JP2008516973A5 - - Google Patents
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- JP2008516973A5 JP2008516973A5 JP2007536949A JP2007536949A JP2008516973A5 JP 2008516973 A5 JP2008516973 A5 JP 2008516973A5 JP 2007536949 A JP2007536949 A JP 2007536949A JP 2007536949 A JP2007536949 A JP 2007536949A JP 2008516973 A5 JP2008516973 A5 JP 2008516973A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- methyl
- imidazo
- pyrimidin
- ylamino
- 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.)
- Withdrawn
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- -1 3- (Ethylsulfonyl) phenyl Chemical group 0.000 claims description 846
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 211
- FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 claims description 174
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 70
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 56
- BOUIZPWBFIVJPD-UHFFFAOYSA-N 3h-1,2,4-triazin-4-amine Chemical class NN1CN=NC=C1 BOUIZPWBFIVJPD-UHFFFAOYSA-N 0.000 claims description 31
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 20
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 16
- 150000001408 amides Chemical class 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 12
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 claims description 10
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 9
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- XRLDSWLMHUQECH-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1CCCC1 XRLDSWLMHUQECH-UHFFFAOYSA-N 0.000 claims description 6
- WMSPXQIQBQAWLL-UHFFFAOYSA-N cyclopropanesulfonamide Chemical compound NS(=O)(=O)C1CC1 WMSPXQIQBQAWLL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 6
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 5
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 claims description 4
- AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 claims description 4
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 4
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 4
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 4
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- QVESPAZTKUYKFE-UHFFFAOYSA-N 7-(3-ethylsulfonylphenyl)-n-(5-methyl-1h-pyrazol-3-yl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound CCS(=O)(=O)C1=CC=CC(C=2N=C(NC=3NN=C(C)C=3)N3C=CN=C3C=2)=C1 QVESPAZTKUYKFE-UHFFFAOYSA-N 0.000 claims description 4
- MTEVLMIUCCLOJF-UHFFFAOYSA-N 7-[3-(ethylsulfonylmethyl)phenyl]-2-methyl-n-(5-methyl-1h-pyrazol-3-yl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound CCS(=O)(=O)CC1=CC=CC(C=2N=C(NC3=NNC(C)=C3)N3C=C(C)N=C3C=2)=C1 MTEVLMIUCCLOJF-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims description 4
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 4
- MFNYBOWJWGPXFM-UHFFFAOYSA-N cyclobutanecarboxamide Chemical compound NC(=O)C1CCC1 MFNYBOWJWGPXFM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 4
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 4
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 4
- ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical compound NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 claims description 4
- 229960003966 nicotinamide Drugs 0.000 claims description 4
- 235000005152 nicotinamide Nutrition 0.000 claims description 4
- 239000011570 nicotinamide Substances 0.000 claims description 4
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 4
- ZFCHNZDUMIOWFV-UHFFFAOYSA-M pyrimidine-2-carboxylate Chemical compound [O-]C(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-M 0.000 claims description 4
- HMKSATPFCVLZAD-KRWDZBQOSA-N (2s)-n-[4-[2-methyl-5-[(5-methyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]sulfanylphenyl]oxolane-2-carboxamide Chemical compound N=1C(SC=2C=CC(NC(=O)[C@H]3OCCC3)=CC=2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 HMKSATPFCVLZAD-KRWDZBQOSA-N 0.000 claims description 2
- CMDUDMQXEVARHF-KRWDZBQOSA-N (2s)-n-[[3-[5-[(5-methyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]phenyl]methyl]pyrrolidine-2-carboxamide Chemical compound N1C(C)=CC(NC=2N3C=CN=C3C=C(N=2)C=2C=C(CNC(=O)[C@H]3NCCC3)C=CC=2)=N1 CMDUDMQXEVARHF-KRWDZBQOSA-N 0.000 claims description 2
- FYLXOUQHGOJJRI-UHFFFAOYSA-N (4-hydroxypiperidin-1-yl)-[3-[5-[(5-methyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]phenyl]methanone Chemical compound N1C(C)=CC(NC=2N3C=CN=C3C=C(N=2)C=2C=C(C=CC=2)C(=O)N2CCC(O)CC2)=N1 FYLXOUQHGOJJRI-UHFFFAOYSA-N 0.000 claims description 2
- OTBFUMSMIVYLAK-UHFFFAOYSA-N 1,3-thiazole-5-sulfonamide Chemical compound NS(=O)(=O)C1=CN=CS1 OTBFUMSMIVYLAK-UHFFFAOYSA-N 0.000 claims description 2
- AFCXECFLGWINNG-UHFFFAOYSA-N 1-[[3-[5-[(5-cyclopropyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]phenyl]methyl]imidazolidin-2-one Chemical compound O=C1NCCN1CC1=CC=CC(C=2N=C(NC3=NNC(=C3)C3CC3)N3C=CN=C3C=2)=C1 AFCXECFLGWINNG-UHFFFAOYSA-N 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- ZZPZQIMGCDVBIX-UHFFFAOYSA-N 2-[4-[2-methyl-5-[(5-methyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]pyrazol-1-yl]-n-phenylacetamide Chemical compound N=1C(C2=CN(CC(=O)NC=3C=CC=CC=3)N=C2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 ZZPZQIMGCDVBIX-UHFFFAOYSA-N 0.000 claims description 2
- DYADDGIMLGZAON-UHFFFAOYSA-N 2-[[4-[2-methyl-5-[(5-methyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]pyrazol-1-yl]methyl]benzonitrile Chemical compound N=1C(C2=CN(CC=3C(=CC=CC=3)C#N)N=C2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 DYADDGIMLGZAON-UHFFFAOYSA-N 0.000 claims description 2
- BJQRCMRGLKTFCX-UHFFFAOYSA-N 2-[[4-[5-[(5-cyclopropyl-1h-pyrazol-3-yl)amino]-2-methylimidazo[1,2-c]pyrimidin-7-yl]pyrazol-1-yl]methyl]benzonitrile Chemical compound N=1C(C2=CN(CC=3C(=CC=CC=3)C#N)N=C2)=CC2=NC(C)=CN2C=1NC(=NN1)C=C1C1CC1 BJQRCMRGLKTFCX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- FMMUQXDMPOTDLB-UHFFFAOYSA-N 2-methyl-7-[1-(2-methylpropyl)pyrazol-4-yl]-n-(5-methyl-1h-pyrazol-3-yl)imidazo[1,2-c]pyrimidin-5-amine Chemical class C1=NN(CC(C)C)C=C1C1=CC2=NC(C)=CN2C(NC2=NNC(C)=C2)=N1 FMMUQXDMPOTDLB-UHFFFAOYSA-N 0.000 claims description 2
- NWUUBYBANOEWNL-UHFFFAOYSA-N 2-methyl-7-[3-(3-methylimidazol-4-yl)phenyl]-n-(5-methyl-1h-pyrazol-3-yl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C=2C=C(C=CC=2)C=2N(C=NC=2)C)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 NWUUBYBANOEWNL-UHFFFAOYSA-N 0.000 claims description 2
- NMSNGWOXZGUXPU-UHFFFAOYSA-N 2-methyl-7-[3-[3-(methylamino)pyrrolidin-1-yl]sulfonylphenyl]-n-(5-methyl-1h-pyrazol-3-yl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound C1C(NC)CCN1S(=O)(=O)C1=CC=CC(C=2N=C(NC3=NNC(C)=C3)N3C=C(C)N=C3C=2)=C1 NMSNGWOXZGUXPU-UHFFFAOYSA-N 0.000 claims description 2
- QHCODFQJYAZFBH-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-(3-piperazin-1-ylsulfonylphenyl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C=2C=C(C=CC=2)S(=O)(=O)N2CCNCC2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 QHCODFQJYAZFBH-UHFFFAOYSA-N 0.000 claims description 2
- HUPVQHYRVNCWRU-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-(3-propan-2-yloxyphenyl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound CC(C)OC1=CC=CC(C=2N=C(NC3=NNC(C)=C3)N3C=C(C)N=C3C=2)=C1 HUPVQHYRVNCWRU-UHFFFAOYSA-N 0.000 claims description 2
- RWXSVGBXJSUDBT-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-(3-propoxyphenyl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound CCCOC1=CC=CC(C=2N=C(NC3=NNC(C)=C3)N3C=C(C)N=C3C=2)=C1 RWXSVGBXJSUDBT-UHFFFAOYSA-N 0.000 claims description 2
- OAZQHPZMYBNBIE-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-(3-pyrrolidin-1-ylsulfonylphenyl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C=2C=C(C=CC=2)S(=O)(=O)N2CCCC2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 OAZQHPZMYBNBIE-UHFFFAOYSA-N 0.000 claims description 2
- QMETZUFLUYJPNN-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-[1-(1-phenylpropan-2-yl)pyrazol-4-yl]imidazo[1,2-c]pyrimidin-5-amine Chemical compound C1=C(C=2N=C(NC3=NNC(C)=C3)N3C=C(C)N=C3C=2)C=NN1C(C)CC1=CC=CC=C1 QMETZUFLUYJPNN-UHFFFAOYSA-N 0.000 claims description 2
- WJXWUUGUOWMEAY-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-[1-(2-piperidin-1-ylethyl)pyrazol-4-yl]imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C2=CN(CCN3CCCCC3)N=C2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 WJXWUUGUOWMEAY-UHFFFAOYSA-N 0.000 claims description 2
- WGMYRTALXBVWPI-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-[1-[[2-(trifluoromethoxy)phenyl]methyl]pyrazol-4-yl]imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C2=CN(CC=3C(=CC=CC=3)OC(F)(F)F)N=C2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 WGMYRTALXBVWPI-UHFFFAOYSA-N 0.000 claims description 2
- HCPAPPQGSRCYQN-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-[3-(1,3,5-trimethylpyrazol-4-yl)phenyl]imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C=2C=C(C=CC=2)C2=C(N(C)N=C2C)C)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 HCPAPPQGSRCYQN-UHFFFAOYSA-N 0.000 claims description 2
- UVPZIMVFHCTSED-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-[3-(1,3-thiazol-2-ylsulfonyl)phenyl]imidazo[1,2-c]pyrimidin-5-amine Chemical class N=1C(C=2C=C(C=CC=2)S(=O)(=O)C=2SC=CN=2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 UVPZIMVFHCTSED-UHFFFAOYSA-N 0.000 claims description 2
- GGVKDZOKPSTLDC-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C=2C=C(C=CC=2)C=2C=3C=CNC=3N=CC=2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 GGVKDZOKPSTLDC-UHFFFAOYSA-N 0.000 claims description 2
- SJXFROBNJHRXJZ-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-[3-(3-methylpyridin-4-yl)phenyl]imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C=2C=C(C=CC=2)C=2C(=CN=CC=2)C)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 SJXFROBNJHRXJZ-UHFFFAOYSA-N 0.000 claims description 2
- CFVGGCMTRZKEGF-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-[3-(piperazin-1-ylmethyl)phenyl]imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C=2C=C(CN3CCNCC3)C=CC=2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 CFVGGCMTRZKEGF-UHFFFAOYSA-N 0.000 claims description 2
- LJWJMBSFNXRTKZ-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-[3-(piperidin-1-ylmethyl)phenyl]imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C=2C=C(CN3CCCCC3)C=CC=2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 LJWJMBSFNXRTKZ-UHFFFAOYSA-N 0.000 claims description 2
- UZYXIAWQWYJODS-KRWDZBQOSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-[3-[(3s)-pyrrolidin-3-yl]sulfonylphenyl]imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C=2C=C(C=CC=2)S(=O)(=O)[C@@H]2CNCC2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 UZYXIAWQWYJODS-KRWDZBQOSA-N 0.000 claims description 2
- OLTXWOKQKOFPJB-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-phenyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C)CN2C=1C=C(C=1C=CC=CC=1)N=C2NC=1C=C(C)NN=1 OLTXWOKQKOFPJB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- JBJDYLNJACPLLX-UHFFFAOYSA-N 3-[2-methyl-5-[(5-methyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]-n-phenylbenzenesulfonamide Chemical compound N=1C(C=2C=C(C=CC=2)S(=O)(=O)NC=2C=CC=CC=2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 JBJDYLNJACPLLX-UHFFFAOYSA-N 0.000 claims description 2
- YVJWNCMKNALEFQ-UHFFFAOYSA-N 3-[3-[2-methyl-5-[(5-methyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]phenyl]propanoic acid Chemical compound N=1C(C=2C=C(CCC(O)=O)C=CC=2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 YVJWNCMKNALEFQ-UHFFFAOYSA-N 0.000 claims description 2
- DVFMQGYTPGZVKT-UHFFFAOYSA-N 3-[5-[(5-methyl-1h-pyrazol-3-yl)amino]-2-(trifluoromethyl)imidazo[1,2-c]pyrimidin-7-yl]-n-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)C1=CC=CC(C=2N=C(NC3=NNC(C)=C3)N3C=C(N=C3C=2)C(F)(F)F)=C1 DVFMQGYTPGZVKT-UHFFFAOYSA-N 0.000 claims description 2
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- 239000002253 acid Substances 0.000 claims description 2
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 2
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- AZIJEPBVMATVKF-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-methyl-7-[1-(3-methylbutyl)pyrazol-4-yl]imidazo[1,2-c]pyrimidin-5-amine Chemical compound C1=NN(CCC(C)C)C=C1C1=CC2=NC(C)=CN2C(NC2=NNC(=C2)C2CC2)=N1 AZIJEPBVMATVKF-UHFFFAOYSA-N 0.000 claims description 2
- UYANHYRKBSXTHC-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-methyl-7-[1-(pyridin-2-ylmethyl)pyrazol-4-yl]imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C2=CN(CC=3N=CC=CC=3)N=C2)=CC2=NC(C)=CN2C=1NC(=NN1)C=C1C1CC1 UYANHYRKBSXTHC-UHFFFAOYSA-N 0.000 claims description 2
- DLQXOLXQCSNNCE-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-methyl-7-[1-(quinolin-8-ylmethyl)pyrazol-4-yl]imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C2=CN(CC=3C4=NC=CC=C4C=CC=3)N=C2)=CC2=NC(C)=CN2C=1NC(=NN1)C=C1C1CC1 DLQXOLXQCSNNCE-UHFFFAOYSA-N 0.000 claims description 2
- VTMWPYSEQYVEKS-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-methyl-7-[1-[(3-nitrophenyl)methyl]pyrazol-4-yl]imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C2=CN(CC=3C=C(C=CC=3)[N+]([O-])=O)N=C2)=CC2=NC(C)=CN2C=1NC(=NN1)C=C1C1CC1 VTMWPYSEQYVEKS-UHFFFAOYSA-N 0.000 claims description 2
- LKRDPFBOIUVFPF-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-methyl-7-[1-[(3-pyrrol-1-ylphenyl)methyl]pyrazol-4-yl]imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C2=CN(CC=3C=C(C=CC=3)N3C=CC=C3)N=C2)=CC2=NC(C)=CN2C=1NC(=NN1)C=C1C1CC1 LKRDPFBOIUVFPF-UHFFFAOYSA-N 0.000 claims description 2
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- MELKKSOYORGVIB-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-7-(2,3-dihydro-1-benzofuran-5-yl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound C1CC1C1=CC(NC=2N3C=CN=C3C=C(N=2)C=2C=C3CCOC3=CC=2)=NN1 MELKKSOYORGVIB-UHFFFAOYSA-N 0.000 claims description 2
- QCLFRXLRKRKCCI-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-7-(2,3-dihydroindol-1-yl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound C1CC1C1=CC(NC=2N3C=CN=C3C=C(N=2)N2C3=CC=CC=C3CC2)=NN1 QCLFRXLRKRKCCI-UHFFFAOYSA-N 0.000 claims description 2
- NGMPKDXNIYGWOQ-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-7-(3,4-dihydro-1h-isoquinolin-2-yl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound C1CC1C1=CC(NC=2N3C=CN=C3C=C(N=2)N2CC3=CC=CC=C3CC2)=NN1 NGMPKDXNIYGWOQ-UHFFFAOYSA-N 0.000 claims description 2
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- YZWBADIZXZDZPW-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-7-[1-[(2,3-dimethoxyphenyl)methyl]pyrazol-4-yl]-2-methylimidazo[1,2-c]pyrimidin-5-amine Chemical compound COC1=CC=CC(CN2N=CC(=C2)C=2N=C(NC3=NNC(=C3)C3CC3)N3C=C(C)N=C3C=2)=C1OC YZWBADIZXZDZPW-UHFFFAOYSA-N 0.000 claims description 2
- RLFRRBJZIHHNGJ-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-7-[1-[(3,5-dimethoxyphenyl)methyl]pyrazol-4-yl]-2-methylimidazo[1,2-c]pyrimidin-5-amine Chemical compound COC1=CC(OC)=CC(CN2N=CC(=C2)C=2N=C(NC3=NNC(=C3)C3CC3)N3C=C(C)N=C3C=2)=C1 RLFRRBJZIHHNGJ-UHFFFAOYSA-N 0.000 claims description 2
- DWFQRZNROTUJJE-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-7-[1-[(3-methoxyphenyl)methyl]pyrazol-4-yl]-2-methylimidazo[1,2-c]pyrimidin-5-amine Chemical compound COC1=CC=CC(CN2N=CC(=C2)C=2N=C(NC3=NNC(=C3)C3CC3)N3C=C(C)N=C3C=2)=C1 DWFQRZNROTUJJE-UHFFFAOYSA-N 0.000 claims description 2
- LGERUKVWJHEAEY-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-7-[1-[(4-methoxyphenyl)methyl]pyrazol-4-yl]-2-methylimidazo[1,2-c]pyrimidin-5-amine Chemical compound C1=CC(OC)=CC=C1CN1N=CC(C=2N=C(NC3=NNC(=C3)C3CC3)N3C=C(C)N=C3C=2)=C1 LGERUKVWJHEAEY-UHFFFAOYSA-N 0.000 claims description 2
- HLOFFXFIJVZECX-UHFFFAOYSA-N n-(5-methyl-1h-pyrazol-3-yl)-2,7-diphenylimidazo[1,2-c]pyrimidin-5-amine Chemical compound N1C(C)=CC(NC=2N3C=C(N=C3C=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 HLOFFXFIJVZECX-UHFFFAOYSA-N 0.000 claims description 2
- VPQBXMMVYAODPG-UHFFFAOYSA-N n-(5-methyl-1h-pyrazol-3-yl)-6-phenylimidazo[1,2-a]pyrazin-8-amine Chemical compound N1C(C)=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=CC=CC=2)=N1 VPQBXMMVYAODPG-UHFFFAOYSA-N 0.000 claims description 2
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- WFWLQEJPFGTKQP-UHFFFAOYSA-N n-(5-methyl-1h-pyrazol-3-yl)-7-(1,2,3,4-tetrahydroisoquinolin-7-yl)imidazo[1,2-c]pyrimidin-5-amine Chemical class N1C(C)=CC(NC=2N3C=CN=C3C=C(N=2)C=2C=C3CNCCC3=CC=2)=N1 WFWLQEJPFGTKQP-UHFFFAOYSA-N 0.000 claims description 2
- LTVLIBKBGHODBB-UHFFFAOYSA-N n-(5-methyl-1h-pyrazol-3-yl)-7-(2-methylsulfonyl-3,4-dihydro-1h-isoquinolin-7-yl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound N1C(C)=CC(NC=2N3C=CN=C3C=C(N=2)C=2C=C3CN(CCC3=CC=2)S(C)(=O)=O)=N1 LTVLIBKBGHODBB-UHFFFAOYSA-N 0.000 claims description 2
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- GZYUZBROUKLZAA-UHFFFAOYSA-N n-(5-methyl-1h-pyrazol-3-yl)-7-piperidin-1-ylimidazo[1,2-c]pyrimidin-5-amine Chemical compound N1C(C)=CC(NC=2N3C=CN=C3C=C(N=2)N2CCCCC2)=N1 GZYUZBROUKLZAA-UHFFFAOYSA-N 0.000 claims description 2
- JNLYNHDNQCEBGQ-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethoxy]-5-[2-methyl-5-[(5-methyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]phenyl]cyclopropanesulfonamide Chemical compound CN(C)CCOC1=CC=C(C=2N=C(NC3=NNC(C)=C3)N3C=C(C)N=C3C=2)C=C1NS(=O)(=O)C1CC1 JNLYNHDNQCEBGQ-UHFFFAOYSA-N 0.000 claims description 2
- WKVNWHBJXLKDMT-UHFFFAOYSA-N n-[2-[2-methyl-5-[(5-methyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1C1=CC2=NC(C)=CN2C(NC2=NNC(C)=C2)=N1 WKVNWHBJXLKDMT-UHFFFAOYSA-N 0.000 claims description 2
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- RHBIBVBVJHEJEW-UHFFFAOYSA-N n-[3-[2-(hydroxymethyl)-5-[(5-methyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]phenyl]methanesulfonamide Chemical compound N1C(C)=CC(NC=2N3C=C(CO)N=C3C=C(N=2)C=2C=C(NS(C)(=O)=O)C=CC=2)=N1 RHBIBVBVJHEJEW-UHFFFAOYSA-N 0.000 claims description 2
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-
2005
- 2005-10-14 EP EP05810353.2A patent/EP1812439B2/en not_active Expired - Lifetime
- 2005-10-14 DE DE602005023333T patent/DE602005023333D1/de not_active Expired - Lifetime
- 2005-10-14 US US11/251,616 patent/US7713973B2/en active Active
- 2005-10-14 JP JP2007536949A patent/JP2008516973A/ja not_active Withdrawn
- 2005-10-14 WO PCT/US2005/037059 patent/WO2006044687A2/en not_active Ceased
- 2005-10-14 AT AT05810353T patent/ATE479687T1/de not_active IP Right Cessation
-
2010
- 2010-04-06 US US12/755,301 patent/US8288536B2/en not_active Expired - Fee Related
-
2011
- 2011-12-26 JP JP2011284364A patent/JP5524171B2/ja not_active Expired - Fee Related
-
2013
- 2013-01-17 JP JP2013006060A patent/JP2013121966A/ja not_active Ceased
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