JP5864589B2 - 細菌トポイソメラーゼｉｉ阻害性２−エチルカルバモイルアミノ−１，３−ベンゾチアゾール−５−イル類 - Google Patents

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Publication number

JP5864589B2

JP5864589B2 JP2013532015A JP2013532015A JP5864589B2 JP 5864589 B2 JP5864589 B2 JP 5864589B2 JP 2013532015 A JP2013532015 A JP 2013532015A JP 2013532015 A JP2013532015 A JP 2013532015A JP 5864589 B2 JP5864589 B2 JP 5864589B2

Authority

JP

Japan

Prior art keywords

ethylcarbamoylamino

benzothiazol

piperidine

pyrimidin

methyl

Prior art date

2010-10-08

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.)

Expired - Fee Related

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• 230000001580 bacterial effect Effects 0.000 title claims description 17
• 102000007537 Type II DNA Topoisomerases Human genes 0.000 title 1
• 108010046308 Type II DNA Topoisomerases Proteins 0.000 title 1
• 230000002401 inhibitory effect Effects 0.000 title 1
• 239000000203 mixture Substances 0.000 claims description 249
• 150000001875 compounds Chemical class 0.000 claims description 224
• 125000000217 alkyl group Chemical group 0.000 claims description 202
• 229910052739 hydrogen Inorganic materials 0.000 claims description 186
• 229920006395 saturated elastomer Polymers 0.000 claims description 107
• -1 Ethylcarbamoylamino Chemical group 0.000 claims description 84
• 239000002243 precursor Substances 0.000 claims description 71
• 150000003839 salts Chemical class 0.000 claims description 60
• 125000000623 heterocyclic group Chemical group 0.000 claims description 58
• 125000005843 halogen group Chemical group 0.000 claims description 51
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 44
• 125000003545 alkoxy group Chemical group 0.000 claims description 43
• 125000002619 bicyclic group Chemical group 0.000 claims description 40
• 229910052757 nitrogen Inorganic materials 0.000 claims description 40
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 35
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 33
• 125000003118 aryl group Chemical group 0.000 claims description 32
• 239000002253 acid Substances 0.000 claims description 30
• 229910052799 carbon Inorganic materials 0.000 claims description 30
• 238000000034 method Methods 0.000 claims description 29
• 125000001475 halogen functional group Chemical group 0.000 claims description 27
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
• 230000008878 coupling Effects 0.000 claims description 22
• 238000010168 coupling process Methods 0.000 claims description 22
• 238000005859 coupling reaction Methods 0.000 claims description 22
• 125000002950 monocyclic group Chemical group 0.000 claims description 22
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 19
• 229910052760 oxygen Inorganic materials 0.000 claims description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 14
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 11
• 239000003242 anti bacterial agent Substances 0.000 claims description 11
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
• 208000035143 Bacterial infection Diseases 0.000 claims description 10
• 125000002947 alkylene group Chemical group 0.000 claims description 10
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
• VWGVZRSKDSKOCX-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 VWGVZRSKDSKOCX-UHFFFAOYSA-N 0.000 claims description 9
• 230000008569 process Effects 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
• 125000004450 alkenylene group Chemical group 0.000 claims description 8
• 125000004419 alkynylene group Chemical group 0.000 claims description 8
• 150000007942 carboxylates Chemical class 0.000 claims description 8
• JSJORNVDZKDKSU-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(4-methylpyridin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC(C)=CC=N1 JSJORNVDZKDKSU-UHFFFAOYSA-N 0.000 claims description 7
• LEQHROIJVSVGKQ-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(pyridine-2-carbonylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1NC(=O)C1=CC=CC=N1 LEQHROIJVSVGKQ-UHFFFAOYSA-N 0.000 claims description 7
• JUYRPCDORFQPQJ-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-4-pyridin-2-yl-[1,3]thiazolo[5,4-c]pyridin-6-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=NC=1C1=CC=CC=N1 JUYRPCDORFQPQJ-UHFFFAOYSA-N 0.000 claims description 6
• LQPRFUISPJLHIA-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(pyrimidine-2-carbonylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1NC(=O)C1=NC=CC=N1 LQPRFUISPJLHIA-UHFFFAOYSA-N 0.000 claims description 6
• XHZIGBLECMTNGL-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-[2-(6-methoxypyridin-2-yl)ethynyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C#CC1=CC=CC(OC)=N1 XHZIGBLECMTNGL-UHFFFAOYSA-N 0.000 claims description 6
• MTAJMFNBGICWOP-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyridazin-3-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=C(N=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 MTAJMFNBGICWOP-UHFFFAOYSA-N 0.000 claims description 6
• HLKACKWVNDSHBX-UHFFFAOYSA-N 1-[5-[7-bromo-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(Br)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 HLKACKWVNDSHBX-UHFFFAOYSA-N 0.000 claims description 6
• SVJMHGIAIUBOET-UHFFFAOYSA-N 7-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]-2-methyl-3-oxo-4h-pyrido[3,2-b][1,4]oxazine-2-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=C3OC(C)(C(=O)NC3=NC=2)C(O)=O)=CC=1C1=CC=CC=N1 SVJMHGIAIUBOET-UHFFFAOYSA-N 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• OXEAADVCNBKSBS-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 OXEAADVCNBKSBS-UHFFFAOYSA-N 0.000 claims description 5
• OASNACIRCRZKGU-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(2-methoxy-1,3-thiazol-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CSC(OC)=N1 OASNACIRCRZKGU-UHFFFAOYSA-N 0.000 claims description 5
• RNPFNBDXZQGQRJ-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(2-methoxyethoxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(COCCOC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 RNPFNBDXZQGQRJ-UHFFFAOYSA-N 0.000 claims description 5
• XUPBYGGPWQXYQB-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-[[methyl(pyrimidin-2-yl)amino]methyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1CN(C)C1=NC=CC=N1 XUPBYGGPWQXYQB-UHFFFAOYSA-N 0.000 claims description 5
• DRMIPWIMPSKYAQ-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-methyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(C)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 DRMIPWIMPSKYAQ-UHFFFAOYSA-N 0.000 claims description 5
• NDKAXLRYJQJEEE-UHFFFAOYSA-N 1-[5-[7-cyclohexyl-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1CCCCC1 NDKAXLRYJQJEEE-UHFFFAOYSA-N 0.000 claims description 5
• DTPGVCZIIMRXML-UHFFFAOYSA-N 1-[5-[7-ethyl-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(CC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 DTPGVCZIIMRXML-UHFFFAOYSA-N 0.000 claims description 5
• 229910014033 C-OH Inorganic materials 0.000 claims description 5
• 229910014570 C—OH Inorganic materials 0.000 claims description 5
• 238000011109 contamination Methods 0.000 claims description 5
• FPXFVAZABUPWIT-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(1-methyltriazol-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CN(C)N=N1 FPXFVAZABUPWIT-UHFFFAOYSA-N 0.000 claims description 4
• ICMDMPKJQUFPDF-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(1-phenyltriazol-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C(N=N1)=CN1C1=CC=CC=C1 ICMDMPKJQUFPDF-UHFFFAOYSA-N 0.000 claims description 4
• FWWLCZIDTDZESJ-AMVVHIIESA-N 1-[5-[2-(ethylcarbamoylamino)-7-[(e)-n-methoxy-c-methylcarbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(\C(C)=N\OC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 FWWLCZIDTDZESJ-AMVVHIIESA-N 0.000 claims description 4
• KLDMGBMNAIRONS-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-hydroxy-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(O)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 KLDMGBMNAIRONS-UHFFFAOYSA-N 0.000 claims description 4
• LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 claims description 4
• QVGBSVRQPUQXSZ-IBBHUPRXSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-[(e)-n-methoxy-c-methylcarbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=1C(\C(C)=N\OC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(O)=O)CC1 QVGBSVRQPUQXSZ-IBBHUPRXSA-N 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 150000001768 cations Chemical class 0.000 claims description 4
• XUVJOQRNPJNTHG-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-4-fluoro-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=C(F)C(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 XUVJOQRNPJNTHG-UHFFFAOYSA-N 0.000 claims description 3
• XYEMQUWUUXZULS-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-ethynyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(C#C)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 XYEMQUWUUXZULS-UHFFFAOYSA-N 0.000 claims description 3
• GVQIMNOYLDVOJX-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyrazin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-prop-2-enylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC=C)(CC2)C(O)=O)=CC=1C1=CN=CC=N1 GVQIMNOYLDVOJX-UHFFFAOYSA-N 0.000 claims description 3
• VMIAHALRMSSYGZ-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-(trifluoromethyl)piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC2)(C(O)=O)C(F)(F)F)=CC=1C1=CC=CC=N1 VMIAHALRMSSYGZ-UHFFFAOYSA-N 0.000 claims description 3
• CFECMZNVTSKBMB-UHFFFAOYSA-N 1-[5-[7-(4,5-dihydro-1,2-oxazol-3-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-ethylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=NOCC1 CFECMZNVTSKBMB-UHFFFAOYSA-N 0.000 claims description 3
• QBIZSRFTNZRMDT-UHFFFAOYSA-N 1-[5-[7-(ethylcarbamoyl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(C(=O)NCC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 QBIZSRFTNZRMDT-UHFFFAOYSA-N 0.000 claims description 3
• XTCZNJQRUBTOSI-UHFFFAOYSA-N 1-[5-[7-cyclopropyl-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1CC1 XTCZNJQRUBTOSI-UHFFFAOYSA-N 0.000 claims description 3
• QUYTUENFVFMKJF-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-formyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=1C(C=O)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(O)=O)CC1 QUYTUENFVFMKJF-UHFFFAOYSA-N 0.000 claims description 3
• 239000005973 Carvone Substances 0.000 claims description 3
• 229910052796 boron Inorganic materials 0.000 claims description 3
• UEAGFZUKGBQFSG-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(oxan-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(=O)OCC)=CC=1C1CCOCC1 UEAGFZUKGBQFSG-UHFFFAOYSA-N 0.000 claims description 3
• 239000002271 gyrase inhibitor Substances 0.000 claims description 3
• 125000003003 spiro group Chemical group 0.000 claims description 3
• VZRLKPOBDKXHEN-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(1,3-thiazol-2-ylcarbamoyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C(=O)NC1=NC=CS1 VZRLKPOBDKXHEN-UHFFFAOYSA-N 0.000 claims description 2
• KOLVVJOFVJGNBD-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(methoxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(COC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 KOLVVJOFVJGNBD-UHFFFAOYSA-N 0.000 claims description 2
• DYVMIAODNIPPKX-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(morpholin-4-ylmethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1CN1CCOCC1 DYVMIAODNIPPKX-UHFFFAOYSA-N 0.000 claims description 2
• ZXJVTCXBSJRTAY-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(morpholine-4-carbonyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C(=O)N1CCOCC1 ZXJVTCXBSJRTAY-UHFFFAOYSA-N 0.000 claims description 2
• BCOKKZLVXVOUBR-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-[ethyl(methyl)carbamoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(C(=O)N(C)CC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 BCOKKZLVXVOUBR-UHFFFAOYSA-N 0.000 claims description 2
• HOHICCCLUXQFKL-UHFFFAOYSA-N 1-[5-[7-(1-acetylpiperidin-4-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1CCN(C(C)=O)CC1 HOHICCCLUXQFKL-UHFFFAOYSA-N 0.000 claims description 2
• XXYZRWMRILLPBR-UHFFFAOYSA-N 1-[5-[7-carbamoyl-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-ethylpiperidine-4-carboxylic acid Chemical compound C=1C(C(N)=O)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(O)=O)CC1 XXYZRWMRILLPBR-UHFFFAOYSA-N 0.000 claims description 2
• FAWKRDYMJYUEKB-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(O)=O)CC1 FAWKRDYMJYUEKB-UHFFFAOYSA-N 0.000 claims description 2
• VYLKCVDNRCETDL-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-morpholin-4-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1N1CCOCC1 VYLKCVDNRCETDL-UHFFFAOYSA-N 0.000 claims description 2
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
• HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 2
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• AFWWNXOSDUHYFQ-UHFFFAOYSA-N 1,3-dioxane-2-carboxylic acid Chemical compound OC(=O)C1OCCCO1 AFWWNXOSDUHYFQ-UHFFFAOYSA-N 0.000 claims 1
• ZDUQPQAZIGLDOX-UHFFFAOYSA-N 1-[4-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyridin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=C(N=CC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 ZDUQPQAZIGLDOX-UHFFFAOYSA-N 0.000 claims 1
• VDQBFVNLOKHTEL-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-5-pyrazol-1-yl-[1,2,4]triazolo[1,5-a]pyridin-7-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound N12N=C(NC(=O)NCC)N=C2C=C(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)C=C1N1C=CC=N1 VDQBFVNLOKHTEL-UHFFFAOYSA-N 0.000 claims 1
• QPNYUROAFAKJGR-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-5-pyrazol-1-ylimidazo[1,2-a]pyridin-7-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C2=NC(NC(=O)NCC)=CN2C(N2N=CC=C2)=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 QPNYUROAFAKJGR-UHFFFAOYSA-N 0.000 claims 1
• SBOXALOUCSXAEY-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-6-methoxy-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound COC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 SBOXALOUCSXAEY-UHFFFAOYSA-N 0.000 claims 1
• HRZPPODWLOBXDJ-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(1,3-oxazol-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=CO1 HRZPPODWLOBXDJ-UHFFFAOYSA-N 0.000 claims 1
• OBVVAQMYRWVXJH-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(1,3-thiazol-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CSC=N1 OBVVAQMYRWVXJH-UHFFFAOYSA-N 0.000 claims 1
• YDYDPEKDUOINGU-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(1,3-thiazol-5-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CN=CS1 YDYDPEKDUOINGU-UHFFFAOYSA-N 0.000 claims 1
• UUFGLKGSUOBNSA-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(1-methyl-2-oxopyridin-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C=1C=CN(C)C(=O)C=1 UUFGLKGSUOBNSA-UHFFFAOYSA-N 0.000 claims 1
• JSBMZEZVRKQZLV-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(1-methylpyrrol-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=CN1C JSBMZEZVRKQZLV-UHFFFAOYSA-N 0.000 claims 1
• OVHSCXCBFSZSNG-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(1h-pyrazol-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C=1C=NNC=1 OVHSCXCBFSZSNG-UHFFFAOYSA-N 0.000 claims 1
• QBQCASRBYYVDRF-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(2-ethyl-1,3-thiazol-5-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CN=C(CC)S1 QBQCASRBYYVDRF-UHFFFAOYSA-N 0.000 claims 1
• YVTUROXWRQKRSE-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(2-methoxypyrimidin-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=NC(OC)=N1 YVTUROXWRQKRSE-UHFFFAOYSA-N 0.000 claims 1
• VXDFZZQXRYBOHG-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(2-methylpyrimidin-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=NC(C)=N1 VXDFZZQXRYBOHG-UHFFFAOYSA-N 0.000 claims 1
• QJRZJUOAYABAMS-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(2-morpholin-4-yl-1,3-thiazol-5-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C(S1)=CN=C1N1CCOCC1 QJRZJUOAYABAMS-UHFFFAOYSA-N 0.000 claims 1
• MEEZWPCKGHOMRD-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(2-pyrazin-2-ylethynyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C#CC1=CN=CC=N1 MEEZWPCKGHOMRD-UHFFFAOYSA-N 0.000 claims 1
• TZUHMJOMWDKWPD-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridin-3-ylethynyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C#CC1=CC=CN=C1 TZUHMJOMWDKWPD-UHFFFAOYSA-N 0.000 claims 1
• BGZGXALJMXKQON-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridin-4-ylethynyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C#CC1=CC=NC=C1 BGZGXALJMXKQON-UHFFFAOYSA-N 0.000 claims 1
• QVNJEAQVVHJSID-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(2-pyrimidin-2-ylethynyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C#CC1=NC=CC=N1 QVNJEAQVVHJSID-UHFFFAOYSA-N 0.000 claims 1
• YASIJTBDSUKURQ-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(2-pyrimidin-4-ylethynyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C#CC1=CC=NC=N1 YASIJTBDSUKURQ-UHFFFAOYSA-N 0.000 claims 1
• AFTLKGYVTIOXTL-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(3-fluoro-4-methoxypyridin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=CC(OC)=C1F AFTLKGYVTIOXTL-UHFFFAOYSA-N 0.000 claims 1
• GQKBXCHOLJDRBG-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(3-fluoro-5-methylpyridin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=C(C)C=C1F GQKBXCHOLJDRBG-UHFFFAOYSA-N 0.000 claims 1
• VDKYTVIOWRBCRJ-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(3-fluoropyridin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=CC=C1F VDKYTVIOWRBCRJ-UHFFFAOYSA-N 0.000 claims 1
• IYQYDKQIMUJUGT-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(3-methoxy-6-methylpyridin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC(C)=CC=C1OC IYQYDKQIMUJUGT-UHFFFAOYSA-N 0.000 claims 1
• HUSFGNCUFNDVTL-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(3-methoxypyrazin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=CN=C1OC HUSFGNCUFNDVTL-UHFFFAOYSA-N 0.000 claims 1
• MAXPDCBPDUUJPC-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(3-methoxypyridin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=CC=C1OC MAXPDCBPDUUJPC-UHFFFAOYSA-N 0.000 claims 1
• SKDCWESIRXHJJF-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(3-methylpyrazin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=CN=C1C SKDCWESIRXHJJF-UHFFFAOYSA-N 0.000 claims 1
• FDKIGQXXNBPAPC-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(4-fluoropyridin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC(F)=CC=N1 FDKIGQXXNBPAPC-UHFFFAOYSA-N 0.000 claims 1
• NKYQSSLUCZYICX-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(4-methoxypyridin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC(OC)=CC=N1 NKYQSSLUCZYICX-UHFFFAOYSA-N 0.000 claims 1
• LJVUHQUMARIXOV-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(4-methoxypyridin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-propylpiperidine-4-carboxylic acid Chemical compound C1CC(CCC)(C(O)=O)CCN1C1=NC=C(C=2C=C3N=C(NC(=O)NCC)SC3=C(C=3N=CC=C(OC)C=3)C=2)C=N1 LJVUHQUMARIXOV-UHFFFAOYSA-N 0.000 claims 1
• SIBLNETVBOYCNW-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(4-methoxypyrimidin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=CC(OC)=N1 SIBLNETVBOYCNW-UHFFFAOYSA-N 0.000 claims 1
• YRAGCRNFBQJOOL-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(4-methoxypyrimidin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-propylpiperidine-4-carboxylic acid Chemical compound C1CC(CCC)(C(O)=O)CCN1C1=NC=C(C=2C=C3N=C(NC(=O)NCC)SC3=C(C=3N=C(OC)C=CN=3)C=2)C=N1 YRAGCRNFBQJOOL-UHFFFAOYSA-N 0.000 claims 1
• OOEDBAUVFRBDGB-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(4-methylpyrimidin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=CC(C)=N1 OOEDBAUVFRBDGB-UHFFFAOYSA-N 0.000 claims 1
• SCYCINRBSVGEHS-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(5-ethylpyrazin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CN=C(CC)C=N1 SCYCINRBSVGEHS-UHFFFAOYSA-N 0.000 claims 1
• KMMKXBJQJRJNMJ-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(5-ethylpyrimidin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=C(CC)C=N1 KMMKXBJQJRJNMJ-UHFFFAOYSA-N 0.000 claims 1
• ZPPQMMLXEXSHAN-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(5-fluoro-4-methylpyridin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC(C)=C(F)C=N1 ZPPQMMLXEXSHAN-UHFFFAOYSA-N 0.000 claims 1
• GPFVDNKQKJAXJD-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(5-fluoro-6-methylpyridin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=C(F)C(C)=N1 GPFVDNKQKJAXJD-UHFFFAOYSA-N 0.000 claims 1
• MGUYYOXVTXRBSM-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(5-fluoropyrimidin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=C(F)C=N1 MGUYYOXVTXRBSM-UHFFFAOYSA-N 0.000 claims 1
• LGQMXKZELLAQEN-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(5-methoxypyrazin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CN=C(OC)C=N1 LGQMXKZELLAQEN-UHFFFAOYSA-N 0.000 claims 1
• SHGFDGWSFRDIGT-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(5-methoxypyrimidin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=C(OC)C=N1 SHGFDGWSFRDIGT-UHFFFAOYSA-N 0.000 claims 1
• OCUHSSUTRYHEEE-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(5-methyl-1,2,4-oxadiazol-3-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NOC(C)=N1 OCUHSSUTRYHEEE-UHFFFAOYSA-N 0.000 claims 1
• IEYHJOZEAWWKPF-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(5-methylpyrazin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CN=C(C)C=N1 IEYHJOZEAWWKPF-UHFFFAOYSA-N 0.000 claims 1
• NSVBZGBQGWZJPC-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(5-methylpyridin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=C(C)C=N1 NSVBZGBQGWZJPC-UHFFFAOYSA-N 0.000 claims 1
• RQYYLZJLVWKJJP-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(5-methylpyrimidin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=C(C)C=N1 RQYYLZJLVWKJJP-UHFFFAOYSA-N 0.000 claims 1
• GAESENQYNKARLM-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(6-methoxypyrazin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CN=CC(OC)=N1 GAESENQYNKARLM-UHFFFAOYSA-N 0.000 claims 1
• JLVZTRLDVATONH-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(6-methoxypyridin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=CC(OC)=N1 JLVZTRLDVATONH-UHFFFAOYSA-N 0.000 claims 1
• IBQZOCHIVKQRFE-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(6-methoxypyrimidin-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC(OC)=NC=N1 IBQZOCHIVKQRFE-UHFFFAOYSA-N 0.000 claims 1
• OHBGLTWHKIAONR-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(6-methoxypyrimidin-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-propylpiperidine-4-carboxylic acid Chemical compound C1CC(CCC)(C(O)=O)CCN1C1=NC=C(C=2C=C3N=C(NC(=O)NCC)SC3=C(C=3N=CN=C(OC)C=3)C=2)C=N1 OHBGLTWHKIAONR-UHFFFAOYSA-N 0.000 claims 1
• CHNMYRMMWYWYEV-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(6-methylpyrimidin-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC(C)=NC=N1 CHNMYRMMWYWYEV-UHFFFAOYSA-N 0.000 claims 1
• KONROZWBHHWXPE-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(6-oxo-1-propan-2-ylpyrimidin-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC(=O)N(C(C)C)C=N1 KONROZWBHHWXPE-UHFFFAOYSA-N 0.000 claims 1
• SHGQPWMQVRIHLW-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(6-propan-2-yloxypyrimidin-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC(OC(C)C)=NC=N1 SHGQPWMQVRIHLW-UHFFFAOYSA-N 0.000 claims 1
• ZUCHLHNWYFNLHD-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-propylpiperidine-4-carboxylic acid Chemical compound C1CC(CCC)(C(O)=O)CCN1C1=NC=C(C=2C=C3N=C(NC(=O)NCC)SC3=C(C=3C=4C=CNC=4N=CN=3)C=2)C=N1 ZUCHLHNWYFNLHD-UHFFFAOYSA-N 0.000 claims 1
• KQNCAVRPKGDCKS-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(oxan-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1CCOCC1 KQNCAVRPKGDCKS-UHFFFAOYSA-N 0.000 claims 1
• ZDDJFBYGXKZOOI-HBHSWBPBSA-N 1-[5-[2-(ethylcarbamoylamino)-7-[(e)-c-methyl-n-(2,2,2-trifluoroethoxy)carbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(\C(C)=N\OCC(F)(F)F)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 ZDDJFBYGXKZOOI-HBHSWBPBSA-N 0.000 claims 1
• GLGVXISUDYLTMU-IBBHUPRXSA-N 1-[5-[2-(ethylcarbamoylamino)-7-[(e)-n-(2-hydroxyethoxy)-c-methylcarbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(\C(C)=N\OCCO)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 GLGVXISUDYLTMU-IBBHUPRXSA-N 0.000 claims 1
• PIXMQGNEPRYBGJ-KPGMTVGESA-N 1-[5-[2-(ethylcarbamoylamino)-7-[(e)-n-(2-methoxyethoxy)-c-methylcarbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(\C(C)=N\OCCOC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 PIXMQGNEPRYBGJ-KPGMTVGESA-N 0.000 claims 1
• GUNCNAJMPJRGCP-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-[1-(2-methoxyethyl)-6-oxopyrimidin-4-yl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC(=O)N(CCOC)C=N1 GUNCNAJMPJRGCP-UHFFFAOYSA-N 0.000 claims 1
• KWQOGTFVUKXYNZ-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-[2-(1,3-thiazol-2-yl)ethynyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C#CC1=NC=CS1 KWQOGTFVUKXYNZ-UHFFFAOYSA-N 0.000 claims 1
• NVVGRGWUINPVHT-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-[2-(5-methyl-1,3,4-thiadiazol-2-yl)ethynyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C#CC1=NN=C(C)S1 NVVGRGWUINPVHT-UHFFFAOYSA-N 0.000 claims 1
• HTTWSINFWVCFJS-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-[4-(hydroxymethyl)-1,3-thiazol-2-yl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC(CO)=CS1 HTTWSINFWVCFJS-UHFFFAOYSA-N 0.000 claims 1
• BLEDCLFQGPCGQI-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C(N=C1)=CC=C1CN1CCOCC1 BLEDCLFQGPCGQI-UHFFFAOYSA-N 0.000 claims 1
• SWDROYBZLHRPJQ-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-[5-(trifluoromethyl)pyridin-2-yl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=C(C(F)(F)F)C=N1 SWDROYBZLHRPJQ-UHFFFAOYSA-N 0.000 claims 1
• SFAJEYKXUYHKHG-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-[6-[(2-methylpropan-2-yl)oxy]pyrazin-2-yl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CN=CC(OC(C)(C)C)=N1 SFAJEYKXUYHKHG-UHFFFAOYSA-N 0.000 claims 1
• OSIZFJHESNPNRM-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-furo[3,2-c]pyridin-4-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(C=2C=3C=COC=3C=CN=2)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 OSIZFJHESNPNRM-UHFFFAOYSA-N 0.000 claims 1
• YCNBLPNWRAXMJC-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-hex-1-ynyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C=2N=C(NC(=O)NCC)SC=2C(C#CCCCC)=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 YCNBLPNWRAXMJC-UHFFFAOYSA-N 0.000 claims 1
• KHEJZFZUKOSVCN-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-imidazol-1-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1N1C=CN=C1 KHEJZFZUKOSVCN-UHFFFAOYSA-N 0.000 claims 1
• LJFMHMRHZQAHGU-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-methoxy-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(OC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 LJFMHMRHZQAHGU-UHFFFAOYSA-N 0.000 claims 1
• VWDJHIIDPMAYAT-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyrazin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CN=CC=N1 VWDJHIIDPMAYAT-UHFFFAOYSA-N 0.000 claims 1
• KEVFMPICOSXSNM-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyrazin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-propylpiperidine-4-carboxylic acid Chemical compound C1CC(CCC)(C(O)=O)CCN1C1=NC=C(C=2C=C3N=C(NC(=O)NCC)SC3=C(C=3N=CC=NC=3)C=2)C=N1 KEVFMPICOSXSNM-UHFFFAOYSA-N 0.000 claims 1
• NRQCOVTWTHVDHH-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyrazol-1-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1N1C=CC=N1 NRQCOVTWTHVDHH-UHFFFAOYSA-N 0.000 claims 1
• XVIKDVDCYZJEQZ-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]-1,2,4-thiadiazol-3-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2SN=C(N=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 XVIKDVDCYZJEQZ-UHFFFAOYSA-N 0.000 claims 1
• VTDLMMPOXPXBEX-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]-3-fluoropyridin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=C(F)C(N3CCC(C)(CC3)C(O)=O)=NC=2)=CC=1C1=CC=CC=N1 VTDLMMPOXPXBEX-UHFFFAOYSA-N 0.000 claims 1
• WTPJBVVUWARAKX-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]-3-methylpyridin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=C(C)C(N3CCC(C)(CC3)C(O)=O)=NC=2)=CC=1C1=CC=CC=N1 WTPJBVVUWARAKX-UHFFFAOYSA-N 0.000 claims 1
• UGAQROKNUXZONK-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]-4-methoxypyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C(=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)OC)=CC=1C1=CC=CC=N1 UGAQROKNUXZONK-UHFFFAOYSA-N 0.000 claims 1
• HJXQDUZLFXATDX-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]-4-methylpyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C(=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)C)=CC=1C1=CC=CC=N1 HJXQDUZLFXATDX-UHFFFAOYSA-N 0.000 claims 1
• BQMMRFSCMNFZSU-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrazin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2N=CC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 BQMMRFSCMNFZSU-UHFFFAOYSA-N 0.000 claims 1
• KDEJGQOKCYEPLC-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyridin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=CC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 KDEJGQOKCYEPLC-UHFFFAOYSA-N 0.000 claims 1
• LURIJXSAKDBXEA-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyridin-3-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=C(C=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 LURIJXSAKDBXEA-UHFFFAOYSA-N 0.000 claims 1
• XQUQYOUBYNTAGV-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-2-methylpiperidine-2-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2C(CCCC2)(C)C(O)=O)=CC=1C1=CC=CC=N1 XQUQYOUBYNTAGV-UHFFFAOYSA-N 0.000 claims 1
• XAKBUJMSYHVSRP-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-2-methylpyrrolidine-2-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2C(CCC2)(C)C(O)=O)=CC=1C1=CC=CC=N1 XAKBUJMSYHVSRP-UHFFFAOYSA-N 0.000 claims 1
• BSAZQPNUYCMTJT-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-3,4-dimethylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CC(C)C(C)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 BSAZQPNUYCMTJT-UHFFFAOYSA-N 0.000 claims 1
• HECGYFDHCWIYHM-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-3-(trifluoromethyl)pyrrolidine-3-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CC(CC2)(C(O)=O)C(F)(F)F)=CC=1C1=CC=CC=N1 HECGYFDHCWIYHM-UHFFFAOYSA-N 0.000 claims 1
• HQJKRWSBBBIPJK-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-3-methylpyrrolidine-3-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CC(C)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 HQJKRWSBBBIPJK-UHFFFAOYSA-N 0.000 claims 1
• DQFPWWTXWBMINF-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-(2,2,2-trifluoroethyl)piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC(F)(F)F)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 DQFPWWTXWBMINF-UHFFFAOYSA-N 0.000 claims 1
• OMKSSHCEHGMQCM-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-(methoxymethyl)piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(COC)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 OMKSSHCEHGMQCM-UHFFFAOYSA-N 0.000 claims 1
• NJNXSCUBTYHSGN-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-fluoropiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(F)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 NJNXSCUBTYHSGN-UHFFFAOYSA-N 0.000 claims 1
• CIVMGLPXLKVJJI-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-hydroxy-3-methylpiperidine-3-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CC(C)(C(O)CC2)C(O)=O)=CC=1C1=CC=CC=N1 CIVMGLPXLKVJJI-UHFFFAOYSA-N 0.000 claims 1
• ZDIKOLMINUXGSX-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-hydroxypiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(O)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 ZDIKOLMINUXGSX-UHFFFAOYSA-N 0.000 claims 1
• NEDZEUWJEDFTFG-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methoxypiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC2)(OC)C(O)=O)=CC=1C1=CC=CC=N1 NEDZEUWJEDFTFG-UHFFFAOYSA-N 0.000 claims 1
• RYGYAXOTBRTNEK-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-n-methylsulfonylpiperidine-4-carboxamide Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(=O)NS(C)(=O)=O)=CC=1C1=CC=CC=N1 RYGYAXOTBRTNEK-UHFFFAOYSA-N 0.000 claims 1
• DVHHHIADFLWGRF-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylazepane-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CCC2)C(O)=O)=CC=1C1=CC=CC=N1 DVHHHIADFLWGRF-UHFFFAOYSA-N 0.000 claims 1
• MIBVQVWSUZXFCA-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylsulfanylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC2)(SC)C(O)=O)=CC=1C1=CC=CC=N1 MIBVQVWSUZXFCA-UHFFFAOYSA-N 0.000 claims 1
• JMDUFIAKFPSXMZ-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylsulfonylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC2)(C(O)=O)S(C)(=O)=O)=CC=1C1=CC=CC=N1 JMDUFIAKFPSXMZ-UHFFFAOYSA-N 0.000 claims 1
• JCAYVDPDWCOPOX-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-phenylpiperidine-4-carboxamide Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC2)(C(N)=O)C=2C=CC=CC=2)=CC=1C1=CC=CC=N1 JCAYVDPDWCOPOX-UHFFFAOYSA-N 0.000 claims 1
• PCQLZNPLABVNRW-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-phenylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC2)(C(O)=O)C=2C=CC=CC=2)=CC=1C1=CC=CC=N1 PCQLZNPLABVNRW-UHFFFAOYSA-N 0.000 claims 1
• COGPNSRZKKKKBG-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-propan-2-ylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC2)(C(C)C)C(O)=O)=CC=1C1=CC=CC=N1 COGPNSRZKKKKBG-UHFFFAOYSA-N 0.000 claims 1
• XWZGNAXIFOXKJQ-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-propylpiperidine-4-carboxylic acid Chemical compound C1CC(CCC)(C(O)=O)CCN1C1=NC=C(C=2C=C3N=C(NC(=O)NCC)SC3=C(C=3N=CC=CC=3)C=2)C=N1 XWZGNAXIFOXKJQ-UHFFFAOYSA-N 0.000 claims 1
• YVQWIPHRMCUJNH-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-4-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=NC=C1 YVQWIPHRMCUJNH-UHFFFAOYSA-N 0.000 claims 1
• MRGDQBIMOXGTEQ-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyrimidin-4-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=NC=N1 MRGDQBIMOXGTEQ-UHFFFAOYSA-N 0.000 claims 1
• NXOQMYUAZNPIOZ-UHFFFAOYSA-N 1-[5-[7-(2-cyanopyrimidin-4-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=NC(C#N)=N1 NXOQMYUAZNPIOZ-UHFFFAOYSA-N 0.000 claims 1
• FNSXITYKZZQJOW-UHFFFAOYSA-N 1-[5-[7-(2-cyclopentylethynyl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C#CC1CCCC1 FNSXITYKZZQJOW-UHFFFAOYSA-N 0.000 claims 1
• MAPUQKJLTBPMPM-UHFFFAOYSA-N 1-[5-[7-(2-ethoxy-1,3-thiazol-5-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CN=C(OCC)S1 MAPUQKJLTBPMPM-UHFFFAOYSA-N 0.000 claims 1
• FNJXYMRQKGDTNM-UHFFFAOYSA-N 1-[5-[7-(3,5-difluoropyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=C(F)C=C1F FNJXYMRQKGDTNM-UHFFFAOYSA-N 0.000 claims 1
• FUPVDXFSCLQKSB-UHFFFAOYSA-N 1-[5-[7-(3-amino-6-methoxypyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC(OC)=CC=C1N FUPVDXFSCLQKSB-UHFFFAOYSA-N 0.000 claims 1
• VRYIQUFCLHGKHD-UHFFFAOYSA-N 1-[5-[7-(3-cyano-4-methoxypyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=CC(OC)=C1C#N VRYIQUFCLHGKHD-UHFFFAOYSA-N 0.000 claims 1
• NLQBPUHUQWDMLD-UHFFFAOYSA-N 1-[5-[7-(3-cyano-5-methylpyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=C(C)C=C1C#N NLQBPUHUQWDMLD-UHFFFAOYSA-N 0.000 claims 1
• MNIRKDMYPAYHSX-UHFFFAOYSA-N 1-[5-[7-(3-cyanopyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-ethylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=NC=CC=C1C#N MNIRKDMYPAYHSX-UHFFFAOYSA-N 0.000 claims 1
• UWRPXNHHUCKZMS-UHFFFAOYSA-N 1-[5-[7-(3-cyanopyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=CC=C1C#N UWRPXNHHUCKZMS-UHFFFAOYSA-N 0.000 claims 1
• SWXYBOOMFRYRSI-UHFFFAOYSA-N 1-[5-[7-(3-cyanopyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-propylpiperidine-4-carboxylic acid Chemical compound C1CC(CCC)(C(O)=O)CCN1C1=NC=C(C=2C=C3N=C(NC(=O)NCC)SC3=C(C=3C(=CC=CN=3)C#N)C=2)C=N1 SWXYBOOMFRYRSI-UHFFFAOYSA-N 0.000 claims 1
• MJGPWHINCULELK-UHFFFAOYSA-N 1-[5-[7-(4-cyanopyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-ethylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=CC(C#N)=CC=N1 MJGPWHINCULELK-UHFFFAOYSA-N 0.000 claims 1
• DZXMLSFUXACTGU-UHFFFAOYSA-N 1-[5-[7-(4-cyanopyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC(C#N)=CC=N1 DZXMLSFUXACTGU-UHFFFAOYSA-N 0.000 claims 1
• HBZMUYLGMPNMTE-UHFFFAOYSA-N 1-[5-[7-(4-cyanopyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-propylpiperidine-4-carboxylic acid Chemical compound C1CC(CCC)(C(O)=O)CCN1C1=NC=C(C=2C=C3N=C(NC(=O)NCC)SC3=C(C=3N=CC=C(C=3)C#N)C=2)C=N1 HBZMUYLGMPNMTE-UHFFFAOYSA-N 0.000 claims 1
• BLXJFFXXCRADJW-UHFFFAOYSA-N 1-[5-[7-(4-ethoxypyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC(OCC)=CC=N1 BLXJFFXXCRADJW-UHFFFAOYSA-N 0.000 claims 1
• QBXWBHJJMQJOQT-UHFFFAOYSA-N 1-[5-[7-(5,6-dimethoxypyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=C(OC)C(OC)=N1 QBXWBHJJMQJOQT-UHFFFAOYSA-N 0.000 claims 1
• SWFFQRRFNOHNQV-UHFFFAOYSA-N 1-[5-[7-(5-cyano-3-fluoropyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=C(C#N)C=C1F SWFFQRRFNOHNQV-UHFFFAOYSA-N 0.000 claims 1
• MPKUAYUJKGMPEE-UHFFFAOYSA-N 1-[5-[7-(5-cyano-3-methylpyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=C(C#N)C=C1C MPKUAYUJKGMPEE-UHFFFAOYSA-N 0.000 claims 1
• RYDIXDHIUHYJDA-UHFFFAOYSA-N 1-[5-[7-(5-cyano-4-methylpyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC(C)=C(C#N)C=N1 RYDIXDHIUHYJDA-UHFFFAOYSA-N 0.000 claims 1
• XRRYLOBTHKJYPK-UHFFFAOYSA-N 1-[5-[7-(5-cyano-6-methylpyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=C(C#N)C(C)=N1 XRRYLOBTHKJYPK-UHFFFAOYSA-N 0.000 claims 1
• QRSBDLNCIPTQSS-UHFFFAOYSA-N 1-[5-[7-(5-cyanopyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-ethylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=CC=C(C#N)C=N1 QRSBDLNCIPTQSS-UHFFFAOYSA-N 0.000 claims 1
• PFMFGYIDJIGMRL-UHFFFAOYSA-N 1-[5-[7-(5-cyanopyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=C(C#N)C=N1 PFMFGYIDJIGMRL-UHFFFAOYSA-N 0.000 claims 1
• KEYRTJWCHQTBGV-UHFFFAOYSA-N 1-[5-[7-(5-cyanopyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-propylpiperidine-4-carboxylic acid Chemical compound C1CC(CCC)(C(O)=O)CCN1C1=NC=C(C=2C=C3N=C(NC(=O)NCC)SC3=C(C=3N=CC(=CC=3)C#N)C=2)C=N1 KEYRTJWCHQTBGV-UHFFFAOYSA-N 0.000 claims 1
• CKXZNDIIPJVGGS-UHFFFAOYSA-N 1-[5-[7-(6-cyanopyridin-2-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=CC(C#N)=N1 CKXZNDIIPJVGGS-UHFFFAOYSA-N 0.000 claims 1
• UEEZCMFSTYORBV-CCVNUDIWSA-N 1-[5-[7-[(e)-ethoxyiminomethyl]-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(\C=N\OCC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 UEEZCMFSTYORBV-CCVNUDIWSA-N 0.000 claims 1
• XZTZEMVCXPLIBS-IBBHUPRXSA-N 1-[5-[7-[(e)-n-ethoxy-c-methylcarbonimidoyl]-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(\C(C)=N\OCC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 XZTZEMVCXPLIBS-IBBHUPRXSA-N 0.000 claims 1
• AVBOTASALZZZPO-UHFFFAOYSA-N 1-[5-[7-[2-(dimethylamino)-1,3-thiazol-5-yl]-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CN=C(N(C)C)S1 AVBOTASALZZZPO-UHFFFAOYSA-N 0.000 claims 1
• CFSJTWQUOAZSJC-UHFFFAOYSA-N 1-[5-[7-[3-cyano-4-(dimethylamino)pyridin-2-yl]-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=NC=CC(N(C)C)=C1C#N CFSJTWQUOAZSJC-UHFFFAOYSA-N 0.000 claims 1
• JACOZHYDYPGGBJ-UHFFFAOYSA-N 1-[5-[7-[5-(cyanomethyl)pyridin-2-yl]-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=C(CC#N)C=N1 JACOZHYDYPGGBJ-UHFFFAOYSA-N 0.000 claims 1
• RBGVTBWFDSOTBB-UHFFFAOYSA-N 1-[5-[7-bromo-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-ethylpiperidine-4-carboxylic acid Chemical compound C=1C(Br)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(O)=O)CC1 RBGVTBWFDSOTBB-UHFFFAOYSA-N 0.000 claims 1
• MNCCWECZKRRJQC-UHFFFAOYSA-N 1-[5-[7-bromo-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-propylpiperidine-4-carboxylic acid Chemical compound C1CC(CCC)(C(O)=O)CCN1C1=NC=C(C=2C=C3N=C(NC(=O)NCC)SC3=C(Br)C=2)C=N1 MNCCWECZKRRJQC-UHFFFAOYSA-N 0.000 claims 1
• AHOCXEKTJIDOMA-UHFFFAOYSA-N 1-[5-[7-bromo-2-(ethylcarbamoylamino)-6-methoxy-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound COC=1C(Br)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 AHOCXEKTJIDOMA-UHFFFAOYSA-N 0.000 claims 1
• GFGKTSGYEFSJPT-UHFFFAOYSA-N 1-[[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]methyl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(CN3CCC(C)(CC3)C(O)=O)=NC=2)=CC=1C1=CC=CC=N1 GFGKTSGYEFSJPT-UHFFFAOYSA-N 0.000 claims 1
• RWSIQFBDFSBCMM-UHFFFAOYSA-N 2-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1,3,4,5,6,6a-hexahydrocyclopenta[c]pyrrole-3a-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CC3(CCCC3C2)C(O)=O)=CC=1C1=CC=CC=N1 RWSIQFBDFSBCMM-UHFFFAOYSA-N 0.000 claims 1
• OYDOPICKYILOLX-UHFFFAOYSA-N 2-ethyl-7-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-7-azaspiro[3.5]nonane-2-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC3(CC(CC)(C3)C(O)=O)CC2)=CC=1C1=CC=CC=N1 OYDOPICKYILOLX-UHFFFAOYSA-N 0.000 claims 1
• JCCMEQDXFMFWSY-UHFFFAOYSA-N 3-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyridin-2-yl]-5-methyl-4h-1,2-oxazole-5-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=CC=2)C=2CC(C)(ON=2)C(O)=O)=CC=1C1=CC=CC=N1 JCCMEQDXFMFWSY-UHFFFAOYSA-N 0.000 claims 1
• AICVCIFWLZLFMO-UHFFFAOYSA-N 4-[[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-methylamino]-1-methylcyclohexane-1-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N(C)C2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 AICVCIFWLZLFMO-UHFFFAOYSA-N 0.000 claims 1
• OLQZKASMDSLNHI-UHFFFAOYSA-N 4-[[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]amino]-1-methylcyclohexane-1-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(NC3CCC(C)(CC3)C(O)=O)=NC=2)=CC=1C1=CC=CC=N1 OLQZKASMDSLNHI-UHFFFAOYSA-N 0.000 claims 1
• JAQPSBDKFLKJAF-UHFFFAOYSA-N 4-benzyl-1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC=3C=CC=CC=3)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 JAQPSBDKFLKJAF-UHFFFAOYSA-N 0.000 claims 1
• RERBMFQIXRURTK-UHFFFAOYSA-N 4-cyano-1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC2)(C#N)C(O)=O)=CC=1C1=CC=CC=N1 RERBMFQIXRURTK-UHFFFAOYSA-N 0.000 claims 1
• XXNFHUQLHUKFJC-UHFFFAOYSA-N 4-cyclopropyl-1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC2)(C2CC2)C(O)=O)=CC=1C1=CC=CC=N1 XXNFHUQLHUKFJC-UHFFFAOYSA-N 0.000 claims 1
• MLABYLQGVDSNEB-UHFFFAOYSA-N 4-ethoxy-1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC2)(OCC)C(O)=O)=CC=1C1=CC=CC=N1 MLABYLQGVDSNEB-UHFFFAOYSA-N 0.000 claims 1
• ZWRJPAHTPARALH-UHFFFAOYSA-N 4-ethyl-1-[3-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]-1,2,4-thiadiazol-5-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2N=C(SN=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 ZWRJPAHTPARALH-UHFFFAOYSA-N 0.000 claims 1
• PMKIIDLYDLXPKN-UHFFFAOYSA-N 4-ethyl-1-[4-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]-1,3-thiazol-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2N=C(SC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 PMKIIDLYDLXPKN-UHFFFAOYSA-N 0.000 claims 1
• WJDVHZMZOPTOIR-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-4-pyridin-2-yl-[1,3]thiazolo[5,4-c]pyridin-6-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=NC=1C1=CC=CC=N1 WJDVHZMZOPTOIR-UHFFFAOYSA-N 0.000 claims 1
• YULATESOHQTMNQ-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-5-pyrazol-1-ylimidazo[1,2-a]pyridin-7-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=1C2=NC(NC(=O)NCC)=CN2C(N2N=CC=C2)=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(O)=O)CC1 YULATESOHQTMNQ-UHFFFAOYSA-N 0.000 claims 1
• PWBBQPMZYQRNQW-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-(4-fluorophenyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=CC=C(F)C=C1 PWBBQPMZYQRNQW-UHFFFAOYSA-N 0.000 claims 1
• HGEXZHKEFSHCLS-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-(4-methoxypyridin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=CC(OC)=CC=N1 HGEXZHKEFSHCLS-UHFFFAOYSA-N 0.000 claims 1
• YATUNNBRTDJPNO-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-(4-methoxypyrimidin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=NC=CC(OC)=N1 YATUNNBRTDJPNO-UHFFFAOYSA-N 0.000 claims 1
• BFZCYWDENDQLQG-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-(4-methylpyrimidin-2-yl)-1,3-benzothiazol-5-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2N=CC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=NC=CC(C)=N1 BFZCYWDENDQLQG-UHFFFAOYSA-N 0.000 claims 1
• ZYVCXNZAFYGWFH-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-(4-methylpyrimidin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=NC=CC(C)=N1 ZYVCXNZAFYGWFH-UHFFFAOYSA-N 0.000 claims 1
• BNKRGEZGEUGARE-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-(4-oxo-1h-pyrimidin-6-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=CC(=O)NC=N1 BNKRGEZGEUGARE-UHFFFAOYSA-N 0.000 claims 1
• UEOTZTNEQXQQHC-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-(5-methylpyrimidin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=NC=C(C)C=N1 UEOTZTNEQXQQHC-UHFFFAOYSA-N 0.000 claims 1
• RYAIMKKRPXXRIP-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-(6-methoxypyrimidin-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=CC(OC)=NC=N1 RYAIMKKRPXXRIP-UHFFFAOYSA-N 0.000 claims 1
• CNXYGMRWMNJHAM-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=1C(C=2C=3C=CNC=3N=CN=2)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(O)=O)CC1 CNXYGMRWMNJHAM-UHFFFAOYSA-N 0.000 claims 1
• QAQBBVBDUKDJTN-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-(C-ethyl-N-methoxycarbonimidoyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=1C(C(CC)=NOC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(O)=O)CC1 QAQBBVBDUKDJTN-UHFFFAOYSA-N 0.000 claims 1
• AUGCRZOOOOCFGR-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-(methoxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=1C(COC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(O)=O)CC1 AUGCRZOOOOCFGR-UHFFFAOYSA-N 0.000 claims 1
• QAQBBVBDUKDJTN-BIZUNTBRSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-[(e)-c-ethyl-n-methoxycarbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=1C(\C(CC)=N\OC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(O)=O)CC1 QAQBBVBDUKDJTN-BIZUNTBRSA-N 0.000 claims 1
• QSSIULGDIOLINI-CCVNUDIWSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-[(e)-methoxyiminomethyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=1C(\C=N\OC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(O)=O)CC1 QSSIULGDIOLINI-CCVNUDIWSA-N 0.000 claims 1
• QAQBBVBDUKDJTN-MZFJOGFUSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-[(z)-c-ethyl-n-methoxycarbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=1C(\C(CC)=N/OC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(O)=O)CC1 QAQBBVBDUKDJTN-MZFJOGFUSA-N 0.000 claims 1
• QSSIULGDIOLINI-MUXKCCDJSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-[(z)-methoxyiminomethyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=1C(\C=N/OC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(O)=O)CC1 QSSIULGDIOLINI-MUXKCCDJSA-N 0.000 claims 1
• VSDAALGBJHRNCR-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-propanoyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=1C(C(=O)CC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(O)=O)CC1 VSDAALGBJHRNCR-UHFFFAOYSA-N 0.000 claims 1
• PNZRDKVNWFGXIM-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-pyrazin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=CN=CC=N1 PNZRDKVNWFGXIM-UHFFFAOYSA-N 0.000 claims 1
• DHRVPWANGFWADD-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]-1,3-thiazol-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2SC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 DHRVPWANGFWADD-UHFFFAOYSA-N 0.000 claims 1
• CEOBYTAJUWIVLD-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2N=CC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 CEOBYTAJUWIVLD-UHFFFAOYSA-N 0.000 claims 1
• GCWPCIHKHREHIS-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyridin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=CC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 GCWPCIHKHREHIS-UHFFFAOYSA-N 0.000 claims 1
• BGDFGUILEKFYGA-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 BGDFGUILEKFYGA-UHFFFAOYSA-N 0.000 claims 1
• PMGZMASQWSAZQZ-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-3h-benzimidazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C=12NC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 PMGZMASQWSAZQZ-UHFFFAOYSA-N 0.000 claims 1
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
• URRFLHQXSXTXQS-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-6-methoxy-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound COC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(=O)OCC)CC1 URRFLHQXSXTXQS-UHFFFAOYSA-N 0.000 claims 1
• MWJDLABAJOIWJU-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical class C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(=O)OCC)=CC=1C1=CC=CC=N1 MWJDLABAJOIWJU-UHFFFAOYSA-N 0.000 claims 1
• CLAQUKVMUVOGMZ-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylsulfonylpiperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC2)(C(=O)OCC)S(C)(=O)=O)=CC=1C1=CC=CC=N1 CLAQUKVMUVOGMZ-UHFFFAOYSA-N 0.000 claims 1
• SGWRIEGDMVMVEH-UHFFFAOYSA-N ethyl 1-[5-[7-(1-acetylpiperidin-4-yl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(=O)OCC)=CC=1C1CCN(C(C)=O)CC1 SGWRIEGDMVMVEH-UHFFFAOYSA-N 0.000 claims 1
• HSWJFXXNRUQKQS-UHFFFAOYSA-N ethyl 3-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyridin-2-yl]-5-methyl-4h-1,2-oxazole-5-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=CC=2)C=2CC(C)(ON=2)C(=O)OCC)=CC=1C1=CC=CC=N1 HSWJFXXNRUQKQS-UHFFFAOYSA-N 0.000 claims 1
• LTWIXGSWLRJXFX-UHFFFAOYSA-N ethyl 5-[[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]amino]-2-methyl-1,3-dioxane-2-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(NC3COC(C)(OC3)C(=O)OCC)=NC=2)=CC=1C1=CC=CC=N1 LTWIXGSWLRJXFX-UHFFFAOYSA-N 0.000 claims 1
• SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims 1
• SHTRGQKBFCVOLF-UHFFFAOYSA-N methyl 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-3-methyl-4-oxopiperidine-3-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CC(C)(C(=O)CC2)C(=O)OC)=CC=1C1=CC=CC=N1 SHTRGQKBFCVOLF-UHFFFAOYSA-N 0.000 claims 1
• CMIGEQOTAHNYGK-UHFFFAOYSA-N methyl 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-hydroxy-3-methylpiperidine-3-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CC(C)(C(O)CC2)C(=O)OC)=CC=1C1=CC=CC=N1 CMIGEQOTAHNYGK-UHFFFAOYSA-N 0.000 claims 1
• LRIIHAFRFBCZMB-UHFFFAOYSA-N methyl 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-hydroxypiperidine-4-carboxylate Chemical class C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(O)(CC2)C(=O)OC)=CC=1C1=CC=CC=N1 LRIIHAFRFBCZMB-UHFFFAOYSA-N 0.000 claims 1
• GECJOBMLBYECOP-UHFFFAOYSA-N methyl 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methoxypiperidine-4-carboxylate Chemical class C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC2)(OC)C(=O)OC)=CC=1C1=CC=CC=N1 GECJOBMLBYECOP-UHFFFAOYSA-N 0.000 claims 1
• QVWDSJAIGUQZHX-UHFFFAOYSA-N methyl 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical class C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(=O)OC)=CC=1C1=CC=CC=N1 QVWDSJAIGUQZHX-UHFFFAOYSA-N 0.000 claims 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
• 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 432
• 239000000243 solution Substances 0.000 description 229
• 239000011541 reaction mixture Substances 0.000 description 225
• 235000019439 ethyl acetate Nutrition 0.000 description 215
• 239000007787 solid Substances 0.000 description 202
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 165
• 239000000047 product Substances 0.000 description 165
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 164
• 238000006243 chemical reaction Methods 0.000 description 153
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 147
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 141
• 230000002829 reductive effect Effects 0.000 description 137
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 120
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 117
• 238000004809 thin layer chromatography Methods 0.000 description 114
• 239000002904 solvent Substances 0.000 description 100
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 99
• 239000011734 sodium Substances 0.000 description 98
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 94
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 94
• 239000012267 brine Substances 0.000 description 89
• 239000000741 silica gel Substances 0.000 description 79
• 229910002027 silica gel Inorganic materials 0.000 description 79
• 238000005481 NMR spectroscopy Methods 0.000 description 75
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
• 239000012044 organic layer Substances 0.000 description 69
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 66
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 66
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 61
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
• 239000000543 intermediate Substances 0.000 description 50
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
• 238000003756 stirring Methods 0.000 description 42
• 238000000746 purification Methods 0.000 description 35
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 29
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 29
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• 239000000706 filtrate Substances 0.000 description 27
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
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• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 25
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 25
• 238000001990 intravenous administration Methods 0.000 description 24
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 24
• 238000010926 purge Methods 0.000 description 24
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 22
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 22
• XPGIBDJXEVAVTO-UHFFFAOYSA-N 5-bromo-2-chloropyrimidine Chemical compound ClC1=NC=C(Br)C=N1 XPGIBDJXEVAVTO-UHFFFAOYSA-N 0.000 description 19
• NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 19
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• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 18
• 238000005160 1H NMR spectroscopy Methods 0.000 description 17
• 239000000463 material Substances 0.000 description 17
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• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
• 239000007858 starting material Substances 0.000 description 16
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 15
• 238000003818 flash chromatography Methods 0.000 description 15
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
• 239000007864 aqueous solution Substances 0.000 description 14
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 13
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• 238000004587 chromatography analysis Methods 0.000 description 13
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• GROSTTZPZYYHEI-UHFFFAOYSA-N ethyl 1-[5-[7-bromo-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=1C(Br)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(=O)OCC)CC1 GROSTTZPZYYHEI-UHFFFAOYSA-N 0.000 description 13
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
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• 235000011056 potassium acetate Nutrition 0.000 description 12
• 239000002244 precipitate Substances 0.000 description 12
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• KWNVFAOEIPOIPW-UHFFFAOYSA-N ethyl 1-(5-bromopyrimidin-2-yl)-4-ethoxypiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(OCC)CCN1C1=NC=C(Br)C=N1 KWNVFAOEIPOIPW-UHFFFAOYSA-N 0.000 description 2
• JBLROONTPUBPMC-UHFFFAOYSA-N ethyl 1-(5-bromopyrimidin-2-yl)-4-ethylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(CC)CCN1C1=NC=C(Br)C=N1 JBLROONTPUBPMC-UHFFFAOYSA-N 0.000 description 2
• LBCFWXROIMCRLN-UHFFFAOYSA-N ethyl 1-(5-bromopyrimidin-2-yl)-4-fluoropiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(F)CCN1C1=NC=C(Br)C=N1 LBCFWXROIMCRLN-UHFFFAOYSA-N 0.000 description 2
• IDMRWFJHAJYZDR-UHFFFAOYSA-N ethyl 1-(5-bromopyrimidin-2-yl)-4-hydroxypiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(O)CCN1C1=NC=C(Br)C=N1 IDMRWFJHAJYZDR-UHFFFAOYSA-N 0.000 description 2
• NVLUIAAXEYPJKZ-UHFFFAOYSA-N ethyl 1-(5-bromopyrimidin-2-yl)-4-methylsulfanylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(SC)CCN1C1=NC=C(Br)C=N1 NVLUIAAXEYPJKZ-UHFFFAOYSA-N 0.000 description 2
• SYMHBBUUFZNONP-UHFFFAOYSA-N ethyl 1-(5-bromopyrimidin-2-yl)-4-methylsulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(C)(=O)=O)CCN1C1=NC=C(Br)C=N1 SYMHBBUUFZNONP-UHFFFAOYSA-N 0.000 description 2
• PHEJRPJQXFMLBV-UHFFFAOYSA-N ethyl 1-(5-bromopyrimidin-2-yl)piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C1=NC=C(Br)C=N1 PHEJRPJQXFMLBV-UHFFFAOYSA-N 0.000 description 2
• UTCPYEBJBHYECT-UHFFFAOYSA-N ethyl 1-[(5-bromopyrimidin-2-yl)methyl]-4-methylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(C)CCN1CC1=NC=C(Br)C=N1 UTCPYEBJBHYECT-UHFFFAOYSA-N 0.000 description 2
• HNUCAJLBLRXDKH-UHFFFAOYSA-N ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(2-methoxyethoxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(C)CCN1C1=NC=C(C=2C=C3N=C(SC3=C(COCCOC)C=2)N2C(N(CC)CN(C)C2)=O)C=N1 HNUCAJLBLRXDKH-UHFFFAOYSA-N 0.000 description 2
• ADXAASQQKAANLE-UHFFFAOYSA-N ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-formyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(C)CCN1C1=NC=C(C=2C=C3N=C(SC3=C(C=O)C=2)N2C(N(CC)CN(C)C2)=O)C=N1 ADXAASQQKAANLE-UHFFFAOYSA-N 0.000 description 2
• JUYWWCNMKSAZPN-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(pyridine-2-carbonylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(=O)OCC)=CC=1NC(=O)C1=CC=CC=N1 JUYWWCNMKSAZPN-UHFFFAOYSA-N 0.000 description 2
• VHZIFEQSSFSDAW-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(pyrimidine-2-carbonylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(=O)OCC)=CC=1NC(=O)C1=NC=CC=N1 VHZIFEQSSFSDAW-UHFFFAOYSA-N 0.000 description 2
• RDRPADFDBYVBQP-KPGMTVGESA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-[(e)-n-methoxy-c-methylcarbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=1C(\C(C)=N\OC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(=O)OCC)CC1 RDRPADFDBYVBQP-KPGMTVGESA-N 0.000 description 2
• FHZDQOZTPBGOME-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-[2-(3-methylimidazol-4-yl)ethynyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(=O)OCC)=CC=1C#CC1=CN=CN1C FHZDQOZTPBGOME-UHFFFAOYSA-N 0.000 description 2
• HDULNEUEZIPKNR-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-[[methyl(pyrimidin-2-yl)amino]methyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(=O)OCC)=CC=1CN(C)C1=NC=CC=N1 HDULNEUEZIPKNR-UHFFFAOYSA-N 0.000 description 2
• WLGAADGJJBTSQT-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-methyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=1C(C)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(=O)OCC)CC1 WLGAADGJJBTSQT-UHFFFAOYSA-N 0.000 description 2
• NMCPABJGAIDNHX-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-pyrazin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-prop-2-enylpiperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC=C)(CC2)C(=O)OCC)=CC=1C1=CN=CC=N1 NMCPABJGAIDNHX-UHFFFAOYSA-N 0.000 description 2
• OZEJMVPPVMIPSS-UHFFFAOYSA-N ethyl 1-[5-[7-(ethylcarbamoyl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=1C(C(=O)NCC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(=O)OCC)CC1 OZEJMVPPVMIPSS-UHFFFAOYSA-N 0.000 description 2
• LWPRIDJHEIMKTE-UHFFFAOYSA-N ethyl 1-[5-[7-ethenyl-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=1C(C=C)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(=O)OCC)CC1 LWPRIDJHEIMKTE-UHFFFAOYSA-N 0.000 description 2
• WKYFVGXGMAVNHS-UHFFFAOYSA-N ethyl 1-[5-[7-ethyl-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=1C(CC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(=O)OCC)CC1 WKYFVGXGMAVNHS-UHFFFAOYSA-N 0.000 description 2
• IWDBYBSDWPMBDZ-UHFFFAOYSA-N ethyl 2-methyl-3-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4h-pyrido[3,2-b][1,4]oxazine-2-carboxylate Chemical compound C=1N=C2NC(=O)C(C(=O)OCC)(C)OC2=CC=1B1OC(C)(C)C(C)(C)O1 IWDBYBSDWPMBDZ-UHFFFAOYSA-N 0.000 description 2
• DBSRQLSGMFNMSQ-UHFFFAOYSA-N ethyl 3-(5-bromopyridin-2-yl)-5-methyl-4h-1,2-oxazole-5-carboxylate Chemical compound O1C(C(=O)OCC)(C)CC(C=2N=CC(Br)=CC=2)=N1 DBSRQLSGMFNMSQ-UHFFFAOYSA-N 0.000 description 2
• HNULXDMNOGMJLB-UHFFFAOYSA-N ethyl 4-(1,3-dioxoisoindol-2-yl)-1-methylcyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OCC)(C)CCC1N1C(=O)C2=CC=CC=C2C1=O HNULXDMNOGMJLB-UHFFFAOYSA-N 0.000 description 2
• VCCAYWSDFKIZEF-UHFFFAOYSA-N ethyl 4-amino-1-methylcyclohexane-1-carboxylate Chemical compound CCOC(=O)C1(C)CCC(N)CC1 VCCAYWSDFKIZEF-UHFFFAOYSA-N 0.000 description 2
• WASRJUXSLHUONH-UHFFFAOYSA-N ethyl 4-aminocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCC(N)CC1 WASRJUXSLHUONH-UHFFFAOYSA-N 0.000 description 2
• ZLMPLZLHGNPJTA-UHFFFAOYSA-N ethyl 4-cyanopiperidine-4-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1(C#N)CCNCC1 ZLMPLZLHGNPJTA-UHFFFAOYSA-N 0.000 description 2
• GLLIUWGRMLCKQK-UHFFFAOYSA-N ethyl 4-cyclopropylpiperidine-4-carboxylate;hydrochloride Chemical compound Cl.C1CC1C1(C(=O)OCC)CCNCC1 GLLIUWGRMLCKQK-UHFFFAOYSA-N 0.000 description 2
• YCYKNLGPLYDJJE-UHFFFAOYSA-N ethyl 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-formyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylate Chemical compound C=1C(C=O)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(=O)OCC)CC1 YCYKNLGPLYDJJE-UHFFFAOYSA-N 0.000 description 2
• WEJQDOQJHKHPNU-UHFFFAOYSA-N ethyl 4-hydroxypiperidine-4-carboxylate Chemical compound CCOC(=O)C1(O)CCNCC1 WEJQDOQJHKHPNU-UHFFFAOYSA-N 0.000 description 2
• VNHLFUMSWZCORK-UHFFFAOYSA-N ethyl 4-methylsulfanylpiperidine-4-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1(SC)CCNCC1 VNHLFUMSWZCORK-UHFFFAOYSA-N 0.000 description 2
• NSNZUKCRKAXQST-UHFFFAOYSA-N ethyl 4-methylsulfonylpiperidine-4-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1(S(C)(=O)=O)CCNCC1 NSNZUKCRKAXQST-UHFFFAOYSA-N 0.000 description 2
• REMKTWLYWWGNEV-UHFFFAOYSA-N ethyl 4-prop-2-enylpiperidine-4-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1(CC=C)CCNCC1 REMKTWLYWWGNEV-UHFFFAOYSA-N 0.000 description 2
• IUYVWBHQRUQKER-UHFFFAOYSA-N ethyl 7-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]-2-methyl-3-oxo-4h-pyrido[3,2-b][1,4]oxazine-2-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=C3OC(C)(C(=O)NC3=NC=2)C(=O)OCC)=CC=1C1=CC=CC=N1 IUYVWBHQRUQKER-UHFFFAOYSA-N 0.000 description 2
• YGPAXFFZCMHLTK-UHFFFAOYSA-N ethyl 7-bromo-2-methyl-3-oxo-4h-pyrido[3,2-b][1,4]oxazine-2-carboxylate Chemical compound BrC1=CN=C2NC(=O)C(C(=O)OCC)(C)OC2=C1 YGPAXFFZCMHLTK-UHFFFAOYSA-N 0.000 description 2
• LWGLDXOPXMASKJ-UHFFFAOYSA-N ethyl 7-bromo-5-chloroimidazo[1,2-a]pyridine-2-carboxylate Chemical compound ClC1=CC(Br)=CC2=NC(C(=O)OCC)=CN21 LWGLDXOPXMASKJ-UHFFFAOYSA-N 0.000 description 2
• BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 2
• 239000011737 fluorine Substances 0.000 description 2
• 229940124307 fluoroquinolone Drugs 0.000 description 2
• 239000006260 foam Substances 0.000 description 2
• BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
• 239000007789 gas Substances 0.000 description 2
• IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
• 239000001257 hydrogen Substances 0.000 description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
• 239000012535 impurity Substances 0.000 description 2
• 239000004615 ingredient Substances 0.000 description 2
• 229940102223 injectable solution Drugs 0.000 description 2
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
• 125000000842 isoxazolyl group Chemical group 0.000 description 2
• 150000002576 ketones Chemical class 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 239000012263 liquid product Substances 0.000 description 2
• 229910052744 lithium Inorganic materials 0.000 description 2
• RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 2
• 239000011777 magnesium Substances 0.000 description 2
• 229910052749 magnesium Inorganic materials 0.000 description 2
• 238000004949 mass spectrometry Methods 0.000 description 2
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
• YFMQGYOIFRMLMJ-UHFFFAOYSA-N methyl 1-(5-bromopyrimidin-2-yl)-3-(trifluoromethyl)pyrrolidine-3-carboxylate Chemical compound C1C(C(=O)OC)(C(F)(F)F)CCN1C1=NC=C(Br)C=N1 YFMQGYOIFRMLMJ-UHFFFAOYSA-N 0.000 description 2
• SIMZEKAJFZJWCP-UHFFFAOYSA-N methyl 1-(5-bromopyrimidin-2-yl)-4-[(2-methylpropan-2-yl)oxycarbonylamino]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)(NC(=O)OC(C)(C)C)CCN1C1=NC=C(Br)C=N1 SIMZEKAJFZJWCP-UHFFFAOYSA-N 0.000 description 2
• WDSKESLDQBMPLD-UHFFFAOYSA-N methyl 1-(5-bromopyrimidin-2-yl)-4-hydroxy-3-methylpiperidine-3-carboxylate Chemical compound C1CC(O)C(C(=O)OC)(C)CN1C1=NC=C(Br)C=N1 WDSKESLDQBMPLD-UHFFFAOYSA-N 0.000 description 2
• HFQYLMMYIGSJBU-UHFFFAOYSA-N methyl 2,3,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrole-3a-carboxylate Chemical compound C1CCC2CNCC21C(=O)OC HFQYLMMYIGSJBU-UHFFFAOYSA-N 0.000 description 2
• WTBMTSLTOFBBET-UHFFFAOYSA-N methyl 2-(5-bromopyrimidin-2-yl)-1,3,4,5,6,6a-hexahydrocyclopenta[c]pyrrole-3a-carboxylate Chemical compound C1C2(C(=O)OC)CCCC2CN1C1=NC=C(Br)C=N1 WTBMTSLTOFBBET-UHFFFAOYSA-N 0.000 description 2
• DFKYQTUJTMSPII-UHFFFAOYSA-N methyl 2-benzyl-1,3,4,5,6,6a-hexahydrocyclopenta[c]pyrrole-3a-carboxylate Chemical compound C1C2(C(=O)OC)CCCC2CN1CC1=CC=CC=C1 DFKYQTUJTMSPII-UHFFFAOYSA-N 0.000 description 2
• VBMHFZJINCOCDH-UHFFFAOYSA-N methyl 3-(trifluoromethyl)pyrrolidine-3-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1(C(F)(F)F)CCNC1 VBMHFZJINCOCDH-UHFFFAOYSA-N 0.000 description 2
• XWBFIPVPQLAHMA-UHFFFAOYSA-N methyl 4-[(2-methylpropan-2-yl)oxycarbonylamino]piperidine-4-carboxylate Chemical compound CC(C)(C)OC(=O)NC1(C(=O)OC)CCNCC1 XWBFIPVPQLAHMA-UHFFFAOYSA-N 0.000 description 2
• MCIOJLAJBZGHGI-UHFFFAOYSA-N methyl 4-hydroxy-3-methylpiperidine-3-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1(C)CNCCC1O MCIOJLAJBZGHGI-UHFFFAOYSA-N 0.000 description 2
• 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 2
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
• BQNSIPJDOWWKNQ-UHFFFAOYSA-N n-(4-bromo-3-fluoro-2-nitro-6-pyridin-2-ylphenyl)-2,2-dimethylpropanamide Chemical compound C1=C(Br)C(F)=C([N+]([O-])=O)C(NC(=O)C(C)(C)C)=C1C1=CC=CC=N1 BQNSIPJDOWWKNQ-UHFFFAOYSA-N 0.000 description 2
• IYYHGHQCLDLPHB-UHFFFAOYSA-N n-(4-bromo-5-fluoro-2-pyridin-2-ylphenyl)-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC(F)=C(Br)C=C1C1=CC=CC=N1 IYYHGHQCLDLPHB-UHFFFAOYSA-N 0.000 description 2
• JDMOBPVQUSTBRF-UHFFFAOYSA-N n-(5-fluoro-2-pyridin-2-ylphenyl)-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC(F)=CC=C1C1=CC=CC=N1 JDMOBPVQUSTBRF-UHFFFAOYSA-N 0.000 description 2
• PUHSWGKSQUHSDT-UHFFFAOYSA-N n-[(2,6-dibromopyridin-4-yl)carbamothioyl]benzamide Chemical compound BrC1=NC(Br)=CC(NC(=S)NC(=O)C=2C=CC=CC=2)=C1 PUHSWGKSQUHSDT-UHFFFAOYSA-N 0.000 description 2
• WQLPHGABHNNMTL-UHFFFAOYSA-N n-[(3-bromo-5-phenylmethoxyphenyl)carbamothioyl]benzamide Chemical compound C=1C(OCC=2C=CC=CC=2)=CC(Br)=CC=1NC(=S)NC(=O)C1=CC=CC=C1 WQLPHGABHNNMTL-UHFFFAOYSA-N 0.000 description 2
• VHDOMZSBOGQSMO-UHFFFAOYSA-N n-[5-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC(F)=CC=C1B1OC(C)(C)C(C)(C)O1 VHDOMZSBOGQSMO-UHFFFAOYSA-N 0.000 description 2
• GEHDCVXPBUTGAR-UHFFFAOYSA-N n-ethyl-2-(ethylcarbamoylamino)-5-hydroxy-1,3-benzothiazole-7-carboxamide Chemical compound OC1=CC(C(=O)NCC)=C2SC(NC(=O)NCC)=NC2=C1 GEHDCVXPBUTGAR-UHFFFAOYSA-N 0.000 description 2
• QNLZQGYGAFQUAF-UHFFFAOYSA-N n-ethyl-2-(ethylcarbamoylamino)-5-methoxy-1,3-benzothiazole-7-carboxamide Chemical compound COC1=CC(C(=O)NCC)=C2SC(NC(=O)NCC)=NC2=C1 QNLZQGYGAFQUAF-UHFFFAOYSA-N 0.000 description 2
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
• IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 2
• 229910017604 nitric acid Inorganic materials 0.000 description 2
• 239000000346 nonvolatile oil Substances 0.000 description 2
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
• 229960002969 oleic acid Drugs 0.000 description 2
• PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 2
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
• 125000003544 oxime group Chemical group 0.000 description 2
• LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
• 235000003270 potassium fluoride Nutrition 0.000 description 2
• TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 2
• 125000002098 pyridazinyl group Chemical group 0.000 description 2
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 2
• 125000000168 pyrrolyl group Chemical group 0.000 description 2
• 150000007660 quinolones Chemical class 0.000 description 2
• 239000011347 resin Substances 0.000 description 2
• 229920005989 resin Polymers 0.000 description 2
• 238000004366 reverse phase liquid chromatography Methods 0.000 description 2
• 238000004007 reversed phase HPLC Methods 0.000 description 2
• 230000002441 reversible effect Effects 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 239000012047 saturated solution Substances 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 235000010378 sodium ascorbate Nutrition 0.000 description 2
• PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 2
• 229960005055 sodium ascorbate Drugs 0.000 description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
• PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 2
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• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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• YSMODUONRAFBET-UHNVWZDZSA-N erythro-5-hydroxy-L-lysine Chemical compound NC[C@H](O)CC[C@H](N)C(O)=O YSMODUONRAFBET-UHNVWZDZSA-N 0.000 description 1
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• XDQNYAJLSMQCIW-UHFFFAOYSA-N ethyl 1-(4-bromo-1,3-thiazol-2-yl)-4-ethylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(CC)CCN1C1=NC(Br)=CS1 XDQNYAJLSMQCIW-UHFFFAOYSA-N 0.000 description 1
• MBUBKDGRAXXYME-UHFFFAOYSA-N ethyl 1-(4-bromopyridin-2-yl)-4-methylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(C)CCN1C1=CC(Br)=CC=N1 MBUBKDGRAXXYME-UHFFFAOYSA-N 0.000 description 1
• BDQYMUXSLLYYFF-UHFFFAOYSA-N ethyl 1-(5-bromo-1,3-thiazol-2-yl)-4-ethylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(CC)CCN1C1=NC=C(Br)S1 BDQYMUXSLLYYFF-UHFFFAOYSA-N 0.000 description 1
• DIISFVIUHBFMLD-UHFFFAOYSA-N ethyl 1-(5-bromopyridin-3-yl)-4-methylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(C)CCN1C1=CN=CC(Br)=C1 DIISFVIUHBFMLD-UHFFFAOYSA-N 0.000 description 1
• OCRLZABSXCDFHW-UHFFFAOYSA-N ethyl 1-(5-bromopyrimidine-2-carbonyl)-4-methylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(C)CCN1C(=O)C1=NC=C(Br)C=N1 OCRLZABSXCDFHW-UHFFFAOYSA-N 0.000 description 1
• NOJYIHASRCBTBX-UHFFFAOYSA-N ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(hydroxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(C)CCN1C1=NC=C(C=2C=C3N=C(SC3=C(CO)C=2)N2C(N(CC)CN(C)C2)=O)C=N1 NOJYIHASRCBTBX-UHFFFAOYSA-N 0.000 description 1
• YDKYCJORKJUGCA-UHFFFAOYSA-N ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(iodomethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(C)CCN1C1=NC=C(C=2C=C3N=C(SC3=C(CI)C=2)N2C(N(CC)CN(C)C2)=O)C=N1 YDKYCJORKJUGCA-UHFFFAOYSA-N 0.000 description 1
• ATXSGVFJJGSVCR-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-4-pyridin-2-yl-[1,3]thiazolo[5,4-c]pyridin-6-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(=O)OCC)=NC=1C1=CC=CC=N1 ATXSGVFJJGSVCR-UHFFFAOYSA-N 0.000 description 1
• HTCSZBUCAVAHCX-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(1-methyltriazol-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(=O)OCC)=CC=1C1=CN(C)N=N1 HTCSZBUCAVAHCX-UHFFFAOYSA-N 0.000 description 1
• LYPYNCKARCZOBZ-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(1-phenyltriazol-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(=O)OCC)=CC=1C(N=N1)=CN1C1=CC=CC=C1 LYPYNCKARCZOBZ-UHFFFAOYSA-N 0.000 description 1
• HOJPOJRAYSGURI-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(2-trimethylsilylethynyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=1C(C#C[Si](C)(C)C)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(=O)OCC)CC1 HOJPOJRAYSGURI-UHFFFAOYSA-N 0.000 description 1
• FZWUEYWUGDOKGO-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(4-methylpyridin-2-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(=O)OCC)=CC=1C1=CC(C)=CC=N1 FZWUEYWUGDOKGO-UHFFFAOYSA-N 0.000 description 1
• CLXOGXXNPUWTGI-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-[1-(trimethylsilylmethyl)triazol-4-yl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(=O)OCC)=CC=1C1=CN(C[Si](C)(C)C)N=N1 CLXOGXXNPUWTGI-UHFFFAOYSA-N 0.000 description 1
• XDJRQLPJARTBIG-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-formyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=1C(C=O)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(=O)OCC)CC1 XDJRQLPJARTBIG-UHFFFAOYSA-N 0.000 description 1
• XMSSBALEOXEDDX-UHFFFAOYSA-N ethyl 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-(trifluoromethyl)piperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC2)(C(=O)OCC)C(F)(F)F)=CC=1C1=CC=CC=N1 XMSSBALEOXEDDX-UHFFFAOYSA-N 0.000 description 1
• HYLAZACPTHMXHD-UHFFFAOYSA-N ethyl 1-[5-[7-(1-ethoxyethenyl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=1C(C(=C)OCC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(=O)OCC)CC1 HYLAZACPTHMXHD-UHFFFAOYSA-N 0.000 description 1
• SAOYDBVIYCQBGN-UHFFFAOYSA-N ethyl 1-[5-[7-(4,5-dihydro-1,3-thiazol-2-ylcarbamoyl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(=O)OCC)=CC=1C(=O)NC1=NCCS1 SAOYDBVIYCQBGN-UHFFFAOYSA-N 0.000 description 1
• ZKHZALBCNHGJPW-UHFFFAOYSA-N ethyl 1-[5-[7-[3-(1,3-dioxoisoindol-2-yl)oxyprop-1-ynyl]-2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-ethylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(CC)CCN1C1=NC=C(C=2C=C3N=C(SC3=C(C#CCON3C(C4=CC=CC=C4C3=O)=O)C=2)N2C(N(CC)CN(C)C2)=O)C=N1 ZKHZALBCNHGJPW-UHFFFAOYSA-N 0.000 description 1
• BLNDYICHICBTNJ-UHFFFAOYSA-N ethyl 1-[5-[7-acetyl-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=1C(C(C)=O)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(=O)OCC)CC1 BLNDYICHICBTNJ-UHFFFAOYSA-N 0.000 description 1
• YYJKGWIOPAFYMR-UHFFFAOYSA-N ethyl 1-[5-[7-bromo-2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-ethylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(CC)CCN1C1=NC=C(C=2C=C3N=C(SC3=C(Br)C=2)N2C(N(CC)CN(C)C2)=O)C=N1 YYJKGWIOPAFYMR-UHFFFAOYSA-N 0.000 description 1
• QXWPKJONVDGFMF-UHFFFAOYSA-N ethyl 1-[5-[7-bromo-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-prop-2-enylpiperidine-4-carboxylate Chemical compound C=1C(Br)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC=C)(C(=O)OCC)CC1 QXWPKJONVDGFMF-UHFFFAOYSA-N 0.000 description 1
• QCMXVVUAXJLYPC-UHFFFAOYSA-N ethyl 1-[5-[7-cyclohexyl-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(C)(CC2)C(=O)OCC)=CC=1C1CCCCC1 QCMXVVUAXJLYPC-UHFFFAOYSA-N 0.000 description 1
• FLUKEWNALZFURC-UHFFFAOYSA-N ethyl 1-benzyl-3,4-dimethylpiperidine-4-carboxylate Chemical compound C1C(C)C(C(=O)OCC)(C)CCN1CC1=CC=CC=C1 FLUKEWNALZFURC-UHFFFAOYSA-N 0.000 description 1
• SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
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• VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 1
• YYNJXQIQHNPOSH-UHFFFAOYSA-N ethyl 4-[(5-bromopyrimidin-2-yl)-methylamino]-1-methylcyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OCC)(C)CCC1N(C)C1=NC=C(Br)C=N1 YYNJXQIQHNPOSH-UHFFFAOYSA-N 0.000 description 1
• XGFRNAHHYBGXIZ-UHFFFAOYSA-N ethyl 4-benzyl-1-(5-bromopyrimidin-2-yl)piperidine-4-carboxylate Chemical compound C1CN(C=2N=CC(Br)=CN=2)CCC1(C(=O)OCC)CC1=CC=CC=C1 XGFRNAHHYBGXIZ-UHFFFAOYSA-N 0.000 description 1
• CAPDUHXHHVMIOJ-UHFFFAOYSA-N ethyl 4-benzylpiperidine-4-carboxylate Chemical compound C=1C=CC=CC=1CC1(C(=O)OCC)CCNCC1 CAPDUHXHHVMIOJ-UHFFFAOYSA-N 0.000 description 1
• WKFHWILNBMRPON-OKCVXOCRSA-N ethyl 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-[(e)-methoxyiminomethyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylate Chemical compound C=1C(\C=N\OC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(=O)OCC)CC1 WKFHWILNBMRPON-OKCVXOCRSA-N 0.000 description 1
• YXDJXSLUZFBZIQ-ATZGPIRCSA-N ethyl 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-[(e)-n-methoxy-c-methylcarbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylate Chemical compound C=1C(\C(C)=N\OC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(=O)OCC)CC1 YXDJXSLUZFBZIQ-ATZGPIRCSA-N 0.000 description 1
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• INWHPEOLADZATF-UHFFFAOYSA-N ethyl 4-prop-2-enyl-1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(CC=C)CCN1C1=NC=C(B2OC(C)(C)C(C)(C)O2)C=N1 INWHPEOLADZATF-UHFFFAOYSA-N 0.000 description 1
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