DE60223715T2 - Glyt1 transporter inhibitoren und deren anwendung in der behandlung von neurologischen und neuropsychiatischen krankheiten - Google Patents
Glyt1 transporter inhibitoren und deren anwendung in der behandlung von neurologischen und neuropsychiatischen krankheiten Download PDFInfo
- Publication number
- DE60223715T2 DE60223715T2 DE60223715T DE60223715T DE60223715T2 DE 60223715 T2 DE60223715 T2 DE 60223715T2 DE 60223715 T DE60223715 T DE 60223715T DE 60223715 T DE60223715 T DE 60223715T DE 60223715 T2 DE60223715 T2 DE 60223715T2
- Authority
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- Germany
- Prior art keywords
- hydroxypropyl
- amide
- sulfonic acid
- dimethylpyrrolidin
- naphthalene
- 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.)
- Expired - Fee Related
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- 238000011282 treatment Methods 0.000 title claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 27
- 230000000926 neurological effect Effects 0.000 title description 7
- 201000010099 disease Diseases 0.000 title description 6
- 239000003112 inhibitor Substances 0.000 title description 3
- 102100022622 Alpha-1,3-mannosyl-glycoprotein 2-beta-N-acetylglucosaminyltransferase Human genes 0.000 title 1
- 101000972916 Homo sapiens Alpha-1,3-mannosyl-glycoprotein 2-beta-N-acetylglucosaminyltransferase Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 205
- -1 R 21 Chemical compound 0.000 claims description 80
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 101710083171 Sodium- and chloride-dependent glycine transporter 1 Proteins 0.000 claims description 25
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 23
- 150000001408 amides Chemical class 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 102100023145 Sodium- and chloride-dependent glycine transporter 1 Human genes 0.000 claims description 19
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 230000001404 mediated effect Effects 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- ZFFSMUXTPWBHPL-UHFFFAOYSA-N n-[3-(2,4-dimethylpyrrolidin-1-yl)-2-hydroxypropyl]naphthalene-1-sulfonamide Chemical compound C1C(C)CC(C)N1CC(O)CNS(=O)(=O)C1=CC=CC2=CC=CC=C12 ZFFSMUXTPWBHPL-UHFFFAOYSA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 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 7
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
- DUOJVRWFIHNZTJ-UHFFFAOYSA-N 2,4-dimethylpyrrolidine Chemical compound CC1CNC(C)C1 DUOJVRWFIHNZTJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- HVJAYFJHJZUVBX-UHFFFAOYSA-N n-(2-hydroxy-3-piperidin-1-ylpropyl)naphthalene-1-sulfonamide Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)NCC(O)CN1CCCCC1 HVJAYFJHJZUVBX-UHFFFAOYSA-N 0.000 claims description 6
- WFUWCFSYNNOABU-UHFFFAOYSA-N n-(2-hydroxy-3-pyrrolidin-1-ylpropyl)naphthalene-1-sulfonamide Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)NCC(O)CN1CCCC1 WFUWCFSYNNOABU-UHFFFAOYSA-N 0.000 claims description 6
- NESOLNYQUNZLFY-XHSDSOJGSA-N n-[(2r)-3-[(2r,6s)-2,6-dimethylpiperidin-1-yl]-2-hydroxypropyl]-5-iodonaphthalene-1-sulfonamide Chemical compound C[C@H]1CCC[C@@H](C)N1C[C@@H](O)CNS(=O)(=O)C1=CC=CC2=C(I)C=CC=C12 NESOLNYQUNZLFY-XHSDSOJGSA-N 0.000 claims description 6
- IFCYHVCTAATODB-UHFFFAOYSA-N n-[2-hydroxy-3-(2-methylpiperidin-1-yl)propyl]naphthalene-1-sulfonamide Chemical compound CC1CCCCN1CC(O)CNS(=O)(=O)C1=CC=CC2=CC=CC=C12 IFCYHVCTAATODB-UHFFFAOYSA-N 0.000 claims description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- NOZBVIXZASBZPN-AXFHLTTASA-N 2,5-dichloro-n-[(2r)-3-[(2s,6r)-2,6-dimethylpiperidin-1-yl]-2-hydroxypropyl]thiophene-3-sulfonamide Chemical compound C[C@H]1CCC[C@@H](C)N1C[C@@H](O)CNS(=O)(=O)C1=C(Cl)SC(Cl)=C1 NOZBVIXZASBZPN-AXFHLTTASA-N 0.000 claims description 4
- DKKQLDRUDXWMJW-AXFHLTTASA-N 4,5-dibromo-n-[(2r)-3-[(2s,6r)-2,6-dimethylpiperidin-1-yl]-2-hydroxypropyl]thiophene-2-sulfonamide Chemical compound C[C@H]1CCC[C@@H](C)N1C[C@@H](O)CNS(=O)(=O)C1=CC(Br)=C(Br)S1 DKKQLDRUDXWMJW-AXFHLTTASA-N 0.000 claims description 4
- HZCJPUADBXZCCG-FVJLSDCUSA-N 4-(4-chlorophenyl)-n-[(2r)-3-[(2r,6s)-2,6-dimethylpiperidin-1-yl]-2-hydroxypropyl]benzenesulfonamide Chemical compound C[C@H]1CCC[C@@H](C)N1C[C@@H](O)CNS(=O)(=O)C1=CC=C(C=2C=CC(Cl)=CC=2)C=C1 HZCJPUADBXZCCG-FVJLSDCUSA-N 0.000 claims description 4
- SYVHMARMCXOYJF-AEJSXWLSSA-N 4-bromo-2,5-dichloro-n-[(2r)-3-[(2s,6r)-2,6-dimethylpiperidin-1-yl]-2-hydroxypropyl]thiophene-3-sulfonamide Chemical compound C[C@H]1CCC[C@@H](C)N1C[C@@H](O)CNS(=O)(=O)C1=C(Cl)SC(Cl)=C1Br SYVHMARMCXOYJF-AEJSXWLSSA-N 0.000 claims description 4
- QAVCGAYWPBAKEH-JZXOWHBKSA-N 4-cyano-n-[(2r)-3-[(2r,6s)-2,6-dimethylpiperidin-1-yl]-2-hydroxypropyl]naphthalene-1-sulfonamide Chemical compound C[C@H]1CCC[C@@H](C)N1C[C@@H](O)CNS(=O)(=O)C1=CC=C(C#N)C2=CC=CC=C12 QAVCGAYWPBAKEH-JZXOWHBKSA-N 0.000 claims description 4
- MOLPUSJKGNBHBG-JZXOWHBKSA-N 5-acetyl-n-[(2r)-3-[(2s,6r)-2,6-dimethylpiperidin-1-yl]-2-hydroxypropyl]naphthalene-1-sulfonamide Chemical compound C[C@H]1CCC[C@@H](C)N1C[C@@H](O)CNS(=O)(=O)C1=CC=CC2=C(C(C)=O)C=CC=C12 MOLPUSJKGNBHBG-JZXOWHBKSA-N 0.000 claims description 4
- NHTGKASFJYAJGD-UXLLHSPISA-N 5-chloro-n-[(2r)-3-[(2s,6r)-2,6-dimethylpiperidin-1-yl]-2-hydroxypropyl]naphthalene-2-sulfonamide Chemical compound C[C@H]1CCC[C@@H](C)N1C[C@@H](O)CNS(=O)(=O)C1=CC=C(C(Cl)=CC=C2)C2=C1 NHTGKASFJYAJGD-UXLLHSPISA-N 0.000 claims description 4
- DHIRAKYHVJGYIG-JZXOWHBKSA-N 5-cyano-n-[(2r)-3-[(2r,6s)-2,6-dimethylpiperidin-1-yl]-2-hydroxypropyl]naphthalene-1-sulfonamide Chemical compound C[C@H]1CCC[C@@H](C)N1C[C@@H](O)CNS(=O)(=O)C1=CC=CC2=C(C#N)C=CC=C12 DHIRAKYHVJGYIG-JZXOWHBKSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- PIOXVFZEJFFVDG-XRZIKPEHSA-N FC(C(=O)O)(F)F.C1(CC1)C1N(CCC1)C[C@H](CNS(=O)(=O)C1=CC=CC2=CC=CC=C12)O Chemical compound FC(C(=O)O)(F)F.C1(CC1)C1N(CCC1)C[C@H](CNS(=O)(=O)C1=CC=CC2=CC=CC=C12)O PIOXVFZEJFFVDG-XRZIKPEHSA-N 0.000 claims description 4
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- XEISCDHNUDSCLM-KQCMKQOESA-N FC(C(=O)O)(F)F.O[C@@H](CNS(=O)(=O)C1=CC=CC2=CC=CC=C12)CN1[C@@H]2CC(C[C@](C1)(C2)C)(C)C Chemical compound FC(C(=O)O)(F)F.O[C@@H](CNS(=O)(=O)C1=CC=CC2=CC=CC=C12)CN1[C@@H]2CC(C[C@](C1)(C2)C)(C)C XEISCDHNUDSCLM-KQCMKQOESA-N 0.000 claims description 4
- HBSSSXSLDXYEHN-BXWZNKKMSA-N FC(C(=O)O)(F)F.O[C@H](CNS(=O)(=O)C1=CC=CC2=CC=CC=C12)CN1C(CCC1)C Chemical compound FC(C(=O)O)(F)F.O[C@H](CNS(=O)(=O)C1=CC=CC2=CC=CC=C12)CN1C(CCC1)C HBSSSXSLDXYEHN-BXWZNKKMSA-N 0.000 claims description 4
- ANRCWSRLFMGBJL-XRZIKPEHSA-N N-[(2R)-2-hydroxy-3-(2-propan-2-ylpyrrolidin-1-yl)propyl]naphthalene-1-sulfonamide 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.O[C@@H](CNS(=O)(=O)C1=CC=CC2=CC=CC=C12)CN1C(CCC1)C(C)C ANRCWSRLFMGBJL-XRZIKPEHSA-N 0.000 claims description 4
- PEXKCWFDHKYFGG-MWVDPUPUSA-N N-[(2R)-3-(2,4-dimethylpyrrolidin-1-yl)-2-hydroxypropyl]naphthalene-1-sulfonamide 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.CC1N(CC(C1)C)C[C@H](CNS(=O)(=O)C1=CC=CC2=CC=CC=C12)O PEXKCWFDHKYFGG-MWVDPUPUSA-N 0.000 claims description 4
- IPTZVPFJYRFMGA-MWVDPUPUSA-N N-[(2R)-3-(2,5-dimethylpyrrolidin-1-yl)-2-hydroxypropyl]naphthalene-1-sulfonamide 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.CC1N(C(CC1)C)C[C@H](CNS(=O)(=O)C1=CC=CC2=CC=CC=C12)O IPTZVPFJYRFMGA-MWVDPUPUSA-N 0.000 claims description 4
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- 125000002619 bicyclic group Chemical group 0.000 claims description 4
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- HVJAYFJHJZUVBX-INIZCTEOSA-N n-[(2r)-2-hydroxy-3-piperidin-1-ylpropyl]naphthalene-1-sulfonamide Chemical compound C([C@H](CNS(=O)(=O)C=1C2=CC=CC=C2C=CC=1)O)N1CCCCC1 HVJAYFJHJZUVBX-INIZCTEOSA-N 0.000 claims description 4
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- DNUPKXDIBVGRIZ-MHJFOBGBSA-N n-[(2r)-3-(2,6-diethylpiperidin-1-yl)-2-hydroxypropyl]naphthalene-1-sulfonamide Chemical compound CCC1CCCC(CC)N1C[C@@H](O)CNS(=O)(=O)C1=CC=CC2=CC=CC=C12 DNUPKXDIBVGRIZ-MHJFOBGBSA-N 0.000 claims description 4
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 to carbon atoms of the hetero ring
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/12—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
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| GB0130696 | 2001-12-21 | ||
| PCT/GB2002/005819 WO2003055478A1 (en) | 2001-12-21 | 2002-12-19 | Glyt1 transporter inhibitors and uses thereof in treatment of neurological and neuropsychiatric disorders |
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| DE60223715D1 DE60223715D1 (de) | 2008-01-03 |
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| DE60223715T Expired - Fee Related DE60223715T2 (de) | 2001-12-21 | 2002-12-19 | Glyt1 transporter inhibitoren und deren anwendung in der behandlung von neurologischen und neuropsychiatischen krankheiten |
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| WO (1) | WO2003055478A1 (enExample) |
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| GB0314479D0 (en) * | 2003-06-20 | 2003-07-23 | Glaxo Group Ltd | Compounds |
| ES2634841T3 (es) * | 2003-10-14 | 2017-09-29 | Pfizer Products Inc. | Derivados bicíclicos [3.1.0] como inhibidores del transportador de glicina |
| GB0326840D0 (en) * | 2003-11-18 | 2003-12-24 | Glaxo Group Ltd | Compounds |
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| GB0408777D0 (en) * | 2004-04-20 | 2004-05-26 | Glaxo Group Ltd | Compounds |
| AU2005292323B2 (en) | 2004-09-30 | 2011-06-09 | Merck Sharp & Dohme Llc | Cyclopropyl piperidine glycine transporter inhibitors |
| WO2006067414A2 (en) * | 2004-12-23 | 2006-06-29 | Glaxo Group Limited | Glycine transport inhibitors |
| PE20061330A1 (es) * | 2004-12-23 | 2006-12-27 | Glaxo Group Ltd | Compuestos derivados de benzamida como inhibidores del transportador de glicina |
| GB0428233D0 (en) * | 2004-12-23 | 2005-01-26 | Glaxo Group Ltd | Compounds |
| GB0428232D0 (en) * | 2004-12-23 | 2005-01-26 | Glaxo Group Ltd | Compounds |
| PE20061156A1 (es) * | 2004-12-23 | 2006-12-16 | Glaxo Group Ltd | Derivados de benzamida como agentes inhibidores del transportador de glicina |
| JP2009503006A (ja) * | 2005-08-02 | 2009-01-29 | グラクソ グループ リミテッド | GlyT1トランスポーター阻害剤ならびに神経および神経精神障害の治療におけるその使用 |
| AR059839A1 (es) | 2006-03-16 | 2008-04-30 | Glaxo Group Ltd | Compuesto derivado de diazaespiro-acetamida, composicion farmaceutica que lo comprende, uso para la preparacion de un medicamento para el tratamiento de un trastorno mediado por glyt1 y proceso para su preparacion |
| GB0612420D0 (en) * | 2006-06-22 | 2006-08-02 | Glaxo Group Ltd | Compounds |
| GB0612425D0 (en) * | 2006-06-22 | 2006-08-02 | Glaxo Group Ltd | Compounds |
| CA2691450A1 (en) * | 2007-08-22 | 2009-02-26 | Abbott Gmbh & Co. Kg | 4-benzylaminoquinolines, pharmaceutical compositions containing them, and their use in therapy |
| ES2397764T3 (es) | 2008-04-01 | 2013-03-11 | Abbott Gmbh & Co. Kg | Tetrahidroisoquinolinas, composiciones farmacéuticas que las contienen, y su uso en terapia |
| AU2009255156B2 (en) | 2008-06-05 | 2013-03-14 | Asahi Kasei Pharma Corporation | Sulfonamide compound and application thereof |
| TW201038569A (en) | 2009-02-16 | 2010-11-01 | Abbott Gmbh & Co Kg | Heterocyclic compounds, pharmaceutical compositions containing them, and their use in therapy |
| AR075442A1 (es) | 2009-02-16 | 2011-03-30 | Abbott Gmbh & Co Kg | Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia |
| WO2011012622A1 (en) | 2009-07-30 | 2011-02-03 | Glaxo Group Limited | Benzoxazinone derivatives for the treatment of glytl mediated disorders |
| WO2011023753A1 (en) | 2009-08-27 | 2011-03-03 | Glaxo Group Limited | Benzoxazine derivatives as glycine transport inhibitors |
| CN101781244B (zh) * | 2010-02-10 | 2014-04-16 | 中国农业大学 | 化合物4-溴-n-(吡啶-2-甲基)萘-1-磺酰胺的制备方法 |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8877794B2 (en) | 2010-08-13 | 2014-11-04 | Abbott Laboratories | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9045459B2 (en) | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9309200B2 (en) | 2011-05-12 | 2016-04-12 | AbbVie Deutschland GmbH & Co. KG | Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| MX2014001457A (es) | 2011-08-05 | 2014-08-21 | Abbvie Deutschland | Derivados de aminocromano, de aminotiocromano y de amino-1,2,3,4-tetrahidroquinolina composiciones farmaceuticas que los contienen, y su uso en terapia. |
| US8846741B2 (en) | 2011-11-18 | 2014-09-30 | Abbvie Inc. | N-substituted aminobenzocycloheptene, aminotetraline, aminoindane and phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9365512B2 (en) | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9656955B2 (en) | 2013-03-15 | 2017-05-23 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9650334B2 (en) | 2013-03-15 | 2017-05-16 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| MX2016004934A (es) | 2013-10-17 | 2016-12-20 | Abbvie Deutschland | Derivados de aminotetralina y aminoindano, composiciones farmaceuticas que los contienen, y su uso en terapia. |
| MX2016004936A (es) | 2013-10-17 | 2016-12-20 | Abbvie Deutschland | Derivados de aminocromano, aminotiocromano y amino-1,2,3,4-tetrahi droquinilina, composiciones farmaceuticas que los contienen, y su uso en terapia. |
| US9550754B2 (en) | 2014-09-11 | 2017-01-24 | AbbVie Deutschland GmbH & Co. KG | 4,5-dihydropyrazole derivatives, pharmaceutical compositions containing them, and their use in therapy |
| WO2016123576A1 (en) * | 2015-01-30 | 2016-08-04 | Lieber Institute For Brain Development | Comt inhibiting methods and compositions |
| EP3380471B8 (en) | 2015-11-25 | 2022-01-19 | Lieber Institute Inc. DBA Lieber Institute For Brain Development | Tetrahydro-8h-pyrido[1,2-a]pyrazine-8-ones as comt inhibitors for the treatment of neurodegenerative disorders |
| CN113194949B (zh) * | 2018-12-18 | 2024-05-31 | 株式会社D.西医疗法研究所 | 异喹啉磺酰氯酸加成盐和其制造方法 |
| CA3184151A1 (en) * | 2020-06-29 | 2022-01-06 | Chris Murphy | Probenecid compounds for the treatment of inflammasome-mediated lung disease |
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| DE3276313D1 (en) * | 1981-09-24 | 1987-06-19 | Beecham Wuelfing Gmbh & Co Kg | Sulphonamides |
| ZA9610745B (en) * | 1995-12-22 | 1997-06-24 | Warner Lambert Co | 4-Subsituted piperidine analogs and their use as subtype selective nmda receptor antagonists |
| EP1138678B1 (en) * | 1997-10-31 | 2004-12-22 | Daiichi Suntory Pharma Co., Ltd. | Process for making N-((4-phenyl) methylphenyl) piperazines |
| AU2030999A (en) * | 1998-01-09 | 1999-07-26 | Allelix Neuroscience, Inc. | Glycine transport inhibitors |
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Also Published As
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|---|---|
| EP1455777B1 (en) | 2007-11-21 |
| ES2297030T3 (es) | 2008-05-01 |
| GB0130696D0 (en) | 2002-02-06 |
| JP2005519048A (ja) | 2005-06-30 |
| AU2002352483A1 (en) | 2003-07-15 |
| DE60223715D1 (de) | 2008-01-03 |
| US20050267152A1 (en) | 2005-12-01 |
| EP1455777A1 (en) | 2004-09-15 |
| WO2003055478A1 (en) | 2003-07-10 |
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Inventor name: COULTON, STEVEN, HARLOW, ESSEX CM19 5 AW, GB Inventor name: HADLEY, MICHAEL STEWART, HARLOW, ESSEX CM19 5A, GB Inventor name: HERDON, HUGH JONATHAN, HARLOW, ESSEX CM19 5AW, GB Inventor name: JIN, JIAN, KING OF PRUSSIA, PA 19406, US Inventor name: JOINER, GRAHAM J., HARLOW, ESSEX CM19 5AW, GB Inventor name: PORTER, RODERICK ALAN, HARLOW, ESSEX CM19 5AW, GB Inventor name: RAHMAN, SHAHZAD SHAROOQ, HARLOW, ESSEX CM19 5A, GB |
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