CA2659701A1 - Benzoxazole and benzothiazole derivatives as 5-hydroxytrytamine-6 ligands - Google Patents
Benzoxazole and benzothiazole derivatives as 5-hydroxytrytamine-6 ligands Download PDFInfo
- Publication number
- CA2659701A1 CA2659701A1 CA002659701A CA2659701A CA2659701A1 CA 2659701 A1 CA2659701 A1 CA 2659701A1 CA 002659701 A CA002659701 A CA 002659701A CA 2659701 A CA2659701 A CA 2659701A CA 2659701 A1 CA2659701 A1 CA 2659701A1
- Authority
- CA
- Canada
- Prior art keywords
- benzoxazole
- piperazin
- naphthylsulfonyl
- group
- compound
- 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
Links
- 239000003446 ligand Substances 0.000 title description 11
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title description 9
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 131
- 238000011282 treatment Methods 0.000 claims abstract description 22
- 108091005435 5-HT6 receptors Proteins 0.000 claims abstract description 20
- 208000015114 central nervous system disease Diseases 0.000 claims abstract description 11
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 17
- 208000035475 disorder Diseases 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002619 bicyclic group Chemical group 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 206010019196 Head injury Diseases 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 208000010877 cognitive disease Diseases 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 206010003805 Autism Diseases 0.000 claims description 3
- 208000020706 Autistic disease Diseases 0.000 claims description 3
- 208000012239 Developmental disease Diseases 0.000 claims description 3
- 201000010374 Down Syndrome Diseases 0.000 claims description 3
- 208000001914 Fragile X syndrome Diseases 0.000 claims description 3
- 206010044688 Trisomy 21 Diseases 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- OQLBUNURUSUBQN-UHFFFAOYSA-N 2-(4-cyclobutylpiperazin-1-yl)-4-naphthalen-1-ylsulfonyl-1,3-benzoxazole Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C=1N=2)=CC=CC=1OC=2N(CC1)CCN1C1CCC1 OQLBUNURUSUBQN-UHFFFAOYSA-N 0.000 claims description 2
- MEWGQTLKSHRSFE-UHFFFAOYSA-N 2-(4-cyclobutylpiperazin-1-yl)-7-naphthalen-1-ylsulfonyl-1,3-benzoxazole Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C=1O2)=CC=CC=1N=C2N(CC1)CCN1C1CCC1 MEWGQTLKSHRSFE-UHFFFAOYSA-N 0.000 claims description 2
- QLSHLXSLTKMHKR-UHFFFAOYSA-N 2-(4-ethylpiperazin-1-yl)-4-naphthalen-1-ylsulfonyl-1,3-benzoxazole Chemical compound C1CN(CC)CCN1C1=NC2=C(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C=CC=C2O1 QLSHLXSLTKMHKR-UHFFFAOYSA-N 0.000 claims description 2
- NJNWBYLIWWNPBC-UHFFFAOYSA-N 2-(4-ethylpiperazin-1-yl)-5-naphthalen-1-ylsulfonyl-1,3-benzoxazole Chemical compound C1CN(CC)CCN1C1=NC2=CC(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)=CC=C2O1 NJNWBYLIWWNPBC-UHFFFAOYSA-N 0.000 claims description 2
- VRQZVFGHYLFLHY-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-4-naphthalen-1-ylsulfonyl-1,3-benzoxazole Chemical compound C1CN(C)CCN1C1=NC2=C(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C=CC=C2O1 VRQZVFGHYLFLHY-UHFFFAOYSA-N 0.000 claims description 2
- ZTTWYNIORHZZGX-UHFFFAOYSA-N 2-piperazin-1-yl-4-[3-(trifluoromethyl)phenyl]sulfonyl-1,3-benzoxazole Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)C=2C=3N=C(OC=3C=CC=2)N2CCNCC2)=C1 ZTTWYNIORHZZGX-UHFFFAOYSA-N 0.000 claims description 2
- UQNAGBJCCFFANN-UHFFFAOYSA-N 2-piperazin-1-yl-7-[3-(trifluoromethyl)phenyl]sulfonyl-1,3-benzoxazole Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)C=2C=3OC(=NC=3C=CC=2)N2CCNCC2)=C1 UQNAGBJCCFFANN-UHFFFAOYSA-N 0.000 claims description 2
- ZKQXPUJOZXCOJC-UHFFFAOYSA-N 4-(2,5-dichlorophenyl)sulfonyl-2-piperazin-1-yl-1,3-benzoxazole;7-naphthalen-1-ylsulfonyl-2-piperazin-1-yl-1,3-benzothiazole Chemical compound ClC1=CC=C(Cl)C(S(=O)(=O)C=2C=3N=C(OC=3C=CC=2)N2CCNCC2)=C1.C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C=1S2)=CC=CC=1N=C2N1CCNCC1 ZKQXPUJOZXCOJC-UHFFFAOYSA-N 0.000 claims description 2
- JEGFNIPTHRCNHC-UHFFFAOYSA-N 4-(3-methoxyphenyl)sulfonyl-2-piperazin-1-yl-1,3-benzoxazole Chemical compound COC1=CC=CC(S(=O)(=O)C=2C=3N=C(OC=3C=CC=2)N2CCNCC2)=C1 JEGFNIPTHRCNHC-UHFFFAOYSA-N 0.000 claims description 2
- JDESGJUPIXKIGD-UHFFFAOYSA-N 4-(benzenesulfonyl)-2-piperazin-1-yl-1,3-benzoxazole Chemical compound C=1C=CC=2OC(N3CCNCC3)=NC=2C=1S(=O)(=O)C1=CC=CC=C1 JDESGJUPIXKIGD-UHFFFAOYSA-N 0.000 claims description 2
- RZSRDRPXXPEKAN-UHFFFAOYSA-N 4-naphthalen-1-ylsulfonyl-2-(4-propan-2-ylpiperazin-1-yl)-1,3-benzoxazole Chemical compound C1CN(C(C)C)CCN1C1=NC2=C(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C=CC=C2O1 RZSRDRPXXPEKAN-UHFFFAOYSA-N 0.000 claims description 2
- UADPBBCFLSQPJT-UHFFFAOYSA-N 4-naphthalen-1-ylsulfonyl-2-piperazin-1-yl-1,3-benzoxazole Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C=1N=2)=CC=CC=1OC=2N1CCNCC1 UADPBBCFLSQPJT-UHFFFAOYSA-N 0.000 claims description 2
- MRXHULXFYOLPGO-UHFFFAOYSA-N 5-(benzenesulfonyl)-2-piperazin-1-yl-1,3-benzoxazole Chemical compound C=1C=C2OC(N3CCNCC3)=NC2=CC=1S(=O)(=O)C1=CC=CC=C1 MRXHULXFYOLPGO-UHFFFAOYSA-N 0.000 claims description 2
- MWBQEVLIDMXMRD-UHFFFAOYSA-N 5-naphthalen-1-ylsulfonyl-2-(4-propan-2-ylpiperazin-1-yl)-1,3-benzoxazole Chemical compound C1CN(C(C)C)CCN1C1=NC2=CC(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)=CC=C2O1 MWBQEVLIDMXMRD-UHFFFAOYSA-N 0.000 claims description 2
- XIXJSYHSMPCRSE-UHFFFAOYSA-N 6-naphthalen-1-ylsulfonyl-2-piperazin-1-yl-1,3-benzoxazole Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C=C1O2)=CC=C1N=C2N1CCNCC1 XIXJSYHSMPCRSE-UHFFFAOYSA-N 0.000 claims description 2
- WVUYNNTVCLPARY-UHFFFAOYSA-N 7-(3-chlorophenyl)sulfonyl-2-piperazin-1-yl-1,3-benzoxazole Chemical compound ClC1=CC=CC(S(=O)(=O)C=2C=3OC(=NC=3C=CC=2)N2CCNCC2)=C1 WVUYNNTVCLPARY-UHFFFAOYSA-N 0.000 claims description 2
- AGOCFGSDFYIAHI-UHFFFAOYSA-N 7-naphthalen-1-ylsulfonyl-2-(4-propan-2-ylpiperazin-1-yl)-1,3-benzoxazole Chemical compound C1CN(C(C)C)CCN1C1=NC2=CC=CC(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)=C2O1 AGOCFGSDFYIAHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- TXBQKUOIYXDCIA-UHFFFAOYSA-N 2-(4-butylpiperazin-1-yl)-4-naphthalen-1-ylsulfonyl-1,3-benzoxazole;4-naphthalen-1-ylsulfonyl-2-(4-propylpiperazin-1-yl)-1,3-benzoxazole Chemical compound C1CN(CCC)CCN1C1=NC2=C(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C=CC=C2O1.C1CN(CCCC)CCN1C1=NC2=C(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C=CC=C2O1 TXBQKUOIYXDCIA-UHFFFAOYSA-N 0.000 claims 1
- LMPQEEPXLZFGFS-UHFFFAOYSA-N 2-(4-ethylpiperazin-1-yl)-7-naphthalen-1-ylsulfonyl-1,3-benzoxazole Chemical compound C1CN(CC)CCN1C1=NC2=CC=CC(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)=C2O1 LMPQEEPXLZFGFS-UHFFFAOYSA-N 0.000 claims 1
- WYXFCADKRYUNOI-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-5-naphthalen-1-ylsulfonyl-1,3-benzoxazole Chemical compound C1CN(C)CCN1C1=NC2=CC(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)=CC=C2O1 WYXFCADKRYUNOI-UHFFFAOYSA-N 0.000 claims 1
- SHZWLYFCLFGIKM-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-7-naphthalen-1-ylsulfonyl-1,3-benzoxazole Chemical compound C1CN(C)CCN1C1=NC2=CC=CC(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)=C2O1 SHZWLYFCLFGIKM-UHFFFAOYSA-N 0.000 claims 1
- UUEFVSXDNJPYCE-UHFFFAOYSA-N 2-(4-tert-butylpiperazin-1-yl)-4-naphthalen-1-ylsulfonyl-1,3-benzoxazole Chemical compound C1CN(C(C)(C)C)CCN1C1=NC2=C(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C=CC=C2O1 UUEFVSXDNJPYCE-UHFFFAOYSA-N 0.000 claims 1
- XUOKRGMHZQARTR-UHFFFAOYSA-N 2-piperazin-1-yl-4-(4-propan-2-ylphenyl)sulfonyl-1,3-benzoxazole Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)C1=CC=CC2=C1N=C(N1CCNCC1)O2 XUOKRGMHZQARTR-UHFFFAOYSA-N 0.000 claims 1
- MNJYTCUEXKDBRM-UHFFFAOYSA-N 2-piperazin-1-yl-7-(4-propan-2-ylphenyl)sulfonyl-1,3-benzoxazole Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)C1=CC=CC2=C1OC(N1CCNCC1)=N2 MNJYTCUEXKDBRM-UHFFFAOYSA-N 0.000 claims 1
- MFSZLULDGKDJNK-UHFFFAOYSA-N 4-(3-chlorophenyl)sulfonyl-2-piperazin-1-yl-1,3-benzoxazole Chemical compound ClC1=CC=CC(S(=O)(=O)C=2C=3N=C(OC=3C=CC=2)N2CCNCC2)=C1 MFSZLULDGKDJNK-UHFFFAOYSA-N 0.000 claims 1
- XLODRHINUUOPLQ-UHFFFAOYSA-N 4-(3-fluorophenyl)sulfonyl-2-piperazin-1-yl-1,3-benzoxazole Chemical compound FC1=CC=CC(S(=O)(=O)C=2C=3N=C(OC=3C=CC=2)N2CCNCC2)=C1 XLODRHINUUOPLQ-UHFFFAOYSA-N 0.000 claims 1
- NHHSRTALXZZTQG-UHFFFAOYSA-N 4-(4-fluorophenyl)sulfonyl-2-piperazin-1-yl-1,3-benzoxazole Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C1=CC=CC2=C1N=C(N1CCNCC1)O2 NHHSRTALXZZTQG-UHFFFAOYSA-N 0.000 claims 1
- BZTDVZOWBVTWMB-UHFFFAOYSA-N 4-naphthalen-1-ylsulfonyl-2-piperazin-1-yl-1,3-benzothiazole;6-naphthalen-1-ylsulfonyl-2-piperazin-1-yl-1,3-benzothiazole Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C=C1S2)=CC=C1N=C2N1CCNCC1.C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C=1N=2)=CC=CC=1SC=2N1CCNCC1 BZTDVZOWBVTWMB-UHFFFAOYSA-N 0.000 claims 1
- DLJBWYFUGPKXID-UHFFFAOYSA-N 5-naphthalen-1-ylsulfonyl-2-piperazin-1-yl-1,3-benzoxazole Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C=C1N=2)=CC=C1OC=2N1CCNCC1 DLJBWYFUGPKXID-UHFFFAOYSA-N 0.000 claims 1
- ACBCDHQUGDZJGJ-UHFFFAOYSA-N 7-(2,5-dichlorophenyl)sulfonyl-2-piperazin-1-yl-1,3-benzoxazole Chemical compound ClC1=CC=C(Cl)C(S(=O)(=O)C=2C=3OC(=NC=3C=CC=2)N2CCNCC2)=C1 ACBCDHQUGDZJGJ-UHFFFAOYSA-N 0.000 claims 1
- MJBRTUJYCXBFKR-UHFFFAOYSA-N 7-(3-fluorophenyl)sulfonyl-2-piperazin-1-yl-1,3-benzoxazole Chemical compound FC1=CC=CC(S(=O)(=O)C=2C=3OC(=NC=3C=CC=2)N2CCNCC2)=C1 MJBRTUJYCXBFKR-UHFFFAOYSA-N 0.000 claims 1
- KZEDJINFQURPNK-UHFFFAOYSA-N 7-(3-methoxyphenyl)sulfonyl-2-piperazin-1-yl-1,3-benzoxazole Chemical compound COC1=CC=CC(S(=O)(=O)C=2C=3OC(=NC=3C=CC=2)N2CCNCC2)=C1 KZEDJINFQURPNK-UHFFFAOYSA-N 0.000 claims 1
- VPKFYBMQHAFZFI-UHFFFAOYSA-N 7-(4-fluorophenyl)sulfonyl-2-piperazin-1-yl-1,3-benzoxazole Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C1=CC=CC2=C1OC(N1CCNCC1)=N2 VPKFYBMQHAFZFI-UHFFFAOYSA-N 0.000 claims 1
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- 231100000027 toxicology Toxicity 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic rings
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80999606P | 2006-06-01 | 2006-06-01 | |
| US60/809,996 | 2006-06-01 | ||
| PCT/US2007/012569 WO2007142904A2 (en) | 2006-06-01 | 2007-05-25 | Benzoxazole and benzothiazole derivatives as 5-hydroxytrytamine-6 ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2659701A1 true CA2659701A1 (en) | 2007-12-13 |
Family
ID=38668755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002659701A Abandoned CA2659701A1 (en) | 2006-06-01 | 2007-05-25 | Benzoxazole and benzothiazole derivatives as 5-hydroxytrytamine-6 ligands |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7501421B2 (enExample) |
| EP (1) | EP2024348A2 (enExample) |
| JP (1) | JP2009538909A (enExample) |
| KR (1) | KR20090023641A (enExample) |
| CN (1) | CN101490022A (enExample) |
| AR (1) | AR061147A1 (enExample) |
| AU (1) | AU2007255041A1 (enExample) |
| BR (1) | BRPI0712444A2 (enExample) |
| CA (1) | CA2659701A1 (enExample) |
| CR (1) | CR10474A (enExample) |
| EC (1) | ECSP088930A (enExample) |
| IL (1) | IL195590A0 (enExample) |
| MX (1) | MX2008015328A (enExample) |
| NO (1) | NO20085045L (enExample) |
| PE (1) | PE20080707A1 (enExample) |
| TW (1) | TW200804310A (enExample) |
| WO (1) | WO2007142904A2 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY159575A (en) * | 2009-04-02 | 2017-01-13 | Merck Serono Sa | Dihydroorotate dehydrogenase inhibitors |
| KR101250606B1 (ko) * | 2011-01-24 | 2013-04-03 | 이화여자대학교 산학협력단 | 5-ｈｔ６ 수용체 억제 작용을 갖는 신규한 벤조티아졸 및 벤즈이소티아졸유도체, 이의 제조 방법 및 이를 포함하는 약학적 조성물 |
| CN105431427B (zh) * | 2013-07-10 | 2017-12-08 | 明治制果药业株式会社 | 新型pde4 抑制剂 |
| US9974785B2 (en) | 2014-07-08 | 2018-05-22 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic derivatives and pharmaceutical applications thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7582635B2 (en) * | 2002-12-24 | 2009-09-01 | Purdue Pharma, L.P. | Therapeutic agents useful for treating pain |
| GB0422263D0 (en) * | 2004-10-07 | 2004-11-10 | Glaxo Group Ltd | Novel compounds |
-
2007
- 2007-05-23 PE PE2007000635A patent/PE20080707A1/es not_active Application Discontinuation
- 2007-05-25 AU AU2007255041A patent/AU2007255041A1/en not_active Abandoned
- 2007-05-25 CA CA002659701A patent/CA2659701A1/en not_active Abandoned
- 2007-05-25 CN CNA2007800261442A patent/CN101490022A/zh active Pending
- 2007-05-25 TW TW096118646A patent/TW200804310A/zh unknown
- 2007-05-25 WO PCT/US2007/012569 patent/WO2007142904A2/en not_active Ceased
- 2007-05-25 EP EP07777299A patent/EP2024348A2/en not_active Withdrawn
- 2007-05-25 JP JP2009513221A patent/JP2009538909A/ja not_active Withdrawn
- 2007-05-25 BR BRPI0712444-9A patent/BRPI0712444A2/pt not_active Application Discontinuation
- 2007-05-25 MX MX2008015328A patent/MX2008015328A/es not_active Application Discontinuation
- 2007-05-25 KR KR1020087031621A patent/KR20090023641A/ko not_active Withdrawn
- 2007-05-31 US US11/809,424 patent/US7501421B2/en not_active Expired - Fee Related
- 2007-05-31 AR ARP070102364A patent/AR061147A1/es unknown
-
2008
- 2008-11-27 IL IL195590A patent/IL195590A0/en unknown
- 2008-12-01 EC EC2008008930A patent/ECSP088930A/es unknown
- 2008-12-01 CR CR10474A patent/CR10474A/es not_active Application Discontinuation
- 2008-12-03 NO NO20085045A patent/NO20085045L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CR10474A (es) | 2009-01-07 |
| US7501421B2 (en) | 2009-03-10 |
| MX2008015328A (es) | 2008-12-12 |
| WO2007142904A3 (en) | 2008-02-07 |
| AR061147A1 (es) | 2008-08-06 |
| PE20080707A1 (es) | 2008-05-22 |
| BRPI0712444A2 (pt) | 2012-06-05 |
| IL195590A0 (en) | 2009-09-01 |
| KR20090023641A (ko) | 2009-03-05 |
| WO2007142904A2 (en) | 2007-12-13 |
| ECSP088930A (es) | 2009-01-30 |
| CN101490022A (zh) | 2009-07-22 |
| US20070281945A1 (en) | 2007-12-06 |
| NO20085045L (no) | 2008-12-12 |
| AU2007255041A1 (en) | 2007-12-13 |
| JP2009538909A (ja) | 2009-11-12 |
| TW200804310A (en) | 2008-01-16 |
| EP2024348A2 (en) | 2009-02-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |