AU2006295397A1 - Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof - Google Patents
Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof Download PDFInfo
- Publication number
- AU2006295397A1 AU2006295397A1 AU2006295397A AU2006295397A AU2006295397A1 AU 2006295397 A1 AU2006295397 A1 AU 2006295397A1 AU 2006295397 A AU2006295397 A AU 2006295397A AU 2006295397 A AU2006295397 A AU 2006295397A AU 2006295397 A1 AU2006295397 A1 AU 2006295397A1
- Authority
- AU
- Australia
- Prior art keywords
- carbon atoms
- alkyl
- azabicyclo
- oct
- carboxamide
- 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.)
- Abandoned
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- 238000002360 preparation method Methods 0.000 title description 12
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 9
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 title description 5
- 150000005229 pyrazolopyridines Chemical class 0.000 title description 2
- YJMPFOXUBAJFFA-UHFFFAOYSA-N [1,2]thiazolo[4,3-b]pyridine Chemical class C1=CC=NC2=CSN=C21 YJMPFOXUBAJFFA-UHFFFAOYSA-N 0.000 title 1
- 150000008316 benzisoxazoles Chemical class 0.000 title 1
- 150000002473 indoazoles Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 1674
- 125000000217 alkyl group Chemical group 0.000 claims description 632
- 150000001875 compounds Chemical class 0.000 claims description 332
- -1 NH 2 Chemical group 0.000 claims description 325
- 125000003545 alkoxy group Chemical group 0.000 claims description 188
- 238000000034 method Methods 0.000 claims description 150
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 150
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 136
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 113
- 125000003342 alkenyl group Chemical group 0.000 claims description 108
- 125000000304 alkynyl group Chemical group 0.000 claims description 108
- 150000003839 salts Chemical class 0.000 claims description 104
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 101
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 101
- 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 98
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 97
- DITBWPUMEUDVLU-UHFFFAOYSA-N 1h-indazole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=NNC2=C1 DITBWPUMEUDVLU-UHFFFAOYSA-N 0.000 claims description 67
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 67
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 66
- 125000004414 alkyl thio group Chemical group 0.000 claims description 60
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 60
- 239000000203 mixture Substances 0.000 claims description 58
- 239000012453 solvate Substances 0.000 claims description 56
- 239000012458 free base Substances 0.000 claims description 55
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 52
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 51
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 51
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 46
- 229920006395 saturated elastomer Polymers 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 44
- 229910052731 fluorine Inorganic materials 0.000 claims description 41
- 229910052801 chlorine Inorganic materials 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- 229910052740 iodine Inorganic materials 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
- 102000005962 receptors Human genes 0.000 claims description 38
- 108020003175 receptors Proteins 0.000 claims description 38
- 125000006413 ring segment Chemical group 0.000 claims description 38
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 37
- 229910052794 bromium Inorganic materials 0.000 claims description 37
- 150000001204 N-oxides Chemical class 0.000 claims description 35
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 34
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 32
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 150000003857 carboxamides Chemical class 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 29
- 125000004429 atom Chemical group 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 27
- 125000004423 acyloxy group Chemical group 0.000 claims description 26
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 26
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 201000010099 disease Diseases 0.000 claims description 23
- 125000003282 alkyl amino group Chemical group 0.000 claims description 20
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 19
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 19
- 125000002252 acyl group Chemical group 0.000 claims description 19
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 19
- 206010012289 Dementia Diseases 0.000 claims description 18
- 208000010877 cognitive disease Diseases 0.000 claims description 17
- 125000004043 oxo group Chemical group O=* 0.000 claims description 17
- 125000004434 sulfur atom Chemical group 0.000 claims description 16
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 16
- 238000011321 prophylaxis Methods 0.000 claims description 15
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 14
- 206010027175 memory impairment Diseases 0.000 claims description 14
- 208000000044 Amnesia Diseases 0.000 claims description 13
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 12
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 10
- 239000000556 agonist Substances 0.000 claims description 10
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 10
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 208000026139 Memory disease Diseases 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- 201000004810 Vascular dementia Diseases 0.000 claims description 8
- 230000004913 activation Effects 0.000 claims description 8
- 229910052786 argon Inorganic materials 0.000 claims description 8
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 8
- 230000006984 memory degeneration Effects 0.000 claims description 8
- 208000023060 memory loss Diseases 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- KORMEWQCUWNSMF-UHFFFAOYSA-N 1,2-benzoxazole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=NOC2=C1 KORMEWQCUWNSMF-UHFFFAOYSA-N 0.000 claims description 7
- LLSRLLPHUVVLQJ-UHFFFAOYSA-N 1-cycloheptyldiazepane Chemical group C1CCCCCC1N1NCCCCC1 LLSRLLPHUVVLQJ-UHFFFAOYSA-N 0.000 claims description 7
- 208000028698 Cognitive impairment Diseases 0.000 claims description 7
- 208000023105 Huntington disease Diseases 0.000 claims description 7
- 208000018737 Parkinson disease Diseases 0.000 claims description 7
- 208000028017 Psychotic disease Diseases 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000005110 aryl thio group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 230000027455 binding Effects 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 7
- 230000001713 cholinergic effect Effects 0.000 claims description 7
- 230000007278 cognition impairment Effects 0.000 claims description 7
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 7
- 230000006735 deficit Effects 0.000 claims description 7
- 206010012601 diabetes mellitus Diseases 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 7
- 230000004770 neurodegeneration Effects 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 6
- 230000004064 dysfunction Effects 0.000 claims description 6
- 208000027866 inflammatory disease Diseases 0.000 claims description 6
- 201000000980 schizophrenia Diseases 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 102100035591 POU domain, class 2, transcription factor 2 Human genes 0.000 claims description 5
- 101710084411 POU domain, class 2, transcription factor 2 Proteins 0.000 claims description 5
- 208000006011 Stroke Diseases 0.000 claims description 5
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims description 5
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 230000005540 biological transmission Effects 0.000 claims description 5
- 125000005047 dihydroimidazolyl group Chemical group N1(CNC=C1)* 0.000 claims description 5
- 230000015654 memory Effects 0.000 claims description 5
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 5
- LJEXBQWZLZFSSN-OAHLLOKOSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1-ethyl-6-methoxyindazole-3-carboxamide Chemical compound C12=CC=C(OC)C=C2N(CC)N=C1C(=O)N[C@H]1C(CC2)CCN2C1 LJEXBQWZLZFSSN-OAHLLOKOSA-N 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000006308 propyl amino group Chemical group 0.000 claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 208000011580 syndromic disease Diseases 0.000 claims description 5
- FWQGELKGKGGDPO-UHFFFAOYSA-N 1,2-benzothiazole-3-carboxamide hydrochloride Chemical compound Cl.S1N=C(C2=C1C=CC=C2)C(=O)N FWQGELKGKGGDPO-UHFFFAOYSA-N 0.000 claims description 4
- GGTBELZDHKHESR-UHFFFAOYSA-N 2-cycloheptyloxazepane Chemical group C1CCCCCC1N1OCCCCC1 GGTBELZDHKHESR-UHFFFAOYSA-N 0.000 claims description 4
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 4
- 206010019196 Head injury Diseases 0.000 claims description 4
- 208000009829 Lewy Body Disease Diseases 0.000 claims description 4
- JLIHVNUIYBYZPX-LLVKDONJSA-N N-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-4-hydroxy-1H-indazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NNC2=C1C(O)=CC=C2 JLIHVNUIYBYZPX-LLVKDONJSA-N 0.000 claims description 4
- 206010029350 Neurotoxicity Diseases 0.000 claims description 4
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- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 230000001939 inductive effect Effects 0.000 claims description 4
- LJEXBQWZLZFSSN-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1-ethyl-6-methoxyindazole-3-carboxamide Chemical compound C12=CC=C(OC)C=C2N(CC)N=C1C(=O)N[C@@H]1C(CC2)CCN2C1 LJEXBQWZLZFSSN-HNNXBMFYSA-N 0.000 claims description 4
- IKXVBFQRYVFHDF-QGZVFWFLSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1-propan-2-yl-6-(1,3-thiazol-2-yl)indazole-3-carboxamide Chemical compound C1=C2N(C(C)C)N=C(C(=O)N[C@H]3C4CCN(CC4)C3)C2=CC=C1C1=NC=CS1 IKXVBFQRYVFHDF-QGZVFWFLSA-N 0.000 claims description 4
- KALULFQIHKKFCX-CYBMUJFWSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5,6-dimethoxy-1h-indazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NNC2=C1C=C(OC)C(OC)=C2 KALULFQIHKKFCX-CYBMUJFWSA-N 0.000 claims description 4
- QANNTZCRFNSNGO-OMOCHNIRSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(3-methoxypyrrolidin-1-yl)-1,2-benzothiazole-3-carboxamide Chemical compound C1C(OC)CCN1C1=CC=C(C(=NS2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 QANNTZCRFNSNGO-OMOCHNIRSA-N 0.000 claims description 4
- LJRMDUSLDCDSLB-QGZVFWFLSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(furan-3-ylmethoxy)-1,2-benzothiazole-3-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NSC1=CC=2OCC=1C=COC=1 LJRMDUSLDCDSLB-QGZVFWFLSA-N 0.000 claims description 4
- KNZGHBOYNALEPF-LLVKDONJSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-7-hydroxy-2h-indazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NNC2=C1C=CC=C2O KNZGHBOYNALEPF-LLVKDONJSA-N 0.000 claims description 4
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- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 4
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
- JPJAHTRBVGIFET-KGLQGEEPSA-N 6-(cyclopropylmethoxy)-n-[(3s)-1-(cyclopropylmethyl)-1-azoniabicyclo[2.2.2]octan-3-yl]-1,2-benzothiazole-3-carboxamide;bromide Chemical compound [Br-].C([C@H](C(CC1)CC2)NC(=O)C=3C4=CC=C(OCC5CC5)C=C4SN=3)[N+]21CC1CC1 JPJAHTRBVGIFET-KGLQGEEPSA-N 0.000 claims description 3
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- XNSPJZRHCSNVAR-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-(2-oxo-3-propylimidazolidin-1-yl)-1,2-benzothiazole-3-carboxamide Chemical compound O=C1N(CCC)CCN1C1=CC=C(C(=NS2)C(=O)N[C@@H]3C4CCN(CC4)C3)C2=C1 XNSPJZRHCSNVAR-KRWDZBQOSA-N 0.000 claims description 3
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- 238000012216 screening Methods 0.000 description 1
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- 238000002864 sequence alignment Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000001148 spastic effect Effects 0.000 description 1
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- FJYZXKYGRCRNNP-UHFFFAOYSA-N tert-butyl 5-bromo-1,2-benzothiazole-3-carboxylate Chemical compound C1=C(Br)C=C2C(C(=O)OC(C)(C)C)=NSC2=C1 FJYZXKYGRCRNNP-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
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- Neurology (AREA)
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- Diabetes (AREA)
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- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Endocrinology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Child & Adolescent Psychology (AREA)
- Psychology (AREA)
- Emergency Medicine (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71955205P | 2005-09-23 | 2005-09-23 | |
| US60/719,552 | 2005-09-23 | ||
| PCT/US2006/037142 WO2007038367A1 (en) | 2005-09-23 | 2006-09-22 | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2006295397A1 true AU2006295397A1 (en) | 2007-04-05 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006295397A Abandoned AU2006295397A1 (en) | 2005-09-23 | 2006-09-22 | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof |
Country Status (12)
Families Citing this family (34)
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| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| US8394842B2 (en) | 2006-03-28 | 2013-03-12 | High Point Pharmaceuticals, Llc | Benzothiazoles having histamine H3 receptor activity |
| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| AU2008322426C1 (en) * | 2007-11-16 | 2014-10-23 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| CN101952278A (zh) * | 2008-02-15 | 2011-01-19 | 弗·哈夫曼-拉罗切有限公司 | 3-烷基-哌嗪衍生物及其用途 |
| SI2346833T1 (sl) * | 2008-10-13 | 2013-06-28 | F. Hoffmann-La Roche Ag | Postopek brez diazonija za pripravo indazolnega intermediata v sintezi bicikliäśnih amidov 5-(trifluorometoksi)-1h-3-indazolkarboksilne kisline |
| WO2010059844A1 (en) | 2008-11-19 | 2010-05-27 | Envivo Pharmaceuticals, Inc. | Treatment of cognitive disorders with (r)-7-chloro-n-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide and pharmaceutically acceptable salts thereof |
| TW201031664A (en) | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| TWI558398B (zh) | 2009-09-22 | 2016-11-21 | 諾華公司 | 菸鹼乙醯膽鹼受體α７活化劑之用途 |
| US20110172428A1 (en) | 2010-01-12 | 2011-07-14 | Shan-Ming Kuang | Methods for the preparation of indazole-3-carboxylic acid and n-(s)-1-azabicyclo[2.2.2]oct-3-yl-1h-indazole-3-carboxamide hydrochloride salt |
| WO2011137313A1 (en) * | 2010-04-30 | 2011-11-03 | Bristol-Myers Squibb Company | Aza-bicyclic amine n-oxide compounds as alpha-7 nicotinic acetylcholine receptor ligand pro-drugs |
| SA111320455B1 (ar) | 2010-05-17 | 2014-10-16 | Envivo Pharmaceuticals Inc | صورة بلورية من (R)-7- كلورو -N- (كينوكليدين -3- يل) بنزو[b] ثيوفين -2- كربوكساميد هيدروكلوريد أحادي الهيدرات |
| US8242276B2 (en) | 2010-06-30 | 2012-08-14 | Hoffmann-La Roche Inc. | Methods for the preparation of N-(S)-1-azabicyclo[2.2.2]oct-3-yl-1H-indazole-3-carboxamide hydrochloride salt |
| BR112013001939A2 (pt) | 2010-07-26 | 2017-07-11 | Envivo Pharmaceuticals Inc | tratamento de distúrbios cognitivos com determinados agonistas receptores de ácido alfa-7-nicotínico em combinação com inibidres de acetilcolinesterase |
| AR086791A1 (es) * | 2011-07-01 | 2014-01-22 | Lundbeck & Co As H | Moduladores alostericos positivos del receptor de acetilcolina nicotinico |
| AU2013259871A1 (en) | 2012-05-08 | 2014-11-20 | Forum Pharmaceuticals Inc. | Methods of maintaining, treating or improving cognitive function |
| JOP20130213B1 (ar) | 2012-07-17 | 2021-08-17 | Takeda Pharmaceuticals Co | معارضات لمستقبلht3-5 |
| MA37975B2 (fr) * | 2012-09-11 | 2021-03-31 | Genzyme Corp | Inhibiteurs de synthase de glucosylcéramide |
| EP2927229B1 (en) | 2012-10-16 | 2018-09-05 | Takeda Pharmaceutical Company Limited | Benzene-fused 5-membered nitrogen-containing heteroaromatic compounds useful for prophylaxis or treatment of neurodegenerative diseases or epilepsy |
| EP3010889B1 (de) | 2013-06-20 | 2018-10-03 | Bayer CropScience Aktiengesellschaft | Arylsulfid- und arylsulfoxid-derivate als akarizide und insektizide |
| JP6449880B2 (ja) * | 2013-08-08 | 2019-01-09 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規ピラジンアミド化合物 |
| JP6586104B2 (ja) | 2014-03-20 | 2019-10-02 | サミュメッド リミテッド ライアビリティ カンパニー | ５−置換インダゾール−３−カルボキサミドならびにその調製および使用の方法 |
| KR101532211B1 (ko) * | 2014-04-30 | 2015-06-30 | 세종대학교산학협력단 | Ampk 억제기능에 기반한 뇌졸중 치료용 약학적 조성물 및 방법 |
| WO2016053947A1 (en) | 2014-09-29 | 2016-04-07 | Takeda Pharmaceutical Company Limited | Crystalline form of 1-(1-methyl-1h-pyrazol-4-yl)-n-((1r,5s,7s)-9-methyl-3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)-1h-indole-3-carboxamide |
| US10370370B2 (en) * | 2015-06-10 | 2019-08-06 | Axovant Sciences Gmbh | Aminobenzisoxazole compounds as agonists of α7-nicotinic acetylcholine receptors |
| EP3334740A4 (en) * | 2015-08-12 | 2019-02-06 | Axovant Sciences GmbH | GEMINAL SUBSTITUTED AMINOBENZISOXAZOLE COMPOUNDS AS AGONISTS OF ALPHA 7-NICOTINIC ACETYLCHOLINE RECEPTORS |
| CA3123260A1 (en) * | 2015-10-16 | 2017-04-20 | Abbvie Inc. | Crystalline hemihydrate of (3s,4r)-3-ethyl-4-(3h-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state form thereof |
| WO2018185266A1 (en) | 2017-04-06 | 2018-10-11 | Inventiva | New compounds inhibitors of the yap/taz-tead interaction and their use in the treatment of malignant mesothelioma. |
| EP3632908A1 (en) | 2018-10-02 | 2020-04-08 | Inventiva | Inhibitors of the yap/taz-tead interaction and their use in the treatment of cancer |
| WO2021156769A1 (en) | 2020-02-03 | 2021-08-12 | Genzyme Corporation | Methods for treating neurological symptoms associated with lysosomal storage diseases |
| US11618751B1 (en) | 2022-03-25 | 2023-04-04 | Ventus Therapeutics U.S., Inc. | Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 derivatives |
| JP2023534322A (ja) | 2020-07-24 | 2023-08-09 | ジェンザイム・コーポレーション | ベングルスタットを含む医薬組成物 |
| US11319319B1 (en) | 2021-04-07 | 2022-05-03 | Ventus Therapeutics U.S., Inc. | Compounds for inhibiting NLRP3 and uses thereof |
| US12331048B2 (en) | 2022-10-31 | 2025-06-17 | Ventus Therapeutics U.S., Inc. | Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 inhibitors |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA93737B (en) * | 1992-02-04 | 1993-09-06 | Eisai Co Ltd | Aminobenzoic acid derivatives. |
| AR036041A1 (es) * | 2001-06-12 | 2004-08-04 | Upjohn Co | Compuestos aromaticos heterociclicos sustituidos con quinuclidina y composiciones farmaceuticas que los contienen |
| AR036040A1 (es) * | 2001-06-12 | 2004-08-04 | Upjohn Co | Compuestos de heteroarilo multiciclicos sustituidos con quinuclidinas y composiciones farmaceuticas que los contienen |
| DE10162375A1 (de) * | 2001-12-19 | 2003-07-10 | Bayer Ag | Bicyclische N-Aryl-amide |
| AU2003250322B2 (en) * | 2002-08-14 | 2010-01-21 | Neurosearch A/S | Novel quinuclidine derivatives and their use |
| BR0314485A (pt) * | 2002-09-25 | 2005-07-26 | Memory Pharm Corp | Indazóis, benzotiazóis e benzoisotiazóis, composto, composição farmacêutica, método desativação/estimulação seletiva de receptores nicotìnicos de a-7 em um mamìfero e método de tratamento e/ou prevenção de uma doença com os mesmos |
| MXPA05007689A (es) * | 2003-01-22 | 2005-09-30 | Pharmacia & Upjohn Co Llc | Tratamiento de enfermedades con agonistas completos del receptor alfa-7 de nach. |
| PT1697378E (pt) * | 2003-12-22 | 2008-02-28 | Memory Pharm Corp | Indoles, 1h-indazoles, 1,2-benzisoxazoles e 1,2-benzisotiazoles, sua preparação e utilizações |
-
2006
- 2006-09-22 BR BRPI0617534-1A patent/BRPI0617534A2/pt not_active IP Right Cessation
- 2006-09-22 CA CA002622677A patent/CA2622677A1/en not_active Abandoned
- 2006-09-22 SG SG201006955-7A patent/SG165417A1/en unknown
- 2006-09-22 CN CNA2006800439794A patent/CN101312968A/zh active Pending
- 2006-09-22 KR KR1020087009574A patent/KR20080048550A/ko not_active Ceased
- 2006-09-22 JP JP2008532459A patent/JP2009509964A/ja active Pending
- 2006-09-22 RU RU2008115268/04A patent/RU2450003C2/ru not_active IP Right Cessation
- 2006-09-22 WO PCT/US2006/037142 patent/WO2007038367A1/en active Application Filing
- 2006-09-22 EP EP06815264A patent/EP1940833A1/en not_active Withdrawn
- 2006-09-22 AU AU2006295397A patent/AU2006295397A1/en not_active Abandoned
-
2008
- 2008-03-12 ZA ZA200802342A patent/ZA200802342B/xx unknown
- 2008-03-20 IL IL190358A patent/IL190358A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SG165417A1 (en) | 2010-10-28 |
| RU2008115268A (ru) | 2009-10-27 |
| KR20080048550A (ko) | 2008-06-02 |
| CA2622677A1 (en) | 2007-04-05 |
| IL190358A0 (en) | 2009-09-22 |
| EP1940833A1 (en) | 2008-07-09 |
| ZA200802342B (en) | 2009-03-25 |
| BRPI0617534A2 (pt) | 2011-07-26 |
| RU2450003C2 (ru) | 2012-05-10 |
| CN101312968A (zh) | 2008-11-26 |
| WO2007038367A1 (en) | 2007-04-05 |
| JP2009509964A (ja) | 2009-03-12 |
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| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |