JP2020536116A5 - - Google Patents
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- JP2020536116A5 JP2020536116A5 JP2020520037A JP2020520037A JP2020536116A5 JP 2020536116 A5 JP2020536116 A5 JP 2020536116A5 JP 2020520037 A JP2020520037 A JP 2020520037A JP 2020520037 A JP2020520037 A JP 2020520037A JP 2020536116 A5 JP2020536116 A5 JP 2020536116A5
- Authority
- JP
- Japan
- Prior art keywords
- benzo
- carboxamide
- thiazol
- fluoro
- cyclopropane
- 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.)
- Pending
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- -1 trimethylsilylethoxymethyl Chemical group 0.000 claims 125
- 150000001875 compounds Chemical class 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 24
- 125000005843 halogen group Chemical group 0.000 claims 12
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims 7
- 230000011987 methylation Effects 0.000 claims 6
- 238000007069 methylation reaction Methods 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 125000000335 thiazolyl group Chemical group 0.000 claims 5
- 125000005605 benzo group Chemical group 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims 2
- PHZKRDKMJHXGBR-UHFFFAOYSA-N 2-fluorocyclopropane-1-carboxamide Chemical compound NC(=O)C1CC1F PHZKRDKMJHXGBR-UHFFFAOYSA-N 0.000 claims 2
- 208000001089 Multiple system atrophy Diseases 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- ZYLLHHUJRGWQAR-BDAKNGLRSA-N (1S,2S)-2-fluoro-N-[6-(1H-pyrazol-5-yl)-1,3-benzothiazol-2-yl]cyclopropane-1-carboxamide Chemical compound N1N=C(C=C1)C1=CC2=C(N=C(S2)NC(=O)[C@H]2[C@H](C2)F)C=C1 ZYLLHHUJRGWQAR-BDAKNGLRSA-N 0.000 claims 1
- WZTMYPNAIZBREW-OLZOCXBDSA-N (1S,2S)-2-fluoro-N-[6-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3-benzothiazol-2-yl]cyclopropane-1-carboxamide Chemical compound N1C=CC=2C1=NC=C(C=2)C1=CC2=C(N=C(S2)NC(=O)[C@H]2[C@H](C2)F)C=C1 WZTMYPNAIZBREW-OLZOCXBDSA-N 0.000 claims 1
- INMYGGVAGYMDSK-CVEARBPZSA-N (1S,2S)-2-fluoro-N-[6-[5-(1H-imidazol-2-yl)-2-methylphenyl]-1,3-benzothiazol-2-yl]cyclopropane-1-carboxamide Chemical compound N1C(=NC=C1)C=1C=CC(=C(C=1)C1=CC2=C(N=C(S2)NC(=O)[C@H]2[C@H](C2)F)C=C1)C INMYGGVAGYMDSK-CVEARBPZSA-N 0.000 claims 1
- MCYIVRQLSUZJFI-CVEARBPZSA-N (1S,2S)-N-[6-(1-acetyl-5-methyl-2,3-dihydroindol-4-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound C(C)(=O)N1CCC2=C(C(=CC=C12)C)C1=CC2=C(N=C(S2)NC(=O)[C@H]2[C@H](C2)F)C=C1 MCYIVRQLSUZJFI-CVEARBPZSA-N 0.000 claims 1
- GBZOMWZVTZAYLZ-OLZOCXBDSA-N (1S,2S)-N-[6-(2,4-dimethylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound CC1=NC=CC(=C1C1=CC2=C(N=C(S2)NC(=O)[C@H]2[C@H](C2)F)C=C1)C GBZOMWZVTZAYLZ-OLZOCXBDSA-N 0.000 claims 1
- AEZMREWUYWLTQN-KGLIPLIRSA-N (1S,2S)-N-[6-(2,6-dimethylphenyl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound CC1=C(C(=CC=C1)C)C1=CC2=C(N=C(S2)NC(=O)[C@H]2[C@H](C2)F)C=C1 AEZMREWUYWLTQN-KGLIPLIRSA-N 0.000 claims 1
- DQYQBMXKLGHNLA-MNOVXSKESA-N (1S,2S)-N-[6-(2-chloro-4-methylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound ClC1=NC=CC(=C1C1=CC2=C(N=C(S2)NC(=O)[C@H]2[C@H](C2)F)C=C1)C DQYQBMXKLGHNLA-MNOVXSKESA-N 0.000 claims 1
- NESWHIPLHKEXOY-YPMHNXCESA-N (1S,2S)-N-[6-(2-chloro-6-methylphenyl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound ClC1=C(C(=CC=C1)C)C1=CC2=C(N=C(S2)NC(=O)[C@H]2[C@H](C2)F)C=C1 NESWHIPLHKEXOY-YPMHNXCESA-N 0.000 claims 1
- CJEHWCVSHXXLJF-OCCSQVGLSA-N (1S,2S)-N-[6-(4,6-dimethylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound CC1=C(C=NC(=C1)C)C1=CC2=C(N=C(S2)NC(=O)[C@H]2[C@H](C2)F)C=C1 CJEHWCVSHXXLJF-OCCSQVGLSA-N 0.000 claims 1
- QWELMJZIRGDRQV-NEPJUHHUSA-N (1S,2S)-N-[6-(4,6-dimethylpyrimidin-5-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound CC1=NC=NC(=C1C1=CC2=C(N=C(S2)NC(=O)[C@H]2[C@H](C2)F)C=C1)C QWELMJZIRGDRQV-NEPJUHHUSA-N 0.000 claims 1
- CAJBURCAFDBVHU-BDAKNGLRSA-N (1S,2S)-N-[6-(4-chloro-3-methyl-1,2-thiazol-5-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound ClC=1C(=NSC=1C1=CC2=C(N=C(S2)NC(=O)[C@H]2[C@H](C2)F)C=C1)C CAJBURCAFDBVHU-BDAKNGLRSA-N 0.000 claims 1
- CTHLILYKCAMGBB-YPMHNXCESA-N (1S,2S)-N-[6-(4-cyanopyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound C(#N)C1=C(C=NC=C1)C1=CC2=C(N=C(S2)NC(=O)[C@H]2[C@H](C2)F)C=C1 CTHLILYKCAMGBB-YPMHNXCESA-N 0.000 claims 1
- NQGODUNKIPTMRT-CABCVRRESA-N (1S,2S)-N-[6-(5-cyano-2-methylphenyl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)C1=CC2=C(N=C(S2)NC(=O)[C@H]2[C@H](C2)F)C=C1)C NQGODUNKIPTMRT-CABCVRRESA-N 0.000 claims 1
- ZBQVFHOPFCBSCE-OCCSQVGLSA-N (1S,2S)-N-[6-(6-acetyl-4-methylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound C(C)(=O)C1=CC(=C(C=N1)C1=CC2=C(N=C(S2)NC(=O)[C@H]2[C@H](C2)F)C=C1)C ZBQVFHOPFCBSCE-OCCSQVGLSA-N 0.000 claims 1
- JJGBCAZQKWQYON-NEPJUHHUSA-N (1S,2S)-N-[6-(6-amino-2,4-dimethylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound NC1=CC(=C(C(=N1)C)C1=CC2=C(N=C(S2)NC(=O)[C@H]2[C@H](C2)F)C=C1)C JJGBCAZQKWQYON-NEPJUHHUSA-N 0.000 claims 1
- WBOFKNDBDSNHFK-PWSUYJOCSA-N (1S,2S)-N-[6-(6-chloro-4-methylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound ClC1=CC(=C(C=N1)C1=CC2=C(N=C(S2)NC(=O)[C@H]2[C@H](C2)F)C=C1)C WBOFKNDBDSNHFK-PWSUYJOCSA-N 0.000 claims 1
- HFCXTEFQLMTHQJ-UHFFFAOYSA-N 2-fluoro-N-[6-(1H-imidazol-2-yl)-1,3-benzothiazol-2-yl]cyclopropane-1-carboxamide Chemical compound N1C(=NC=C1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 HFCXTEFQLMTHQJ-UHFFFAOYSA-N 0.000 claims 1
- ZJQBQHALLFJKAY-UHFFFAOYSA-N 2-fluoro-N-[6-(1H-imidazol-5-yl)-1,3-benzothiazol-2-yl]cyclopropane-1-carboxamide Chemical compound N1C=NC(=C1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 ZJQBQHALLFJKAY-UHFFFAOYSA-N 0.000 claims 1
- ZYLLHHUJRGWQAR-UHFFFAOYSA-N 2-fluoro-N-[6-(1H-pyrazol-5-yl)-1,3-benzothiazol-2-yl]cyclopropane-1-carboxamide Chemical compound N1N=C(C=C1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 ZYLLHHUJRGWQAR-UHFFFAOYSA-N 0.000 claims 1
- JFQJLPMMPKJMKQ-UHFFFAOYSA-N 2-fluoro-N-[6-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1,3-benzothiazol-2-yl]cyclopropane-1-carboxamide Chemical compound N1C=CC=2C1=NC=CC=2C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 JFQJLPMMPKJMKQ-UHFFFAOYSA-N 0.000 claims 1
- WZTMYPNAIZBREW-UHFFFAOYSA-N 2-fluoro-N-[6-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3-benzothiazol-2-yl]cyclopropane-1-carboxamide Chemical compound N1C=CC=2C1=NC=C(C=2)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 WZTMYPNAIZBREW-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 206010067889 Dementia with Lewy bodies Diseases 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- ZAOXQERVRUZSIS-UHFFFAOYSA-N N-[4-chloro-6-(4-methylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound ClC1=CC(=CC2=C1N=C(S2)NC(=O)C1C(C1)F)C=1C=NC=CC=1C ZAOXQERVRUZSIS-UHFFFAOYSA-N 0.000 claims 1
- GTIMPAJBGXUYOT-UHFFFAOYSA-N N-[5-chloro-6-(4-methylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound ClC=1C(=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=1)C=1C=NC=CC=1C GTIMPAJBGXUYOT-UHFFFAOYSA-N 0.000 claims 1
- MCYIVRQLSUZJFI-UHFFFAOYSA-N N-[6-(1-acetyl-5-methyl-2,3-dihydroindol-4-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound C(C)(=O)N1CCC2=C(C(=CC=C12)C)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 MCYIVRQLSUZJFI-UHFFFAOYSA-N 0.000 claims 1
- BYDQBLXKGPBIIU-UHFFFAOYSA-N N-[6-(1H-benzimidazol-4-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound N1C=NC2=C1C=CC=C2C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 BYDQBLXKGPBIIU-UHFFFAOYSA-N 0.000 claims 1
- NNAQWGNCNULAMF-UHFFFAOYSA-N N-[6-(2,3-dimethylphenyl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound CC1=C(C=CC=C1C)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 NNAQWGNCNULAMF-UHFFFAOYSA-N 0.000 claims 1
- GBZOMWZVTZAYLZ-UHFFFAOYSA-N N-[6-(2,4-dimethylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound CC1=NC=CC(=C1C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1)C GBZOMWZVTZAYLZ-UHFFFAOYSA-N 0.000 claims 1
- AEZMREWUYWLTQN-UHFFFAOYSA-N N-[6-(2,6-dimethylphenyl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound CC1=C(C(=CC=C1)C)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 AEZMREWUYWLTQN-UHFFFAOYSA-N 0.000 claims 1
- ZKFLBKPDAQSORY-UHFFFAOYSA-N N-[6-(2-bromophenyl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound BrC1=C(C=CC=C1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 ZKFLBKPDAQSORY-UHFFFAOYSA-N 0.000 claims 1
- DQYQBMXKLGHNLA-UHFFFAOYSA-N N-[6-(2-chloro-4-methylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound ClC1=NC=CC(=C1C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1)C DQYQBMXKLGHNLA-UHFFFAOYSA-N 0.000 claims 1
- NESWHIPLHKEXOY-UHFFFAOYSA-N N-[6-(2-chloro-6-methylphenyl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound ClC1=C(C(=CC=C1)C)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 NESWHIPLHKEXOY-UHFFFAOYSA-N 0.000 claims 1
- NBHMCZKNYZRZNA-UHFFFAOYSA-N N-[6-(2-ethylphenyl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound C(C)C1=C(C=CC=C1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 NBHMCZKNYZRZNA-UHFFFAOYSA-N 0.000 claims 1
- AWNKPNRUFDRIHY-UHFFFAOYSA-N N-[6-(2-ethynylphenyl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound C(#C)C1=C(C=CC=C1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 AWNKPNRUFDRIHY-UHFFFAOYSA-N 0.000 claims 1
- QRAPYTBEQQQOFW-UHFFFAOYSA-N N-[6-(3,4-dimethyl-1,2-thiazol-5-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound CC1=NSC(=C1C)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 QRAPYTBEQQQOFW-UHFFFAOYSA-N 0.000 claims 1
- MDLAARMERPZKMW-UHFFFAOYSA-N N-[6-(3-chloro-2-methylphenyl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound ClC=1C(=C(C=CC=1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1)C MDLAARMERPZKMW-UHFFFAOYSA-N 0.000 claims 1
- RBHRLFIFAMSDCJ-UHFFFAOYSA-N N-[6-(4,5-dimethylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound CC1=C(C=NC=C1C)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 RBHRLFIFAMSDCJ-UHFFFAOYSA-N 0.000 claims 1
- CJEHWCVSHXXLJF-UHFFFAOYSA-N N-[6-(4,6-dimethylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound CC1=C(C=NC(=C1)C)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 CJEHWCVSHXXLJF-UHFFFAOYSA-N 0.000 claims 1
- QWELMJZIRGDRQV-UHFFFAOYSA-N N-[6-(4,6-dimethylpyrimidin-5-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound CC1=NC=NC(=C1C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1)C QWELMJZIRGDRQV-UHFFFAOYSA-N 0.000 claims 1
- SQAYIXHDDPGMEM-UHFFFAOYSA-N N-[6-(4-bromopyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound BrC1=C(C=NC=C1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 SQAYIXHDDPGMEM-UHFFFAOYSA-N 0.000 claims 1
- CAJBURCAFDBVHU-UHFFFAOYSA-N N-[6-(4-chloro-3-methyl-1,2-thiazol-5-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound ClC=1C(=NSC=1C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1)C CAJBURCAFDBVHU-UHFFFAOYSA-N 0.000 claims 1
- NQCQCGGOVSEMRM-UHFFFAOYSA-N N-[6-(4-chloropyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound ClC1=C(C=NC=C1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 NQCQCGGOVSEMRM-UHFFFAOYSA-N 0.000 claims 1
- GCJVENOSHGELRV-UHFFFAOYSA-N N-[6-(4-ethylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound C(C)C1=C(C=NC=C1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 GCJVENOSHGELRV-UHFFFAOYSA-N 0.000 claims 1
- XWIYGTTWTGHLGH-UHFFFAOYSA-N N-[6-(4-ethynylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound C(#C)C1=C(C=NC=C1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1 XWIYGTTWTGHLGH-UHFFFAOYSA-N 0.000 claims 1
- JHDSITICBSAFEJ-UHFFFAOYSA-N N-[6-(4-methylpyridin-3-yl)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide Chemical compound CC1=C(C=NC=C1)C1=CC2=C(N=C(S2)NC(=O)C2CC2)C=C1 JHDSITICBSAFEJ-UHFFFAOYSA-N 0.000 claims 1
- REWJFRSETNEPIT-UHFFFAOYSA-N N-[6-(5-chloro-4-methylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound ClC=1C(=C(C=NC=1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1)C REWJFRSETNEPIT-UHFFFAOYSA-N 0.000 claims 1
- NQGODUNKIPTMRT-UHFFFAOYSA-N N-[6-(5-cyano-2-methylphenyl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1)C NQGODUNKIPTMRT-UHFFFAOYSA-N 0.000 claims 1
- HBSDZKHKWNFFHJ-UHFFFAOYSA-N N-[6-(5-ethynyl-2-methylphenyl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound C(#C)C=1C=CC(=C(C=1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1)C HBSDZKHKWNFFHJ-UHFFFAOYSA-N 0.000 claims 1
- ZBQVFHOPFCBSCE-UHFFFAOYSA-N N-[6-(6-acetyl-4-methylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound C(C)(=O)C1=CC(=C(C=N1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1)C ZBQVFHOPFCBSCE-UHFFFAOYSA-N 0.000 claims 1
- JJGBCAZQKWQYON-UHFFFAOYSA-N N-[6-(6-amino-2,4-dimethylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound NC1=CC(=C(C(=N1)C)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1)C JJGBCAZQKWQYON-UHFFFAOYSA-N 0.000 claims 1
- WBOFKNDBDSNHFK-UHFFFAOYSA-N N-[6-(6-chloro-4-methylpyridin-3-yl)-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound ClC1=CC(=C(C=N1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1)C WBOFKNDBDSNHFK-UHFFFAOYSA-N 0.000 claims 1
- UJECCFNPOCWFOC-UHFFFAOYSA-N N-[6-[2-(difluoromethyl)phenyl]-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound FC(C1=C(C=CC=C1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1)F UJECCFNPOCWFOC-UHFFFAOYSA-N 0.000 claims 1
- BVKFWHKQQPRDBF-UHFFFAOYSA-N N-[6-[4-(difluoromethyl)pyridin-3-yl]-1,3-benzothiazol-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound FC(C1=C(C=NC=C1)C1=CC2=C(N=C(S2)NC(=O)C2C(C2)F)C=C1)F BVKFWHKQQPRDBF-UHFFFAOYSA-N 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000032859 Synucleinopathies Diseases 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 125000006419 fluorocyclopropyl group Chemical group 0.000 claims 1
- 125000003838 furazanyl group Chemical group 0.000 claims 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 *[C@](C1)[C@@]1C(Nc1nc(c(*)c(*)c(*)c2)c2[s]1)=O Chemical compound *[C@](C1)[C@@]1C(Nc1nc(c(*)c(*)c(*)c2)c2[s]1)=O 0.000 description 1
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| MX2021010122A (es) | 2019-02-22 | 2021-09-23 | 1St Biotherapeutics Inc | Compuestos de imidazopiridinilo y su uso para el tratamiento de trastornos neurodegenerativos. |
| EP3934702B1 (en) * | 2019-03-07 | 2024-05-08 | 1st Biotherapeutics, Inc. | [ 18f]-labeled benzothiazole derivative as pet radiotracer |
| US10385046B1 (en) * | 2019-03-19 | 2019-08-20 | 1ST Biotherapeutics, Inc. | Processes for preparing benzothiazol compounds and methods of using the same for treating neurodegenerative disorders |
| CN113631554B (zh) * | 2019-03-28 | 2024-06-21 | 第一生物治疗股份有限公司 | 苯并噻唑化合物的药用盐、多晶型物及其制备方法 |
| CN110483402B (zh) * | 2019-08-12 | 2021-07-23 | 上海毕得医药科技股份有限公司 | 一种3-溴-5-苯基-1h-吡唑的合成方法 |
| CN115968362B (zh) * | 2020-08-21 | 2025-06-13 | 第一生物治疗股份有限公司 | 作为pet放射性示踪剂的[18f]-标记的咪唑并吡啶衍生物 |
| US12398156B2 (en) | 2020-08-21 | 2025-08-26 | 1ST Biotherapeutics, Inc. | Compounds for prevention or treatment of neurodegenerative disorders |
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| EP4223750B1 (en) * | 2020-09-30 | 2025-06-25 | Asahi Kasei Pharma Corporation | Nitrogen-containing bicyclic compounds which contain pyrimidine as interleukin 1 receptor-associated kinase 4 (irak-4) inhibitors to be used in the treatment of inflammatory or autoimmune diseases |
| TWI898106B (zh) * | 2022-01-11 | 2025-09-21 | 日商旭化成製藥股份有限公司 | 含有嘧啶之含氮雙環化合物 |
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| US7091227B2 (en) * | 2000-02-07 | 2006-08-15 | Abbott Gmbh & Co. Kg | Benzothiazole derivatives |
| PE20070978A1 (es) | 2006-02-14 | 2007-11-15 | Novartis Ag | COMPUESTOS HETEROCICLICOS COMO INHIBIDORES DE FOSFATIDILINOSITOL 3-QUINASAS (PI3Ks) |
| CN101384586A (zh) * | 2006-02-14 | 2009-03-11 | 诺华公司 | Pi-3激酶抑制剂及其应用方法 |
| EP2058309A4 (en) | 2006-08-04 | 2010-12-22 | Takeda Pharmaceutical | CONDENSED HETEROCYCLIC COMPOUND |
| AU2008277628B2 (en) | 2007-07-18 | 2012-03-15 | Novartis Ag | Bicyclic heteroaryl compounds and their use as kinase inhibitors |
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| WO2009114874A2 (en) * | 2008-03-14 | 2009-09-17 | Intellikine, Inc. | Benzothiazole kinase inhibitors and methods of use |
| AR071523A1 (es) | 2008-04-30 | 2010-06-23 | Merck Serono Sa | Compuestos biciclicos fusionados, un proceso para su preparacion, el compuesto para ser utilizado como medicamento en el tratamiento y profilaxis de enfermedades, una composicion farmaceutica y un conjunto que comprende paquetes separados del compuesto y de un ingrediente activo del medicamento |
| JP2011525535A (ja) | 2008-06-24 | 2011-09-22 | 武田薬品工業株式会社 | ＰＩ３Ｋ／ｍＴＯＲ阻害剤 |
| JP5788316B2 (ja) * | 2008-07-08 | 2015-09-30 | インテリカイン， エルエルシー | キナーゼインヒビターおよび使用方法 |
| JP4528849B2 (ja) * | 2008-07-14 | 2010-08-25 | シャープ株式会社 | 引出し型加熱調理器 |
| WO2010100144A1 (en) * | 2009-03-04 | 2010-09-10 | Merck Serono S.A. | Fused bicyclic compounds as inhibitors for pi3 kinase |
| EP2440058A4 (en) * | 2009-06-12 | 2012-11-21 | Dana Farber Cancer Inst Inc | MELTED HETEROCYCLIC COMPOUNDS AND APPLICATIONS THEREOF |
| CN103261167B (zh) * | 2010-12-17 | 2016-05-04 | 霍夫曼-拉罗奇有限公司 | 取代的6，6-稠合含氮杂环化合物及其用途 |
| KR20140107153A (ko) * | 2014-07-23 | 2014-09-04 | 한국과학기술원 | 인돌 유도체 화합물, 이를 포함하는 Ａｂｌ 키나제 저해제 조성물 및 이상세포 성장 질환의 예방 및 치료용 약학 조성물 |
| EP3692023B1 (en) | 2017-10-02 | 2023-05-17 | 1st Biotherapeutics, Inc. | Benzothiazol compounds and methods using the same for treating neurodegenerative disorders |
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