NZ586508A - Antibacterial condensed thiazoles - Google Patents

Info

Publication number

NZ586508A

NZ586508A NZ586508A NZ58650808A NZ586508A NZ 586508 A NZ586508 A NZ 586508A NZ 586508 A NZ586508 A NZ 586508A NZ 58650808 A NZ58650808 A NZ 58650808A NZ 586508 A NZ586508 A NZ 586508A

Authority

NZ

New Zealand

Prior art keywords

thiazol

ethyl

mmol

urea

benzo

Prior art date

2007-12-13

Links

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• Global Dossier
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• 230000000844 anti-bacterial effect Effects 0.000 title abstract description 14
• 150000003557 thiazoles Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 108
• -1 benzothiazol derivative compounds Chemical class 0.000 claims abstract description 86
• 150000003839 salts Chemical class 0.000 claims abstract description 13
• 208000035143 Bacterial infection Diseases 0.000 claims abstract description 7
• 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 7
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 5
• 238000002360 preparation method Methods 0.000 claims description 170
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 37
• 239000000203 mixture Substances 0.000 claims description 27
• 125000001424 substituent group Chemical group 0.000 claims description 21
• 239000001257 hydrogen Substances 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• 230000001580 bacterial effect Effects 0.000 claims description 19
• 230000000694 effects Effects 0.000 claims description 19
• 125000006413 ring segment Chemical group 0.000 claims description 18
• 125000000217 alkyl group Chemical group 0.000 claims description 17
• 238000000034 method Methods 0.000 claims description 14
• 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 13
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• YQEOHQLMFVMQRC-UHFFFAOYSA-N 1-ethyl-3-[5-[2-methyl-1-[(6-methylpyridin-2-yl)methyl]-6-oxopyridin-4-yl]-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(=CC1=O)C=C(C)N1CC1=CC=CC(C)=N1 YQEOHQLMFVMQRC-UHFFFAOYSA-N 0.000 claims description 9
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
• 239000004202 carbamide Substances 0.000 claims description 9
• 238000011109 contamination Methods 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 125000005605 benzo group Chemical group 0.000 claims description 7
• 125000003386 piperidinyl group Chemical group 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical class C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
• HDIHJDRBCDWCQH-UHFFFAOYSA-N 1-ethyl-3-[5-[2-methyl-6-oxo-1-(1-pyridin-2-ylethyl)pyridin-4-yl]-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(=CC1=O)C=C(C)N1C(C)C1=CC=CC=N1 HDIHJDRBCDWCQH-UHFFFAOYSA-N 0.000 claims description 5
• ZWMXKXNCZAXWND-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-[2-methyl-1-[1-(6-methylpyridin-3-yl)ethyl]-6-oxopyridin-4-yl]-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(=CC1=O)C=C(C)N1C(C)C1=CC=C(C)N=C1 ZWMXKXNCZAXWND-UHFFFAOYSA-N 0.000 claims description 5
• 241000194032 Enterococcus faecalis Species 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 125000002837 carbocyclic group Chemical group 0.000 claims description 5
• 229940032049 enterococcus faecalis Drugs 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 241000894007 species Species 0.000 claims description 5
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 4
• 241000194031 Enterococcus faecium Species 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 241000191967 Staphylococcus aureus Species 0.000 claims description 4
• 241000193998 Streptococcus pneumoniae Species 0.000 claims description 4
• 241000193996 Streptococcus pyogenes Species 0.000 claims description 4
• 125000004450 alkenylene group Chemical group 0.000 claims description 4
• 125000002947 alkylene group Chemical group 0.000 claims description 4
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
• 150000002825 nitriles Chemical class 0.000 claims description 4
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 4
• 229940031000 streptococcus pneumoniae Drugs 0.000 claims description 4
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 4
• 150000003568 thioethers Chemical class 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• FEZCMLSGFJEISW-UHFFFAOYSA-N 1-[5-[1-[3-(dimethylamino)propyl]-2-methyl-6-oxopyridin-4-yl]-6-fluoro-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=C(C)N(CCCN(C)C)C(=O)C=1 FEZCMLSGFJEISW-UHFFFAOYSA-N 0.000 claims description 3
• LCRAXLYNKHWKRF-UHFFFAOYSA-N 1-ethyl-3-(6-methyl-5-pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound CC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 LCRAXLYNKHWKRF-UHFFFAOYSA-N 0.000 claims description 3
• WEGXUOREFKMSHG-UHFFFAOYSA-N 1-ethyl-3-[5-(4-methyl-2,3-dihydropyrido[3,2-b][1,4]oxazin-7-yl)-1,3-benzothiazol-2-yl]urea Chemical compound CN1CCOC2=CC(C=3C=C4N=C(SC4=CC=3)NC(=O)NCC)=CN=C21 WEGXUOREFKMSHG-UHFFFAOYSA-N 0.000 claims description 3
• TWXZFBTXRMNCGO-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-[2-methyl-1-[(1-methylpiperidin-2-yl)methyl]-6-oxopyridin-4-yl]-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(=CC1=O)C=C(C)N1CC1CCCCN1C TWXZFBTXRMNCGO-UHFFFAOYSA-N 0.000 claims description 3
• UYOBBWGXWSFJIQ-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-[2-methyl-1-[(1-methylpyrrolidin-3-yl)methyl]-6-oxopyridin-4-yl]-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(=CC1=O)C=C(C)N1CC1CCN(C)C1 UYOBBWGXWSFJIQ-UHFFFAOYSA-N 0.000 claims description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
• 241000186427 Cutibacterium acnes Species 0.000 claims description 3
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical class C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
• 241000191963 Staphylococcus epidermidis Species 0.000 claims description 3
• 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 3
• UDENJDSANWBPKI-UHFFFAOYSA-N methyl 1-[5-[2-(ethylcarbamoylamino)-6-fluoro-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylate Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C(=O)OC)CC1 UDENJDSANWBPKI-UHFFFAOYSA-N 0.000 claims description 3
• NEDNPDQFFWXYMP-UHFFFAOYSA-N n-[5-[2-(ethylcarbamoylamino)-6-fluoro-1,3-benzothiazol-5-yl]pyridin-2-yl]acetamide Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=C(NC(C)=O)N=C1 NEDNPDQFFWXYMP-UHFFFAOYSA-N 0.000 claims description 3
• 229940055019 propionibacterium acne Drugs 0.000 claims description 3
• 229910052701 rubidium Inorganic materials 0.000 claims description 3
• KDXZKBAHQKXWHE-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-6-fluoro-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-3-carboxylic acid Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCCC(C(O)=O)C1 KDXZKBAHQKXWHE-UHFFFAOYSA-N 0.000 claims description 2
• JUZOPGNAEFIKMI-UHFFFAOYSA-N 1-ethyl-3-(5-pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 JUZOPGNAEFIKMI-UHFFFAOYSA-N 0.000 claims description 2
• SESBOEYJZCQDBQ-UHFFFAOYSA-N 1-ethyl-3-(6-fluoro-5-pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 SESBOEYJZCQDBQ-UHFFFAOYSA-N 0.000 claims description 2
• KBYWLNLMISYCJJ-UHFFFAOYSA-N 1-ethyl-3-[5-(1-methylpyrazol-4-yl)-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=NN(C)C=1 KBYWLNLMISYCJJ-UHFFFAOYSA-N 0.000 claims description 2
• RTGPBFZARVRBQG-UHFFFAOYSA-N 1-ethyl-3-[5-[1-(2-hydroxyethyl)-2-methyl-6-oxopyridin-4-yl]-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=C(C)N(CCO)C(=O)C=1 RTGPBFZARVRBQG-UHFFFAOYSA-N 0.000 claims description 2
• RWBYPNPZWLOZBK-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-(5-hydroxypyridin-3-yl)-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CN=CC(O)=C1 RWBYPNPZWLOZBK-UHFFFAOYSA-N 0.000 claims description 2
• WBXQNQAKOAPQIS-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-[1-(2-morpholin-4-ylethyl)-2-oxopyridin-4-yl]-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(=CC1=O)C=CN1CCN1CCOCC1 WBXQNQAKOAPQIS-UHFFFAOYSA-N 0.000 claims description 2
• CCKSWMJYOYEDBJ-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-[6-[(Z)-N'-hydroxycarbamimidoyl]pyridin-3-yl]-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=C(C(N)=NO)N=C1 CCKSWMJYOYEDBJ-UHFFFAOYSA-N 0.000 claims description 2
• JWQRMITVLGIGCV-UHFFFAOYSA-N 2-[5-[2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyridin-2-yl]-n-methylacetamide Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=C(CC(=O)NC)N=C1 JWQRMITVLGIGCV-UHFFFAOYSA-N 0.000 claims description 2
• ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• HHHNOETWBQNCSX-UHFFFAOYSA-N methyl 2-[4-[2-(ethylcarbamoylamino)-6-fluoro-1,3-benzothiazol-5-yl]pyrazol-1-yl]propanoate Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=NN(C(C)C(=O)OC)C=1 HHHNOETWBQNCSX-UHFFFAOYSA-N 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
• 150000003222 pyridines Chemical class 0.000 claims description 2
• 239000000758 substrate Substances 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 4
• DVLHFOLCJLLICM-UHFFFAOYSA-N 1-ethyl-3-[5-(6-morpholin-4-ylpyridin-3-yl)-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CC=C1N1CCOCC1 DVLHFOLCJLLICM-UHFFFAOYSA-N 0.000 claims 1
• OLSGHGOPECHRLT-UHFFFAOYSA-N C(C)NC(=O)NC=1SC2=C(N1)C=C(C(=C2)F)C2=CC(OC(=C2)C)=O.C(C)NC(NC=2SC1=C(N2)C=C(C(=C1)F)C=1C=NN(C1)CC(=O)OCC)=O Chemical compound C(C)NC(=O)NC=1SC2=C(N1)C=C(C(=C2)F)C2=CC(OC(=C2)C)=O.C(C)NC(NC=2SC1=C(N2)C=C(C(=C1)F)C=1C=NN(C1)CC(=O)OCC)=O OLSGHGOPECHRLT-UHFFFAOYSA-N 0.000 claims 1
• MYWWEZDAPIRFGF-UHFFFAOYSA-N C(C)NC(=O)NC=1SC2=C(N1)C=C(C(=C2)F)C2=NC=CC(=C2)OC.C(C)NC(=O)NC=2SC1=C(N2)C=C(C(=C1)F)C=1C=NC(=CC1)C1=NOC(=N1)C Chemical compound C(C)NC(=O)NC=1SC2=C(N1)C=C(C(=C2)F)C2=NC=CC(=C2)OC.C(C)NC(=O)NC=2SC1=C(N2)C=C(C(=C1)F)C=1C=NC(=CC1)C1=NOC(=N1)C MYWWEZDAPIRFGF-UHFFFAOYSA-N 0.000 claims 1
• DZGTWVQODMVIQC-UHFFFAOYSA-N C(C)NC(=O)NC=1SC2=C(N1)C=C(C(=C2)F)C=2C=NC(=CC2)CN2CCOCC2.C(C)NC(=O)NC=2SC1=C(N2)C=C(C(=C1)F)C=1C=NC(=CC1)CO Chemical compound C(C)NC(=O)NC=1SC2=C(N1)C=C(C(=C2)F)C=2C=NC(=CC2)CN2CCOCC2.C(C)NC(=O)NC=2SC1=C(N2)C=C(C(=C1)F)C=1C=NC(=CC1)CO DZGTWVQODMVIQC-UHFFFAOYSA-N 0.000 claims 1
• WKCFOWVZICUKTO-UHFFFAOYSA-N C(C)NC(=O)NC=1SC2=C(N1)C=C(C(=C2)F)C=2C=NC(=NC2)S(=O)(=O)C.C(C)NC(=O)NC=2SC1=C(N2)C=C(C(=C1)F)C1=CN=CS1 Chemical compound C(C)NC(=O)NC=1SC2=C(N1)C=C(C(=C2)F)C=2C=NC(=NC2)S(=O)(=O)C.C(C)NC(=O)NC=2SC1=C(N2)C=C(C(=C1)F)C1=CN=CS1 WKCFOWVZICUKTO-UHFFFAOYSA-N 0.000 claims 1
• FONNEKNWJKNBQL-UHFFFAOYSA-N C(C)NC(=O)NC=1SC2=C(N1)C=C(C(=C2)F)C=2C=NC=C(C2)OC.C(C)NC(=O)NC=2SC1=C(N2)C=C(C(=C1)F)C=1C=NC(=NC1)N1CCN(CC1)C Chemical compound C(C)NC(=O)NC=1SC2=C(N1)C=C(C(=C2)F)C=2C=NC=C(C2)OC.C(C)NC(=O)NC=2SC1=C(N2)C=C(C(=C1)F)C=1C=NC(=NC1)N1CCN(CC1)C FONNEKNWJKNBQL-UHFFFAOYSA-N 0.000 claims 1
• VXRIDLAXYLKGPT-UHFFFAOYSA-N C(C)NC(=O)NC=1SC2=C(N1)C=C(C(=C2)OC)C2=CC(N(C=C2)C)=O.C(C)NC(=O)NC=2SC1=C(N2)C=C(C(=C1)OC)C=1C=NC=CC1 Chemical compound C(C)NC(=O)NC=1SC2=C(N1)C=C(C(=C2)OC)C2=CC(N(C=C2)C)=O.C(C)NC(=O)NC=2SC1=C(N2)C=C(C(=C1)OC)C=1C=NC=CC1 VXRIDLAXYLKGPT-UHFFFAOYSA-N 0.000 claims 1
• QJZDTSHMKJFJPO-UHFFFAOYSA-N C(C)NC(=O)NC=1SC2=C(N1)C=C(C=C2)C2=CC(OC(=C2)C)=O.C(C)OCCN2C=C(C=CC2=O)C=2C=CC1=C(N=C(S1)NC(=O)NCC)C2 Chemical compound C(C)NC(=O)NC=1SC2=C(N1)C=C(C=C2)C2=CC(OC(=C2)C)=O.C(C)OCCN2C=C(C=CC2=O)C=2C=CC1=C(N=C(S1)NC(=O)NCC)C2 QJZDTSHMKJFJPO-UHFFFAOYSA-N 0.000 claims 1
• AWAPBMOXFTYRQB-UHFFFAOYSA-N C(C)NC(=O)NC=1SC2=C(N1)C=C(C=C2)C2=CN=C1N2C=CC=C1.C(C)NC(=O)NC=1SC2=C(N1)C=C(C=C2)C2=CN=C(S2)O Chemical compound C(C)NC(=O)NC=1SC2=C(N1)C=C(C=C2)C2=CN=C1N2C=CC=C1.C(C)NC(=O)NC=1SC2=C(N1)C=C(C=C2)C2=CN=C(S2)O AWAPBMOXFTYRQB-UHFFFAOYSA-N 0.000 claims 1
• BMXXKSDONGUVQM-UHFFFAOYSA-N C(C)NC(=O)NC=1SC2=C(N1)C=C(C=C2)C2=NC=C(N=C2)N2C(C=CC=C2)=O.C(C)NC(=O)NC=2SC1=C(N2)C=C(C=C1)C=1C=NC(=CC1)CO Chemical compound C(C)NC(=O)NC=1SC2=C(N1)C=C(C=C2)C2=NC=C(N=C2)N2C(C=CC=C2)=O.C(C)NC(=O)NC=2SC1=C(N2)C=C(C=C1)C=1C=NC(=CC1)CO BMXXKSDONGUVQM-UHFFFAOYSA-N 0.000 claims 1
• DCFRXPZOKZTFMJ-UHFFFAOYSA-N C(C)NC(=O)NC=1SC2=C(N1)C=C(C=C2)C=2C=CC=1N(C2)C=CN1.N=1N=CN2C1C=CC(=C2)C=2C=CC1=C(N=C(S1)NC(=O)NCC)C2 Chemical compound C(C)NC(=O)NC=1SC2=C(N1)C=C(C=C2)C=2C=CC=1N(C2)C=CN1.N=1N=CN2C1C=CC(=C2)C=2C=CC1=C(N=C(S1)NC(=O)NCC)C2 DCFRXPZOKZTFMJ-UHFFFAOYSA-N 0.000 claims 1
• JNZCMAPGOOGBPW-UHFFFAOYSA-N C(C)NC(NC=1SC2=C(N1)C=C(C(=C2)F)C=2C=CC(=NC2)CC(=O)NC)=O.C(C)NC(=O)NC=2SC1=C(N2)C=C(C(=C1)F)C1=CC(N(C=C1)C1CNCC1)=O Chemical compound C(C)NC(NC=1SC2=C(N1)C=C(C(=C2)F)C=2C=CC(=NC2)CC(=O)NC)=O.C(C)NC(=O)NC=2SC1=C(N2)C=C(C(=C1)F)C1=CC(N(C=C1)C1CNCC1)=O JNZCMAPGOOGBPW-UHFFFAOYSA-N 0.000 claims 1
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• IXHLLGYVJJUMSS-UHFFFAOYSA-N Cl.C(C)NC(=O)NC=1SC2=C(N1)C=C(C(=C2)F)C=2C=NC(=NC2)N2CCNCC2.C(C)NC(=O)NC=2SC1=C(N2)C=C(C(=C1)F)C=1C=NC(=NC1)N1CCN(CC1)CCO Chemical compound Cl.C(C)NC(=O)NC=1SC2=C(N1)C=C(C(=C2)F)C=2C=NC(=NC2)N2CCNCC2.C(C)NC(=O)NC=2SC1=C(N2)C=C(C(=C1)F)C=1C=NC(=NC1)N1CCN(CC1)CCO IXHLLGYVJJUMSS-UHFFFAOYSA-N 0.000 claims 1
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