WO2020045941A1 - Nouveau dérivé d'amine hétérocyclique et composition pharmaceutique le comprenant - Google Patents
Nouveau dérivé d'amine hétérocyclique et composition pharmaceutique le comprenant Download PDFInfo
- Publication number
- WO2020045941A1 WO2020045941A1 PCT/KR2019/010894 KR2019010894W WO2020045941A1 WO 2020045941 A1 WO2020045941 A1 WO 2020045941A1 KR 2019010894 W KR2019010894 W KR 2019010894W WO 2020045941 A1 WO2020045941 A1 WO 2020045941A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- amino
- methylthiazol
- pyridin
- morpholinomethyl
- prop
- Prior art date
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- -1 heterocyclic amine Chemical class 0.000 title claims abstract description 84
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 184
- 239000000126 substance Substances 0.000 claims abstract description 49
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 7
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 7
- 201000011510 cancer Diseases 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 33
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 27
- 125000004193 piperazinyl group Chemical group 0.000 claims description 24
- 125000003386 piperidinyl group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- AJSAXQJLWVWVJD-UHFFFAOYSA-N 1-[4-[[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)NC1CCN(CC1)C(C=C)=O)CN1CCOCC1 AJSAXQJLWVWVJD-UHFFFAOYSA-N 0.000 claims description 4
- MPESXHUFUDSCJX-UHFFFAOYSA-N 5-methyl-N-[6-methyl-4-(morpholin-4-ylmethyl)pyridin-2-yl]-1,3-thiazol-2-amine Chemical compound CC1=CN=C(S1)NC1=NC(=CC(=C1)CN1CCOCC1)C MPESXHUFUDSCJX-UHFFFAOYSA-N 0.000 claims description 4
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- AWYUOBJWJZXPEK-ONEGZZNKSA-N (E)-1-[3-[[2-[(5-methyl-1,3-thiazol-2-yl)amino]-6-(morpholin-4-ylmethyl)pyrimidin-4-yl]amino]pyrrolidin-1-yl]but-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=NC(=CC(=N1)NC1CN(CC1)C(\C=C\C)=O)CN1CCOCC1 AWYUOBJWJZXPEK-ONEGZZNKSA-N 0.000 claims description 3
- QBICJTDAZRFGHD-SFHVURJKSA-N 1-[(3S)-3-[[4-(1-methylpiperidin-4-yl)oxy-6-[(5-methyl-1,3-thiazol-2-yl)amino]pyridin-2-yl]amino]piperidin-1-yl]but-2-yn-1-one Chemical compound CN1CCC(CC1)OC1=CC(=NC(=C1)NC=1SC(=CN1)C)N[C@@H]1CN(CCC1)C(C#CC)=O QBICJTDAZRFGHD-SFHVURJKSA-N 0.000 claims description 3
- OHODATKLBRVXKJ-KRWDZBQOSA-N 1-[(3S)-3-[[4-(1-methylpiperidin-4-yl)oxy-6-[(5-methyl-1,3-thiazol-2-yl)amino]pyridin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound CN1CCC(CC1)OC1=CC(=NC(=C1)NC=1SC(=CN1)C)N[C@@H]1CN(CCC1)C(C=C)=O OHODATKLBRVXKJ-KRWDZBQOSA-N 0.000 claims description 3
- AHRSWKWTRFAUDI-KRWDZBQOSA-N 1-[(3S)-3-[[4-(1-methylpiperidin-4-yl)oxy-6-[(5-methyl-1,3-thiazol-2-yl)amino]pyridin-2-yl]amino]piperidin-1-yl]prop-2-yn-1-one Chemical compound CN1CCC(CC1)OC1=CC(=NC(=C1)NC=1SC(=CN1)C)N[C@@H]1CN(CCC1)C(C#C)=O AHRSWKWTRFAUDI-KRWDZBQOSA-N 0.000 claims description 3
- NVQOBRIJVCGAMR-SFHVURJKSA-N 1-[(3S)-3-[[4-[(4-ethylpiperazin-1-yl)methyl]-6-[(5-methyl-1,3-thiazol-2-yl)amino]pyrimidin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound C(C)N1CCN(CC1)CC1=NC(=NC(=C1)NC=1SC(=CN1)C)N[C@@H]1CN(CCC1)C(C=C)=O NVQOBRIJVCGAMR-SFHVURJKSA-N 0.000 claims description 3
- NRNATCSARBVXOX-KRWDZBQOSA-N 1-[(3S)-3-[[4-[(5-methyl-1,3-thiazol-2-yl)amino]-6-(piperidin-1-ylmethyl)pyrimidin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=NC(=NC(=C1)CN1CCCCC1)N[C@@H]1CN(CCC1)C(C=C)=O NRNATCSARBVXOX-KRWDZBQOSA-N 0.000 claims description 3
- MKQUPJKYOFYFPL-UHFFFAOYSA-N 1-[3-[[4-[(5-methyl-1,3-thiazol-2-yl)amino]-6-(morpholin-4-ylmethyl)pyrimidin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=NC(=NC(=C1)CN1CCOCC1)NC1CN(CCC1)C(C=C)=O MKQUPJKYOFYFPL-UHFFFAOYSA-N 0.000 claims description 3
- WFDCXXRJRKBMFT-AWEZNQCLSA-N 2-[(5-methyl-1,3-thiazol-2-yl)amino]-6-[[(3S)-1-prop-2-enoylpiperidin-3-yl]amino]pyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1C[C@H](CCC1)NC=1C=C(C#N)C=C(N1)NC=1SC(=CN1)C WFDCXXRJRKBMFT-AWEZNQCLSA-N 0.000 claims description 3
- HCRIXQNJIWLPBT-NRFANRHFSA-N 3-[4-[[2-[(5-methyl-1,3-thiazol-2-yl)amino]-6-[[(3S)-1-prop-2-enoylpiperidin-3-yl]amino]pyridin-4-yl]methyl]piperazin-1-yl]propanenitrile Chemical compound C(C=C)(=O)N1C[C@H](CCC1)NC1=NC(=CC(=C1)CN1CCN(CC1)CCC#N)NC=1SC(=CN1)C HCRIXQNJIWLPBT-NRFANRHFSA-N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- CQDFDHWMURAJMX-WRFKIARRSA-N (E)-3-chloro-1-[(3S)-3-[[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound Cl/C=C/C(=O)N1C[C@H](CCC1)NC1=NC(=CC(=C1)CN1CCOCC1)NC=1SC(=CN1)C CQDFDHWMURAJMX-WRFKIARRSA-N 0.000 claims description 2
- XYNGXOBHDVDZEC-GOSISDBHSA-N 1-[(3R)-3-[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]oxypiperidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)O[C@H]1CN(CCC1)C(C=C)=O)CN1CCOCC1 XYNGXOBHDVDZEC-GOSISDBHSA-N 0.000 claims description 2
- MKQUPJKYOFYFPL-MRXNPFEDSA-N 1-[(3R)-3-[[4-[(5-methyl-1,3-thiazol-2-yl)amino]-6-(morpholin-4-ylmethyl)pyrimidin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=NC(=NC(=C1)CN1CCOCC1)N[C@H]1CN(CCC1)C(C=C)=O MKQUPJKYOFYFPL-MRXNPFEDSA-N 0.000 claims description 2
- GNXIHWLECJIKNB-LJQANCHMSA-N 1-[(3R)-3-[[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]amino]piperidin-1-yl]but-2-yn-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)N[C@H]1CN(CCC1)C(C#CC)=O)CN1CCOCC1 GNXIHWLECJIKNB-LJQANCHMSA-N 0.000 claims description 2
- RVBWFVYCYPOETA-GOSISDBHSA-N 1-[(3R)-3-[[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)N[C@H]1CN(CCC1)C(C=C)=O)CN1CCOCC1 RVBWFVYCYPOETA-GOSISDBHSA-N 0.000 claims description 2
- NATKWXMFQTVAJG-QGZVFWFLSA-N 1-[(3R)-3-[[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]amino]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)N[C@H]1CN(CC1)C(C=C)=O)CN1CCOCC1 NATKWXMFQTVAJG-QGZVFWFLSA-N 0.000 claims description 2
- XYNGXOBHDVDZEC-SFHVURJKSA-N 1-[(3S)-3-[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]oxypiperidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)O[C@@H]1CN(CCC1)C(C=C)=O)CN1CCOCC1 XYNGXOBHDVDZEC-SFHVURJKSA-N 0.000 claims description 2
- NNPXIZPXWLNHEF-KRWDZBQOSA-N 1-[(3S)-3-[[3-fluoro-6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound FC=1C(=NC(=CC1CN1CCOCC1)NC=1SC(=CN1)C)N[C@@H]1CN(CCC1)C(C=C)=O NNPXIZPXWLNHEF-KRWDZBQOSA-N 0.000 claims description 2
- WTSKFCWCCLOYTI-KRWDZBQOSA-N 1-[(3S)-3-[[4-(morpholin-4-ylmethyl)-6-(1,3-thiazol-2-ylamino)pyridin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound O1CCN(CC1)CC1=CC(=NC(=C1)NC=1SC=CN1)N[C@@H]1CN(CCC1)C(C=C)=O WTSKFCWCCLOYTI-KRWDZBQOSA-N 0.000 claims description 2
- YDSUUUSGAAONPZ-IBGZPJMESA-N 1-[(3S)-3-[[4-(morpholin-4-ylmethyl)-6-(pyridin-2-ylamino)pyridin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound O1CCN(CC1)CC1=CC(=NC(=C1)NC1=NC=CC=C1)N[C@@H]1CN(CCC1)C(C=C)=O YDSUUUSGAAONPZ-IBGZPJMESA-N 0.000 claims description 2
- WXQXOJDYWXFBQP-SFHVURJKSA-N 1-[(3S)-3-[[4-(morpholin-4-ylmethyl)-6-(pyrimidin-2-ylamino)pyridin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound O1CCN(CC1)CC1=CC(=NC(=C1)NC1=NC=CC=N1)N[C@@H]1CN(CCC1)C(C=C)=O WXQXOJDYWXFBQP-SFHVURJKSA-N 0.000 claims description 2
- YBFUZFSNBDVIBS-INIZCTEOSA-N 1-[(3S)-3-[[4-(morpholin-4-ylmethyl)-6-[[5-(trifluoromethyl)-1,3-thiazol-2-yl]amino]pyridin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound O1CCN(CC1)CC1=CC(=NC(=C1)NC=1SC(=CN1)C(F)(F)F)N[C@@H]1CN(CCC1)C(C=C)=O YBFUZFSNBDVIBS-INIZCTEOSA-N 0.000 claims description 2
- NIJQUCVWHUEDPZ-KRWDZBQOSA-N 1-[(3S)-3-[[4-[(5-methyl-1,3-thiazol-2-yl)amino]-6-(morpholin-4-ylmethyl)pyrimidin-2-yl]amino]piperidin-1-yl]but-2-yn-1-one Chemical compound CC1=CN=C(S1)NC1=NC(=NC(=C1)CN1CCOCC1)N[C@@H]1CN(CCC1)C(C#CC)=O NIJQUCVWHUEDPZ-KRWDZBQOSA-N 0.000 claims description 2
- MKQUPJKYOFYFPL-INIZCTEOSA-N 1-[(3S)-3-[[4-[(5-methyl-1,3-thiazol-2-yl)amino]-6-(morpholin-4-ylmethyl)pyrimidin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=NC(=NC(=C1)CN1CCOCC1)N[C@@H]1CN(CCC1)C(C=C)=O MKQUPJKYOFYFPL-INIZCTEOSA-N 0.000 claims description 2
- VWWRTQBLBBYABT-NRFANRHFSA-N 1-[(3S)-3-[[4-[[4-(2-methoxyethyl)piperazin-1-yl]methyl]-6-[(5-methyl-1,3-thiazol-2-yl)amino]pyridin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound COCCN1CCN(CC1)CC1=CC(=NC(=C1)NC=1SC(=CN1)C)N[C@@H]1CN(CCC1)C(C=C)=O VWWRTQBLBBYABT-NRFANRHFSA-N 0.000 claims description 2
- VEMCQSSGPFHANF-INIZCTEOSA-N 1-[(3S)-3-[[6-[(5-chloro-1H-pyrazol-3-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound ClC1=CC(=NN1)NC1=CC(=CC(=N1)N[C@@H]1CN(CCC1)C(C=C)=O)CN1CCOCC1 VEMCQSSGPFHANF-INIZCTEOSA-N 0.000 claims description 2
- GNXIHWLECJIKNB-IBGZPJMESA-N 1-[(3S)-3-[[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]amino]piperidin-1-yl]but-2-yn-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)N[C@@H]1CN(CCC1)C(C#CC)=O)CN1CCOCC1 GNXIHWLECJIKNB-IBGZPJMESA-N 0.000 claims description 2
- RVBWFVYCYPOETA-SFHVURJKSA-N 1-[(3S)-3-[[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)N[C@@H]1CN(CCC1)C(C=C)=O)CN1CCOCC1 RVBWFVYCYPOETA-SFHVURJKSA-N 0.000 claims description 2
- NATKWXMFQTVAJG-KRWDZBQOSA-N 1-[(3S)-3-[[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]amino]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)N[C@@H]1CN(CC1)C(C=C)=O)CN1CCOCC1 NATKWXMFQTVAJG-KRWDZBQOSA-N 0.000 claims description 2
- BEXLVVWBJNBJLQ-IBGZPJMESA-N 1-[(3S)-3-[[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(pyridin-2-ylmethyl)pyridin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)N[C@@H]1CN(CCC1)C(C=C)=O)CC1=NC=CC=C1 BEXLVVWBJNBJLQ-IBGZPJMESA-N 0.000 claims description 2
- QSTHCTSZHLOKOV-IBGZPJMESA-N 1-[(3S)-3-[[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(pyridin-3-ylmethyl)pyridin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)N[C@@H]1CN(CCC1)C(C=C)=O)CC=1C=NC=CC1 QSTHCTSZHLOKOV-IBGZPJMESA-N 0.000 claims description 2
- HJGSVSBNCKJWRQ-IBGZPJMESA-N 1-[(3S)-3-[methyl-[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound CN([C@@H]1CN(CCC1)C(C=C)=O)C1=NC(=CC(=C1)CN1CCOCC1)NC=1SC(=CN1)C HJGSVSBNCKJWRQ-IBGZPJMESA-N 0.000 claims description 2
- XYNGXOBHDVDZEC-UHFFFAOYSA-N 1-[3-[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]oxypiperidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)OC1CN(CCC1)C(C=C)=O)CN1CCOCC1 XYNGXOBHDVDZEC-UHFFFAOYSA-N 0.000 claims description 2
- ZUDVPIFNMIUHFV-UHFFFAOYSA-N 1-[3-[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]oxypyrrolidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)OC1CN(CC1)C(C=C)=O)CN1CCOCC1 ZUDVPIFNMIUHFV-UHFFFAOYSA-N 0.000 claims description 2
- DKNNAABVLCVLSC-UHFFFAOYSA-N 1-[3-[[2-[(5-methyl-1,3-thiazol-2-yl)amino]-6-(morpholin-4-ylmethyl)pyrimidin-4-yl]amino]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=NC(=CC(=N1)NC1CN(CC1)C(C=C)=O)CN1CCOCC1 DKNNAABVLCVLSC-UHFFFAOYSA-N 0.000 claims description 2
- RVBWFVYCYPOETA-UHFFFAOYSA-N 1-[3-[[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)NC1CN(CCC1)C(C=C)=O)CN1CCOCC1 RVBWFVYCYPOETA-UHFFFAOYSA-N 0.000 claims description 2
- NATKWXMFQTVAJG-UHFFFAOYSA-N 1-[3-[[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]amino]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)NC1CN(CC1)C(C=C)=O)CN1CCOCC1 NATKWXMFQTVAJG-UHFFFAOYSA-N 0.000 claims description 2
- ZEGZZOYWOPSHBD-UHFFFAOYSA-N 1-[4-[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]oxypiperidin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)OC1CCN(CC1)C(C=C)=O)CN1CCOCC1 ZEGZZOYWOPSHBD-UHFFFAOYSA-N 0.000 claims description 2
- SSOLZFZRZMFFSF-UHFFFAOYSA-N 1-[6-[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]-3,3a,4,5,7,7a-hexahydro-2H-pyrrolo[2,3-c]pyridin-1-yl]but-2-yn-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)N1CC2C(CC1)CCN2C(C#CC)=O)CN2CCOCC2 SSOLZFZRZMFFSF-UHFFFAOYSA-N 0.000 claims description 2
- KUPFVPACKRDDQP-UHFFFAOYSA-N 1-[6-[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]-3,3a,4,5,7,7a-hexahydro-2H-pyrrolo[2,3-c]pyridin-1-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)N1CC2C(CC1)CCN2C(C=C)=O)CN2CCOCC2 KUPFVPACKRDDQP-UHFFFAOYSA-N 0.000 claims description 2
- YMCAZUDQAYIMCD-UHFFFAOYSA-N 1-[6-[[6-[(5-methyl-1,3-thiazol-2-yl)amino]-4-(morpholin-4-ylmethyl)pyridin-2-yl]amino]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound CC1=CN=C(S1)NC1=CC(=CC(=N1)NC1CC2(CN(C2)C(C=C)=O)C1)CN1CCOCC1 YMCAZUDQAYIMCD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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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
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
La présente invention concerne un nouveau dérivé d'amine hétérocyclique représenté par la formule 1 ci-dessous et une composition pharmaceutique le comprenant, et un composé selon la présente invention peut être utilisé pour la prévention ou le traitement de maladies auto-immunes ou du cancer. [Formule 1] Dans la formule 1, les significations de R1, R2, X1, X2, L, Y, A et B sont telles que définies dans la description.
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021534102A JP7162741B2 (ja) | 2018-08-27 | 2019-08-27 | 新規なヘテロサイクリックアミン誘導体およびこれを含む薬学組成物 |
| PE2021000205A PE20210417A1 (es) | 2018-08-27 | 2019-08-27 | Nuevo derivado de amina heterociclico y composicion farmaceutica que lo comprende |
| CA3108856A CA3108856C (fr) | 2018-08-27 | 2019-08-27 | Nouveau derive d'amine heterocyclique et composition pharmaceutique le comprenant |
| BR112021003652-0A BR112021003652B1 (pt) | 2018-08-27 | 2019-08-27 | Composto derivado de amina heterocíclica, composição farmacêutica compreendendo o mesmo e uso do dito composto para prevenir ou tratar doenças autoimunes ou cânceres |
| MX2021002188A MX2021002188A (es) | 2018-08-27 | 2019-08-27 | Nuevo derivado de amina heterociclica y composicion farmaceutica que la comprende. |
| BR122022001938-2A BR122022001938B1 (pt) | 2018-08-27 | 2019-08-27 | Composto derivado de amina heterocíclica, composição farmacêutica compreendendo o mesmo e uso do dito composto para prevenir ou tratar doenças autoimunes ou cânceres |
| US17/269,325 US20220064155A1 (en) | 2018-08-27 | 2019-08-27 | Novel heterocyclic amine derivative and pharmaceutical composition comprising same |
| AU2019331328A AU2019331328B2 (en) | 2018-08-27 | 2019-08-27 | Novel heterocyclic amine derivative and pharmaceutical composition comprising same |
| EP19855534.4A EP3845530A4 (fr) | 2018-08-27 | 2019-08-27 | Nouveau dérivé d'amine hétérocyclique et composition pharmaceutique le comprenant |
| CN201980056437.8A CN112638910A (zh) | 2018-08-27 | 2019-08-27 | 新的杂环胺衍生物及包含其的药物组合物 |
| RU2021107433A RU2760184C1 (ru) | 2018-08-27 | 2019-08-27 | Новое производное гетероциклического амина и содержащая его фармацевтическая композиция |
| SG11202101451QA SG11202101451QA (en) | 2018-08-27 | 2019-08-27 | Novel heterocyclic amine derivative and pharmaceutical composition comprising same |
| TNP/2021/000025A TN2021000025A1 (en) | 2018-08-27 | 2019-08-27 | Novel heterocyclic amine derivative and pharmaceutical composition comprising same |
| PH12021550329A PH12021550329A1 (en) | 2018-08-27 | 2021-02-16 | Novel heterocyclic amine derivative and pharmaceutical composition comprising same |
| CONC2021/0001849A CO2021001849A2 (es) | 2018-08-27 | 2021-02-16 | Nuevo derivado de amina heterocíclico y composición farmacéutica que lo comprende |
| DO2021000030A DOP2021000030A (es) | 2018-08-27 | 2021-02-17 | Nuevo derivado de amina heterocíclico y composición farmacéutica que lo comprende |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2018-0100359 | 2018-08-27 | ||
| KR20180100359 | 2018-08-27 | ||
| KR1020190104641A KR102328682B1 (ko) | 2018-08-27 | 2019-08-26 | 신규한 헤테로사이클릭아민 유도체 및 이를 포함하는 약학 조성물 |
| KR10-2019-0104641 | 2019-08-26 |
Publications (1)
| Publication Number | Publication Date |
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| WO2020045941A1 true WO2020045941A1 (fr) | 2020-03-05 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2019/010894 WO2020045941A1 (fr) | 2018-08-27 | 2019-08-27 | Nouveau dérivé d'amine hétérocyclique et composition pharmaceutique le comprenant |
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| Country | Link |
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| WO (1) | WO2020045941A1 (fr) |
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