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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| EP2663558A1 (en) | 2011-01-14 | 2013-11-20 | Vertex Pharmaceuticals Incorporated | Solid forms of gyrase inhibitor (r)-1-ethyl-3-[5-[2-{1-hydroxy-1-methyl-ethyl}pyrimidin-5-yl]-7-(tetrahydrofuran-2-yl}-1h-benzimidazol-2-yl]urea |
| PT2663556E (pt) | 2011-01-14 | 2014-11-27 | Vertex Pharma | Processo de fabrico de inibidores de girase e topoisomerase iv |
| RU2625305C2 (ru) | 2011-01-14 | 2017-07-13 | Сперо Тринем, Инк. | Твердые формы ингибитора гиразы (r)-1-этил-3-[6-фтор-5[2-(1-гидрокси-1-метил-этил) пиримидин-5-ил]-7-(тетрагидрофуран-2-ил)-1н-бензимидазол-2-ил] мочевины |
| JP6085829B2 (ja) | 2011-01-14 | 2017-03-01 | スペロ トリネム， インコーポレイテッド | ピリミジンジャイレースおよびトポイソメラーゼｉｖ阻害剤 |
| WO2012177707A1 (en) | 2011-06-20 | 2012-12-27 | Vertex Pharmaceuticals Incorporated | Phosphate esters of gyrase and topoisomerase inhibitors |
| WO2013138860A1 (en) | 2012-03-22 | 2013-09-26 | Biota Europe Limited | Antibacterial compounds |
| US9018216B2 (en) | 2012-07-18 | 2015-04-28 | 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 |
| WO2014014845A1 (en) | 2012-07-18 | 2014-01-23 | Vertex Pharmaceuticals Incorporated | Combination therapy comprising|1 -ethyl-3-[5-[2-{1 -hydroxy-1 -methyl-ethyl}pyrimidin-5-yl]-7-(tetra hydrofuran-2-|yl}-1 h-benzimidazol-2-yl]urea and derivatives thereof to treat mycobacterium|diseases |
| EP3102203A2 (en) | 2014-02-03 | 2016-12-14 | Spero Gyrase, Inc. | Antibacterial combinations comprising polymyxin |
| 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 |
| CN107428749B (zh) | 2015-01-28 | 2020-07-24 | 上海复旦张江生物医药股份有限公司 | 取代的咪唑并[1,2-α]吡啶-2-基胺化合物及其药物组合物和使用方法 |
| 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 |
| CN114456176B (zh) | 2016-03-28 | 2024-08-30 | 因赛特公司 | 作为tam抑制剂的吡咯并三嗪化合物 |
| US11168090B2 (en) * | 2017-01-18 | 2021-11-09 | Array Biopharma Inc. | Substituted pyrazolo[1,5-a]pyrazines as RET kinase inhibitors |
| US20210070747A1 (en) | 2017-03-24 | 2021-03-11 | Taisho Pharmaceutical Co., Ltd. | 2(1h)-quinolinone derivative |
| WO2019057946A1 (en) | 2017-09-25 | 2019-03-28 | F. Hoffmann-La Roche Ag | MULTI-CYCLIC AROMATIC COMPOUNDS AS D-FACTOR INHIBITORS |
| EP3728228A1 (en) | 2017-12-22 | 2020-10-28 | Ravenna Pharmaceuticals, Inc. | Aminopyridine derivatives as phosphatidylinositol phosphate kinase inhibitors |
| 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 |
| KR20220047294A (ko) * | 2019-08-15 | 2022-04-15 | 바이엘 악티엔게젤샤프트 | 2-(페닐이미노)-3-알킬-1,3-티아졸리딘-4-온의 제조 방법 |
| WO2022032644A1 (zh) * | 2020-08-14 | 2022-02-17 | 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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| US7618974B2 (en) * | 2003-01-31 | 2009-11-17 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| US7569591B2 (en) * | 2003-01-31 | 2009-08-04 | 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 US US13/268,154 patent/US9181234B2/en not_active Expired - Fee Related
- 2011-10-07 WO PCT/AU2011/001284 patent/WO2012045124A1/en not_active Ceased
- 2011-10-07 AU AU2011313820A patent/AU2011313820A1/en not_active Abandoned
- 2011-10-07 CN CN201180059188.1A patent/CN103249732B/zh not_active Expired - Fee Related
- 2011-10-07 EP EP11830125.8A patent/EP2625178A4/en not_active Withdrawn
- 2011-10-07 JP JP2013532015A patent/JP5864589B2/ja not_active Expired - Fee Related
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