HRP20050266A2 - Indazoles, benzothiazoles, and benzoisothiazoles, and uses thereof - Google Patents
Indazoles, benzothiazoles, and benzoisothiazoles, and uses thereof Download PDFInfo
- Publication number
- HRP20050266A2 HRP20050266A2 HR20050266A HRP20050266A HRP20050266A2 HR P20050266 A2 HRP20050266 A2 HR P20050266A2 HR 20050266 A HR20050266 A HR 20050266A HR P20050266 A HRP20050266 A HR P20050266A HR P20050266 A2 HRP20050266 A2 HR P20050266A2
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- Croatia
- Prior art keywords
- oct
- azabicyclo
- group
- carbon atoms
- carboxamide
- Prior art date
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims description 9
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 title description 2
- 150000002473 indoazoles Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 228
- 238000000034 method Methods 0.000 claims description 222
- 150000001875 compounds Chemical class 0.000 claims description 163
- -1 benzoisothiazolyl group Chemical group 0.000 claims description 120
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 43
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 43
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- 229910052801 chlorine Inorganic materials 0.000 claims description 34
- 229910052731 fluorine Inorganic materials 0.000 claims description 32
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 229910052794 bromium Inorganic materials 0.000 claims description 29
- 241000124008 Mammalia Species 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 23
- 229910052740 iodine Inorganic materials 0.000 claims description 22
- SABOFVOVHYJWCO-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-bromo-1,2-benzothiazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NSC2=CC(Br)=CC=C21 SABOFVOVHYJWCO-LBPRGKRZSA-N 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- OEFLOIIPWWSINC-ZETCQYMHSA-N (3r)-1-azabicyclo[2.2.2]octane-3-carboxamide Chemical compound C1CC2[C@@H](C(=O)N)CN1CC2 OEFLOIIPWWSINC-ZETCQYMHSA-N 0.000 claims description 19
- OEFLOIIPWWSINC-SSDOTTSWSA-N (3s)-1-azabicyclo[2.2.2]octane-3-carboxamide Chemical compound C1CC2[C@H](C(=O)N)CN1CC2 OEFLOIIPWWSINC-SSDOTTSWSA-N 0.000 claims description 19
- 208000000044 Amnesia Diseases 0.000 claims description 18
- 208000026139 Memory disease Diseases 0.000 claims description 18
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 18
- OEFLOIIPWWSINC-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octane-3-carboxamide Chemical compound C1CC2C(C(=O)N)CN1CC2 OEFLOIIPWWSINC-UHFFFAOYSA-N 0.000 claims description 17
- 206010012289 Dementia Diseases 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 208000010877 cognitive disease Diseases 0.000 claims description 16
- 230000006984 memory degeneration Effects 0.000 claims description 16
- 208000023060 memory loss Diseases 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 15
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 15
- SABOFVOVHYJWCO-GFCCVEGCSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-bromo-1,2-benzothiazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NSC2=CC(Br)=CC=C21 SABOFVOVHYJWCO-GFCCVEGCSA-N 0.000 claims description 15
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 14
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 14
- 208000024827 Alzheimer disease Diseases 0.000 claims description 12
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- CHIMYIMDQJTEAR-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-bromo-1h-indazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NNC2=CC=C(Br)C=C21 CHIMYIMDQJTEAR-ZDUSSCGKSA-N 0.000 claims description 11
- BAKAGHXBJJLTDB-UHFFFAOYSA-N 1,2-benzothiazole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=NSC2=C1 BAKAGHXBJJLTDB-UHFFFAOYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 230000002829 reductive effect Effects 0.000 claims description 10
- 125000006413 ring segment Chemical group 0.000 claims description 10
- MXAAPXJMDOYGCQ-UHFFFAOYSA-N 1,3-benzothiazole-4-carboxamide Chemical compound NC(=O)C1=CC=CC2=C1N=CS2 MXAAPXJMDOYGCQ-UHFFFAOYSA-N 0.000 claims description 9
- PVROETJHCUDAFG-UHFFFAOYSA-N 1-methylindazole-3-carboxamide Chemical compound C1=CC=C2N(C)N=C(C(N)=O)C2=C1 PVROETJHCUDAFG-UHFFFAOYSA-N 0.000 claims description 9
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims description 9
- 229960004373 acetylcholine Drugs 0.000 claims description 9
- MRLQHKJQIGQMLM-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-bromo-1h-indazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NNC2=CC(Br)=CC=C21 MRLQHKJQIGQMLM-ZDUSSCGKSA-N 0.000 claims description 9
- 201000004810 Vascular dementia Diseases 0.000 claims description 8
- 230000004913 activation Effects 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- RXRRDQFTRFFCBX-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-thiophen-2-yl-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2C1=CC=CS1 RXRRDQFTRFFCBX-INIZCTEOSA-N 0.000 claims description 8
- WKIYKLLNLNJSFA-SFHVURJKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-(2-fluorophenyl)-1,2-benzothiazole-3-carboxamide Chemical compound FC1=CC=CC=C1C1=CC=C(C(=NS2)C(=O)N[C@@H]3C4CCN(CC4)C3)C2=C1 WKIYKLLNLNJSFA-SFHVURJKSA-N 0.000 claims description 8
- HNEKXGJJBDSHNS-SFHVURJKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-(3-fluorophenyl)-1,2-benzothiazole-3-carboxamide Chemical compound FC1=CC=CC(C=2C=C3SN=C(C3=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 HNEKXGJJBDSHNS-SFHVURJKSA-N 0.000 claims description 8
- FEBALDANULNCKJ-SFHVURJKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-(4-fluorophenyl)-1,2-benzothiazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1C1=CC=C(C(=NS2)C(=O)N[C@@H]3C4CCN(CC4)C3)C2=C1 FEBALDANULNCKJ-SFHVURJKSA-N 0.000 claims description 8
- AAFPSKNSBSFTFJ-SFHVURJKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-phenyl-1,2-benzothiazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NSC1=CC=2C1=CC=CC=C1 AAFPSKNSBSFTFJ-SFHVURJKSA-N 0.000 claims description 8
- FXAAMMPZQFZLSF-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-pyridin-3-yl-1,2-benzothiazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NSC1=CC=2C1=CC=CN=C1 FXAAMMPZQFZLSF-KRWDZBQOSA-N 0.000 claims description 8
- UCSIXQKDYLPESL-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-pyridin-4-yl-1,2-benzothiazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NSC1=CC=2C1=CC=NC=C1 UCSIXQKDYLPESL-KRWDZBQOSA-N 0.000 claims description 8
- CHIMYIMDQJTEAR-CYBMUJFWSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-bromo-1h-indazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NNC2=CC=C(Br)C=C21 CHIMYIMDQJTEAR-CYBMUJFWSA-N 0.000 claims description 8
- MRLQHKJQIGQMLM-CYBMUJFWSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-bromo-1h-indazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NNC2=CC(Br)=CC=C21 MRLQHKJQIGQMLM-CYBMUJFWSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- WNWYMORIBRNPIX-HNNXBMFYSA-N (3r)-n-(2h-indazol-3-ylmethyl)-1-azabicyclo[2.2.2]octan-3-amine Chemical compound C1=CC=C2C(CN[C@@H]3C4CCN(CC4)C3)=NNC2=C1 WNWYMORIBRNPIX-HNNXBMFYSA-N 0.000 claims description 7
- WNWYMORIBRNPIX-OAHLLOKOSA-N (3s)-n-(2h-indazol-3-ylmethyl)-1-azabicyclo[2.2.2]octan-3-amine Chemical compound C1=CC=C2C(CN[C@H]3C4CCN(CC4)C3)=NNC2=C1 WNWYMORIBRNPIX-OAHLLOKOSA-N 0.000 claims description 7
- 208000028017 Psychotic disease Diseases 0.000 claims description 7
- 230000027455 binding Effects 0.000 claims description 7
- 208000028698 Cognitive impairment Diseases 0.000 claims description 6
- 208000023105 Huntington disease Diseases 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 6
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- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
- 230000001713 cholinergic effect Effects 0.000 claims description 6
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 230000004770 neurodegeneration Effects 0.000 claims description 6
- 206010039966 Senile dementia Diseases 0.000 claims description 5
- 208000006011 Stroke Diseases 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 230000019771 cognition Effects 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 230000004064 dysfunction Effects 0.000 claims description 5
- VWKPWKPFWQLBNQ-UHFFFAOYSA-N n-(1h-indazol-4-ylmethyl)-1-azabicyclo[2.2.2]octan-3-amine Chemical compound C1N(CC2)CCC2C1NCC1=CC=CC2=C1C=NN2 VWKPWKPFWQLBNQ-UHFFFAOYSA-N 0.000 claims description 5
- KQCWYRVMYYAYGT-ZOWNYOTGSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzothiazole-7-carboxamide;hydrochloride Chemical compound Cl.N([C@@H]1C2CCN(CC2)C1)C(=O)C1=CC=CC2=C1SC=N2 KQCWYRVMYYAYGT-ZOWNYOTGSA-N 0.000 claims description 5
- OZDWSZJHOSFRKG-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1h-indazole-4-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C1=CC=CC2=C1C=NN2 OZDWSZJHOSFRKG-AWEZNQCLSA-N 0.000 claims description 5
- XOLHBLOXMOMVET-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1h-indazole-7-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C1=CC=CC2=C1NN=C2 XOLHBLOXMOMVET-ZDUSSCGKSA-N 0.000 claims description 5
- XGCLESQPHQWSCE-ZOWNYOTGSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1h-indazole-7-carboxamide;hydrochloride Chemical compound Cl.N([C@@H]1C2CCN(CC2)C1)C(=O)C1=CC=CC2=C1NN=C2 XGCLESQPHQWSCE-ZOWNYOTGSA-N 0.000 claims description 5
- LMUPWJRROXDVJF-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-bromo-1,2-benzothiazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NSC2=CC=C(Br)C=C21 LMUPWJRROXDVJF-LBPRGKRZSA-N 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 4
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims description 4
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- 230000032683 aging Effects 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
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- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
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- 208000027061 mild cognitive impairment Diseases 0.000 claims description 4
- TXCYUSKWBHUVEP-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-1h-indazole-3-carboxamide Chemical compound C1=CC=C2C(C(NC3C4CCN(CC4)C3)=O)=NNC2=C1 TXCYUSKWBHUVEP-UHFFFAOYSA-N 0.000 claims description 4
- PWSQABYFZFMBBK-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-ylmethyl)-1h-indazol-3-amine Chemical compound C1N(CC2)CCC2C1CNC1=NNC2=CC=CC=C12 PWSQABYFZFMBBK-UHFFFAOYSA-N 0.000 claims description 4
- MJLXMLRFZNKRIO-UHFFFAOYSA-N n-(1h-indazol-4-yl)-1-azabicyclo[2.2.2]octane-3-carboxamide Chemical compound C1N(CC2)CCC2C1C(=O)NC1=CC=CC2=C1C=NN2 MJLXMLRFZNKRIO-UHFFFAOYSA-N 0.000 claims description 4
- SWWBCULPVVRVKA-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1=CC=C2C(C(N[C@@H]3C4CCN(CC4)C3)=O)=NSC2=C1 SWWBCULPVVRVKA-LBPRGKRZSA-N 0.000 claims description 4
- PNLGYCHEUIMVGW-YDALLXLXSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,2-benzothiazole-3-carboxamide;hydrochloride Chemical compound Cl.C1=CC=C2C(C(N[C@@H]3C4CCN(CC4)C3)=O)=NSC2=C1 PNLGYCHEUIMVGW-YDALLXLXSA-N 0.000 claims description 4
- CMRLNEYJEPELSM-ZOWNYOTGSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1h-indazole-3-carboxamide;hydrochloride Chemical compound Cl.C1=CC=C2C(C(N[C@@H]3C4CCN(CC4)C3)=O)=NNC2=C1 CMRLNEYJEPELSM-ZOWNYOTGSA-N 0.000 claims description 4
- ZDHWXFFZXTWIJC-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(furan-3-yl)-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2C=1C=COC=1 ZDHWXFFZXTWIJC-KRWDZBQOSA-N 0.000 claims description 4
- JNRQAYFUWDRETJ-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-cyclopropyl-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2C1CC1 JNRQAYFUWDRETJ-INIZCTEOSA-N 0.000 claims description 4
- XIBDASVCLSAVOS-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-methoxy-1,2-benzothiazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NSC2=CC=C(OC)C=C21 XIBDASVCLSAVOS-ZDUSSCGKSA-N 0.000 claims description 4
- JKOFQQLMAUBDEP-IBGZPJMESA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-phenyl-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2C1=CC=CC=C1 JKOFQQLMAUBDEP-IBGZPJMESA-N 0.000 claims description 4
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- UVRGSLUELPZVJF-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-morpholin-4-yl-1,2-benzothiazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NSC1=CC=2N1CCOCC1 UVRGSLUELPZVJF-INIZCTEOSA-N 0.000 claims description 4
- CKAVMUTUDGXMOJ-IBGZPJMESA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-phenyl-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NNC1=CC=2C1=CC=CC=C1 CKAVMUTUDGXMOJ-IBGZPJMESA-N 0.000 claims description 4
- ABQXDHCEHRPVQH-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-thiophen-2-yl-1,2-benzothiazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NSC1=CC=2C1=CC=CS1 ABQXDHCEHRPVQH-HNNXBMFYSA-N 0.000 claims description 4
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Classifications
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US41315102P | 2002-09-25 | 2002-09-25 | |
US44846903P | 2003-02-21 | 2003-02-21 | |
PCT/US2003/029976 WO2004029050A1 (en) | 2002-09-25 | 2003-09-25 | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
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HR20050266A HRP20050266A2 (en) | 2002-09-25 | 2005-03-18 | Indazoles, benzothiazoles, and benzoisothiazoles, and uses thereof |
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US (6) | US7429664B2 (pt) |
EP (2) | EP1543000B1 (pt) |
JP (2) | JP4890762B2 (pt) |
KR (1) | KR101129933B1 (pt) |
CN (1) | CN100484937C (pt) |
AU (1) | AU2003276919B2 (pt) |
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