AU2011313820A1 - Antibacterial compounds - Google Patents

Info

Publication number

AU2011313820A1

AU2011313820A1 AU2011313820A AU2011313820A AU2011313820A1 AU 2011313820 A1 AU2011313820 A1 AU 2011313820A1 AU 2011313820 A AU2011313820 A AU 2011313820A AU 2011313820 A AU2011313820 A AU 2011313820A AU 2011313820 A1 AU2011313820 A1 AU 2011313820A1

Authority

AU

Australia

Prior art keywords

benzothiazol

ethylcarbamoylamino

pyrimidin

piperidine

carboxylic acid

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 206
• 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 13
• 239000000203 mixture Substances 0.000 claims abstract description 218
• 150000003839 salts Chemical class 0.000 claims abstract description 61
• 238000000034 method Methods 0.000 claims abstract description 24
• 230000008569 process Effects 0.000 claims abstract description 9
• 238000004519 manufacturing process Methods 0.000 claims abstract description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 199
• 229920006395 saturated elastomer Polymers 0.000 claims description 102
• 229910052757 nitrogen Inorganic materials 0.000 claims description 73
• 239000002243 precursor Substances 0.000 claims description 72
• 125000000623 heterocyclic group Chemical group 0.000 claims description 64
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 61
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 60
• 125000003545 alkoxy group Chemical group 0.000 claims description 42
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
• 125000002619 bicyclic group Chemical group 0.000 claims description 39
• 125000002950 monocyclic group Chemical group 0.000 claims description 37
• 125000005843 halogen group Chemical group 0.000 claims description 35
• -1 4,4-difluoro-1-piperidyl Chemical group 0.000 claims description 34
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 21
• 230000008878 coupling Effects 0.000 claims description 21
• 238000010168 coupling process Methods 0.000 claims description 21
• 238000005859 coupling reaction Methods 0.000 claims description 21
• 125000001475 halogen functional group Chemical group 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 12
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 239000003242 anti bacterial agent Substances 0.000 claims description 11
• 230000001580 bacterial effect Effects 0.000 claims description 11
• 208000015181 infectious disease Diseases 0.000 claims description 11
• 125000004450 alkenylene group Chemical group 0.000 claims description 10
• 125000002947 alkylene group Chemical group 0.000 claims description 10
• 125000004419 alkynylene group Chemical group 0.000 claims description 10
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 10
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 9
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 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
• 229910014033 C-OH Inorganic materials 0.000 claims description 5
• 229910014570 C—OH Inorganic materials 0.000 claims description 5
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
• 238000011109 contamination Methods 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 4
• 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 4
• 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 4
• 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 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
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 229910052796 boron Inorganic materials 0.000 claims description 4
• 150000001768 cations Chemical class 0.000 claims description 4
• SRJOCJYGOFTFLH-UHFFFAOYSA-M piperidine-4-carboxylate Chemical compound [O-]C(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-M 0.000 claims description 4
• 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 3
• 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 3
• CGBXIJUBUMBYPB-UVHMKAGCSA-N 1-[5-[2-(ethylcarbamoylamino)-7-[(e)-methoxyiminomethyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(\C=N\OC)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 CGBXIJUBUMBYPB-UVHMKAGCSA-N 0.000 claims description 3
• 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 3
• 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 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
• 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 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
• HCUGEMXYLZKDPO-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-[2-(3-methylimidazol-4-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=CN=CN1C HCUGEMXYLZKDPO-UHFFFAOYSA-N 0.000 claims description 2
• 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 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
• 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
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
• 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 compound 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 description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
• 125000006413 ring segment Chemical group 0.000 claims description 2
• 125000003003 spiro group Chemical group 0.000 claims description 2
• 239000000758 substrate Substances 0.000 claims description 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
• 125000004540 benzothiazol-5-yl group Chemical group S1C=NC2=C1C=CC(=C2)* 0.000 claims 5
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
• HCKNAJXCHMACDN-UHFFFAOYSA-N 1-methylpiperidine-4-carboxylic acid Chemical compound CN1CCC(C(O)=O)CC1 HCKNAJXCHMACDN-UHFFFAOYSA-N 0.000 claims 2
• 125000000473 carbonimidoyl group Chemical group [H]\N=C(/*)* 0.000 claims 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• 125000006272 (C3-C7) cycloalkyl group Chemical group 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
• 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 1
• 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 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
• 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 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
• JKICTKFXYRXQSJ-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(1-methylpyrazol-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=NN(C)C=1 JKICTKFXYRXQSJ-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
• 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
• 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 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
• 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
• 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
• 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
• 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 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
• LFDQGRCBVUPVGX-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-(4-methylpyrimidin-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(C)C=CN=3)C=2)C=N1 LFDQGRCBVUPVGX-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
• 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
• 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
• 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
• 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 1
• 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 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
• 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 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
• ZBCAWBJRXPONFH-VFLNYLIXSA-N 1-[5-[2-(ethylcarbamoylamino)-7-[(e)-n-hydroxy-c-methylcarbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=1C(\C(C)=N\O)=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C)(C(O)=O)CC1 ZBCAWBJRXPONFH-VFLNYLIXSA-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
• 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
• 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 1
• 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 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
• 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
• 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 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
• 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
• 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 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
• 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
• 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
• 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
• 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 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
• MJKBYJXHCKAMKG-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidine-2-carbonyl]-4-methylpiperidine-4-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)C(=O)N2CCC(C)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 MJKBYJXHCKAMKG-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
• 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
• 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
• 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
• 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 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
• 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 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
• 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
• 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 1
• 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 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
• 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
• QLQOUJUHABLQSQ-UHFFFAOYSA-N 3-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]pyrrolidine-3-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CC(CC)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 QLQOUJUHABLQSQ-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
• CZMDWZPSXYKKPY-UHFFFAOYSA-N 4-amino-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(N)(CC2)C(O)=O)=CC=1C1=CC=CC=N1 CZMDWZPSXYKKPY-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
• 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
• 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
• 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
• 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
• 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 1
• 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 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
• 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
• LAAYXYZFTCBCAV-UHFFFAOYSA-N 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-pyrimidin-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=N1 LAAYXYZFTCBCAV-UHFFFAOYSA-N 0.000 claims 1
• QBYURIZMKXSHIT-UHFFFAOYSA-N 5-[[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]amino]-2-methyl-1,3-dioxane-2-carboxylic acid Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(NC3COC(C)(OC3)C(O)=O)=NC=2)=CC=1C1=CC=CC=N1 QBYURIZMKXSHIT-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• 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
• JXDCDURWDRVLAQ-UHFFFAOYSA-N ethyl 1-[5-[7-[2-(4-ethoxycarbonyl-4-ethylpiperidin-1-yl)pyrimidin-5-yl]-2-(ethylcarbamoylamino)-1,3-benzoxazol-5-yl]pyrimidin-2-yl]-4-ethylpiperidine-4-carboxylate Chemical compound C=12OC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC)(CC2)C(=O)OCC)=CC=1C(C=N1)=CN=C1N1CCC(CC)(C(=O)OCC)CC1 JXDCDURWDRVLAQ-UHFFFAOYSA-N 0.000 claims 1
• MPDODIPWPHESFY-UHFFFAOYSA-N ethyl 4-cyano-1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CCC(CC2)(C#N)C(=O)OCC)=CC=1C1=CC=CC=N1 MPDODIPWPHESFY-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
• CSIWSRBCVMJUMM-UHFFFAOYSA-N methyl 1-[5-[2-(ethylcarbamoylamino)-7-pyridin-2-yl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-3-(trifluoromethyl)pyrrolidine-3-carboxylate Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N2CC(CC2)(C(=O)OC)C(F)(F)F)=CC=1C1=CC=CC=N1 CSIWSRBCVMJUMM-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
• 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 compound 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
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• HWFGRGYTYHGKRY-UHFFFAOYSA-N ethyl 1-(3-chloro-1,2,4-thiadiazol-5-yl)-4-ethylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(CC)CCN1C1=NC(Cl)=NS1 HWFGRGYTYHGKRY-UHFFFAOYSA-N 0.000 description 2
• JTVJKPUZZYFBEN-UHFFFAOYSA-N ethyl 1-(5-bromopyrimidin-2-yl)-3,4-dimethylpiperidine-4-carboxylate Chemical compound C1C(C)C(C(=O)OCC)(C)CCN1C1=NC=C(Br)C=N1 JTVJKPUZZYFBEN-UHFFFAOYSA-N 0.000 description 2
• MRBANNMIEAVJAW-UHFFFAOYSA-N ethyl 1-(5-bromopyrimidin-2-yl)-4-cyanopiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(C#N)CCN1C1=NC=C(Br)C=N1 MRBANNMIEAVJAW-UHFFFAOYSA-N 0.000 description 2
• 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
• 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
• 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
• QKGDDLXPSBUUIO-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-methylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(C)CCN1C1=NC=C(C=2C=C3N=C(SC3=C(Br)C=2)N2C(N(CC)CN(C)C2)=O)C=N1 QKGDDLXPSBUUIO-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
• KDDYYOJWCYJQLF-UHFFFAOYSA-N ethyl 4-(1,3-dioxoisoindol-2-yl)cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OCC)CCC1N1C(=O)C2=CC=CC=C2C1=O KDDYYOJWCYJQLF-UHFFFAOYSA-N 0.000 description 2
• PVAYYKRNIQMUNB-UHFFFAOYSA-N ethyl 4-(trifluoromethyl)piperidine-4-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1(C(F)(F)F)CCNCC1 PVAYYKRNIQMUNB-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
• 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 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
• NBELYFILOKZYJZ-UHFFFAOYSA-N ethyl 5-[(5-bromopyrimidin-2-yl)amino]-2-methyl-1,3-dioxane-2-carboxylate Chemical compound C1OC(C(=O)OCC)(C)OCC1NC1=NC=C(Br)C=N1 NBELYFILOKZYJZ-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
• TUXCQKQMKGATPB-UHFFFAOYSA-N ethyl n-[(4,6-dichloropyridin-2-yl)carbamothioyl]carbamate Chemical compound CCOC(=O)NC(=S)NC1=CC(Cl)=CC(Cl)=N1 TUXCQKQMKGATPB-UHFFFAOYSA-N 0.000 description 2
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
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• 239000007789 gas Substances 0.000 description 2
• 125000006038 hexenyl group Chemical group 0.000 description 2
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
• 235000011167 hydrochloric acid Nutrition 0.000 description 2
• 239000001257 hydrogen Substances 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• 239000012535 impurity Substances 0.000 description 2
• 238000007918 intramuscular administration Methods 0.000 description 2
• 125000000842 isoxazolyl group Chemical group 0.000 description 2
• 150000002576 ketones Chemical class 0.000 description 2
• 239000012263 liquid product Substances 0.000 description 2
• 229910052744 lithium Inorganic materials 0.000 description 2
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• 239000011777 magnesium Substances 0.000 description 2
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• 238000004949 mass spectrometry Methods 0.000 description 2
• SPUACDWLOLSOQO-UHFFFAOYSA-M methoxyazanium;chloride Chemical compound [Cl-].CO[NH3+] SPUACDWLOLSOQO-UHFFFAOYSA-M 0.000 description 2
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• 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
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• 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
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• 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
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• 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
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• 235000010262 sodium metabisulphite Nutrition 0.000 description 2
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• XPYLJGVHPLMDHY-UHFFFAOYSA-N (2,3,5-tribromo-4-methoxyphenyl)thiourea Chemical compound COC1=C(Br)C=C(NC(N)=S)C(Br)=C1Br XPYLJGVHPLMDHY-UHFFFAOYSA-N 0.000 description 1
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
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• STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 description 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
• XUBOMFCQGDBHNK-JTQLQIEISA-N (S)-gatifloxacin Chemical compound FC1=CC(C(C(C(O)=O)=CN2C3CC3)=O)=C2C(OC)=C1N1CCN[C@@H](C)C1 XUBOMFCQGDBHNK-JTQLQIEISA-N 0.000 description 1
• UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 1
• ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 1
• APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
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• PAXUSHNWLIUWOV-UHFFFAOYSA-N 1-(4,6-dibromo-[1,3]thiazolo[5,4-c]pyridin-2-yl)-3-ethylurea Chemical compound BrC1=NC(Br)=C2SC(NC(=O)NCC)=NC2=C1 PAXUSHNWLIUWOV-UHFFFAOYSA-N 0.000 description 1
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• 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
• 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 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
• 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 1
• 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 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
• 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
• 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 1
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• 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
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• PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical compound FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 description 1
• QXXHXTRTGZBOGD-UHFFFAOYSA-M trifluoromethanesulfonate;5-(trifluoromethyl)dibenzothiophen-5-ium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=C2[S+](C(F)(F)F)C3=CC=CC=C3C2=C1 QXXHXTRTGZBOGD-UHFFFAOYSA-M 0.000 description 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
• SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
• CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
• 238000001665 trituration Methods 0.000 description 1
• 238000002525 ultrasonication Methods 0.000 description 1
• 238000003828 vacuum filtration Methods 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 238000010792 warming Methods 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 238000010626 work up procedure Methods 0.000 description 1
• 229910052727 yttrium Inorganic materials 0.000 description 1
• 239000004246 zinc acetate Substances 0.000 description 1
• 239000011592 zinc chloride Substances 0.000 description 1
• 235000005074 zinc chloride Nutrition 0.000 description 1
• GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1