JP4533138B2 - キナーゼ阻害剤としての縮環ヘテロ環式ピラゾール誘導体 - Google Patents
キナーゼ阻害剤としての縮環ヘテロ環式ピラゾール誘導体 Download PDFInfo
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- JP4533138B2 JP4533138B2 JP2004525180A JP2004525180A JP4533138B2 JP 4533138 B2 JP4533138 B2 JP 4533138B2 JP 2004525180 A JP2004525180 A JP 2004525180A JP 2004525180 A JP2004525180 A JP 2004525180A JP 4533138 B2 JP4533138 B2 JP 4533138B2
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- Prior art keywords
- thieno
- pyrazole
- carboxamide
- amino
- formula
- Prior art date
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- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 102000009076 src-Family Kinases Human genes 0.000 description 1
- 108010087686 src-Family Kinases Proteins 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 102000013498 tau Proteins Human genes 0.000 description 1
- 108010026424 tau Proteins Proteins 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ZGOVQMMKMXMZSH-UHFFFAOYSA-N tert-butyl 4-cyano-5-hydrazinylthiophene-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CC(C#N)=C(NN)S1 ZGOVQMMKMXMZSH-UHFFFAOYSA-N 0.000 description 1
- RKSOPLXZQNSWAS-UHFFFAOYSA-N tert-butyl bromide Chemical compound CC(C)(C)Br RKSOPLXZQNSWAS-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- OJJOFKKOLNCPOX-UHFFFAOYSA-N thiophen-2-ylhydrazine Chemical compound NNC1=CC=CS1 OJJOFKKOLNCPOX-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 229960002004 valdecoxib Drugs 0.000 description 1
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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Description
XはNR', O, S, SO又はSO2から選択される基であり;
R及びR1のそれぞれは、同一であるか又は異なって、独立的に、水素、若しくはR',-COR',-COOR',-CONHR',-CONR'R",-SO2R',-SO2NHR'又は-SO2NR'R"から選択される任意に置換された基であり;
ここで、R'及びR"のそれぞれは、同一であるか又は異なって、水素、若しくは任意にさらに置換された直鎖又は分枝鎖の、C1-C6アルキル、ヘテロシクリル、アリール又はアリール-C1-C6アルキル基から独立的に選択される;
R2は、R',-CH2OR'及びOR'から選択される任意に置換された基であり、ここでR'は、上記で定義されたものである。
XはNR', O, S, SO又はSO2であり;
R及びR1のそれぞれは、同一であるか又は異なって、独立的に、水素原子若しくはR',-COR',-COOR',-CONHR',-CONR'R",-SO2R',-SO2NHR'又は-SO2NR'R"から選択される任意に置換された基であり;
ここで、R'及びR"のそれぞれは、同一であるか又は異なって、水素若しくは任意にさらに置換された直鎖又は分枝鎖の、C1-C6アルキル、ヘテロシクリル、アリール、又はアリール-C1-C6アルキル基から独立的に選択される;
R2は、R',-CH2OR'及びOR'から選択される任意に置換された基であり、ここでR'は、上記で定義されたものである。
b)このようにして得られた式(I)の化合物を、他の式(I)の化合物(ここで、Rは水素原子以外である)に転換すること;及び/又は、必要であれば、該式(I)の化合物を薬学的に許容されるそれらの塩に転換すること、及び/又は該式(I)の化合物の塩をそれらの遊離化合物に転換することを含む。
a)上記で定義された式(II)の化合物を、ヒドラジン又はヒドラジン塩と反応させ、式(I)の化合物(ここで、Rは水素であり、R1、R2及びXは上記で定義されたものである)を得ること;
a’)このようにして得られた式(I)の化合物を、式(III)のアルキルクロロカルボネートと反応させ、
R3-O-CO-Cl (III)
(ここで、R3は低級アルキルである)、ヘテロ環ピラゾール窒素原子で保護された式(IV)の化合物を得ること:
c)アルカリ性条件下で保護基を切断して、所望の式(I)の化合物を得ること、及び、必要であれば、このようにして得られた式(I)の化合物を、他の式(I)の化合物に転換すること;及び/又は、必要であれば、該式(I)の化合物を薬学的に許容されるそれらの塩に転換すること、及び/又は該それらの塩を、式(I)の遊離化合物に転換することを含む。
a'')上記工程(a)で得られ、Rが水素原子である式(I)の化合物を、クロロギ酸のeccess、或いは式(IIIa)又は(IIIb)のそれぞれの塩化アシル誘導体と反応させ、
R’-O-CO-Cl (IIIa) R’-CO-Cl (IIIb)
(ここで、R’は上記で定義されたものである)
それぞれ式(Va)又は(Vb)の化合物を得ること:
a''')式(I)の化合物(ここで、Rは水素原子であり、R1、R2及びXは上記で定義されたものである)を、式(VI)のイソシアネートポリスチレン樹脂と反応させ、
c'')アルカリ性条件下で、式(VIII)の化合物を切断して樹脂を除去すること、及び、そのように所望の式(I)の化合物を得ること、及び、必要であれば、得られた式(I)の化合物を他の式(I)の化合物に転換すること;及び/又は、必要であれば、式(I)の化合物を薬学的に許容されるそれらの塩に、及び/又は該それらの塩を式(I)の遊離化合物に転換すること、を含む。
R−Y (IX)
(ここでRは水素以外の上記された意味であり、Yは適切な脱離基、好ましくは塩素又は臭素である)と反応させることによって調製され得る。
R’NCO (X)
(ここで、R’は水素以外の上記で定義されたものである)と反応させることによって調製されうる。
R''−Y (XI)
(ここでR'’は、水素以外の上記で定義されたものであり、Yは適切な脱離基、好ましくは塩素又は臭素である)、対応する式(I)、(V)又は(VIII)の化合物(ここでRは−CONR'R''であり、R’及びR''は水素以外である)を得ることができる。
R’R''NH (XII)
(ここで、R’及びR''は水素以外の上記で定義されたものである)と反応させることによって調製され得る。
R’-CHO (XIII)
(ここでR’は、水素以外の上記定義されたものである)と反応されて、対応する式(I)又は(V)の化合物(ここでRはR’CH2-基であり、R’は水素以外の上記定義されたものである)を得ることができる。
R’R''NH (XII)
(ここで、R’及びR''は、上記定義のとおりである)と反応させることによって調製され得る。
R’Li (XIV)
(ここで、R’は水素以外の上記で定義されたものである)と反応させることによって調製され得る。
R’OH (XV)
(ここでR’は、水素以外の上記定義のとおりである)と反応させることによって調製される。
R’−Y (XVI)
(ここでR’は、水素以外の上記定義のとおりであり、Yは適切な脱離基、好ましくは塩素又は臭素である)との反応を介して都合よく調製され得る。
R’−Y (XVI)
(ここでR’は、水素以外の上記定義のとおりであり、Yは適切な脱離基、好ましくは塩素又は臭素である)との反応を介して、都合よく調製されうる。後者の反応は、水素化ナトリウム、tBuOK、炭酸カリウム、水酸化カリウムなどのような塩基の存在下において、トルエン、ジクロロメタン、クロロホルム、ジエチルエーテル、テトラヒドロフラン、アセトニトリル、N,N−ジメチルホルムアミド又はジメチルスルホキシドのような適切な溶媒中において、約−10℃から還流の温度範囲において実行されうる。
R’-Y (XVI)
(ここで、R’は水素以外の上記定義のとおりであり、Yは上記定義の通りの適切な脱離基である)と反応させ、R2として-CH2OR’又はOR’基を有する対応する化合物を得ることができる。
(ここにおいて、
Xは、NR', O, S, SO又はSO2であり;
R及びR1のそれぞれは、同一であるか又は異なって、独立的に、水素原子若しくはR',-COR',-COOR',-CONHR',-CONR'R",-SO2R',-SO2NHR'又は-SO2NR'R"から選択される任意に置換された基であり;
ここで、R'及びR"のそれぞれは、同一であるか又は異なって、水素若しくは任意にさらに置換された直鎖又は分枝鎖のC1-C6アルキル、ヘテロシクリル、アリール、又はアリール-C1-C6アルキル基から独立的に選択される;
R2は、R',-CH2OR'及びOR'から選択される任意に置換された基であり、ここでR'は上記で定義されたものである)は、本発明のさらなる目的である。
XはNR', O, S, SO又はSO2であり;
R及びR1のそれぞれは、同一であるか又は異なって、独立的に、水素原子若しくはR',-COR',-COOR',-CONHR',-CONR'R",-SO2R',-SO2NHR'又は-SO2NR'R"から選択される任意に置換された基であり;
ここで、R'及びR"のそれぞれは、同一であるか又は異なって、水素若しくは任意にさらに置換された直鎖又は分枝鎖の、C1-C6アルキル、ヘテロシクリル、アリール、又はアリール-C1-C6アルキル基から独立的に選択される;
R2は、R',-CH2OR'及びOR'から選択される任意に置換された基であり、ここでR'は、上記で定義されたものである。
式(I)の化合物は、タンパク質キナーゼ阻害剤として活性であり、それ故、例えば腫瘍細胞の制御されない増殖を制限するのに有用である。
キナーゼ反応:最終容積30 μlのバッファー(トリスHCl 10 mM pH 7.5、MgCl2 10 mM, DTT 7.5 mM + 0.2 mg/ml BSA)中の4 μMの自社製ビオチン化ヒストンH1 (Sigma# H-5505)基質、10μM ATP (0.1マイクロCiP33γ-ATP), 1.1 nM サイクリン A/CDK2 複合体、阻害剤を、96 U底のそれぞれのウェルに添加した。室温で60分インキュベーションした後、32 mM EDTA、500μM コールドATP、0.1% トリトンX100 及び10mg/mlの ストレプトアビジンでコーティングしたSPAビーズを含む100μlのPBS バッファーを加えて反応を停止した。20分のインキュベーションの後、110μLの懸濁液を回収し、100μlの5M CsClを含む96穴オプティプレートに移した。4時間後、パッカードTOP-カウント放射能リーダーで該プレートを2分間読み取った。
y = 最低+(最高−最低)/(1+10^((logIC50-x)*傾き))
ここで、Xは阻害剤濃度の対数であり、yは応答であり;yは最低から開始してシグモイド形状で最高に達する。
実験方法:反応は、3.7 nM 酵素、ヒストン及びATP (コールド/標識ATPの一定割合 1/3000)を含むバッファー(10 mM Tris, pH 7.5, 10 mM MgCl2, 0.2 mg/ml BSA, 7.5 mM DTT)中で行った。反応をEDTAで停止し、基質をリン酸膜(ミリポア製マルチスクリーン96穴プレート)で捕捉した。広範に洗浄した後、マルチスクリーンプレートをトップカウンターで読み取った。ATP及びヒストン濃度のそれぞれの対照(時間0)を測定した。
キナーゼ反応:最終容積30μlのバッファー (トリスHCl 10 mM pH 7.5, MgCl2 10 mM, DTT 7.5 mM + 0.2 mg/ml BSA)中の、10μMの自社製のビオチン標識化ヒストンH1 (Sigma# H-5505) 基質, 30μMのATP (0.3マイクロCiP33γ-ATP), 4 ng GST-サイクリンE/CDK2複合体、阻害剤を、96 U 底の各ウェルに添加した。室温で60分インキュベーションした後、32 mM EDTA、500μMのコールドATP、0.1% トリトンX100 及び10mg/mlのストレプトアビジンでコーティングされたSPAビーズを含む、100μlのPBS バッファーを添加して反応を停止した。20分のインキュベーションの後、110μLの懸濁液を回収し、100μlの5M CsClを含む、96-ウェルオプティプレート(OPTIPLATEs)に移した。4時間後、このプレートを、パッカードTOP-カウント放射能リーダーで2分間読み取った。
キナーゼ反応: 最終容積が30μlのバッファー(トリス HCl 10 mM pH 7.5、MgCl2 10 mM, DTT 7.5 mM + 0.2 mg/ml BSA) 中の、4μMの 自社製のビオチン標識化ヒストンH1 (Sigma# H-5505) 基質, 20μM ATP (0.2マイクロCiP33γ-ATP), 3 ng サイクリンB/CDK1複合体、阻害剤を、96 U 底の各ウェルに添加した。室温で20分インキュベーションした後、1 mgのSPAビーズを含む、100μl PBS + 32 mM EDTA + 0.1% トリトンX-100 + 500μM ATPを添加して反応を停止した。次いで、容積110μlをオプティプレートに移した。基質を捕捉するための20分のインキュベーションの後、100μlの5M CsCl を添加して、ビーズのスタティフィケーション(statification)をオプティプレートの最高(top)にし、そしてトップ−カウント装置で放射能をカウントする前に4時間静置した。
cdk5/p25活性の阻害アッセイは、以下のプロトコルに従って行われる。
キナーゼ反応:最終容積50μlのバッファー(トリスHCl 10 mM pH 7.5, MgCl2 10mM, 7.5 mM DTT+0.2 mg/ml BSA)中の、0.4μMのマウスGST-Rb(769-921)(# sc-4112、Santa Cruz製)基質、10μM ATP(0.5μCi P33γ-ATP)、100 ngのバキュロウイルス発現GST-cdk4/GST-サイクリン D1、適切な濃度の阻害剤を、96U底ウェルプレートの各ウェルに添加した。37℃で40分間インキュベーションした後、20μlのEDTA 120 mMで反応を停止した。
キナーゼ反応:最終容積が30μlのバッファー (トリスHCl 10 mM pH 7.5、MgCl2 10 mM, DTT 7.5 mM + 0.2 mg/ml BSA)中の、10 μMの自社製ビオチン標識化MBP (Sigma# M-1891) 基質, 15μM ATP (0.15 マイクロCiP33γ-ATP), 30 ng GST-MAPK (Upstate Biothecnology# 14-173)、阻害剤を、96 U 底の各ウェルに添加した。室温で35分間インキュベーションした後、32 mM EDTA, 500 μMコールドATP、0.1% トリトンX100 及びlOmg/ml ストレプトアビジンでコーティングされたSPAビーズを含む、100 μlの PBS バッファーを加えて反応を停止した。20分のインキュベーション後、110μlの懸濁液を回収し、100μlの5M CsClを含む、96-穴オプティプレートに移した。4時間後、このプレートを、パッカードTOP-カウント放射能リーダーで2分間読み取った。
キナーゼ反応:最終容積が30 μlのバッファー(トリスHCl 10 mM pH 7.5, MgCl2 10 mM, DTT 7.5 mM + 0.2 mg/ml BSA)中の、10μMの自社製のビオチン標識化ヒストンH1 (Sigma# H-5505) 基質、10μMのATP (0.2マイクロMP33γ-ATP)、0.45 UのPKA (Sigma# 2645)、阻害剤を、96 U底の各ウェルに添加した。室温で90分インキュベーションした後、32 mM EDTA, 500 μMコールドATP, 0.1% トリトンX100 及び10mg/ml ストレプトアビジンでコーティングされたSPAビーズを含む、100μlのPBSバッファーを添加して反応を停止した。20分のインキュベーション後、110μlの懸濁液を回収し、100μlの5M CsClを含む、96-穴オプティプレートに移した。4時間後、このプレートを、パッカードTOP-カウント放射能リーダーで2分間読み取った。
キナーゼ反応:最終容積30μlのバッファー (Hepes 50 mM pH 7.5, MgCl2 3 mM,MnCl2 3 mM, DTT 1 mM,NaVO3 3μM, + 0.2 mg/ml BSA)中の、10 μMの自社製ビオチン標識化MBP (Sigma# M-1891) 基質, 2μM ATP (0.04 マイクロCiP33γ-ATP), 36 ng 昆虫細胞発現GST-EGFR,阻害剤を、96 U 底の各ウェルに添加した。室温で20分インキュベーションした後、32 mM EDTA, 500μM コールドATP, 0.1% トリトンX100 及び10mg/ml ストレプトアビジンでコーティングされたSPAビーズを含む100 μl PBS バッファーを添加して反応を停止した。20分インキュベーションした後、110μLの懸濁液を回収し、100 μlの5M CsClを含む96穴オプティプレートに移した。4時間後、このプレートを、パッカードTOP-カウント放射能リーダーで2分間読み取った。
IGF1-R活性の阻害アッセイは、以下のプロトコルで行った。
キナーゼ反応:最終容積30μlのバッファー(HEPES 50 mM pH 7.0,MgCl2 10 mM,1 mM DTT, 0.2 mg/ml BSA, 3 μM オルトバナデート)中の、8μM ビオチン標識化ペプチド (LRRWSLGの4回繰り返し), 10μM ATP (0.5 uCi P33γ-ATP), 7.5 ng アウロラ2, 阻害剤を、96U底ウェルプレートの各ウェルに添加した。室温で60分インキュベーションした後、100 μlのビーズ懸濁液を加えて反応を停止し、ビオチン標識化ペプチドを捕捉した。
Cdc7/dbf4活性の阻害アッセイは、以下のプロトコルで行われる。
− 10 μlの基質(ビオチン標識化MCM2、6μM 最終濃度)
− 10 μlの酵素(Cdc7/Dbf4、17.9 nM 最終濃度)
− 10 μlの試験化合物(投与-応答曲線を作成するために、nM〜μMの範囲で増加する12の濃度)
− 10 μlのコールドATP(2μM 最終濃度)と放射能活性ATP(コールドATPと1/5000モーラーの割合)の混合物を、37℃で起こる反応を開始させるために用いた。
下記の合成例で特定される化合物の分析において、以下のHPLC法を用いた。ここで用いられる用語「Rt」は、特定されたHPLC法を用いての、化合物の保持時間を表す。
HPLC/MSは、996ウォーターズPDA検出器及びマイクロマス mod. ZQ シングル四極子質量分析器スペクトロメータを装備し、エレクトロスプレー(ESI)イオン源を装備した、ウォーターズ2790 HPLCシステムを用いて、ウォーターズXテラRP 18 (4.6 x 50 mm, 3. 5μm)カラムで行った。移動相Aは、酢酸アンモニウム5 mM バッファー (pH 5.5 、酢酸/アセトニトリル95:5)であり、移動相Bは、H2O/アセトニトリル(5:95)であった。勾配は8分で10〜90%B、90%Bを2分間保持。UV検出は220 nm及び254 nm。流速1 ml/分。注入容量10 μl。フルスキャン、質量範囲100〜800 amu。キャピラリ電位は2.5 KV;ソース温度は120℃;コーンは10V。保持時間(HPLC r.t.)は、220 nm又は254 nmで数分与えられる。質量は、m/z比で与えられる。
HPLC/MSは、ポリマーLabs PL1000 蒸発光散乱検出器及びマイクロマスZMD質量スペクトロメータを装備し、エレクトロスプレー(ESI)イオン源を装備した、ヒューレットパッカード1312A HPLC システムを用いて、ハイパーシルC18 BDS (2 x 50 mm, 5μm)カラムを用いて行った。移動相Aは、トリフルオロ酢酸の水溶液(0.1% v/v)であり、移動相Bはトリフルオロ酢酸のアセトニトリル溶液(0.1% v/v)であった。勾配は0〜95%B、1.8分、95%Bで0.3分保持。流速1 ml/分。注入容量3 μl。フルスキャン、質量範囲150〜800 amu。ソース温度は140℃;コーンは25V。保持時間(HPLC r.t.)は、数分与えられる。質量は、m/z比で与えられる。
4-シアノ-5-(メチルチオ)チオフェン-2-カルボン酸
水酸化ナトリウム水溶液(20% w/w 溶液, 9mL)を、1,4-ジオキサン(100mL)中の4-シアノ-5-(メチルチオ)チオフェン-2-カルボン酸エチル(10g,44mmol)の溶液に5℃で添加した。
tert-ブチル 4-シアノ-5-(メチルチオ)チオフェン-2-カルボキシレート
ジメチルアセトアミド(100mL)中の4-シアノ-5-(メチルチオ)チオフェン-2-カルボン酸(2.0g,10mmol)、塩化ベンジルトリメチルアンモニウム(2.25g,10mmol)、tertブチルブロミド(54mL,480mmol)、及び無水炭酸カリウム(36g,260mmol)の混合物を60℃で6時間撹拌した。
tert-ブチル 4-シアノ-5-(メチルスルホニル)チオフェン-2-カルボキシレート
ジメチルホルムアミド(100mL)中のtert-ブチル4-シアノ-5-(メチルチオ)チオフェン-2-カルボキシレート (1.4g,5.5mmol)及びオキソン(14.4g,21.5mmol)の混合物を室温で16時間撹拌した。次いでこの反応混合物を氷/水(400mL)中に注ぎ、酢酸エチルを用いて抽出した。有機層を水で洗浄し、無水硫酸ナトリウムで乾燥させ、蒸発させて1.5gの標題化合物を得た。
tert-ブチル 4-シアノ-5-ヒドラジノチオフェン-2-カルボキシレート
メチルアルコール(30mL)中のtert-ブチル4-シアノ-5-(メチルスルホニル)チオフェン-2-カルボキシレート (2.0g,7.0mmol)及び水酸化ヒドラジン(1.7mL)の混合物を60℃で2時間撹拌した。この反応混合物を酢酸エチル(100mL)を用いて希釈し、水を用いて洗浄した。有機層を分離し、無水硫酸ナトリウムで乾燥させ、蒸発させた。クロマトグラフィー(n-ヘキサン/酢酸エチル 3:2)により精製して1gの標題化合物を得た。
tert-ブチル3-アミノ-1H-チエノ[2,3-c]ピラゾール-5-カルボキシレート
メチルアルコール(15mL)中のtert-ブチル4-シアノ-5-ヒドラジノチオフェン-2-カルボキシレート (1.0g,4.2mmol)及び塩酸(0.7mLの37%溶液)の混合物を室温で14時間撹拌した。この反応混合物を酢酸エチル(50mL)を用いて希釈し、重炭酸ナトリウム水溶液を用いて洗浄した。有機層を分離し、無水硫酸ナトリウムで乾燥させ、蒸発させて0.9gの標題化合物を得た。
本発明の目的である方法に従い、上述の例に記載のとおりに操作することにより、かつ適切な開始物質から開始することにより、以下の式(I)の化合物を得ることができる:
1.N-ベンジル-3-[(4-フルオロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
2.N-エチル-3-{[4-(4-エチルピペラジン-1-イル)ベンゾイル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
3.3-{[4-(4-エチルピペラジン-1-イル)ベンゾイル]アミノ}-N-イソプロピル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
4.N-ベンジル-3-{[4-(4-エチルピペラジン-1-イル)ベンゾイル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
5.N-{5-[(4-メチルピペラジン-1-イル)カルボニル]-1H-チエノ[2,3-c]ピラゾール-3-イル}ベンズアミド;
6.N-[5-(モルホリン-4-イルカルボニル)-1H-チエノ[2,3-c]ピラゾール-3-イル]ベンズアミド;
7.3-(ベンゾイルアミノ)-N-(2-モルホリン-4-イルエチル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
8.3-(ベンゾイルアミノ)-N-フェニル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
9.3-(ベンゾイルアミノ)-N-(2-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
10.3-(ベンゾイルアミノ)-N-(4-シアノフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
11.3-(ベンゾイルアミノ)-N-(4-フルオロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
12.3-(ベンゾイルアミノ)-N-(4-クロロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
13.3-(ベンゾイルアミノ)-N-(4-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
14.3-(ベンゾイルアミノ)-N-(4-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
15.3-(ベンゾイルアミノ)-N-(tert-ブチル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
16.3-(ベンゾイルアミノ)-N-イソプロピル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
17.3-(ベンゾイルアミノ)-N-エチル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
18.2-フルオロ-N-{5-[(4-メチルピペラジン-1-イル)カルボニル]-1H-チエノ[2,3-c]ピラゾール-3-イル}ベンズアミド;
19.2-フルオロ-N-[5-(モルホリン-4-イルカルボニル)-1H-チエノ[2,3-c]ピラゾール-3-イル]ベンズアミド;
20.3-[(2-フルオロベンゾイル)アミノ]-N-(2-モルホリン-4-イルエチル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
21.3-[(2-フルオロベンゾイル)アミノ]-N-フェニル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
22.3-[(2-フルオロベンゾイル)アミノ]-N-(2-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
23.N-(4-シアノフェニル)-3-[(2-フルオロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
24.3-[(2-フルオロベンゾイル)アミノ]-N-(4-フルオロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
25.N-(4-クロロフェニル)-3-[(2-フルオロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
26.3-[(2-フルオロベンゾイル)アミノ]-N-(4-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
27.3-[(2-フルオロベンゾイル)アミノ]-N-(4-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
28.N-(tert-ブチル)-3-[(2-フルオロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
29.3-[(2-フルオロベンゾイル)アミノ]-N-イソプロピル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
30.N-エチル-3-[(2-フルオロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
31.2-クロロ-N-{5-[(4-メチルピペラジン-1-イル)カルボニル]-1H-チエノ[2,3-c]ピラゾール-3-イル}ベンズアミド;
32.2-クロロ-N-[5-(モルホリン-4-イルカルボニル)-1H-チエノ[2,3-c]ピラゾール-3-イル]ベンズアミド;
33.3-[(2-クロロベンゾイル)アミノ]-N-(2-モルホリン-4-イルエチル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
34.3-[(2-クロロベンゾイル)アミノ]-N-フェニル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
35.3-[(2-クロロベンゾイル)アミノ]-N-(2-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
36.3-[(2-クロロベンゾイル)アミノ]-N-(4-シアノフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
37.3-[(2-クロロベンゾイル)アミノ]-N-(4-フルオロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
38.3-[(2-クロロベンゾイル)アミノ]-N-(4-クロロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
39.3-[(2-クロロベンゾイル)アミノ]-N-(4-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
40.3-[(2-クロロベンゾイル)アミノ]-N-(4-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
41.N-(tert-ブチル)-3-[(2-クロロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
42.3-[(2-クロロベンゾイル)アミノ]-N-イソプロピル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
43.3-[(2-クロロベンゾイル)アミノ]-N-エチル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
44.2-メトキシ-N-{5-[(4-メチルピペラジン-1-イル)カルボニル]-1H-チエノ[2,3-c]ピラゾール-3-イル}ベンズアミド;
45.2-メトキシ-N-[5-(モルホリン-4-イルカルボニル)-1H-チエノ[2,3-c]ピラゾール-3-イル]ベンズアミド;
46.3-[(2-メトキシベンゾイル)アミノ]-N-(2-モルホリン-4-イルエチル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
47.3-[(2-メトキシベンゾイル)アミノ]-N-フェニル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
48.3-[(2-メトキシベンゾイル)アミノ]-N-(2-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
49.N-(4-シアノフェニル)-3-[(2-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
50.N-(4-フルオロフェニル)-3-[(2-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
51.N-(4-クロロフェニル)-3-[(2-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
52.3-[(2-メトキシベンゾイル)アミノ]-N-(4-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
53.3-[(2-メトキシベンゾイル)アミノ]-N-(4-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
54.N-(tert-ブチル)-3-[(2-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
55.N-イソプロピル-3-[(2-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
56.N-エチル-3-[(2-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
57.2-メチル-N-{5-[(4-メチルピペラジン-1-イル)カルボニル]-1H-チエノ[2,3-c]ピラゾール-3-イル}ベンズアミド;
58.2-メチル-N-[5-(モルホリン-4-イルカルボニル)-1H-チエノ[2,3-c]ピラゾール-3-イル]ベンズアミド;
59.3-[(2-メチルベンゾイル)アミノ]-N-(2-モルホリン-4-イルエチル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
60.3-[(2-メチルベンゾイル)アミノ]-N-フェニル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
61.3-[(2-メチルベンゾイル)アミノ]-N-(2-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
62.N-(4-シアノフェニル)-3-[(2-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
63.N-(4-フルオロフェニル)-3-[(2-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
64.N-(4-クロロフェニル)-3-[(2-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
65.N-(4-メトキシフェニル)-3-[(2-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
66.3-[(2-メチルベンゾイル)アミノ]-N-(4-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
67.N-(tert-ブチル)-3-[(2-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
68.N-イソプロピル-3-[(2-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
69.N-エチル-3-[(2-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
70.3-メチル-N-{5-[(4-メチルピペラジン-1-イル)カルボニル]-1H-チエノ[2,3-c]ピラゾール-3-イル}ベンズアミド;
71.3-メチル-N-[5-(モルホリン-4-イルカルボニル)-1H-チエノ[2,3-c]ピラゾール-3-イル]ベンズアミド;
72.3-[(3-メチルベンゾイル)アミノ]-N-(2-モルホリン-4-イルエチル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
73.3-[(3-メチルベンゾイル)アミノ]-N-フェニル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
74.3-[(3-メチルベンゾイル)アミノ]-N-(2-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
75.N-(4-シアノフェニル)-3-[(3-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
76.N-(4-フルオロフェニル)-3-[(3-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
77.N-(4-クロロフェニル)-3-[(3-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
78.N-(4-メトキシフェニル)-3-[(3-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
79.3-[(3-メチルベンゾイル)アミノ]-N-(4-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
80.N-(tert-ブチル)-3-[(3-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
81.N-イソプロピル-3-[(3-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
82.N-エチル-3-[(3-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
83.4-フルオロ-N-{5-[(4-メチルピペラジン-1-イル)カルボニル]-1H-チエノ[2,3-c]ピラゾール-3-イル}ベンズアミド;
84.4-フルオロ-N-[5-(モルホリン-4-イルカルボニル)-1H-チエノ[2,3-c]ピラゾール-3-イル]ベンズアミド;
85.3-[(4-フルオロベンゾイル)アミノ]-N-(2-モルホリン-4-イルエチル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
86.3-[(4-フルオロベンゾイル)アミノ]-N-フェニル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
87.3-[(4-フルオロベンゾイル)アミノ]-N-(2-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
88.N-(4-シアノフェニル)-3-[(4-フルオロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
89.3-[(4-フルオロベンゾイル)アミノ]-N-(4-フルオロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
90. N-(4-クロロフェニル)-3-[(4-フルオロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
91. 3-[(4-フルオロベンゾイル)アミノ]-N-(4-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
92. 3-[(4-フルオロベンゾイル)アミノ]-N-(4-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
93.N-(tert-ブチル)-3-[(4-フルオロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
94.3-[(4-フルオロベンゾイル)アミノ]-N-イソプロピル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
95.N-エチル-3-[(4-フルオロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
96.4-クロロ-N-{5-[(4-メチルピペラジン-1-イル)カルボニル]-1H-チエノ[2,3-c]ピラゾール-3-イル}ベンズアミド;
97.4-クロロ-N-[5-(モルホリン-4-イルカルボニル)-1H-チエノ[2,3-c]ピラゾール-3-イル]ベンズアミド;
98.3-[(4-クロロベンゾイル)アミノ]-N-(2-モルホリン-4-イルエチル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
99.3-[(4-クロロベンゾイル)アミノ]-N-フェニル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
100.3-[(4-クロロベンゾイル)アミノ]-N-(2-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
101.3-[(4-クロロベンゾイル)アミノ]-N-(4-シアノフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
102.3-[(4-クロロベンゾイル)アミノ]-N-(4-フルオロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
103.3-[(4-クロロベンゾイル)アミノ]-N-(4-クロロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
104.3-[(4-クロロベンゾイル)アミノ]-N-(4-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
105.3-[(4-クロロベンゾイル)アミノ]-N-(4-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
106.N-(tert-ブチル)-3-[(4-クロロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
107.3-[(4-クロロベンゾイル)アミノ]-N-イソプロピル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
108.3-[(4-クロロベンゾイル)アミノ]-N-エチル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
109.4-メトキシ-N-5-[(4-メチルピペラジン-1-イル)カルボニル]-1H-チエノ[2,3-c]ピラゾール-3-イル}ベンズアミド;
110.4-メトキシ-N-[5-(モルホリン-4-イルカルボニル)]-1H-チエノ[2,3-c]ピラゾール-3-イル]ベンズアミド;
111.3-[(4-メトキシベンゾイル)アミノ]-N-(2-モルホリン-4-イルエチル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
112.3-[(4-メトキシベンゾイル)アミノ]-N-フェニル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
113.3-[(4-メトキシベンゾイル)アミノ]-N-(2-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
114.N-(4-シアノフェニル)-3-[(4-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
115.N-(4-フルオロフェニル)-3-[(4-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
116.N-(4-クロロフェニル)-3-[(4-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
117.3-[(4-メトキシベンゾイル)アミノ]-N-(4-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
118.3-[(4-メトキシベンゾイル)アミノ]-N-(4-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
119.N-(tert-ブチル)-3-[(4-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
120.N-イソプロピル-3-[(4-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
121.N-エチル-3-[(4-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
122.4-tert-ブチル-N-{5-[(4-メチルピペラジン-1-イル)カルボニル]-1H-チエノ[2,3-c]ピラゾール-3-イル}ベンズアミド;
123.4-tert-ブチル-N-[5-(モルホリン-4-イルカルボニル)-1H-チエノ[2,3-c]ピラゾール-3-イル]ベンズアミド;
124.3-[(4-tert-ブチルベンゾイル)アミノ]-N-(2-モルホリン-4-イルエチル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
125.3-[(4-tert-ブチルベンゾイル)アミノ]-N-フェニル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
126.3-[(4-tert-ブチルベンゾイル)アミノ]-N-(2-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
127.3-[(4-tert-ブチルベンゾイル)アミノ]-N-(4-シアノフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
128.3-[(4-tert-ブチルベンゾイル)アミノ]-N-(4-フルオロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
129.3-[(4-tert-ブチルベンゾイル)アミノ]-N-(4-クロロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
130.3-[(4-tert-ブチルベンゾイル)アミノ]-N-(4-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
131.3-[(4-tert-ブチルベンゾイル)アミノ]-N-(4-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
132.N-(tert-ブチル)-3-[(4-tert-ブチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
133.3-[(4-tert-ブチルベンゾイル)アミノ]-N-イソプロピル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
134.3-[(4-tert-ブチルベンゾイル)アミノ]-N-エチル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
135.4-メチル-N-{5-[(4-メチルピペラジン-1-イル)カルボニル]-1H-チエノ[2,3-c]ピラゾール-3-イル}ベンズアミド;
136.4-メチル-N-[5-(モルホリン-4-イルカルボニル)-1H-チエノ[2,3-c]ピラゾール-3-イル]ベンズアミド;
137.3-[(4-メチルベンゾイル)アミノ]-N-(2-モルホリン-4-イルエチル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
138.3-[(4-メチルベンゾイル)アミノ]-N-フェニル-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
139.3-[(4-メチルベンゾイル)アミノ]-N-(2-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
140.N-(4-シアノフェニル)-3-[(4-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
141.N-(4-フルオロフェニル)-3-[(4-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
142.N-(4-クロロフェニル)-3-[(4-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
143.N-(4-メトキシフェニル)-3-[(4-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
144.3-[(4-メチルベンゾイル)アミノ]-N-(4-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
145.N-(tert-ブチル)-3-[(4-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
146.N-イソプロピル-3-[(4-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
147.N-エチル-3-[(4-メチルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
148.3-[(3-フルオロベンゾイル)アミノ]-N-(4-モルホリン-4-イルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
149.N-(2-シアノフェニル)-3-[(3-フルオロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
150.3-[(3-フルオロベンゾイル)アミノ]-N-(2-フルオロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
151.N-(2-クロロフェニル)-3-[(3-フルオロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
152.N-(2,6-ジクロロフェニル)-3-[(3-フルオロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
153.3-[(3-フルオロベンゾイル)アミノ]-N-(2-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
154.N-(2,6-ジエチルフェニル)-3-[(3-フルオロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
155.N-(3-シアノフェニル)-3-[(3-フルオロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
156.3-[(3-フルオロベンゾイル)アミノ]-N-(3-フルオロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
157.N-(3-クロロフェニル)-3-[(3-フルオロベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
158.3-[(3-フルオロベンゾイル)アミノ]-N-(3-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
159.3-[(3-フルオロベンゾイル)アミノ]-N-(3-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
160.3-[(3-フルオロベンゾイル)アミノ]-N-[4-(4-メチルピペラジン-1-イル)フェニル]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
161.3-[(3-クロロベンゾイル)アミノ]-N-(4-モルホリン-4-イルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
162.3-[(3-クロロベンゾイル)アミノ]-N-(2-シアノフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
163.3-[(3-クロロベンゾイル)アミノ]-N-(2-フルオロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
164.3-[(3-クロロベンゾイル)アミノ]-N-(2-クロロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
165.3-[(3-クロロベンゾイル)アミノ]-N-(2,6-ジクロロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
166.3-[(3-クロロベンゾイル)アミノ]-N-(2-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
167.3-[(3-クロロベンゾイル)アミノ]-N-(2,6-ジエチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
168.3-[(3-クロロベンゾイル)アミノ]-N-(3-シアノフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
169.3-[(3-クロロベンゾイル)アミノ]-N-(3-フルオロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
170.3-[(3-クロロベンゾイル)アミノ]-N-(3-クロロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
171.3-[(3-クロロベンゾイル)アミノ]-N-(3-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
172.3-[(3-クロロベンゾイル)アミノ]-N-(3-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
173.3-[(3-クロロベンゾイル)アミノ]-N-[4-(4-メチルピペラジン-1-イル)フェニル]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
174.3-[(3-メトキシベンゾイル)アミノ]-N-(4-モルホリン-4-イルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
175.N-(2-シアノフェニル)-3-[(3-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
176.N-(2-フルオロフェニル)-3-[(3-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
177.N-(2-クロロフェニル)-3-[(3-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
178.N-(2,6-ジクロロフェニル)-3-[(3-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
179.3-[(3-メトキシベンゾイル)アミノ]-N-(2-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
180.N-(2,6-ジエチルフェニル)-3-[(3-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
181.N-(3-シアノフェニル)-3-[(3-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
182.N-(3-フルオロフェニル)-3-[(3-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
183.N-(3-クロロフェニル)-3-[(3-メトキシベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
184.3-[(3-メトキシベンゾイル)アミノ]-N-(3-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
185.3-[(3-メトキシベンゾイル)アミノ]-N-(3-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
186.3-[(3-メトキシベンゾイル)アミノ]-N-[4-(4-メチルピペラジン-1-イル)フェニル]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
187.N-(4-モルホリン-4-イルフェニル)-3-[(フェニルアセチル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
188.N-(2-シアノフェニル)-3-[(フェニルアセチル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
189.N-(2-フルオロフェニル)-3-[(フェニルアセチル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
190.N-(2-クロロフェニル)-3-[(フェニルアセチル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
191.N-(2,6-ジクロロフェニル)-3-[(フェニルアセチル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
192.N-(2-メトキシフェニル)-3-[(フェニルアセチル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
193.N-(2,6-ジエチルフェニル)-3-[(フェニルアセチル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
194.N-(3-シアノフェニル)-3-[(フェニルアセチル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
195.N-(3-フルオロフェニル)-3-[(フェニルアセチル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
196.N-(3-クロロフェニル)-3-[(フェニルアセチル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
197.N-(3-メトキシフェニル)-3-[(フェニルアセチル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
198.N-(3-メチルフェニル)-3-[(フェニルアセチル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
199.N-[4-(4-メチルピペラジン-1-イル)フェニル]-3-[(フェニルアセチル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
200.3-{[(2-フルオロフェニル)アセチル]アミノ}-N-(4-モルホリン-4-イルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
201.N-(2-シアノフェニル)-3-{[(2-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
202.N-(2-フルオロフェニル)-3-{[(2-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
203.N-(2-クロロフェニル)-3-{[(2-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
204.N-(2,6-ジクロロフェニル)-3-{[(2-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
205.3-{[(2-フルオロフェニル)アセチル]アミノ}-N-(2-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
206.N-(2,6-ジエチルフェニル)-3-{[(2-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
207.N-(3-シアノフェニル)-3-{[(2-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
208.N-(3-フルオロフェニル)-3-{[(2-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
209.N-(3-クロロフェニル)-3-{[(2-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
210.3-{[(2-フルオロフェニル)アセチル]アミノ}-N-(3-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
211.3-{[(2-フルオロフェニル)アセチル]アミノ}-N-(3-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
212.3-{[(2-フルオロフェニル)アセチル]アミノ}-N-[4-(4-メチルピペラジン-1-イル)フェニル]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
213.3-{[(2-メチルフェニル)アセチル]アミノ}-N-(4-モルホリン-4-イルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
214.N-(2-シアノフェニル)-3-{[(2-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
215.N-(2-フルオロフェニル)-3-{[(2-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
216.N-(2-クロロフェニル)-3-{[(2-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
217.N-(2,6-ジクロロフェニル)-3-{[(2-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
218.N-(2-メトキシフェニル)-3-{[(2-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
219.N-(2,6-ジエチルフェニル)-3-{[(2-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
220.N-(3-シアノフェニル)-3-{[(2-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
221.N-(3-フルオロフェニル)-3-{[(2-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
222.N-(3-クロロフェニル)-3-{[(2-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
223.N-(3-メトキシフェニル)-3-{[(2-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
224.N-(3-メチルフェニル)-3-{[(2-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
225.3-{[(2-メチルフェニル)アセチル]アミノ}-N-[4-(4-メチルピペラジン-1-イル)フェニル]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
226.3-{[(4-フルオロフェニル)アセチル]アミノ}-N-(4-モルホリン-4-イルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
227.N-(2-シアノフェニル)-3-{[(4-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
228.N-(2-フルオロフェニル)-3-{[(4-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
229.N-(2-クロロフェニル)-3-{[(4-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
230.N-(2,6-ジクロロフェニル)-3-{[(4-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
231.3-{[(4-フルオロフェニル)アセチル]アミノ}-N-(2-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
232.N-(2,6-ジエチルフェニル)-3-{[(4-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
233.N-(3-シアノフェニル)-3-{[(4-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
234.N-(3-フルオロフェニル)-3-{[(4-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
235.N-(3-クロロフェニル)-3-{[(4-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
236.3-{[(4-フルオロフェニル)アセチル]アミノ}-N-(3-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
237.3-{[(4-フルオロフェニル)アセチル]アミノ}-N-(3-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
238.3-{[(4-フルオロフェニル)アセチル]アミノ}-N-[4-(4-メチルピペラジン-1-イル)フェニル]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
239.3-{[(4-クロロフェニル)アセチル]アミノ}-N-(4-モルホリン-4-イルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
240.3-{[(4-クロロフェニル)アセチル]アミノ}-N-(2-シアノフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
241.3-{[(4-クロロフェニル)アセチル]アミノ}-N-(2-フルオロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
242.N-(2-クロロフェニル)-3-{[(4-クロロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
243.3-{[(4-クロロフェニル)アセチル]アミノ}-N-(2,6-ジクロロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
244.3-{[(4-クロロフェニル)アセチル]アミノ}-N-(2-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
245.3-{[(4-クロロフェニル)アセチル]アミノ}-N-(2,6-ジエチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
246.3-{[(4-クロロフェニル)アセチル]アミノ}-N-(3-シアノフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
247.3-{[(4-クロロフェニル)アセチル]アミノ}-N-(3-フルオロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
248.N-(3-クロロフェニル)-3-{[(4-クロロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
249.3-{[(4-クロロフェニル)アセチル]アミノ}-N-(3-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
250.3-{[(4-クロロフェニル)アセチル]アミノ}-N-(3-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
251.3-{[(4-クロロフェニル)アセチル]アミノ}-N-[4-(4-メチルピペラジン-1-イル)フェニル]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
252.3-{[(4-メトキシフェニル)アセチル]アミノ}-N-(4-モルホリン-4-イルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
253.N-(2-シアノフェニル)-3-{[(4-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
254.N-(2-フルオロフェニル)-3-{[(4-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
255.N-(2-クロロフェニル)-3-{[(4-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
256.N-(2,6-ジクロロフェニル)-3-{[(4-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
257.N-(2-メトキシフェニル)-3-{[(4-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
258.N-(2,6-ジエチルフェニル)-3-{[(4-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
259.N-(3-シアノフェニル)-3-{[(4-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
260.N-(3-フルオロフェニル)-3-{[(4-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
261.N-(3-クロロフェニル)-3-{[(4-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
262.N-(3-メトキシフェニル)-3-{[(4-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
263.3-{[(4-メトキシフェニル)アセチル]アミノ}-N-(3-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
264.3-{[(4-メトキシフェニル)アセチル]アミノ}-N-[4-(4-メチルピペラジン-1-イル)フェニル]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
265.3-{[(4-メチルフェニル)アセチル]アミノ}-N-(4-モルホリン-4-イルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
266.N-(2-シアノフェニル)-3-{[(4-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
267.N-(2-フルオロフェニル)-3-{[(4-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
268.N-(2-クロロフェニル)-3-{[(4-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
269.N-(2,6-ジクロロフェニル)-3-{[(4-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
270.N-(2-メトキシフェニル)-3-{[(4-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
271.N-(2,6-ジエチルフェニル)-3-{[(4-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
272.N-(3-シアノフェニル)-3-{[(4-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
273.N-(3-フルオロフェニル)-3-{[(4-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
274.N-(3-クロロフェニル)-3-{[(4-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
275.N-(3-メトキシフェニル)-3-{[(4-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
276.N-(3-メチルフェニル)-3-{[(4-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
277.3-{[(4-メチルフェニル)アセチル]アミノ}-N-[4-(4-メチルピペラジン-1-イル)フェニル]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
278.3-{[(4-tert-ブチルフェニル)アセチル]アミノ}-N-(4-モルホリン-4-イルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
279.3-{[(4-tert-ブチルフェニル)アセチル]アミノ}-N-(2-シアノフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
280.3-{[(4-tert-ブチルフェニル)アセチル]アミノ}-N-(2-フルオロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
281.3-{[(4-tert-ブチルフェニル)アセチル]アミノ}-N-(2-クロロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
282.3-{[(4-tert-ブチルフェニル)アセチル]アミノ}-N-(2,6-ジクロロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
283.3-{[(4-tert-ブチルフェニル)アセチル]アミノ}-N-(2-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
284.3-{[(4-tert-ブチルフェニル)アセチル]アミノ}-N-(2,6-ジエチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
285.3-[(4-tert-ブチルフェニル)アセチル]アミノ}-N-(3-シアノフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
286.3-{[(4-tert-ブチルフェニル)アセチル]アミノ}-N-(3-フルオロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
287.3-{[(4-tert-ブチルフェニル)アセチル]アミノ}-N-(3-クロロフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
288.3-{[(4-tert-ブチルフェニル)アセチル]アミノ}-N-(3-メトキシフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
289.3-{[(4-tert-ブチルフェニル)アセチル]アミノ}-N-(3-メチルフェニル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
290.3-{[(4-tert-ブチルフェニル)アセチル]アミノ}-N-[4-(4-メチルピペラジン-1-イル)フェニル]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
291.N-ベンジル-3-{[(2-クロロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
292.3-{[(2-クロロフェニル)アセチル]アミノ}-N-(2-フルオロベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
293.N-(2-クロロベンジル)-3-{[(2-クロロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
294.3-{[(2-クロロフェニル)アセチル]アミノ}-N-(2-メトキシベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
295.3-{[(2-クロロフェニル)アセチル]アミノ}-N-(2-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
296.3-{[(2-クロロフェニル)アセチル]アミノ}-N-(3-フルオロベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
297.3-{[(2-クロロフェニル)アセチル]アミノ}-N-(3-メトキシベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
298.3-{[(2-クロロフェニル)アセチル]アミノ}-N-(3-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
299.3-{[(2-クロロフェニル)アセチル]アミノ}-N-(4-フルオロベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
300.N-(4-クロロベンジル)-3-{[(2-クロロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
301.3-{[(2-クロロフェニル)アセチル]アミノ}-N-(4-メトキシベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
302.3-{[(2-クロロフェニル)アセチル]アミノ}-N-(4-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
303.N-(3-クロロベンジル)-3-{[(2-クロロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
304.N-ベンジル-3-{[(2-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
305.N-(2-フルオロベンジル)-3-{[(2-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
306.N-(2-クロロベンジル)-3-{[(2-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
307.N-(2-メトキシベンジル)-3-{[(2-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
308.3-{[(2-メトキシフェニル)アセチル]アミノ}-N-(2-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
309.N-(3-フルオロベンジル)-3-{[(2-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
310.N-(3-メトキシベンジル)-3-{[(2-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
311.3-{[(2-メトキシフェニル)アセチル]アミノ}-N-(3-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
312.N-(4-フルオロベンジル)-3-{[(2-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
313.N-(4-クロロベンジル)-3-{[(2-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
314.N-(4-メトキシベンジル)-3-{[(2-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
315.3-{[(2-メトキシフェニル)アセチル]アミノ}-N-(4-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
316.N-(3-クロロベンジル)-3-{[(2-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
317.N-ベンジル-3-{[(3-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
318.N-(2-フルオロベンジル)-3-{[(3-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
319.N-(2-クロロベンジル)-3-{[(3-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
320.3-{[(3-フルオロフェニル)アセチル]アミノ}-N-(2-メトキシベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
321.3-{[(3-フルオロフェニル)アセチル]アミノ}-N-(2-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
322.N-(3-フルオロベンジル)-3-{[(3-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
323.3-{[(3-フルオロフェニル)アセチル]アミノ}-N-(3-メトキシベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
324.3-{[(3-フルオロフェニル)アセチル]アミノ}-N-(3-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
325.N-(4-フルオロベンジル)-3-{[(3-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
326.N-(4-クロロベンジル)-3-{[(3-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
327.3-{[(3-フルオロフェニル)アセチル]アミノ}-N-(4-メトキシベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
328.3-{[(3-フルオロフェニル)アセチル]アミノ}-N-(4-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
329.N-(3-クロロベンジル)-3-{[(3-フルオロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
330.N-ベンジル-3-{[(3-クロロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
331.3-{[(3-クロロフェニル)アセチル]アミノ}-N-(2-フルオロベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
332.N-(2-クロロベンジル)-3-{[(3-クロロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
333.3-{[(3-クロロフェニル)アセチル]アミノ}-N-(2-メトキシベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
334.3-{[(3-クロロフェニル)アセチル]アミノ}-N-(2-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
335.3-{[(3-クロロフェニル)アセチル]アミノ}-N-(3-フルオロベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
336.3-{[(3-クロロフェニル)アセチル]アミノ}-N-(3-メトキシベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
337.3-{[(3-クロロフェニル)アセチル]アミノ}-N-(3-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
338.3-{[(3-クロロフェニル)アセチル]アミノ}-N-(4-フルオロベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
339.N-(4-クロロベンジル)-3-{[(3-クロロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
340.3-{[(3-クロロフェニル)アセチル]アミノ}-N-(4-メトキシベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
341.3-{[(3-クロロフェニル)アセチル]アミノ}-N-(4-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
342.N-(3-クロロベンジル)-3-{[(3-クロロフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
343.N-ベンジル-3-{[(3-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
344.N-(2-フルオロベンジル)-3-{[(3-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
345.N-(2-クロロベンジル)-3-{[(3-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
346.N-(2-メトキシベンジル)-3-{[(3-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
347.3-{[(3-メトキシフェニル)アセチル]アミノ}-N-(2-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
348.N-(3-フルオロベンジル)-3-{[(3-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
349.N-(3-メトキシベンジル)-3-{[(3-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
350.3-{[(3-メトキシフェニル)アセチル]アミノ}-N-(3-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
351.N-(4-フルオロベンジル)-3-{[(3-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
352.N-(4-クロロベンジル)-3-{[(3-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
353.N-(4-メトキシベンジル)-3-{[(3-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
354.3-[(3-メトキシフェニル)アセチル]アミノ}-N-(4-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
355.N-(3-クロロベンジル)-3-{[(3-メトキシフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
356.N-ベンジル-3-{[(3-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
357.N-(2-フルオロベンジル)-3-{[(3-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
358.N-(2-クロロベンジル)-3-{[(3-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
359.N-(2-メトキシベンジル)-3-{[(3-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
360.N-(2-メチルベンジル)-3-{[(3-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
361.N-(3-フルオロベンジル)-3-{[(3-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
362.N-(3-メトキシベンジル)-3-{[(3-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
363.N-(3-メチルベンジル)-3-{[(3-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
364.N-(4-フルオロベンジル)-3-{[(3-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
365.N-(4-クロロベンジル)-3-{[(3-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
366.N-(4-メトキシベンジル)-3-{[(3-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
367.N-(4-メチルベンジル)-3-{[(3-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
368.N-(3-クロロベンジル)-3-{[(3-メチルフェニル)アセチル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
369.N-ベンジル-3-[(チエン-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
370.N-(2-フルオロベンジル)-3-[(チエン-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
371.N-(2-クロロベンジル)-3-[(チエン-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
372.N-(2-メトキシベンジル)-3-[(チエン-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
373.N-(2-メチルベンジル)-3-[(チエン-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
374.N-(3-フルオロベンジル)-3-[(チエン-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
375.N-(3-メトキシベンジル)-3-[(チエン-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
376.N-(3-メチルベンジル)-3-[(チエン-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
377.N-(4-フルオロベンジル)-3-[(チエン-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
378.N-(4-クロロベンジル)-3-[(チエン-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
379.N-(4-メトキシベンジル)-3-[(チエン-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
380.N-(4-メチルベンジル)-3-[(チエン-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
381.N-(3-クロロベンジル)-3-[(チエン-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
382.N-ベンジル-3-(イソニコチノイルアミノ)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
383.N-(2-フルオロベンジル)-3-(イソニコチノイルアミノ)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
384.N-(2-クロロベンジル)-3-(イソニコチノイルアミノ)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
385.3-(イソニコチノイルアミノ)-N-(2-メトキシベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
386.3-(イソニコチノイルアミノ)-N-(2-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
387.N-(3-フルオロベンジル)-3-(イソニコチノイルアミノ)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
388.3-(イソニコチノイルアミノ)-N-(3-メトキシベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
389.3-(イソニコチノイルアミノ)-N-(3-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
390.N-(4-フルオロベンジル)-3-(イソニコチノイルアミノ)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
391.N-(4-クロロベンジル)-3-(イソニコチノイルアミノ)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
392.3-(イソニコチノイルアミノ)-N-(4-メトキシベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
393.3-(イソニコチノイルアミノ)-N-(4-メチルベンジル)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
394.N-(3-クロロベンジル)-3-(イソニコチノイルアミノ)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
395.N-ベンジル-3-[(1,3-チアゾール-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
396.N-(2-フルオロベンジル)-3-[(1,3-チアゾール-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
397.N-(2-クロロベンジル)-3-[(1,3-チアゾール-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
398.N-(2-メトキシベンジル)-3-[(1,3-チアゾール-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
399.N-(2-メチルベンジル)-3-[(1,3-チアゾール-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
400.N-(3-フルオロベンジル)-3-[(1,3-チアゾール-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
401.N-(3-メトキシベンジル)-3-[(1,3-チアゾール-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
402.N-(3-メチルベンジル)-3-[(1,3-チアゾール-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
403.N-(4-フルオロベンジル)-3-[(1,3-チアゾール-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
404.N-(4-クロロベンジル)-3-[(1,3-チアゾール-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
405.N-(4-メトキシベンジル)-3-[(1,3-チアゾール-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
406.N-(4-メチルベンジル)-3-[(1,3-チアゾール-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
407.N-(3-クロロベンジル)-3-[(1,3-チアゾール-2-イルカルボニル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
408.N-ベンジル-3-{[4-(4-メチルピペラジン-1-イル)ベンゾイル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
409.N-(2-フルオロベンジル)-3-{[4-(4-メチルピペラジン-1-イル)ベンゾイル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
410.N-(2-クロロベンジル)-3-{[4-(4-メチルピペラジン-1-イル)ベンゾイル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
411.N-(2-メトキシベンジル)-3-{[4-(4-メチルピペラジン-1-イル)ベンゾイル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
412.N-(2-メチルベンジル)-3-{[4-(4-メチルピペラジン-1-イル)ベンゾイル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
413.N-(3-フルオロベンジル)-3-{[4-(4-メチルピペラジン-1-イル)ベンゾイル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
414.N-(3-メトキシベンジル)-3-{[4-(4-メチルピペラジン-1-イル)ベンゾイル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
415.N-(3-メチルベンジル)-3-{[4-(4-メチルピペラジン-1-イル)ベンゾイル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
416.N-(4-フルオロベンジル)-3-{[4-(4-メチルピペラジン-1-イル)ベンゾイル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
417.N-(4-クロロベンジル)-3-{[4-(4-メチルピペラジン-1-イル)ベンゾイル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
418.N-(4-メトキシベンジル)-3-{[4-(4-メチルピペラジン-1-イル)ベンゾイル]アミノ)-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
419.N-(4-メチルベンジル)-3-{[4-(4-メチルピペラジン-1-イル)ベンゾイル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
420.N-(3-クロロベンジル)-3-{[4-(4-メチルピペラジン-1-イル)ベンゾイル]アミノ}-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
421.N-ベンジル-3-[(4-モルホリン-4-イルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
422.N-(2-フルオロベンジル)-3-[(4-モルホリン-4-イルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
423.N-(2-クロロベンジル)-3-[(4-モルホリン-4-イルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
424.N-(2-メトキシベンジル)-3-[(4-モルホリン-4-イルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
425.N-(2-メチルベンジル)-3-[(4-モルホリン-4-イルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
426.N-(3-フルオロベンジル)-3-[(4-モルホリン-4-イルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
427.N-(3-メトキシベンジル)-3-[(4-モルホリン-4-イルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
428.N-(3-メチルベンジル)-3-[(4-モルホリン-4-イルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
429.N-(4-フルオロベンジル)-3-[(4-モルホリン-4-イルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
430.N-(4-クロロベンジル)-3-[(4-モルホリン-4-イルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
431.N-(4-メトキシベンジル)-3-[(4-モルホリン-4-イルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
432.N-(4-メチルベンジル)-3-[(4-モルホリン-4-イルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド;
433.N-(3-クロロベンジル)-3-[(4-モルホリン-4-イルベンゾイル)アミノ]-1H-チエノ[2,3-c]ピラゾール-5-カルボキシアミド。
Claims (4)
- tert−ブチル 3−アミノ−1H−チエノ[2,3−c]ピラゾール−5−カルボキシレートである、請求項1に記載の式(I)の化合物又は薬学的に許容されるそれらの塩。
- 薬剤として使用するための、請求項1に記載の式(I)の化合物又は薬学的に許容されるそれらの塩。
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US39812102P | 2002-07-25 | 2002-07-25 | |
PCT/EP2003/007531 WO2004013146A1 (en) | 2002-07-25 | 2003-07-11 | Condensed heterocyclic pyrazole derivatives as kinase inhibitors |
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EP (1) | EP1530573B1 (ja) |
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AR (1) | AR040520A1 (ja) |
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AU (1) | AU2003250040A1 (ja) |
BR (1) | BR0312961A (ja) |
CA (1) | CA2493680C (ja) |
DE (1) | DE60319836T2 (ja) |
ES (1) | ES2303601T3 (ja) |
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TW200526204A (en) * | 2004-02-03 | 2005-08-16 | Pharmacia Italia Spa | 1h-thieno[2,3-c]pyrazole derivatives useful as kinase inhibitors |
DE602005023333D1 (de) | 2004-10-15 | 2010-10-14 | Takeda Pharmaceutical | Kinaseinhibitoren |
FR2878442B1 (fr) * | 2004-11-29 | 2008-10-24 | Aventis Pharma Sa | THIENO(2,3-c)PYRAZOLES SUBSTITUES, PROCEDE DE PREPARATION, COMPOSITIONS LES CONTENANT ET UTILISATION |
US7485661B2 (en) * | 2005-01-18 | 2009-02-03 | Pfizer Italia S.R.L. | Heterobicyclic pyrazole derivatives as kinase inhibitors |
FR2882751B1 (fr) * | 2005-03-04 | 2007-09-14 | Aventis Pharma Sa | Hydrazinocarbonyl-thieno[2,3-c]pyrazoles, procede de preparation, compositions les contenant et utilisation |
JP5303271B2 (ja) * | 2005-07-19 | 2013-10-02 | ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ | キナーゼ阻害剤として有用な1H−チエノ[2,3−c]ピラゾール化合物 |
WO2007039773A1 (en) * | 2005-10-06 | 2007-04-12 | Merck Sharp & Dohme Limited | Use of fused pyrrole carboxylic acids for the treatment of neurodegenerative and psychiatric diseases as d-amino acid oxidase inhibitors |
US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
FR2904626B1 (fr) | 2006-08-03 | 2008-09-19 | Sanofi Aventis | Derives de pyrazolo[4,3]thiazole, leur preparation et leur application en therapeutique |
EA200970361A1 (ru) | 2006-10-09 | 2010-02-26 | Такеда Фармасьютикал Компани Лимитед | Ингибиторы киназы |
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CZ2003591A3 (cs) * | 2000-08-10 | 2003-06-18 | Pharmacia Italia S. P. A. | Bicyklopyrazoly účinné jako kinázové inhibitory, způsob jejich přípravy a farmaceutické prostředky, které je obsahují |
WO2002024694A1 (en) * | 2000-09-22 | 2002-03-28 | Smithkline Beecham, P.L.C. | Pyrazolopyridines and pyrazolopyridazines as antidiabetics |
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BR0312961A (pt) | 2005-06-14 |
ATE389658T1 (de) | 2008-04-15 |
CA2493680C (en) | 2010-09-07 |
TW200413383A (en) | 2004-08-01 |
DE60319836D1 (de) | 2008-04-30 |
WO2004013146A1 (en) | 2004-02-12 |
US20090233813A1 (en) | 2009-09-17 |
AU2003250040A1 (en) | 2004-02-23 |
AR040520A1 (es) | 2005-04-06 |
EP1530573B1 (en) | 2008-03-19 |
DE60319836T2 (de) | 2009-05-07 |
ES2303601T3 (es) | 2008-08-16 |
US20060122249A1 (en) | 2006-06-08 |
MXPA05000946A (es) | 2005-05-16 |
US8017643B2 (en) | 2011-09-13 |
US7541378B2 (en) | 2009-06-02 |
US7786048B2 (en) | 2010-08-31 |
JP2005537288A (ja) | 2005-12-08 |
CA2493680A1 (en) | 2004-02-12 |
US20100286223A1 (en) | 2010-11-11 |
EP1530573A1 (en) | 2005-05-18 |
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