JP2020511542A5 - - Google Patents
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- Publication number
- JP2020511542A5 JP2020511542A5 JP2020500788A JP2020500788A JP2020511542A5 JP 2020511542 A5 JP2020511542 A5 JP 2020511542A5 JP 2020500788 A JP2020500788 A JP 2020500788A JP 2020500788 A JP2020500788 A JP 2020500788A JP 2020511542 A5 JP2020511542 A5 JP 2020511542A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- pyrimidin
- thieno
- amino
- methylpropyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 229930195733 hydrocarbon Natural products 0.000 claims 4
- 150000002430 hydrocarbons Chemical class 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims 1
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims 1
- VUDZSIYXZUYWSC-DBRKOABJSA-N (4r)-1-[(2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one Chemical compound FC1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N[C@H](O)CC1 VUDZSIYXZUYWSC-DBRKOABJSA-N 0.000 claims 1
- NCLDZLRHMNRUFR-UHFFFAOYSA-N 2-(2-aminopropan-2-yl)-6-(2-fluoropyridin-4-yl)-3H-thieno[3,2-d]pyrimidin-4-one Chemical compound C1(C(C)(C)N)=NC=2C=C(C3=CC=NC(=C3)F)SC=2C(=O)N1 NCLDZLRHMNRUFR-UHFFFAOYSA-N 0.000 claims 1
- CVTALVOGXLDJKN-JTQLQIEISA-N 2-[(1S)-1-amino-2-methylpropyl]-6-(1,2-oxazol-4-yl)-3H-thieno[3,2-d]pyrimidin-4-one Chemical compound N1=C(NC(=O)C=2SC(C=3C=NOC=3)=CC1=2)[C@@H](N)C(C)C CVTALVOGXLDJKN-JTQLQIEISA-N 0.000 claims 1
- HRMMCJAJKHXCGC-JTQLQIEISA-N 2-[(1S)-1-amino-2-methylpropyl]-6-(1H-imidazol-5-yl)-3H-thieno[3,2-d]pyrimidin-4-one Chemical compound C1([C@@H](N)C(C)C)=NC=2C=C(C=3N=CNC=3)SC=2C(=O)N1 HRMMCJAJKHXCGC-JTQLQIEISA-N 0.000 claims 1
- BHFYJEOUSGMTBT-JTQLQIEISA-N 2-[(1S)-1-amino-2-methylpropyl]-6-(1H-pyrazol-5-yl)-3H-thieno[3,2-d]pyrimidin-4-one Chemical compound C1([C@@H](N)C(C)C)=NC=2C=C(C=3C=CNN=3)SC=2C(=O)N1 BHFYJEOUSGMTBT-JTQLQIEISA-N 0.000 claims 1
- PWRMZHCQYGGTCP-LBPRGKRZSA-N 2-[(1S)-1-amino-2-methylpropyl]-6-(2,5-difluoropyridin-4-yl)-3H-thieno[3,2-d]pyrimidin-4-one Chemical compound N1=C(NC(=O)C=2SC(C3=CC(=NC=C3F)F)=CC1=2)[C@@H](N)C(C)C PWRMZHCQYGGTCP-LBPRGKRZSA-N 0.000 claims 1
- RNOVPZFKWOWKKH-LBPRGKRZSA-N 2-[(1S)-1-amino-2-methylpropyl]-6-(2-chloropyridin-4-yl)-3H-thieno[3,2-d]pyrimidin-4-one Chemical compound N1=C(NC(=O)C=2SC(C3=CC(=NC=C3)Cl)=CC1=2)[C@H](C(C)C)N RNOVPZFKWOWKKH-LBPRGKRZSA-N 0.000 claims 1
- GZFWZLVDZVGSHA-ZDUSSCGKSA-N 2-[(1S)-1-amino-2-methylpropyl]-6-(2-methylpyridin-4-yl)-3H-thieno[3,2-d]pyrimidin-4-one Chemical compound C1([C@@H](N)C(C)C)=NC=2C=C(C3=CC=NC(=C3)C)SC=2C(=O)N1 GZFWZLVDZVGSHA-ZDUSSCGKSA-N 0.000 claims 1
- XPLGSPWXFUDFOU-NSHDSACASA-N 2-[(1S)-1-amino-2-methylpropyl]-6-piperazin-1-yl-3H-thieno[3,2-d]pyrimidin-4-one Chemical compound N1=C(NC(=O)C=2SC(N3CCNCC3)=CC1=2)[C@@H](N)C(C)C XPLGSPWXFUDFOU-NSHDSACASA-N 0.000 claims 1
- YIIVXYZQODJIKJ-NSHDSACASA-N 2-[(1S)-1-amino-2-methylpropyl]-6-pyridazin-4-yl-3H-thieno[3,2-d]pyrimidin-4-one Chemical compound N1=C(NC(=O)C=2SC(C3=CN=NC=C3)=CC1=2)[C@@H](N)C(C)C YIIVXYZQODJIKJ-NSHDSACASA-N 0.000 claims 1
- NXGRRTNELYXSSC-NSHDSACASA-N 2-[(1S)-1-amino-2-methylpropyl]-6-pyrimidin-4-yl-3H-thieno[3,2-d]pyrimidin-4-one Chemical compound N1=C(NC(=O)C=2SC(C3=CC=NC=N3)=CC1=2)[C@H](C(C)C)N NXGRRTNELYXSSC-NSHDSACASA-N 0.000 claims 1
- FGFDHZACFIPRLZ-LURJTMIESA-N 2-[(1S)-1-aminoethyl]-6-(3-fluoropyridin-4-yl)-3H-thieno[3,2-d]pyrimidin-4-one Chemical compound N1=C(NC(=O)C=2SC(C3=CC=NC=C3F)=CC1=2)[C@@H](N)C FGFDHZACFIPRLZ-LURJTMIESA-N 0.000 claims 1
- ZPEYQJFUBZIYBI-QMMMGPOBSA-N 2-[(1S)-1-aminopropyl]-6-(2-fluoropyridin-4-yl)-3H-thieno[3,2-d]pyrimidin-4-one Chemical compound C1([C@@H](N)CC)=NC=2C=C(C3=CC(=NC=C3)F)SC=2C(=O)N1 ZPEYQJFUBZIYBI-QMMMGPOBSA-N 0.000 claims 1
- HSIDKOBEZTZATI-VIFPVBQESA-N 2-[(1S)-1-aminopropyl]-6-(3-fluoropyridin-4-yl)-3H-thieno[3,2-d]pyrimidin-4-one Chemical compound C1([C@@H](N)CC)=NC=2C=C(C3=CC=NC=C3F)SC=2C(=O)N1 HSIDKOBEZTZATI-VIFPVBQESA-N 0.000 claims 1
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 claims 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims 1
- MWDVCHRYCKXEBY-LBPRGKRZSA-N 3-chloro-n-[2-oxo-2-[[(1s)-1-phenylethyl]amino]ethyl]benzamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(=O)CNC(=O)C1=CC=CC(Cl)=C1 MWDVCHRYCKXEBY-LBPRGKRZSA-N 0.000 claims 1
- WCDLCPLAAKUJNY-UHFFFAOYSA-N 4-[4-[3-(1h-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenyl]morpholine Chemical compound C1COCCN1C1=CC=C(C2=CN3N=CC(=C3N=C2)C2=CNN=C2)C=C1 WCDLCPLAAKUJNY-UHFFFAOYSA-N 0.000 claims 1
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 claims 1
- CYQIYUJAEWYPKM-ZDUSSCGKSA-N 6-(2-fluoropyridin-4-yl)-2-[(1S)-2-methyl-1-(methylamino)propyl]-3H-thieno[3,2-d]pyrimidin-4-one Chemical compound C1([C@@H](NC)C(C)C)=NC=2C=C(C3=CC=NC(F)=C3)SC=2C(=O)N1 CYQIYUJAEWYPKM-ZDUSSCGKSA-N 0.000 claims 1
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 claims 1
- LDIOUQIXNSSOGU-UHFFFAOYSA-N 8-(3-pentylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrazolo[1,5-a]pyrimidine Chemical compound CC1=NN2C(NC(CC)CC)=C3CCCC3=NC2=C1C1=CC=C(OC)C=C1Cl LDIOUQIXNSSOGU-UHFFFAOYSA-N 0.000 claims 1
- WNJDXXYDTOZGIQ-NSHDSACASA-N CC(C)[C@H](N)c1nc(=O)c2sc(cc2[nH]1)-c1cc[nH]c1 Chemical compound CC(C)[C@H](N)c1nc(=O)c2sc(cc2[nH]1)-c1cc[nH]c1 WNJDXXYDTOZGIQ-NSHDSACASA-N 0.000 claims 1
- JYFNBEZEBRTZAA-VIFPVBQESA-N CC(C)[C@H](N)c1nc(=O)c2sc(cc2[nH]1)-c1cn[nH]n1 Chemical compound CC(C)[C@H](N)c1nc(=O)c2sc(cc2[nH]1)-c1cn[nH]n1 JYFNBEZEBRTZAA-VIFPVBQESA-N 0.000 claims 1
- 102100034744 Cell division cycle 7-related protein kinase Human genes 0.000 claims 1
- 229940127007 Compound 39 Drugs 0.000 claims 1
- 101000945740 Homo sapiens Cell division cycle 7-related protein kinase Proteins 0.000 claims 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 claims 1
- QLWDQSUMIZMRRZ-LBPRGKRZSA-N N[C@@H](C1CC1)c1nc(=O)c2sc(cc2[nH]1)-c1ccncc1F Chemical compound N[C@@H](C1CC1)c1nc(=O)c2sc(cc2[nH]1)-c1ccncc1F QLWDQSUMIZMRRZ-LBPRGKRZSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 claims 1
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229940126086 compound 21 Drugs 0.000 claims 1
- 229940125846 compound 25 Drugs 0.000 claims 1
- 229940127271 compound 49 Drugs 0.000 claims 1
- 229940126545 compound 53 Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001288 lysyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- RCSBCWXPGSPJNF-UHFFFAOYSA-N n-[4-[5-[3-chloro-4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-yl]butyl]-4-(1,8-naphthyridin-2-yl)butanamide Chemical compound C1=C(Cl)C(OC(F)(F)F)=CC=C1C(O1)=NN=C1CCCCNC(=O)CCCC1=CC=C(C=CC=N2)C2=N1 RCSBCWXPGSPJNF-UHFFFAOYSA-N 0.000 claims 1
- HBEDNENASUYMPO-LJQANCHMSA-N n-hydroxy-4-[[(2r)-3-oxo-2-(thiophen-2-ylmethyl)-2,4-dihydroquinoxalin-1-yl]methyl]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1CN1C2=CC=CC=C2NC(=O)[C@H]1CC1=CC=CS1 HBEDNENASUYMPO-LJQANCHMSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- FRACPXUHUTXLCX-BELIEFIBSA-N tert-butyl N-{1-[(1S)-1-{[(1R,2S)-1-(benzylcarbamoyl)-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]carbamoyl}-2-cyclopropylethyl]-2-oxopyridin-3-yl}carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CN(C1=O)[C@@H](CC2CC2)C(=O)N[C@@H](C[C@@H]3CCNC3=O)[C@H](C(=O)NCC4=CC=CC=C4)O FRACPXUHUTXLCX-BELIEFIBSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762509128P | 2017-05-21 | 2017-05-21 | |
| US62/509,128 | 2017-05-21 | ||
| PCT/US2018/031474 WO2018217439A1 (en) | 2017-05-21 | 2018-05-08 | Substituted [5,6]cyclic-4(3h)-pyrimidinones as anticancer agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020511542A JP2020511542A (ja) | 2020-04-16 |
| JP2020511542A5 true JP2020511542A5 (https=) | 2020-05-28 |
| JP6825163B2 JP6825163B2 (ja) | 2021-02-03 |
Family
ID=64395863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020500788A Expired - Fee Related JP6825163B2 (ja) | 2017-05-21 | 2018-05-08 | 抗癌剤としての置換［５，６］シクロ−４（３ｈ）−ピリミジノン |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US10745410B2 (https=) |
| JP (1) | JP6825163B2 (https=) |
| CN (2) | CN112409373A (https=) |
| WO (1) | WO2018217439A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116490507A (zh) * | 2020-09-10 | 2023-07-25 | 薛定谔公司 | 用于治疗癌症的杂环包缩合cdc7激酶抑制剂 |
| CN112661770B (zh) * | 2020-12-24 | 2022-11-08 | 南京正济医药研究有限公司 | 一种化合物及利用其制备取代的[5,6]环-4(3h)-嘧啶酮化合物的方法 |
| TW202300150A (zh) * | 2021-03-18 | 2023-01-01 | 美商薛定諤公司 | 環狀化合物及其使用方法 |
| CN114544811B (zh) * | 2022-02-17 | 2023-10-20 | 南京正济医药研究有限公司 | 一种cdc7抑制剂有关物质的检测方法 |
| CN121021530A (zh) * | 2022-05-19 | 2025-11-28 | 南京正济医药研究有限公司 | 一种[5,6]环-4(3h)-嘧啶酮类化合物的晶型iii及其药物组合物、用途 |
| WO2025239965A1 (en) * | 2024-05-17 | 2025-11-20 | Purdue Research Foundation | Inhibitors of cdc14 phosphatases and related compositions and methods of use |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090030196A1 (en) * | 2006-12-29 | 2009-01-29 | Abbott Laboratories | Pim kinase inhibitors as cancer chemotherapeutics |
| WO2010101302A1 (en) * | 2009-03-05 | 2010-09-10 | Takeda Pharmaceutical Company Limited | Thienopyrimidine as cdc7 kinase inhibitors |
| SG183304A1 (en) * | 2010-02-17 | 2012-09-27 | Takeda Pharmaceutical | Heterocyclic compound |
| DK3436463T3 (da) * | 2016-03-28 | 2021-08-30 | Takeda Pharmaceuticals Co | Krystalline former af 2-[(2s)-1-azabicyclo[2.2.2]oct-2-yl]-6-(3-methyl-1h-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3h)-on hemi-hydrat |
-
2018
- 2018-05-08 WO PCT/US2018/031474 patent/WO2018217439A1/en not_active Ceased
- 2018-05-08 JP JP2020500788A patent/JP6825163B2/ja not_active Expired - Fee Related
- 2018-05-08 US US16/487,832 patent/US10745410B2/en not_active Expired - Fee Related
- 2018-05-08 CN CN202011093268.6A patent/CN112409373A/zh active Pending
- 2018-05-08 CN CN201880014693.6A patent/CN110381950B/zh active Active
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