TWI396689B - 作為磷酸二酯酶１０抑制劑之吡衍生物 - Google Patents

Info

Publication number

TWI396689B

TWI396689B TW098138718A TW98138718A TWI396689B TW I396689 B TWI396689 B TW I396689B TW 098138718 A TW098138718 A TW 098138718A TW 98138718 A TW98138718 A TW 98138718A TW I396689 B TWI396689 B TW I396689B

Authority

TW

Taiwan

Prior art keywords

alkyl

benzo

phenyl

yloxy

imidazol

Prior art date

2008-11-14

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• 239000003112 inhibitor Substances 0.000 title claims description 31
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 title description 8
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 title description 6
• 150000003216 pyrazines Chemical class 0.000 title 1
• 125000000217 alkyl group Chemical group 0.000 claims description 731
• -1 nitratetradecyl Chemical group 0.000 claims description 601
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 337
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 247
• 150000001875 compounds Chemical class 0.000 claims description 242
• 229920006395 saturated elastomer Polymers 0.000 claims description 129
• 229910052799 carbon Inorganic materials 0.000 claims description 114
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 101
• 229910052731 fluorine Inorganic materials 0.000 claims description 99
• 229910052801 chlorine Inorganic materials 0.000 claims description 98
• 229910052794 bromium Inorganic materials 0.000 claims description 90
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 89
• 125000000468 ketone group Chemical group 0.000 claims description 83
• 229910052757 nitrogen Inorganic materials 0.000 claims description 76
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 75
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 71
• 229910052717 sulfur Inorganic materials 0.000 claims description 66
• 125000001424 substituent group Chemical group 0.000 claims description 65
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 59
• 201000010099 disease Diseases 0.000 claims description 54
• BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 51
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 49
• 150000003839 salts Chemical class 0.000 claims description 49
• 125000001188 haloalkyl group Chemical group 0.000 claims description 48
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 41
• 125000005605 benzo group Chemical group 0.000 claims description 40
• 125000002837 carbocyclic group Chemical group 0.000 claims description 40
• 229910052760 oxygen Inorganic materials 0.000 claims description 37
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims description 29
• JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 29
• 125000002950 monocyclic group Chemical group 0.000 claims description 28
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 28
• 125000004434 sulfur atom Chemical group 0.000 claims description 28
• 125000004429 atom Chemical group 0.000 claims description 27
• 125000000623 heterocyclic group Chemical group 0.000 claims description 27
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 26
• GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 26
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims description 24
• 206010012289 Dementia Diseases 0.000 claims description 23
• 238000011282 treatment Methods 0.000 claims description 22
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 21
• 239000003814 drug Substances 0.000 claims description 21
• 201000000980 schizophrenia Diseases 0.000 claims description 21
• 125000002619 bicyclic group Chemical group 0.000 claims description 19
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 19
• 230000000694 effects Effects 0.000 claims description 18
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
• 208000024891 symptom Diseases 0.000 claims description 16
• 208000020925 Bipolar disease Diseases 0.000 claims description 15
• 210000001159 caudate nucleus Anatomy 0.000 claims description 15
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 14
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 14
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 14
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 14
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 125000004076 pyridyl group Chemical group 0.000 claims description 13
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
• 208000028017 Psychotic disease Diseases 0.000 claims description 11
• 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 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 10
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 10
• 125000004122 cyclic group Chemical group 0.000 claims description 10
• 125000005493 quinolyl group Chemical group 0.000 claims description 10
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
• 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 9
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 9
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 229910052740 iodine Inorganic materials 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 206010008748 Chorea Diseases 0.000 claims description 8
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 125000002757 morpholinyl group Chemical group 0.000 claims description 8
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
• 208000011117 substance-related disease Diseases 0.000 claims description 8
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 8
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 8
• 125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 8
• 206010026749 Mania Diseases 0.000 claims description 7
• 208000019022 Mood disease Diseases 0.000 claims description 7
• 206010034719 Personality change Diseases 0.000 claims description 7
• 208000012601 choreatic disease Diseases 0.000 claims description 7
• 230000003111 delayed effect Effects 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• 206010013663 drug dependence Diseases 0.000 claims description 7
• 230000033001 locomotion Effects 0.000 claims description 7
• UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 claims description 6
• 150000002148 esters Chemical class 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• 208000018737 Parkinson disease Diseases 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 5
• 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 4
• 229930194542 Keto Natural products 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• VBYOFWWEQOSKGN-UHFFFAOYSA-N n-[4-[3-(4-fluorooxan-4-yl)pyridin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C=1C=CN=C(OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=1C1(F)CCOCC1 VBYOFWWEQOSKGN-UHFFFAOYSA-N 0.000 claims description 4
• NYQRKBPJZGVWOL-UHFFFAOYSA-N n-[4-[3-(oxan-4-yl)pyridin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1COCCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 NYQRKBPJZGVWOL-UHFFFAOYSA-N 0.000 claims description 4
• 239000011593 sulfur Substances 0.000 claims description 4
• NQQHFVCQMJVYTB-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(oxan-4-yl)pyridin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CC=C1C1CCOCC1 NQQHFVCQMJVYTB-UHFFFAOYSA-N 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 3
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• FRVHJNLDJAFIMG-UHFFFAOYSA-N n-[4-[3-(2-methylpyridin-4-yl)pyridin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(C)=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)=C1 FRVHJNLDJAFIMG-UHFFFAOYSA-N 0.000 claims description 3
• YSLAFYVBQHFKGE-UHFFFAOYSA-N n-[4-[3-(oxan-4-yl)pyridin-2-yl]oxyphenyl]-1h-benzimidazol-2-amine Chemical compound C1COCCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2N1 YSLAFYVBQHFKGE-UHFFFAOYSA-N 0.000 claims description 3
• 208000020016 psychiatric disease Diseases 0.000 claims description 3
• 125000004297 tetrahydropyrrol-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 3
• HZXVWJIMVWUESM-UHFFFAOYSA-N (1-methylbenzimidazol-2-yl)-[4-[3-(oxan-4-yl)pyridin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2N(C)C=1C(=O)C(C=C1)=CC=C1OC1=NC=CC=C1C1CCOCC1 HZXVWJIMVWUESM-UHFFFAOYSA-N 0.000 claims description 2
• LDLNYSPLFIODTR-UHFFFAOYSA-N (6-fluoro-1h-benzimidazol-2-yl)-[4-[3-(oxan-4-yl)pyridin-2-yl]oxyphenyl]methanone Chemical compound N1C2=CC(F)=CC=C2N=C1C(=O)C(C=C1)=CC=C1OC1=NC=CC=C1C1CCOCC1 LDLNYSPLFIODTR-UHFFFAOYSA-N 0.000 claims description 2
• UOFAHOBPBWETOM-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-piperidin-1-ylpyridin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CC=C1N1CCCCC1 UOFAHOBPBWETOM-UHFFFAOYSA-N 0.000 claims description 2
• BXCJWQKBCQEGBY-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-piperidin-4-ylpyridin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CC=C1C1CCNCC1 BXCJWQKBCQEGBY-UHFFFAOYSA-N 0.000 claims description 2
• RSKNLGXYHGTAMA-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-pyridin-3-ylpyridin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CC=C1C1=CC=CN=C1 RSKNLGXYHGTAMA-UHFFFAOYSA-N 0.000 claims description 2
• NWFKNDRADJHJJH-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-pyridin-4-ylpyridin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CC=C1C1=CC=NC=C1 NWFKNDRADJHJJH-UHFFFAOYSA-N 0.000 claims description 2
• WUMGXAKVADGPKJ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-pyrrolidin-1-ylpyridin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CC=C1N1CCCC1 WUMGXAKVADGPKJ-UHFFFAOYSA-N 0.000 claims description 2
• HWRTUAYLKPDZRX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-quinolin-4-ylpyridin-2-yl)oxyphenyl]methanone Chemical compound C1=CC=C2C(C3=CC=CN=C3OC3=CC=C(C=C3)C(C=3NC4=CC=CC=C4N=3)=O)=CC=NC2=C1 HWRTUAYLKPDZRX-UHFFFAOYSA-N 0.000 claims description 2
• DLBPVNHHKYFSQS-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-quinolin-5-ylpyridin-2-yl)oxyphenyl]methanone Chemical compound C1=CC=C2C(C3=CC=CN=C3OC3=CC=C(C=C3)C(C=3NC4=CC=CC=C4N=3)=O)=CC=CC2=N1 DLBPVNHHKYFSQS-UHFFFAOYSA-N 0.000 claims description 2
• QVXHOMACGITSNO-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2,6-dimethoxypyridin-3-yl)pyridin-2-yl]oxyphenyl]methanone Chemical compound COC1=NC(OC)=CC=C1C1=CC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 QVXHOMACGITSNO-UHFFFAOYSA-N 0.000 claims description 2
• AERXVVORRCWHIC-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxypyridin-3-yl)pyridin-2-yl]oxyphenyl]methanone Chemical compound COC1=NC=CC=C1C1=CC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 AERXVVORRCWHIC-UHFFFAOYSA-N 0.000 claims description 2
• FHVFZRUFTUAPMD-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxypyridin-4-yl)pyridin-2-yl]oxyphenyl]methanone Chemical compound C1=NC(OC)=CC(C=2C(=NC=CC=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 FHVFZRUFTUAPMD-UHFFFAOYSA-N 0.000 claims description 2
• DZPYVQSUTHHSJB-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxyquinolin-3-yl)pyridin-2-yl]oxyphenyl]methanone Chemical compound C1=CC=C2NC(C(=O)C3=CC=C(C=C3)OC3=NC=CC=C3C3=CC4=CC=CC=C4N=C3OC)=NC2=C1 DZPYVQSUTHHSJB-UHFFFAOYSA-N 0.000 claims description 2
• JDOYGGXRQKERCW-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methylpyridin-4-yl)pyridin-2-yl]oxyphenyl]methanone Chemical compound C1=NC(C)=CC(C=2C(=NC=CC=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 JDOYGGXRQKERCW-UHFFFAOYSA-N 0.000 claims description 2
• DTJXXOGYWRSCDC-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-methoxyphenyl)pyridin-2-yl]oxyphenyl]methanone Chemical compound COC1=CC=CC(C=2C(=NC=CC=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 DTJXXOGYWRSCDC-UHFFFAOYSA-N 0.000 claims description 2
• WXUBBIPFLOMBBH-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-methoxypyridin-4-yl)pyridin-2-yl]oxyphenyl]methanone Chemical compound COC1=CN=CC=C1C1=CC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 WXUBBIPFLOMBBH-UHFFFAOYSA-N 0.000 claims description 2
• LAIZEVKNUZLXHG-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-methoxypyridin-3-yl)pyridin-2-yl]oxyphenyl]methanone Chemical compound COC1=CC=NC=C1C1=CC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 LAIZEVKNUZLXHG-UHFFFAOYSA-N 0.000 claims description 2
• FHFVIEDTDRRJAN-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(5-methoxypyridin-3-yl)pyridin-2-yl]oxyphenyl]methanone Chemical compound COC1=CN=CC(C=2C(=NC=CC=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 FHFVIEDTDRRJAN-UHFFFAOYSA-N 0.000 claims description 2
• OHBQMKIWEAMRDM-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(6-methoxypyridin-3-yl)pyridin-2-yl]oxyphenyl]methanone Chemical compound C1=NC(OC)=CC=C1C1=CC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 OHBQMKIWEAMRDM-UHFFFAOYSA-N 0.000 claims description 2
• 229910005965 SO 2 Inorganic materials 0.000 claims description 2
• QKCKYMBAYOHBLF-UHFFFAOYSA-N [4-[3-(3,6-dihydro-2h-pyran-4-yl)pyridin-2-yl]oxyphenyl]-(1h-imidazo[4,5-b]pyridin-2-yl)methanone Chemical compound N=1C2=NC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CC=C1C1=CCOCC1 QKCKYMBAYOHBLF-UHFFFAOYSA-N 0.000 claims description 2
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
• 150000002576 ketones Chemical class 0.000 claims description 2
• ZJEDXHLRLLAMNS-UHFFFAOYSA-N n-[4-(3-pyridin-3-ylpyridin-2-yl)oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1NC(C=C1)=CC=C1OC1=NC=CC=C1C1=CC=CN=C1 ZJEDXHLRLLAMNS-UHFFFAOYSA-N 0.000 claims description 2
• IGTBVZOHYVSJLD-UHFFFAOYSA-N n-[4-[3-(2-methoxypyridin-3-yl)pyridin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=NC=CC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 IGTBVZOHYVSJLD-UHFFFAOYSA-N 0.000 claims description 2
• HCVSKHSKZJXAKP-UHFFFAOYSA-N n-[4-[3-(2-methoxypyridin-4-yl)pyridin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(OC)=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)=C1 HCVSKHSKZJXAKP-UHFFFAOYSA-N 0.000 claims description 2
• HWNDQGJOSDUASO-UHFFFAOYSA-N n-[4-[3-(3-methoxypyridin-4-yl)pyridin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=CN=CC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 HWNDQGJOSDUASO-UHFFFAOYSA-N 0.000 claims description 2
• VZFUGMMBNIQUMI-UHFFFAOYSA-N n-[4-[3-(5-methoxypyridin-3-yl)pyridin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=CN=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)=C1 VZFUGMMBNIQUMI-UHFFFAOYSA-N 0.000 claims description 2
• ZJLVYBVTJXOZNT-UHFFFAOYSA-N n-[4-[3-(6-chloropyridin-3-yl)pyridin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(Cl)=CC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 ZJLVYBVTJXOZNT-UHFFFAOYSA-N 0.000 claims description 2
• JRUSNWSHZKTZAE-UHFFFAOYSA-N n-[4-[3-(6-methylpyridin-3-yl)pyridin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(C)=CC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 JRUSNWSHZKTZAE-UHFFFAOYSA-N 0.000 claims description 2
• HEDHWRMJTFXNQL-UHFFFAOYSA-N n-[4-[3-(oxolan-3-yl)pyridin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1OCCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 HEDHWRMJTFXNQL-UHFFFAOYSA-N 0.000 claims description 2
• PJMKKSGLJJBQMY-UHFFFAOYSA-N nonan-1-one Chemical compound CCCCCCCC[C]=O PJMKKSGLJJBQMY-UHFFFAOYSA-N 0.000 claims description 2
• FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical class CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 2
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 58
• 239000003937 drug carrier Substances 0.000 claims 8
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
• 125000001845 4 membered carbocyclic group Chemical group 0.000 claims 2
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