AU2009313768B2 - Pyrazine compounds as phosphodiesterase 10 inhibitors - Google Patents

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Publication number

AU2009313768B2

AU2009313768B2 AU2009313768A AU2009313768A AU2009313768B2 AU 2009313768 B2 AU2009313768 B2 AU 2009313768B2 AU 2009313768 A AU2009313768 A AU 2009313768A AU 2009313768 A AU2009313768 A AU 2009313768A AU 2009313768 B2 AU2009313768 B2 AU 2009313768B2

Authority

AU

Australia

Prior art keywords

benzo

pyrazin

phenyl

yloxy

nrara

Prior art date

2008-11-14

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.)

Ceased

Links

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• 239000003112 inhibitor Substances 0.000 title claims description 35
• 150000003216 pyrazines Chemical class 0.000 title abstract description 4
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 title description 39
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 title description 37
• 150000001875 compounds Chemical class 0.000 claims abstract description 188
• 239000000203 mixture Substances 0.000 claims abstract description 166
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 54
• 201000010099 disease Diseases 0.000 claims abstract description 42
• 238000000034 method Methods 0.000 claims abstract description 40
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 28
• 201000000980 schizophrenia Diseases 0.000 claims abstract description 25
• 208000020925 Bipolar disease Diseases 0.000 claims abstract description 19
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 208
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 144
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 140
• 229920006395 saturated elastomer Polymers 0.000 claims description 135
• -1 oxaspiro[3.5]nonyl Chemical group 0.000 claims description 134
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 92
• 229910052731 fluorine Inorganic materials 0.000 claims description 90
• 229910052801 chlorine Inorganic materials 0.000 claims description 89
• 125000005605 benzo group Chemical group 0.000 claims description 85
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 81
• 229910052794 bromium Inorganic materials 0.000 claims description 81
• 229910052757 nitrogen Inorganic materials 0.000 claims description 80
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 75
• 229910052799 carbon Inorganic materials 0.000 claims description 69
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 59
• 101100055332 Pseudomonas oleovorans alkN gene Proteins 0.000 claims description 53
• 125000004429 atom Chemical group 0.000 claims description 46
• 150000003839 salts Chemical class 0.000 claims description 42
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 40
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 125000002950 monocyclic group Chemical group 0.000 claims description 29
• UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 claims description 26
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
• 125000002619 bicyclic group Chemical group 0.000 claims description 21
• 125000000623 heterocyclic group Chemical group 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims description 20
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 18
• 206010012289 Dementia Diseases 0.000 claims description 17
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 16
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 16
• 238000002360 preparation method Methods 0.000 claims description 16
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 15
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 12
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 11
• 208000018737 Parkinson disease Diseases 0.000 claims description 11
• 208000028017 Psychotic disease Diseases 0.000 claims description 11
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
• 230000001898 pallidal effect Effects 0.000 claims description 10
• YWFDAAMTUBHJGI-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 YWFDAAMTUBHJGI-UHFFFAOYSA-N 0.000 claims description 9
• 230000001404 mediated effect Effects 0.000 claims description 9
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
• VIZVTXGNPQLHRZ-DLBZAZTESA-N 1h-benzimidazol-2-yl-[4-[3-[(1s,3r)-3-hydroxycyclohexyl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1[C@H](O)CCC[C@@H]1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VIZVTXGNPQLHRZ-DLBZAZTESA-N 0.000 claims description 7
• 206010008748 Chorea Diseases 0.000 claims description 7
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• 229910052701 rubidium Inorganic materials 0.000 claims description 7
• XDJJEQSKDPNXSQ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-cyclopentylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCCC1 XDJJEQSKDPNXSQ-UHFFFAOYSA-N 0.000 claims description 6
• NVZBDCOGNZHANV-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(oxepan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCCOCC1 NVZBDCOGNZHANV-UHFFFAOYSA-N 0.000 claims description 6
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 6
• 125000003725 azepanyl group Chemical group 0.000 claims description 6
• 125000002393 azetidinyl group Chemical group 0.000 claims description 6
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 6
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 6
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000002346 iodo group Chemical group I* 0.000 claims description 6
• 125000002757 morpholinyl group Chemical group 0.000 claims description 6
• CSQHJQJUFABKBU-UHFFFAOYSA-N n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1COCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 CSQHJQJUFABKBU-UHFFFAOYSA-N 0.000 claims description 6
• KRRMOUBLHUGKFX-KRWDZBQOSA-N n-[4-[3-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC[C@@H]1CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 KRRMOUBLHUGKFX-KRWDZBQOSA-N 0.000 claims description 6
• 125000003551 oxepanyl group Chemical group 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• 208000011117 substance-related disease Diseases 0.000 claims description 6
• LKOZXUZYHCPBES-UHFFFAOYSA-N tert-butyl 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]-4-(hydroxymethyl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(CO)C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LKOZXUZYHCPBES-UHFFFAOYSA-N 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 6
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 6
• PODKIINFHOBJKF-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]-4-methylpiperidin-4-ol Chemical compound C1CC(C)(O)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 PODKIINFHOBJKF-UHFFFAOYSA-N 0.000 claims description 5
• VOFJMVKNCQVTIF-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(thian-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCSCC1 VOFJMVKNCQVTIF-UHFFFAOYSA-N 0.000 claims description 5
• VIZVTXGNPQLHRZ-IRXDYDNUSA-N 1h-benzimidazol-2-yl-[4-[3-[(1s,3s)-3-hydroxycyclohexyl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1[C@@H](O)CCC[C@@H]1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VIZVTXGNPQLHRZ-IRXDYDNUSA-N 0.000 claims description 5
• PYCDSETUWLDZCK-UHFFFAOYSA-N 3-[3-[4-(1,3-benzothiazol-2-ylamino)-3-fluorophenoxy]pyrazin-2-yl]cyclohex-2-en-1-ol Chemical compound OC1CCCC(C=2C(=NC=CN=2)OC=2C=C(F)C(NC=3SC4=CC=CC=C4N=3)=CC=2)=C1 PYCDSETUWLDZCK-UHFFFAOYSA-N 0.000 claims description 5
• KLDFOQPHBRUMBD-UHFFFAOYSA-N 3-[3-[4-(1,3-benzothiazol-2-ylamino)-3-fluorophenoxy]pyrazin-2-yl]cyclohex-2-en-1-one Chemical compound C=1C=C(NC=2SC3=CC=CC=C3N=2)C(F)=CC=1OC1=NC=CN=C1C1=CC(=O)CCC1 KLDFOQPHBRUMBD-UHFFFAOYSA-N 0.000 claims description 5
• 206010010219 Compulsions Diseases 0.000 claims description 5
• 206010026749 Mania Diseases 0.000 claims description 5
• 208000019022 Mood disease Diseases 0.000 claims description 5
• 206010034719 Personality change Diseases 0.000 claims description 5
• UESDQIHAOCLDAK-UHFFFAOYSA-N [4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]-(1-propan-2-ylbenzimidazol-2-yl)methanone Chemical compound N=1C2=CC=CC=C2N(C(C)C)C=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 UESDQIHAOCLDAK-UHFFFAOYSA-N 0.000 claims description 5
• 206010013663 drug dependence Diseases 0.000 claims description 5
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
• SOOCRXWTSFOYSK-UHFFFAOYSA-N n-[4-[3-(4-fluorooxan-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound N=1C=CN=C(OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=1C1(F)CCOCC1 SOOCRXWTSFOYSK-UHFFFAOYSA-N 0.000 claims description 5
• YWNIKPNVTJLBHN-UHFFFAOYSA-N n-[4-[3-(oxan-3-ylamino)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CCOCC1NC1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 YWNIKPNVTJLBHN-UHFFFAOYSA-N 0.000 claims description 5
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 210000002637 putamen Anatomy 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• DVBCTQVDMKFPPK-UHFFFAOYSA-N 1,3-benzothiazol-2-yl-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2SC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 DVBCTQVDMKFPPK-UHFFFAOYSA-N 0.000 claims description 4
• BHGBMGVTLFZRCP-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-methoxypiperidin-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(OC)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 BHGBMGVTLFZRCP-UHFFFAOYSA-N 0.000 claims description 4
• ADMPHCQUPDYFKW-VWLOTQADSA-N 1h-benzimidazol-2-yl-[4-[3-[4-[(2s)-1,1,1-trifluoro-2-hydroxypropan-2-yl]piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC([C@@](O)(C)C(F)(F)F)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 ADMPHCQUPDYFKW-VWLOTQADSA-N 0.000 claims description 4
• BLLKHCJAOCXHCW-UHFFFAOYSA-N 3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-one Chemical compound C1C(=O)CCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 BLLKHCJAOCXHCW-UHFFFAOYSA-N 0.000 claims description 4
• GFIJTCIBSLRCRB-UHFFFAOYSA-N 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]oxan-4-ol Chemical compound N=1C=CN=C(OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=1C1(O)CCOCC1 GFIJTCIBSLRCRB-UHFFFAOYSA-N 0.000 claims description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
• 108010011222 cyclo(Arg-Pro) Proteins 0.000 claims description 4
• UJVGWVCHGJXURF-UHFFFAOYSA-N n-[4-[3-(oxolan-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1OCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 UJVGWVCHGJXURF-UHFFFAOYSA-N 0.000 claims description 4
• RLZJFTOYCVIYLE-UHFFFAOYSA-N oxane-4-carbonitrile Chemical compound N#CC1CCOCC1 RLZJFTOYCVIYLE-UHFFFAOYSA-N 0.000 claims description 4
• DATJETPTDKFEEF-UHFFFAOYSA-N pyrrolidine-3-carbonitrile Chemical compound N#CC1CCNC1 DATJETPTDKFEEF-UHFFFAOYSA-N 0.000 claims description 4
• LIUKTCWPZUWMKH-RDJZCZTQSA-N (1s,3s)-3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-ol Chemical compound C1[C@@H](O)CCC[C@@H]1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LIUKTCWPZUWMKH-RDJZCZTQSA-N 0.000 claims description 3
• QHDKAYNNBNHBEI-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4,4-difluorocyclohexen-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1C(F)(F)CCC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 QHDKAYNNBNHBEI-UHFFFAOYSA-N 0.000 claims description 3
• BIFVLRHOLAYNMO-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]cyclohexan-1-one Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCC(=O)CC1 BIFVLRHOLAYNMO-UHFFFAOYSA-N 0.000 claims description 3
• ANYKNJNYLGGMOX-UHFFFAOYSA-N n-[4-[3-(2-methylpyridin-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(C)=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)=C1 ANYKNJNYLGGMOX-UHFFFAOYSA-N 0.000 claims description 3
• NFJWUVZWQQNUEZ-MRXNPFEDSA-N (2r)-1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-fluoropropan-1-one Chemical compound C1CN(C(=O)[C@H](F)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 NFJWUVZWQQNUEZ-MRXNPFEDSA-N 0.000 claims description 2
• NFJWUVZWQQNUEZ-INIZCTEOSA-N (2s)-1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-fluoropropan-1-one Chemical compound C1CN(C(=O)[C@@H](F)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 NFJWUVZWQQNUEZ-INIZCTEOSA-N 0.000 claims description 2
• BLLKHCJAOCXHCW-OAHLLOKOSA-N (3r)-3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-one Chemical compound C1C(=O)CCC[C@H]1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 BLLKHCJAOCXHCW-OAHLLOKOSA-N 0.000 claims description 2
• UHRZMABESCXDJW-OAHLLOKOSA-N (3s)-1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]pyrrolidine-3-carbonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CC[C@H](C#N)C1 UHRZMABESCXDJW-OAHLLOKOSA-N 0.000 claims description 2
• BLLKHCJAOCXHCW-HNNXBMFYSA-N (3s)-3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-one Chemical compound C1C(=O)CCC[C@@H]1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 BLLKHCJAOCXHCW-HNNXBMFYSA-N 0.000 claims description 2
• UHSVYLFWFQNXRY-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-4-ol Chemical compound C1CC(O)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 UHSVYLFWFQNXRY-UHFFFAOYSA-N 0.000 claims description 2
• YVTPALHJEBAVFC-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidine-4-carbonitrile Chemical compound C1CC(C#N)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 YVTPALHJEBAVFC-UHFFFAOYSA-N 0.000 claims description 2
• OLXGCABQYDQRKC-UHFFFAOYSA-N 1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 OLXGCABQYDQRKC-UHFFFAOYSA-N 0.000 claims description 2
• JVXPQSSXFIEQET-UHFFFAOYSA-N 1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 JVXPQSSXFIEQET-UHFFFAOYSA-N 0.000 claims description 2
• LYBQDBKBWCXHLB-UHFFFAOYSA-N 1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LYBQDBKBWCXHLB-UHFFFAOYSA-N 0.000 claims description 2
• CDKHCVAKJVNZMB-UHFFFAOYSA-N 1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 CDKHCVAKJVNZMB-UHFFFAOYSA-N 0.000 claims description 2
• YZVPBDASJFHUAL-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-piperidin-1-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCCCC1 YZVPBDASJFHUAL-UHFFFAOYSA-N 0.000 claims description 2
• RETLSFLATJJXAP-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-piperidin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCNCC1 RETLSFLATJJXAP-UHFFFAOYSA-N 0.000 claims description 2
• ZCFIQKOLFBWTNU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-pyridin-3-yloxypyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OC1=CC=CN=C1 ZCFIQKOLFBWTNU-UHFFFAOYSA-N 0.000 claims description 2
• BXZUDQZZCUTONO-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-pyridin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=NC=C1 BXZUDQZZCUTONO-UHFFFAOYSA-N 0.000 claims description 2
• HTWNAFJOAGRRBM-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-quinolin-5-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound C1=CC=C2C(C3=NC=CN=C3OC3=CC=C(C=C3)C(C=3NC4=CC=CC=C4N=3)=O)=CC=CC2=N1 HTWNAFJOAGRRBM-UHFFFAOYSA-N 0.000 claims description 2
• RPOWDMWZGNQSBU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2,6-dimethoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=NC(OC)=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 RPOWDMWZGNQSBU-UHFFFAOYSA-N 0.000 claims description 2
• VLYJRGUWIXOODC-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxyphenyl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=CC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VLYJRGUWIXOODC-UHFFFAOYSA-N 0.000 claims description 2
• VLBHJGKQIHPSBA-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VLBHJGKQIHPSBA-UHFFFAOYSA-N 0.000 claims description 2
• YLASKEPHIYXYHN-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxypyridin-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1=NC(OC)=CC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 YLASKEPHIYXYHN-UHFFFAOYSA-N 0.000 claims description 2
• NASLEEKYYZHLMU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxyquinolin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1=CC=C2NC(C(=O)C3=CC=C(C=C3)OC3=NC=CN=C3C3=CC4=CC=CC=C4N=C3OC)=NC2=C1 NASLEEKYYZHLMU-UHFFFAOYSA-N 0.000 claims description 2
• WINCBLQQJITJLB-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methylpyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound CC1=NC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 WINCBLQQJITJLB-UHFFFAOYSA-N 0.000 claims description 2
• MOMKNNQNCSGNRV-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methylpyridin-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1=NC(C)=CC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 MOMKNNQNCSGNRV-UHFFFAOYSA-N 0.000 claims description 2
• OBRWVGKIAUHLFT-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-pyridin-2-ylethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCCC1=CC=CC=N1 OBRWVGKIAUHLFT-UHFFFAOYSA-N 0.000 claims description 2
• GYAHJLWOOSIHGS-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-methoxyphenyl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=CC=CC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 GYAHJLWOOSIHGS-UHFFFAOYSA-N 0.000 claims description 2
• AXMKWTHOPXEJGI-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-methoxypyridin-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=CN=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 AXMKWTHOPXEJGI-UHFFFAOYSA-N 0.000 claims description 2
• XDFYJILYPSGECF-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-methyl-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1=CC=C2NC(C(=O)C3=CC=C(C=C3)OC3=NC=CN=C3N3CC4=NN=C(N4CC3)C)=NC2=C1 XDFYJILYPSGECF-UHFFFAOYSA-N 0.000 claims description 2
• PIBYUXDUMHDTHI-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-pyridin-3-ylpropoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCCCC1=CC=CN=C1 PIBYUXDUMHDTHI-UHFFFAOYSA-N 0.000 claims description 2
• DEPGKFSRVIIJKU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-methylpiperazin-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CN(C)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 DEPGKFSRVIIJKU-UHFFFAOYSA-N 0.000 claims description 2
• BXRWUPRQTKCGON-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(5-fluoro-2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=NC=C(F)C=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 BXRWUPRQTKCGON-UHFFFAOYSA-N 0.000 claims description 2
• QBFPMCPDBZLNIY-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(5-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=CN=CC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 QBFPMCPDBZLNIY-UHFFFAOYSA-N 0.000 claims description 2
• UYKPWRCLQFWBMS-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(6-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1=NC(OC)=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 UYKPWRCLQFWBMS-UHFFFAOYSA-N 0.000 claims description 2
• VJEDECJAJOUHQS-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(oxan-3-ylamino)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1NC1CCCOC1 VJEDECJAJOUHQS-UHFFFAOYSA-N 0.000 claims description 2
• YAQXVILTNUOAIK-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(oxan-4-ylamino)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1NC1CCOCC1 YAQXVILTNUOAIK-UHFFFAOYSA-N 0.000 claims description 2
• KUWDSKWHERONCX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(pyridin-2-ylmethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCC1=CC=CC=N1 KUWDSKWHERONCX-UHFFFAOYSA-N 0.000 claims description 2
• JEUOFPDZFFENPA-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(pyridin-3-ylmethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCC1=CC=CN=C1 JEUOFPDZFFENPA-UHFFFAOYSA-N 0.000 claims description 2
• PCUFMTNTOOPRHU-INIZCTEOSA-N 1h-benzimidazol-2-yl-[4-[3-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound OC[C@@H]1CCCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 PCUFMTNTOOPRHU-INIZCTEOSA-N 0.000 claims description 2
• QRHDFAZLVIKPOI-HNNXBMFYSA-N 1h-benzimidazol-2-yl-[4-[3-[(3s)-3-hydroxypyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1[C@@H](O)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 QRHDFAZLVIKPOI-HNNXBMFYSA-N 0.000 claims description 2
• PLJXWUBEQUVCBH-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[2-(1-methylpyrrolidin-2-yl)ethoxy]pyrazin-2-yl]oxyphenyl]methanone Chemical compound CN1CCCC1CCOC1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 PLJXWUBEQUVCBH-UHFFFAOYSA-N 0.000 claims description 2
• XQFKWIKPJOIRMC-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[2-(4-methyl-1,3-thiazol-5-yl)ethoxy]pyrazin-2-yl]oxyphenyl]methanone Chemical compound N1=CSC(CCOC=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1C XQFKWIKPJOIRMC-UHFFFAOYSA-N 0.000 claims description 2
• QJEPBHICDVQIMD-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(2-hydroxyethyl)piperazin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CN(CCO)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 QJEPBHICDVQIMD-UHFFFAOYSA-N 0.000 claims description 2
• OVOUUAFYHZWGSH-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(hydroxymethyl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(CO)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 OVOUUAFYHZWGSH-UHFFFAOYSA-N 0.000 claims description 2
• OZUQEIMBSCUUPC-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(methoxymethyl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(COC)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 OZUQEIMBSCUUPC-UHFFFAOYSA-N 0.000 claims description 2
• ILOXGTYENJEMOX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(trifluoromethyl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(C(F)(F)F)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 ILOXGTYENJEMOX-UHFFFAOYSA-N 0.000 claims description 2
• SGVADHZEXLKTJV-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyridin-2-yl-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=NC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 SGVADHZEXLKTJV-UHFFFAOYSA-N 0.000 claims description 2
• QAKJQHVIJCQZKR-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyridin-2-yl-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=NC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 QAKJQHVIJCQZKR-UHFFFAOYSA-N 0.000 claims description 2
• LSXLNZAVKKFYLI-UHFFFAOYSA-N 2-[1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-4-yl]ethanol Chemical compound C1CC(CCO)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LSXLNZAVKKFYLI-UHFFFAOYSA-N 0.000 claims description 2
• HTFXSBUOJAQECG-UHFFFAOYSA-N 2-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-4,4-dimethylcyclohex-2-en-1-one Chemical compound CC1(C)CCC(=O)C(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 HTFXSBUOJAQECG-UHFFFAOYSA-N 0.000 claims description 2
• AFVMYKZMYQFDLR-UHFFFAOYSA-N 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]-6-methylpiperazin-2-one Chemical compound C1C(=O)NC(C)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 AFVMYKZMYQFDLR-UHFFFAOYSA-N 0.000 claims description 2
• PHKDBPOGMAQERV-UHFFFAOYSA-N 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperazin-2-one Chemical compound C1CNC(=O)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 PHKDBPOGMAQERV-UHFFFAOYSA-N 0.000 claims description 2
• IBBNCEJNFIIDIK-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-6-methylpiperazin-2-one Chemical compound C1C(=O)NC(C)CN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 IBBNCEJNFIIDIK-UHFFFAOYSA-N 0.000 claims description 2
• ZXQSIZFCBGTLEV-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 ZXQSIZFCBGTLEV-UHFFFAOYSA-N 0.000 claims description 2
• VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims description 2
• IWEVCNNWMFEVKS-UHFFFAOYSA-N 5-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]pyridine-2-carbonitrile;n-[4-(3-pyrimidin-5-ylpyrazin-2-yl)oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1NC(C=C1)=CC=C1OC1=NC=CN=C1C1=CN=CN=C1.C1=NC(C#N)=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 IWEVCNNWMFEVKS-UHFFFAOYSA-N 0.000 claims description 2
• HRQSHDCWHGQGAC-UHFFFAOYSA-N 6-fluoro-n-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]-1h-benzimidazol-2-amine Chemical compound N=1C2=CC(F)=CC=C2NC=1NC(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 HRQSHDCWHGQGAC-UHFFFAOYSA-N 0.000 claims description 2
• 101100139845 Caenorhabditis elegans rac-2 gene Proteins 0.000 claims description 2
• KSDGDEIZWGGUDZ-UHFFFAOYSA-N [1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-2-yl]methanol Chemical compound OCC1CCCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 KSDGDEIZWGGUDZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
• QSVXRNXNORDCIH-GOSISDBHSA-N ethyl (3r)-1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidine-3-carboxylate Chemical compound C1[C@H](C(=O)OCC)CCCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 QSVXRNXNORDCIH-GOSISDBHSA-N 0.000 claims description 2
• QSVXRNXNORDCIH-SFHVURJKSA-N ethyl (3s)-1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidine-3-carboxylate Chemical compound C1[C@@H](C(=O)OCC)CCCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 QSVXRNXNORDCIH-SFHVURJKSA-N 0.000 claims description 2
• FMHDJTFIHBVWDS-UHFFFAOYSA-N ethyl 1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 FMHDJTFIHBVWDS-UHFFFAOYSA-N 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
• SQZRXWUIHAQLRV-UHFFFAOYSA-N methyl 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]azetidine-3-carboxylate Chemical compound C1C(C(=O)OC)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 SQZRXWUIHAQLRV-UHFFFAOYSA-N 0.000 claims description 2
• OYEMMCMQHPPZRE-UHFFFAOYSA-N methyl 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]oxane-4-carboxylate Chemical compound N=1C=CN=C(OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=1C1(C(=O)OC)CCOCC1 OYEMMCMQHPPZRE-UHFFFAOYSA-N 0.000 claims description 2
• QHQXBNYKAMDUDS-UHFFFAOYSA-N n-[4-(3-cyclopentylpyrazin-2-yl)oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 QHQXBNYKAMDUDS-UHFFFAOYSA-N 0.000 claims description 2
• MCPHJRVZGYLLFS-UHFFFAOYSA-N n-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1COCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 MCPHJRVZGYLLFS-UHFFFAOYSA-N 0.000 claims description 2
• KZQUGAMNOZLLRA-UHFFFAOYSA-N n-[4-(3-pyridin-3-ylpyrazin-2-yl)oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1NC(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=CN=C1 KZQUGAMNOZLLRA-UHFFFAOYSA-N 0.000 claims description 2
• LHQWYDHZOBIFCY-UHFFFAOYSA-N n-[4-(3-quinolin-5-ylpyrazin-2-yl)oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2C(C3=NC=CN=C3OC3=CC=C(C=C3)NC=3SC4=CC=CC=C4N=3)=CC=CC2=N1 LHQWYDHZOBIFCY-UHFFFAOYSA-N 0.000 claims description 2
• DLBUCAJUNWPCLY-UHFFFAOYSA-N n-[4-[3-(1-methylpiperidin-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CN(C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 DLBUCAJUNWPCLY-UHFFFAOYSA-N 0.000 claims description 2
• YLSRTMOLPMOJMY-UHFFFAOYSA-N n-[4-[3-(2,6-dimethylmorpholin-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1C(C)OC(C)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 YLSRTMOLPMOJMY-UHFFFAOYSA-N 0.000 claims description 2
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