1〜9のいずれか1項に記載の式(I)のピリミジン誘導体、またはその薬学的に許容しうる塩または in vivo 加水分解性エステルを薬学的に許容しうる希釈剤または担体と一緒に含む医薬組成物。
- 温血動物の予防的または治療的処置の方法で用いるための請求項1〜9のいずれか1項に記載の式(I)のピリミジン誘導体、またはその薬学的に許容しうる塩または in vivo 加水分解性エステル。
- 薬剤として用いるための請求項1〜9のいずれか1項に記載の式(I)のピリミジン誘導体、またはその薬学的に許容しうる塩または in vivo 加水分解性エステル。
- 温血動物の抗癌細胞周期阻害(抗細胞増殖)作用および/またはFAK阻害(抗細胞移動および/またはアポトーシス誘発)作用の産生で用いるための薬剤の製造における請求項1〜9のいずれか1項に記載の式(I)のピリミジン誘導体、またはその薬学的に許容しうる塩または in vivo 加水分解性エステルの使用。
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