TW201211031A - Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy - Google Patents
Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy Download PDFInfo
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- TW201211031A TW201211031A TW100128764A TW100128764A TW201211031A TW 201211031 A TW201211031 A TW 201211031A TW 100128764 A TW100128764 A TW 100128764A TW 100128764 A TW100128764 A TW 100128764A TW 201211031 A TW201211031 A TW 201211031A
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- Prior art keywords
- alkyl
- group
- ethyl
- benzyl
- hydrogen
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 15
- 238000002560 therapeutic procedure Methods 0.000 title description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- -1 bromo-1H-imidazole-4-sulfonic acid {2-[5-(2-amino-1-benzyl-ethyl)-2-fluoro -phenoxy]-ethyl}-decylamine Chemical compound 0.000 claims description 386
- 125000000217 alkyl group Chemical group 0.000 claims description 319
- 150000001875 compounds Chemical class 0.000 claims description 180
- 229910052739 hydrogen Inorganic materials 0.000 claims description 163
- 239000001257 hydrogen Substances 0.000 claims description 159
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 127
- 125000003545 alkoxy group Chemical group 0.000 claims description 81
- 208000002193 Pain Diseases 0.000 claims description 68
- 238000011282 treatment Methods 0.000 claims description 62
- 125000000623 heterocyclic group Chemical group 0.000 claims description 60
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 59
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 58
- 239000002253 acid Substances 0.000 claims description 54
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 48
- 239000003814 drug Substances 0.000 claims description 43
- 150000001412 amines Chemical class 0.000 claims description 40
- 125000003282 alkyl amino group Chemical group 0.000 claims description 34
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 32
- 125000003277 amino group Chemical group 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 125000002947 alkylene group Chemical group 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 26
- 150000002367 halogens Chemical group 0.000 claims description 26
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 25
- 239000007789 gas Substances 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 20
- KSZCAGWHZCZJLZ-UHFFFAOYSA-N 1-methylimidazole-4-sulfonic acid Chemical compound CN1C=NC(S(O)(=O)=O)=C1 KSZCAGWHZCZJLZ-UHFFFAOYSA-N 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 150000001721 carbon Chemical group 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 10
- HYZWXCKJXJLMHO-UHFFFAOYSA-N C1=C(N=CN1S)S(=O)(=O)O Chemical compound C1=C(N=CN1S)S(=O)(=O)O HYZWXCKJXJLMHO-UHFFFAOYSA-N 0.000 claims description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 8
- 206010036790 Productive cough Diseases 0.000 claims description 8
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 229910052707 ruthenium Inorganic materials 0.000 claims description 8
- 208000024794 sputum Diseases 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 7
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 230000000926 neurological effect Effects 0.000 claims description 7
- 210000003802 sputum Anatomy 0.000 claims description 7
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 7
- ZMPAPJBFYQSNFM-UHFFFAOYSA-N 1-sulfanylimidazole Chemical compound SN1C=CN=C1 ZMPAPJBFYQSNFM-UHFFFAOYSA-N 0.000 claims description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
- GIBYKOOMNLJCSV-UHFFFAOYSA-N SN1N=CC(=C1)S(=O)(=O)O Chemical compound SN1N=CC(=C1)S(=O)(=O)O GIBYKOOMNLJCSV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- 150000003973 alkyl amines Chemical class 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 claims description 3
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 2
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- XPSBXNCOQGDLQP-UHFFFAOYSA-N NC(=O)c1cccc(c1)C1(Cc2ccccc2)CNC(=O)C1 Chemical compound NC(=O)c1cccc(c1)C1(Cc2ccccc2)CNC(=O)C1 XPSBXNCOQGDLQP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims 1
- GLTYLULZRHMGJB-UHFFFAOYSA-N 3-(3-benzylpyrrolidin-3-yl)benzamide Chemical compound NC(=O)c1cccc(c1)C1(Cc2ccccc2)CCNC1 GLTYLULZRHMGJB-UHFFFAOYSA-N 0.000 claims 1
- CJFOKWNHNZBRRU-UHFFFAOYSA-N Base A Natural products CC1CC2NC(C)NC3NC(C)CC(N1)C23 CJFOKWNHNZBRRU-UHFFFAOYSA-N 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- GTPINKYWKTZDBU-UHFFFAOYSA-N cyclopropylmethanesulfonamide Chemical compound NS(=O)(=O)CC1CC1 GTPINKYWKTZDBU-UHFFFAOYSA-N 0.000 claims 1
- 238000006073 displacement reaction Methods 0.000 claims 1
- 239000000796 flavoring agent Substances 0.000 claims 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- 235000015097 nutrients Nutrition 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 abstract description 45
- 239000003112 inhibitor Substances 0.000 abstract description 20
- 102100023145 Sodium- and chloride-dependent glycine transporter 1 Human genes 0.000 abstract description 3
- 101710083171 Sodium- and chloride-dependent glycine transporter 1 Proteins 0.000 abstract description 3
- 239000002585 base Substances 0.000 description 102
- 125000004432 carbon atom Chemical group C* 0.000 description 102
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 97
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 80
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 71
- 239000000203 mixture Substances 0.000 description 50
- 239000000243 solution Substances 0.000 description 48
- 235000019439 ethyl acetate Nutrition 0.000 description 44
- 238000000034 method Methods 0.000 description 43
- 125000001424 substituent group Chemical group 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 125000004429 atom Chemical group 0.000 description 32
- 239000003795 chemical substances by application Substances 0.000 description 32
- 201000010099 disease Diseases 0.000 description 31
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 30
- 239000012044 organic layer Substances 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 24
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 23
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- 208000020016 psychiatric disease Diseases 0.000 description 23
- 229910052757 nitrogen Chemical group 0.000 description 22
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 18
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- 239000011541 reaction mixture Substances 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- 229940079593 drug Drugs 0.000 description 17
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- 125000004093 cyano group Chemical group *C#N 0.000 description 14
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- 238000006243 chemical reaction Methods 0.000 description 13
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 125000003107 substituted aryl group Chemical group 0.000 description 12
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- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
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Classifications
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- 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
- C07D295/135—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 separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
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Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2397764T3 (es) | 2008-04-01 | 2013-03-11 | Abbott Gmbh & Co. Kg | Tetrahidroisoquinolinas, composiciones farmacéuticas que las contienen, y su uso en terapia |
| 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 |
| US8877794B2 (en) | 2010-08-13 | 2014-11-04 | Abbott Laboratories | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | 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 |
| US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane 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 |
| US9309200B2 (en) | 2011-05-12 | 2016-04-12 | AbbVie Deutschland GmbH & Co. KG | Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8853196B2 (en) | 2011-08-05 | 2014-10-07 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| CA2853254A1 (en) | 2011-11-18 | 2013-05-23 | 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 |
| CN105209457A (zh) * | 2013-03-15 | 2015-12-30 | 艾伯维德国有限责任两合公司 | 吡咯烷衍生物,含有其的药物组合物及其在治疗中的用途 |
| US9650334B2 (en) | 2013-03-15 | 2017-05-16 | Abbvie Inc. | Pyrrolidine 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 |
| CA2924699A1 (en) | 2013-10-17 | 2015-04-23 | AbbVie Deutschland GmbH & Co. KG | Aminotetraline and aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| 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 |
| JPWO2019059244A1 (ja) | 2017-09-21 | 2020-11-05 | 日本農薬株式会社 | シクロプロピルピリジル基を有するベンゾイミダゾール化合物又はその塩類、及びそれらの化合物を含有する農園芸用殺虫剤並びにその使用方法 |
| AR130467A1 (es) * | 2022-09-12 | 2024-12-11 | Gilgamesh Pharmaceuticals Inc | Fenalquilaminas y métodos para fabricar y usar las mismas |
Family Cites Families (134)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3867391A (en) | 1973-08-09 | 1975-02-18 | Pfizer | Cyclic n-substituted derivatives of 1,4-benzene disulphonamide |
| SE8004002L (sv) | 1980-05-29 | 1981-11-30 | Arvidsson Folke Lars Erik | Terapeutiskt anvendbara tetralinderivat |
| ATE39483T1 (de) | 1982-04-02 | 1989-01-15 | Takeda Chemical Industries Ltd | Kondensierte pyrrolinon-derivate, und ihre herstellung. |
| US4789678A (en) | 1986-08-25 | 1988-12-06 | Hoechst-Roussel Pharmaceuticals, Inc. | Memory enhancing α-alkyl-4-amino-3-quinolinemethanols and 1-(4-aralkylamino-3-quinolinyl)alkanones and related compounds |
| US4927838A (en) | 1987-07-10 | 1990-05-22 | Hoffman-La Roche Inc. | Pyridine compounds which are useful in treating a disease state characterized by an excess of platelet activating factors |
| CA1327795C (en) | 1987-08-14 | 1994-03-15 | Jules Freedman | Antidepressants which are aryloxy inadanamines |
| US5300523A (en) | 1988-07-28 | 1994-04-05 | Bayer Aktiengesellschaft | Substituted aminomethyltetralins and their heterocyclic analogues |
| US5545755A (en) | 1989-05-31 | 1996-08-13 | The Upjohn Company | Therapeutically useful 2-aminotetralin derivatives |
| AU654653B2 (en) | 1989-05-31 | 1994-11-17 | Pharmacia & Upjohn Company | Therapeutically useful 2-aminotetralin derivatives |
| US5071875A (en) | 1989-09-25 | 1991-12-10 | Northwestern University | Substituted 2-amidotetralins as melatonin agonists and antagonists |
| JPH06502165A (ja) | 1990-10-12 | 1994-03-10 | ファルマシア・アンド・アップジョン・カンパニー | 治療上有用な2−アミノテトラリン誘導体 |
| JPH06506951A (ja) | 1991-04-26 | 1994-08-04 | ジ・アップジョン・カンパニー | 物質乱用の治療/予防方法 |
| JPH05213884A (ja) | 1991-06-14 | 1993-08-24 | Upjohn Co:The | 新規な4−アミノキノリン類およびこれを有効成分とする高血圧・鬱血性心不全の予防・治療剤 |
| GB9127306D0 (en) | 1991-12-23 | 1992-02-19 | Boots Co Plc | Therapeutic agents |
| MY115155A (en) | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
| EP1019385B1 (en) | 1995-09-15 | 2004-01-14 | PHARMACIA & UPJOHN COMPANY | Aminoaryl oxazolidinone n-oxides |
| CA2619901A1 (en) | 1996-05-31 | 1997-12-04 | Allelix Neuroscience Inc. | Pharmaceutical for treatment of neurological and neuropsychiatric disorders |
| US6083986A (en) | 1996-07-26 | 2000-07-04 | Icagen, Inc. | Potassium channel inhibitors |
| DE19740785A1 (de) * | 1997-02-21 | 1998-08-27 | Bayer Ag | Arylsulfonamide und Analoga |
| US6057357A (en) * | 1997-04-30 | 2000-05-02 | Warner-Lambert Company | Peripherally selective kappa opioid agonists |
| AU6878298A (en) * | 1997-04-30 | 1998-11-24 | Warner-Lambert Company | Peripherally selective kappa opioid agonists |
| WO1998056757A1 (fr) | 1997-06-11 | 1998-12-17 | Sankyo Company, Limited | Derives de benzylamine |
| US20030220234A1 (en) | 1998-11-02 | 2003-11-27 | Selvaraj Naicker | Deuterated cyclosporine analogs and their use as immunodulating agents |
| US6197798B1 (en) | 1998-07-21 | 2001-03-06 | Novartis Ag | Amino-benzocycloalkane derivatives |
| TW555757B (en) | 1998-07-31 | 2003-10-01 | Akzo Nobel Nv | Aminomethylcarboxylic acid derivatives |
| EP1119543B1 (en) | 1998-10-07 | 2004-12-15 | Ortho-McNeil Pharmaceutical, Inc. | N-aralkylaminotetralins as ligands for the neuropeptide y y5 receptor |
| DE60024631T2 (de) | 1999-07-26 | 2006-06-14 | Banyu Pharma Co Ltd | Biaryl-harnstoff-derivate |
| EP1202986B1 (en) | 1999-07-28 | 2005-10-12 | Ortho-McNeil Pharmaceutical, Inc. | Amine and amide derivatives as ligands for the neuropeptide y y5 receptor useful in the treatment of obesity and other disorders |
| GB9918037D0 (en) | 1999-07-30 | 1999-09-29 | Biochemie Gmbh | Organic compounds |
| US6426364B1 (en) | 1999-11-01 | 2002-07-30 | Nps Allelix Corp. | Diaryl-enynes |
| AU781365B2 (en) | 1999-12-21 | 2005-05-19 | Icagen, Inc. | Potassium channel inhibitors |
| DK1283830T3 (da) * | 2000-05-08 | 2008-08-25 | Hoffmann La Roche | Para-amin-substituerede phenylamidglucokinase-aktivatorer |
| JP4850332B2 (ja) | 2000-10-18 | 2012-01-11 | 東京エレクトロン株式会社 | デュアルダマシン構造のエッチング方法 |
| US6815451B2 (en) | 2001-03-27 | 2004-11-09 | Actelion Pharmaceuticals Ltd. | 1,2,3,4-Tetrahydroisoquinolines derivatives as urotensin II receptor antagonists |
| AU2756602A (en) | 2001-04-25 | 2002-10-31 | Pfizer Products Inc. | Methods and kits for treating depression or preventing deterioration of cognitive function |
| US6831193B2 (en) | 2001-05-18 | 2004-12-14 | Abbott Laboratories | Trisubstituted-N-[(1S)-1,2,3,4-Tetrahydro-1-naphthalenyl]benzamides which inhibit P2X3 and P2X2/3 containing receptors |
| ATE305917T1 (de) | 2001-08-16 | 2005-10-15 | Pfizer Prod Inc | Difluormethylen aromatische ether und ihre verwendung als inhibitoren des glycin-typ-1- transporters |
| DE10149370A1 (de) | 2001-10-06 | 2003-04-10 | Merck Patent Gmbh | Pyrazolderivate |
| ATE447561T1 (de) | 2001-11-21 | 2009-11-15 | Pharmacia & Upjohn Co Llc | Substituierte aryl 1,4-pyrazin derivate |
| CN100457738C (zh) | 2001-12-20 | 2009-02-04 | H·隆德贝克有限公司 | 芳氧基苯基和芳硫基苯基衍生物 |
| GB0130696D0 (en) | 2001-12-21 | 2002-02-06 | Smithkline Beecham Plc | Chemical Compounds |
| WO2003068220A1 (en) | 2002-02-12 | 2003-08-21 | Akzo Nobel N.V. | 1-arylsulfonyl-3-substituted indole and indoline derivatives useful in the treatment of central nervous system disorders |
| DE10210779A1 (de) | 2002-03-12 | 2003-10-09 | Merck Patent Gmbh | Cyclische Amide |
| DE10217006A1 (de) | 2002-04-16 | 2003-11-06 | Merck Patent Gmbh | Substituierte Indole |
| FR2838739B1 (fr) | 2002-04-19 | 2004-05-28 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl)benzamide, leur preparation et leur application en therapeutique |
| ATE533743T1 (de) | 2002-05-17 | 2011-12-15 | Janssen Pharmaceutica Nv | Harnstoffderivate von aminotetralin als modulatoren des vanilloid-rezeptors vr1 |
| WO2004007468A1 (en) | 2002-07-15 | 2004-01-22 | Merck & Co., Inc. | Piperidino pyrimidine dipeptidyl peptidase inhibitors for the treatment of diabetes |
| FR2842805A1 (fr) | 2002-07-29 | 2004-01-30 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide,leur preparation et leur application et therapeutique |
| FR2842804B1 (fr) | 2002-07-29 | 2004-09-03 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique |
| US20040152741A1 (en) | 2002-09-09 | 2004-08-05 | Nps Allelix Corporation | Arylglycine derivatives and their use as glycine transport inhibitors |
| PL378117A1 (pl) * | 2003-02-11 | 2006-03-06 | Prosidion Limited | Tricyklopodstawione związki amidowe |
| US7084154B2 (en) | 2003-02-11 | 2006-08-01 | Pharmacopeia Drug Disclovery, Inc. | 2-(aminomethyl) arylamide analgesics |
| CN100372838C (zh) | 2003-02-17 | 2008-03-05 | 弗·哈夫曼-拉罗切有限公司 | 哌啶-苯磺酰胺衍生物 |
| AU2004220112A1 (en) | 2003-03-07 | 2004-09-23 | Eli Lilly And Company | 6-substituted nicotinamide derivatives as opioid receptor antagonists |
| DE10315570A1 (de) | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Triazolderivate |
| JP2006524642A (ja) | 2003-04-30 | 2006-11-02 | ハー・ルンドベック・アクチエゼルスカベット | 芳香族オキシフェニルおよび芳香族スルファニルフェニル誘導体 |
| JP2004359633A (ja) | 2003-06-06 | 2004-12-24 | Bayer Cropscience Ag | イソインドリノン誘導体の殺虫剤としての利用 |
| GB0314478D0 (en) | 2003-06-20 | 2003-07-23 | Glaxo Group Ltd | Compounds |
| GB0314476D0 (en) | 2003-06-20 | 2003-07-23 | Glaxo Group Ltd | Compounds |
| GB0314479D0 (en) | 2003-06-20 | 2003-07-23 | Glaxo Group Ltd | Compounds |
| BRPI0412809A (pt) | 2003-07-23 | 2006-09-26 | Wyeth Corp | compostos de sulfonildihidrobenzimidazolona como ligantes a 5-hidróxitriptamina-6 |
| RS53252B (sr) | 2003-08-11 | 2014-08-29 | F.Hoffmann-La Roche Ag. | Piperazin sa or-supstituisanom fenil grupom i njihova upotreba kao inhibitora glyt1 |
| DK1703909T3 (da) | 2003-09-09 | 2009-06-22 | Hoffmann La Roche | 1-benzoyl-piperazinderivater som glycinoptagelsesinhibitorer til behandling af psykoser |
| WO2005023260A1 (en) | 2003-09-09 | 2005-03-17 | F. Hoffmann-La Roche Ag | 1- (2-amino-benzol) -piperazine derivatives as glycine uptake inhibitors for the treatment of psychoses |
| CN1956949A (zh) * | 2003-09-18 | 2007-05-02 | 默克公司 | 取代的磺酰胺 |
| FR2861070B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[phenyl(pyrrolidin-2-yl)methyl]benzamide et n-[(azepan-2-yl)phenylmethyl]benzamide, leur preparation et leur application en therapeutique |
| FR2861074B1 (fr) | 2003-10-17 | 2006-04-07 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique |
| FR2861071B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[phenyl(alkylpiperidin-2-yl) methyl]benzamide, leur prepartation et leur application en therapeutique |
| FR2861076B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-heterocyclymethylbenzamide, leur preparation et leur application en therapeutique |
| FR2861073B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[heteroaryl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique |
| WO2005040166A1 (en) | 2003-10-23 | 2005-05-06 | F.Hoffmann-La Roche Ag | Triaza-spiropiperidine derivatives for use as glyt-1 inhibitors in the treatment of neurological and neuropsychiatric disorders |
| AU2004289290A1 (en) | 2003-11-12 | 2005-05-26 | Merck & Co., Inc. | 4-phenyl piperdine sulfonyl glycine transporter inhibitors |
| GB0326840D0 (en) | 2003-11-18 | 2003-12-24 | Glaxo Group Ltd | Compounds |
| GB0329362D0 (en) | 2003-12-18 | 2004-01-21 | Glaxo Group Ltd | Compounds |
| WO2005058885A2 (en) | 2003-12-18 | 2005-06-30 | Glaxo Group Limited | Piperidine derivatives and their use as glycine transporter inhibitors |
| WO2005058317A1 (en) | 2003-12-18 | 2005-06-30 | Glaxo Group Limited | Glycine transporter-1 inhibirors |
| MXPA06011328A (es) * | 2004-04-02 | 2006-12-15 | Vertex Pharma | Azaindoles utiles como inhibidotes de roca y otras proteinas cinasas. |
| PL1737850T3 (pl) | 2004-04-19 | 2008-02-29 | Symed Labs Ltd | Nowy sposób wytwarzania linezolidu i związków pokrewnych |
| DE102004030099A1 (de) | 2004-06-22 | 2006-01-12 | Grünenthal GmbH | Gesättigte und ungesättigte 3-Pyridyl-benzocycloalkylmethyl-amine als Serotonin- und/oder Noradrenalin-Reuptake-Hemmer und/oder µ-Opioidrezeptor-Modulatoren |
| DE602004020812D1 (de) | 2004-07-20 | 2009-06-04 | Symed Labs Ltd | Neue zwischenprodukte für linezolid und verwandte verbindungen |
| CN101036158A (zh) | 2004-08-31 | 2007-09-12 | 松下电器产业株式会社 | 内容购买处理终端和其方法及程序 |
| US20060074105A1 (en) | 2004-09-20 | 2006-04-06 | Serenex, Inc. | Substituted quinoline and quinazoline inhibitors of quinone reductase 2 |
| US7511013B2 (en) | 2004-09-29 | 2009-03-31 | Amr Technology, Inc. | Cyclosporin analogues and their pharmaceutical uses |
| NZ555121A (en) | 2004-10-14 | 2011-01-28 | Abbott Gmbh & Co Kg | 6-amino(aza)indane compounds suitable for treating disorders that respond to modulation of the dopamine d3 recptor |
| BRPI0519054A2 (pt) | 2004-12-15 | 2008-12-23 | Hoffmann La Roche | fenil metanonas bi e tricÍclicas substituÍdas como inibidores de transportador i de glicina (glyt-1) para o tratamento de doenÇa de alzheimer |
| DE102005000666B3 (de) | 2005-01-04 | 2006-10-05 | Sanofi-Aventis Deutschland Gmbh | Sulfonylpyrrolidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| HRP20100076T1 (hr) | 2005-02-07 | 2010-03-31 | F. Hoffmann - La Roche Ag | Heterociklički supstituirani fenil metanoni kao inhibitori glicin transportera 1 |
| AU2006228957A1 (en) | 2005-04-01 | 2006-10-05 | Methylgene Inc. | Inhibitors of histone deacetylase |
| US20090221624A1 (en) | 2005-05-06 | 2009-09-03 | Olivo Paul D | 4-aminoquinoline compounds for treating virus-related conditions |
| TW200716636A (en) | 2005-05-31 | 2007-05-01 | Speedel Experimenta Ag | Heterocyclic spiro-compounds |
| EA019115B1 (ru) | 2005-07-15 | 2014-01-30 | Олбани Молекьюлар Рисерч, Инк. | Арил- и гетероарилзамещенные тетрагидробензазепины и их применение для блокировки обратного захвата норэпинефрина, допамина и серотонина |
| US7514068B2 (en) | 2005-09-14 | 2009-04-07 | Concert Pharmaceuticals Inc. | Biphenyl-pyrazolecarboxamide compounds |
| KR20080073359A (ko) | 2005-12-01 | 2008-08-08 | 엘란 파마슈티칼스, 인크. | 5(아릴설포닐)피라졸로피페리딘 |
| US7592461B2 (en) | 2005-12-21 | 2009-09-22 | Bristol-Myers Squibb Company | Indane modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
| CA2654792A1 (en) | 2006-06-12 | 2007-12-21 | Merck Frosst Canada Ltd. | Azetidine derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| GB0619176D0 (en) | 2006-09-29 | 2006-11-08 | Lectus Therapeutics Ltd | Ion channel modulators & uses thereof |
| WO2008038841A1 (en) | 2006-09-30 | 2008-04-03 | Japan Tobacco Inc. | Thiadiazolone derivative and use thereof |
| US8796267B2 (en) | 2006-10-23 | 2014-08-05 | Concert Pharmaceuticals, Inc. | Oxazolidinone derivatives and methods of use |
| BRPI0807813A2 (pt) | 2007-02-15 | 2014-08-05 | Hoffmann La Roche | 2-amino-oxazolinas como ligantes de taar1 |
| WO2008131259A1 (en) | 2007-04-19 | 2008-10-30 | Concert Pharmaceuticals Inc. | Deuterated morpholinyl compounds |
| US7531685B2 (en) | 2007-06-01 | 2009-05-12 | Protia, Llc | Deuterium-enriched oxybutynin |
| HRP20120460T1 (hr) | 2007-06-06 | 2012-06-30 | Dsm Sinochem Pharmaceuticals Netherlands B.V. | Novi 5-supstituirani hidantoini |
| CN101784533B (zh) | 2007-08-22 | 2013-08-21 | 艾博特股份有限两合公司 | 4-苄基氨基喹啉、含有它们的药物组合物和它们在治疗中的用途 |
| WO2009035598A1 (en) | 2007-09-10 | 2009-03-19 | Concert Pharmaceuticals, Inc. | Deuterated pirfenidone |
| US20090118238A1 (en) | 2007-09-17 | 2009-05-07 | Protia, Llc | Deuterium-enriched alendronate |
| US20090082471A1 (en) | 2007-09-26 | 2009-03-26 | Protia, Llc | Deuterium-enriched fingolimod |
| US20090088416A1 (en) | 2007-09-26 | 2009-04-02 | Protia, Llc | Deuterium-enriched lapaquistat |
| EP2209774A1 (en) | 2007-10-02 | 2010-07-28 | Concert Pharmaceuticals Inc. | Pyrimidinedione derivatives |
| WO2009051782A1 (en) | 2007-10-18 | 2009-04-23 | Concert Pharmaceuticals Inc. | Deuterated etravirine |
| US20090105338A1 (en) | 2007-10-18 | 2009-04-23 | Protia, Llc | Deuterium-enriched gabexate mesylate |
| AU2008317375B2 (en) | 2007-10-26 | 2013-02-28 | Concert Pharmaceuticals, Inc. | Deuterated darunavir |
| JP2009185008A (ja) * | 2008-02-08 | 2009-08-20 | Taisho Pharmaceutical Co Ltd | グリシントランスポーター阻害活性を有する化合物 |
| JP2009185010A (ja) * | 2008-02-08 | 2009-08-20 | Taisho Pharmaceutical Co Ltd | グリシントランスポーター阻害剤を含有する医薬 |
| ES2397764T3 (es) | 2008-04-01 | 2013-03-11 | Abbott Gmbh & Co. Kg | Tetrahidroisoquinolinas, composiciones farmacéuticas que las contienen, y su uso en terapia |
| WO2010020548A1 (en) | 2008-08-20 | 2010-02-25 | F. Hoffmann-La Roche Ag | Glyt1 receptor antagonists |
| CA2735842A1 (en) | 2008-09-02 | 2010-03-11 | Sanofi-Aventis | Substituted aminoindanes and analogs thereof, and the pharmaceutical use thereof |
| DE102008047162A1 (de) | 2008-09-15 | 2010-03-25 | Institut Für Solarenergieforschung Gmbh | Rückkontaktsolarzelle mit integrierter Bypass-Diode sowie Herstellungsverfahren hierfür |
| 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 |
| TW201038569A (en) | 2009-02-16 | 2010-11-01 | Abbott Gmbh & Co Kg | Heterocyclic compounds, pharmaceutical compositions containing them, and their use in therapy |
| EP2246331A1 (en) | 2009-04-24 | 2010-11-03 | Westfälische Wilhelms-Universität Münster | NR2B-selective NMDA-receptor antagonists |
| WO2010138901A1 (en) | 2009-05-29 | 2010-12-02 | Biogen Idec Ma Inc | Carboxylic acid-containing compounds, derivatives thereof, and related methods of use |
| US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane 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 |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane 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 |
| 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 |
| US8853196B2 (en) | 2011-08-05 | 2014-10-07 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| CA2853254A1 (en) | 2011-11-18 | 2013-05-23 | 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 |
| CA2924699A1 (en) | 2013-10-17 | 2015-04-23 | AbbVie Deutschland GmbH & Co. KG | Aminotetraline and aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| 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. |
-
2011
- 2011-08-10 US US13/206,937 patent/US8877794B2/en not_active Expired - Fee Related
- 2011-08-11 TW TW100128764A patent/TW201211031A/zh unknown
- 2011-08-12 EP EP11748621.7A patent/EP2603487A1/en not_active Withdrawn
- 2011-08-12 WO PCT/EP2011/063971 patent/WO2012020130A1/en not_active Ceased
- 2011-08-12 MX MX2013001790A patent/MX2013001790A/es active IP Right Grant
- 2011-08-12 JP JP2013523638A patent/JP2013538198A/ja active Pending
- 2011-08-12 CA CA2806643A patent/CA2806643A1/en not_active Abandoned
- 2011-08-12 CN CN201180039735XA patent/CN103237788A/zh active Pending
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2014
- 2014-05-20 US US14/282,712 patent/US9238619B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2806643A1 (en) | 2012-02-16 |
| US9238619B2 (en) | 2016-01-19 |
| EP2603487A1 (en) | 2013-06-19 |
| US20120077796A1 (en) | 2012-03-29 |
| JP2013538198A (ja) | 2013-10-10 |
| US8877794B2 (en) | 2014-11-04 |
| US20140256701A1 (en) | 2014-09-11 |
| WO2012020130A1 (en) | 2012-02-16 |
| MX2013001790A (es) | 2013-10-03 |
| CN103237788A (zh) | 2013-08-07 |
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