JP2013542204A5 - - Google Patents
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- JP2013542204A5 JP2013542204A5 JP2013532015A JP2013532015A JP2013542204A5 JP 2013542204 A5 JP2013542204 A5 JP 2013542204A5 JP 2013532015 A JP2013532015 A JP 2013532015A JP 2013532015 A JP2013532015 A JP 2013532015A JP 2013542204 A5 JP2013542204 A5 JP 2013542204A5
- Authority
- JP
- Japan
- Prior art keywords
- ethylcarbamoylamino
- benzothiazol
- pyrimidin
- piperidine
- carboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 229920006395 saturated elastomer Polymers 0.000 claims description 32
- 125000002619 bicyclic group Chemical group 0.000 claims description 19
- 125000001475 halogen functional group Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 229910014033 C-OH Inorganic materials 0.000 claims description 5
- 229910014570 C—OH Inorganic materials 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 29
- 239000002253 acid Substances 0.000 claims 19
- -1 Ethylcarbamoylamino Chemical group 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 230000008878 coupling Effects 0.000 claims 4
- 238000010168 coupling process Methods 0.000 claims 4
- 238000005859 coupling reaction Methods 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000004450 alkenylene group Chemical group 0.000 claims 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 239000002243 precursor Substances 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 239000005973 Carvone Substances 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 230000001580 bacterial effect Effects 0.000 claims 2
- 238000011109 contamination Methods 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 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
- 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
- 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 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
- 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
- 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
- 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
- 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 1
- 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 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
- 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 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
- 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
- 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
- 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
- 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
- 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 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
- 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 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
- 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 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
- 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 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
- 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 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
- 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 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
- 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 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
- 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
- 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
- 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
- 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 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
- 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
- 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
- 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 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
- 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
- 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
- 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
- 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
- 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 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
- 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 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
- 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 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
- 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 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
- 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 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
- 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 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
- 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
- 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
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 150000001768 cations Chemical class 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
- 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 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
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 239000002271 gyrase inhibitor Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 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
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 claims 1
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| ES2705923T3 (es) | 2011-01-14 | 2019-03-27 | Spero Trinem Inc | Formas sólidas de inhibidor de girasa (R)-1-etil-3-[6-fluoro-5-[2-(1-hidroxi-1-metil-etil)pirimidin-5-il]-7-(tetrahidrofuran-2-il)-1H-bencimidazol-2-il]urea |
| EP2663556B1 (en) | 2011-01-14 | 2014-10-15 | Vertex Pharmaceuticals Incorporated | Process of making gyrase and topoisomerase iv inhibitors |
| SG191946A1 (en) | 2011-01-14 | 2013-08-30 | Vertex Pharma | Pyrimidine gyrase and topoisomerase iv inhibitors |
| CN103702994B (zh) | 2011-06-20 | 2016-03-23 | 沃泰克斯药物股份有限公司 | 旋转酶和拓扑异构酶抑制剂的磷酸酯 |
| CN104302645A (zh) * | 2012-03-22 | 2015-01-21 | 生物区欧洲有限公司 | 抗菌化合物 |
| WO2014015105A1 (en) | 2012-07-18 | 2014-01-23 | Vertex Pharmaceuticals Incorporated | Solid forms of (r)-2-(5-(2-(3-ethylureido)-6-fluoro-7-(tetrahydrofuran-2-yl)-1h-benzo[d]imidazol-5-yl)pyrimidin-2-yl)propan-2-yl dihydrogen phosphate and salts thereof |
| US9572809B2 (en) | 2012-07-18 | 2017-02-21 | Spero Trinem, Inc. | Combination therapy to treat Mycobacterium diseases |
| BR112016018048A2 (pt) | 2014-02-03 | 2017-08-08 | Spero Gyrase Inc | Método para o tratamento ou prevenção de uma infecção bacteriana, uso de um inibidor de topoisomerase tipo ii bacteriana em combinação com uma polimixina ou derivado de polimixina no tratamento ou prevenção de uma infecção bacteriana, uso de um inibidor de topoisomerase tipo ii bacteriana em combinação com uma polimixina ou derivado de polimixina na preparação de um medicamento para o tratamento ou prevenção de uma infecção bacteriana, método para melhorar a atividade antibacteriana de um inibidor de topoisomerase tipo ii bacteriana, método para melhorar a eficácia bactericida de um inibidor de topoisomerase tipo ii bacteriana, composição, agente antibacteriano, processo, e, composto |
| CN104230991A (zh) * | 2014-08-25 | 2014-12-24 | 亿腾药业（泰州）有限公司 | 一种控制福沙吡坦二甲葡胺中钯残留的方法 |
| WO2016119700A1 (en) | 2015-01-28 | 2016-08-04 | Jn Therapeutics | Substituted imidazo [1, 2-a] pyridin-2-ylamine compounds, and pharmaceutical compositions and methods of use thereof |
| CN106167486B (zh) * | 2015-05-22 | 2019-06-14 | 北京四环制药有限公司 | 单环类回旋酶和拓扑异构酶iv抑制剂 |
| PT3436461T (pt) | 2016-03-28 | 2024-01-23 | Incyte Corp | Compostos de pirrolotriazina como inibidores de tam |
| ES2948194T3 (es) * | 2017-01-18 | 2023-09-01 | Array Biopharma Inc | Compuestos de pirazolo[1,5-a]pirazina sustituida como inhibidores de la cinasa RET |
| RU2019133662A (ru) | 2017-03-24 | 2021-04-26 | Тайсо Фармасьютикал Ко., Лтд. | Производное 2(1h)-хинолинона |
| WO2019057946A1 (en) | 2017-09-25 | 2019-03-28 | F. Hoffmann-La Roche Ag | MULTI-CYCLIC AROMATIC COMPOUNDS AS D-FACTOR INHIBITORS |
| JP7569688B2 (ja) | 2017-12-22 | 2024-10-18 | ハイバーセル，インコーポレイテッド | ホスファチジルイノシトールリン酸キナーゼ阻害剤としてのアミノピリジン誘導体 |
| TW202112767A (zh) | 2019-06-17 | 2021-04-01 | 美商佩特拉製藥公司 | 作為磷脂酸肌醇磷酸激酶抑制劑之胺基吡啶衍生物 |
| EP4013744A1 (de) * | 2019-08-15 | 2022-06-22 | Bayer Aktiengesellschaft | Verfahren zur herstellung von 2-(phenylimino)-3-alkyl-1,3-thiazolidin-4-onen |
| CN115315425B (zh) * | 2020-08-14 | 2025-03-28 | 上海复旦张江生物医药股份有限公司 | 一种取代的咪唑并[1,2-a]吡啶-2-基酰胺化合物的制备方法及其中间体 |
| CN115073358B (zh) * | 2022-07-21 | 2023-09-26 | 安徽德诺医药股份有限公司 | 一种n-苄基-4-哌啶甲酸乙酯的制备方法 |
| CN118955404A (zh) * | 2024-07-30 | 2024-11-15 | 凯美克(上海)医药科技有限公司 | 一种化合物3,5-二溴哒嗪的合成方法 |
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| SI1341769T1 (sl) | 2000-12-15 | 2008-02-29 | Vertex Pharma | Inhibitorji bakterijske giraze in njihove uporabe |
| US7569591B2 (en) * | 2003-01-31 | 2009-08-04 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| US7618974B2 (en) * | 2003-01-31 | 2009-11-17 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| US8404852B2 (en) * | 2003-01-31 | 2013-03-26 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| JPWO2007119833A1 (ja) * | 2006-04-14 | 2009-08-27 | 武田薬品工業株式会社 | 含窒素複素環化合物 |
| GB0724342D0 (en) * | 2007-12-13 | 2008-01-30 | Prolysis Ltd | Anitbacterial compositions |
| US20110166088A1 (en) * | 2008-06-25 | 2011-07-07 | Ranbaxy Laboratories Limited | Benzothiazoles and aza-analogues thereof use as antibacterial agents |
| WO2010100144A1 (en) * | 2009-03-04 | 2010-09-10 | Merck Serono S.A. | Fused bicyclic compounds as inhibitors for pi3 kinase |
-
2011
- 2011-10-07 AU AU2011313820A patent/AU2011313820A1/en not_active Abandoned
- 2011-10-07 US US13/268,154 patent/US9181234B2/en not_active Expired - Fee Related
- 2011-10-07 EP EP11830125.8A patent/EP2625178A4/en not_active Withdrawn
- 2011-10-07 WO PCT/AU2011/001284 patent/WO2012045124A1/en not_active Ceased
- 2011-10-07 JP JP2013532015A patent/JP5864589B2/ja not_active Expired - Fee Related
- 2011-10-07 CN CN201180059188.1A patent/CN103249732B/zh not_active Expired - Fee Related
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