TW200530217A - Amino-benzazoles as P2Y1 receptor inhibitors - Google Patents

Info

Publication number

TW200530217A

TW200530217A TW094101691A TW94101691A TW200530217A TW 200530217 A TW200530217 A TW 200530217A TW 094101691 A TW094101691 A TW 094101691A TW 94101691 A TW94101691 A TW 94101691A TW 200530217 A TW200530217 A TW 200530217A

Authority

TW

Taiwan

Prior art keywords

methyl

alkyl

benzyl

pyridin

benzo

Prior art date

2004-01-21

Links

• Espacenet
• Global Dossier
• Discuss

• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical class C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 title claims abstract 3
• 102000016927 Purinergic P2Y1 Receptors Human genes 0.000 title abstract 3
• 108010028935 Purinergic P2Y1 Receptors Proteins 0.000 title abstract 2
• 239000003112 inhibitor Substances 0.000 title description 2
• 238000000034 method Methods 0.000 claims abstract description 66
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 34
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• -1 benzyl Chemical group 0.000 claims description 570
• 125000000217 alkyl group Chemical group 0.000 claims description 458
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 457
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 419
• 150000001875 compounds Chemical class 0.000 claims description 301
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 163
• 125000005842 heteroatom Chemical group 0.000 claims description 127
• 125000000623 heterocyclic group Chemical group 0.000 claims description 127
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 126
• 125000004432 carbon atom Chemical group C* 0.000 claims description 120
• 229910052796 boron Inorganic materials 0.000 claims description 109
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 98
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 90
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 82
• 229910052794 bromium Inorganic materials 0.000 claims description 75
• 229910052731 fluorine Inorganic materials 0.000 claims description 74
• 229910052801 chlorine Inorganic materials 0.000 claims description 70
• 229910052799 carbon Inorganic materials 0.000 claims description 65
• 150000003839 salts Chemical class 0.000 claims description 56
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 54
• 125000002837 carbocyclic group Chemical group 0.000 claims description 54
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 53
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 52
• 125000003118 aryl group Chemical group 0.000 claims description 47
• 229910052739 hydrogen Inorganic materials 0.000 claims description 43
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 42
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 41
• 229910052757 nitrogen Inorganic materials 0.000 claims description 41
• DEPDDPLQZYCHOH-UHFFFAOYSA-N 1h-imidazol-2-amine Chemical compound NC1=NC=CN1 DEPDDPLQZYCHOH-UHFFFAOYSA-N 0.000 claims description 38
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 38
• 229910052740 iodine Inorganic materials 0.000 claims description 36
• 125000003342 alkenyl group Chemical group 0.000 claims description 34
• 150000001721 carbon Chemical group 0.000 claims description 34
• 239000012453 solvate Substances 0.000 claims description 33
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 32
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 32
• 125000001072 heteroaryl group Chemical group 0.000 claims description 31
• 125000004429 atom Chemical group 0.000 claims description 29
• 125000000304 alkynyl group Chemical group 0.000 claims description 27
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 25
• 238000011282 treatment Methods 0.000 claims description 24
• 208000035475 disorder Diseases 0.000 claims description 23
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 23
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
• 125000001544 thienyl group Chemical group 0.000 claims description 19
• 150000001412 amines Chemical class 0.000 claims description 18
• 125000002971 oxazolyl group Chemical group 0.000 claims description 18
• BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 18
• 125000005605 benzo group Chemical group 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 17
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 17
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 16
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
• 125000004076 pyridyl group Chemical group 0.000 claims description 16
• 230000009424 thromboembolic effect Effects 0.000 claims description 16
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 15
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 14
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 14
• 125000002883 imidazolyl group Chemical group 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
• ZBNZAJFNDPPMDT-UHFFFAOYSA-N 1h-imidazole-5-carboxamide Chemical compound NC(=O)C1=CNC=N1 ZBNZAJFNDPPMDT-UHFFFAOYSA-N 0.000 claims description 13
• 208000005189 Embolism Diseases 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 125000002541 furyl group Chemical group 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
• 230000001732 thrombotic effect Effects 0.000 claims description 13
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 12
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
• 239000000126 substance Substances 0.000 claims description 12
• XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims description 11
• 150000001335 aliphatic alkanes Chemical group 0.000 claims description 11
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 11
• UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 claims description 10
• CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims description 9
• 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
• GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 9
• 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 9
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
• 125000000335 thiazolyl group Chemical group 0.000 claims description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
• 208000010125 myocardial infarction Diseases 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
• 150000003254 radicals Chemical class 0.000 claims description 8
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
• 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 7
• 229910052685 Curium Inorganic materials 0.000 claims description 7
• 125000001188 haloalkyl group Chemical group 0.000 claims description 7
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 7
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 6
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 6
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 6
• 206010014513 Embolism arterial Diseases 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
• 239000008280 blood Substances 0.000 claims description 6
• 210000004369 blood Anatomy 0.000 claims description 6
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
• MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 6
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 5
• 206010003210 Arteriosclerosis Diseases 0.000 claims description 5
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
• 208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
• 230000002490 cerebral effect Effects 0.000 claims description 5
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
• FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 5
• 229910052701 rubidium Inorganic materials 0.000 claims description 5
• 125000004306 triazinyl group Chemical group 0.000 claims description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• 229920002554 vinyl polymer Polymers 0.000 claims description 5
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 4
• JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• 125000002528 4-isopropyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• 230000002008 hemorrhagic effect Effects 0.000 claims description 4
• CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 4
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 229910052698 phosphorus Inorganic materials 0.000 claims description 4
• 238000012360 testing method Methods 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• JPBLHOJFMBOCAF-UHFFFAOYSA-N 1,3-benzoxazol-2-amine Chemical compound C1=CC=C2OC(N)=NC2=C1 JPBLHOJFMBOCAF-UHFFFAOYSA-N 0.000 claims description 3
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 3
• 208000007814 Unstable Angina Diseases 0.000 claims description 3
• 125000003277 amino group Chemical group 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 229910052802 copper Inorganic materials 0.000 claims description 3
• 230000034994 death Effects 0.000 claims description 3
• 230000002526 effect on cardiovascular system Effects 0.000 claims description 3
• 229910052702 rhenium Inorganic materials 0.000 claims description 3
• 230000001052 transient effect Effects 0.000 claims description 3
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
• RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 claims description 2
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000003352 4-tert-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 2
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 2
• 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 2
• 200000000007 Arterial disease Diseases 0.000 claims description 2
• 208000007536 Thrombosis Diseases 0.000 claims description 2
• 230000002612 cardiopulmonary effect Effects 0.000 claims description 2
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims description 2
• 150000007857 hydrazones Chemical class 0.000 claims description 2
• 239000007943 implant Substances 0.000 claims description 2
• 230000002093 peripheral effect Effects 0.000 claims description 2
• 239000002689 soil Substances 0.000 claims description 2
• 238000007614 solvation Methods 0.000 claims description 2
• 201000005060 thrombophlebitis Diseases 0.000 claims description 2
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 8
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
• ACTKAGSPIFDCMF-UHFFFAOYSA-N 1,3-oxazol-2-amine Chemical compound NC1=NC=CO1 ACTKAGSPIFDCMF-UHFFFAOYSA-N 0.000 claims 3
• BMKPQMSDSWZWKA-UHFFFAOYSA-N N1=C(NC2=C1C=CC=C2)N.C2=CC=CC=1C3=CC=CC=C3CC21 Chemical compound N1=C(NC2=C1C=CC=C2)N.C2=CC=CC=1C3=CC=CC=C3CC21 BMKPQMSDSWZWKA-UHFFFAOYSA-N 0.000 claims 3
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 3
• OIRCRBMUOZOQRK-UHFFFAOYSA-N 1,3-benzoxazole-2,4-diamine Chemical compound C1=CC=C2OC(N)=NC2=C1N OIRCRBMUOZOQRK-UHFFFAOYSA-N 0.000 claims 2
• DRLOWZIEXKEVNU-UHFFFAOYSA-N 1h-imidazole-2,5-diamine Chemical compound NC1=CN=C(N)N1 DRLOWZIEXKEVNU-UHFFFAOYSA-N 0.000 claims 2
• WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 claims 2
• XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims 2
• MZZZAWDOYQWKMR-UHFFFAOYSA-N 6-methyl-1h-benzimidazol-2-amine Chemical compound CC1=CC=C2N=C(N)NC2=C1 MZZZAWDOYQWKMR-UHFFFAOYSA-N 0.000 claims 2
• 229920003026 Acene Polymers 0.000 claims 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
• 229910021529 ammonia Inorganic materials 0.000 claims 2
• CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 claims 2
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
• ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims 1
• CBTVJPLCLOPCAB-UHFFFAOYSA-N 1-[2-[[2-(2-tert-butylphenoxy)pyridin-3-yl]amino]-3h-benzimidazol-5-yl]ethanone Chemical class N1C2=CC(C(=O)C)=CC=C2N=C1NC1=CC=CN=C1OC1=CC=CC=C1C(C)(C)C CBTVJPLCLOPCAB-UHFFFAOYSA-N 0.000 claims 1
• LLWFGFRHJREOHH-UHFFFAOYSA-N 1-pyridin-3-ylbenzimidazol-2-amine Chemical compound N1=CC(=CC=C1)N1C(=NC2=C1C=CC=C2)N LLWFGFRHJREOHH-UHFFFAOYSA-N 0.000 claims 1
• WYCRHXXXNNXXQH-UHFFFAOYSA-N 1H-imidazole-5-carboximidamide Chemical compound NC(=N)C1=CN=CN1 WYCRHXXXNNXXQH-UHFFFAOYSA-N 0.000 claims 1
• NKWCGTOZTHZDHB-UHFFFAOYSA-N 1h-imidazol-1-ium-4-carboxylate Chemical compound OC(=O)C1=CNC=N1 NKWCGTOZTHZDHB-UHFFFAOYSA-N 0.000 claims 1
• NWVGXXPWOYZODV-UHFFFAOYSA-N 1h-imidazole-5-carbonitrile Chemical compound N#CC1=CN=CN1 NWVGXXPWOYZODV-UHFFFAOYSA-N 0.000 claims 1
• VFCGSOKPVOGQRX-UHFFFAOYSA-N 2,2-dibromo-1-[2-[[2-(2-tert-butylphenoxy)pyridin-3-yl]amino]-1,3-benzothiazol-6-yl]ethanone Chemical compound CC(C)(C)C1=CC=CC=C1OC1=NC=CC=C1NC1=NC2=CC=C(C(=O)C(Br)Br)C=C2S1 VFCGSOKPVOGQRX-UHFFFAOYSA-N 0.000 claims 1
• AYHYNRPXJQZNHV-UHFFFAOYSA-N 2-[[2-(2-tert-butylphenoxy)pyridin-3-yl]amino]-1h-benzimidazole-4-carboxamide Chemical compound CC(C)(C)C1=CC=CC=C1OC1=NC=CC=C1NC1=NC2=CC=CC(C(N)=O)=C2N1 AYHYNRPXJQZNHV-UHFFFAOYSA-N 0.000 claims 1
• ASMFFMMOISULSQ-UHFFFAOYSA-N 2-[[2-(2-tert-butylphenoxy)pyridin-3-yl]amino]-3h-benzimidazol-5-ol Chemical compound CC(C)(C)C1=CC=CC=C1OC1=NC=CC=C1NC1=NC2=CC=C(O)C=C2N1 ASMFFMMOISULSQ-UHFFFAOYSA-N 0.000 claims 1
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
• WFRXSXUDWCVSPI-UHFFFAOYSA-N 3h-benzimidazol-5-amine Chemical compound NC1=CC=C2NC=NC2=C1 WFRXSXUDWCVSPI-UHFFFAOYSA-N 0.000 claims 1
• BYVQLSSDJMTRIE-UHFFFAOYSA-N 4,5-dimethyl-n-[2-[3-(trifluoromethyl)phenoxy]pyridin-3-yl]-1h-benzimidazol-2-amine Chemical compound N1C2=C(C)C(C)=CC=C2N=C1NC1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 BYVQLSSDJMTRIE-UHFFFAOYSA-N 0.000 claims 1
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