ES2326638T3 - Compuestos heterociclicos. - Google Patents
Compuestos heterociclicos. Download PDFInfo
- Publication number
- ES2326638T3 ES2326638T3 ES03721209T ES03721209T ES2326638T3 ES 2326638 T3 ES2326638 T3 ES 2326638T3 ES 03721209 T ES03721209 T ES 03721209T ES 03721209 T ES03721209 T ES 03721209T ES 2326638 T3 ES2326638 T3 ES 2326638T3
- Authority
- ES
- Spain
- Prior art keywords
- pyridine
- furo
- azabicyclo
- octane
- spiro
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 110
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
- 208000035475 disorder Diseases 0.000 claims description 26
- 238000011282 treatment Methods 0.000 claims description 26
- 230000006735 deficit Effects 0.000 claims description 20
- 238000011321 prophylaxis Methods 0.000 claims description 20
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 19
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229960002715 nicotine Drugs 0.000 claims description 11
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 10
- 208000016620 Tourette disease Diseases 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 208000028017 Psychotic disease Diseases 0.000 claims description 9
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 8
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229910052722 tritium Inorganic materials 0.000 claims description 8
- 208000019901 Anxiety disease Diseases 0.000 claims description 7
- 206010026749 Mania Diseases 0.000 claims description 7
- 208000002193 Pain Diseases 0.000 claims description 7
- 230000036506 anxiety Effects 0.000 claims description 7
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 7
- 201000000980 schizophrenia Diseases 0.000 claims description 7
- 208000000044 Amnesia Diseases 0.000 claims description 6
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- 125000004429 atom Chemical group 0.000 claims description 6
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- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 5
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
- 230000007278 cognition impairment Effects 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- UTNQUMOIHZDNPR-FQEVSTJZSA-N (3r)-5'-(1,3-benzothiazol-2-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C1=CC=C2SC(C=3C=C4C[C@]5(C6CCN(CC6)C5)OC4=NC=3)=NC2=C1 UTNQUMOIHZDNPR-FQEVSTJZSA-N 0.000 claims description 4
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- 206010057852 Nicotine dependence Diseases 0.000 claims description 4
- 208000025569 Tobacco Use disease Diseases 0.000 claims description 4
- 230000008484 agonism Effects 0.000 claims description 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
- 208000028683 bipolar I disease Diseases 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 230000006984 memory degeneration Effects 0.000 claims description 4
- 208000023060 memory loss Diseases 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- OPNPJEFFAANXTO-KRWDZBQOSA-N (3r)-5'-(2-methyl-1,3-thiazol-4-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound S1C(C)=NC(C=2C=C3C[C@@]4(OC3=NC=2)C2CCN(CC2)C4)=C1 OPNPJEFFAANXTO-KRWDZBQOSA-N 0.000 claims description 3
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims description 3
- 229960004373 acetylcholine Drugs 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 2
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 230000008485 antagonism Effects 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 231100000863 loss of memory Toxicity 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- 208000012287 Prolapse Diseases 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 230000019771 cognition Effects 0.000 claims 1
- 208000013403 hyperactivity Diseases 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 18
- 238000002560 therapeutic procedure Methods 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 description 34
- 238000000034 method Methods 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
- -1 trimethylstannyl Chemical group 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 201000010099 disease Diseases 0.000 description 10
- 125000002524 organometallic group Chemical group 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 229930182840 (S)-nicotine Natural products 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 101000783401 Bungarus multicinctus Alpha-bungarotoxin Proteins 0.000 description 3
- 229920002873 Polyethylenimine Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 229940098773 bovine serum albumin Drugs 0.000 description 3
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- 125000000524 functional group Chemical group 0.000 description 3
- 210000001320 hippocampus Anatomy 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000000626 neurodegenerative effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- WLQGXFSBIGJXDA-UHFFFAOYSA-N (4-bromo-1,3-thiazol-2-yl)-trimethylsilane Chemical compound C[Si](C)(C)C1=NC(Br)=CS1 WLQGXFSBIGJXDA-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MKEJZKKVVUZXIS-UHFFFAOYSA-N 2,4-dibromo-1,3-thiazole Chemical compound BrC1=CSC(Br)=N1 MKEJZKKVVUZXIS-UHFFFAOYSA-N 0.000 description 2
- LYRXILTUZBBMNS-UHFFFAOYSA-N 4-bromo-2-methyl-1,3-thiazole Chemical compound CC1=NC(Br)=CS1 LYRXILTUZBBMNS-UHFFFAOYSA-N 0.000 description 2
- 101710195183 Alpha-bungarotoxin Proteins 0.000 description 2
- 101100149678 Caenorhabditis elegans snr-3 gene Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 2
- 230000009471 action Effects 0.000 description 2
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- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
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- 239000003365 glass fiber Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
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- 239000000543 intermediate Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
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- XLTANAWLDBYGFU-UHFFFAOYSA-N methyllycaconitine hydrochloride Natural products C1CC(OC)C2(C3C4OC)C5CC(C(C6)OC)C(OC)C5C6(O)C4(O)C2N(CC)CC31COC(=O)C1=CC=CC=C1N1C(=O)CC(C)C1=O XLTANAWLDBYGFU-UHFFFAOYSA-N 0.000 description 2
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- YYQKQPYPLADFMK-UHFFFAOYSA-N tributyl(1,3-thiazol-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CSC=N1 YYQKQPYPLADFMK-UHFFFAOYSA-N 0.000 description 2
- GOWNSHUNTJWVOM-UHFFFAOYSA-N tributyl(1,3-thiazol-5-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CN=CS1 GOWNSHUNTJWVOM-UHFFFAOYSA-N 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
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- DIIFZCPZIRQDIJ-UHFFFAOYSA-N (3,5-dimethyl-1,2-oxazol-4-yl)boronic acid Chemical compound CC1=NOC(C)=C1B(O)O DIIFZCPZIRQDIJ-UHFFFAOYSA-N 0.000 description 1
- BIXRSCVOWFUPML-UHFFFAOYSA-N 1,3-benzothiazol-2-yl(tributyl)stannane Chemical compound C1=CC=C2SC([Sn](CCCC)(CCCC)CCCC)=NC2=C1 BIXRSCVOWFUPML-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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Landscapes
- Health & Medical Sciences (AREA)
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- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Addiction (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0201185A SE0201185D0 (sv) | 2002-04-18 | 2002-04-18 | Heterocyclic compounds |
| SE2002101185 | 2002-04-18 | ||
| SE2002103606 | 2002-12-04 | ||
| SE0203606A SE0203606D0 (sv) | 2002-12-04 | 2002-12-04 | Heterocyclic compounds |
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| ES2326638T3 true ES2326638T3 (es) | 2009-10-16 |
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| ES03721209T Expired - Lifetime ES2326638T3 (es) | 2002-04-18 | 2003-04-15 | Compuestos heterociclicos. |
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| AR036040A1 (es) | 2001-06-12 | 2004-08-04 | Upjohn Co | Compuestos de heteroarilo multiciclicos sustituidos con quinuclidinas y composiciones farmaceuticas que los contienen |
| KR100614900B1 (ko) | 2001-10-02 | 2006-08-25 | 파마시아 앤드 업존 캄파니 엘엘씨 | 질병의 치료를 위한 아자비시클릭-치환된 융합-헤테로아릴화합물 |
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| US8785403B2 (en) | 2003-08-01 | 2014-07-22 | Mitsubishi Tanabe Pharma Corporation | Glucopyranoside compound |
| ES2649737T5 (es) | 2003-08-01 | 2021-07-07 | Mitsubishi Tanabe Pharma Corp | Compuestos novedosos que tienen actividad inhibidora frente a transportador de glucosa dependiente de sodio |
| CN1856497A (zh) * | 2003-09-25 | 2006-11-01 | 阿斯利康(瑞典)有限公司 | 配体 |
| KR20060094962A (ko) * | 2003-10-21 | 2006-08-30 | 아스트라제네카 아베 | 스피로푸로피리딘 아릴 유도체 |
| US7045530B2 (en) | 2003-12-22 | 2006-05-16 | Abbott Laboratories | Spirocyclic quinuclidinic ether derivatives |
| TW200813067A (en) | 2006-05-17 | 2008-03-16 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| UY30730A1 (es) | 2006-12-04 | 2008-07-03 | Mitsubishi Tanabe Pharma Corp | Forma cristalina del hemihidrato de 1-(b (beta)-d-glucopiranosil) -4-metil-3-[5-(4-fluorofenil) -2-tienilmetil]benceno |
| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| CA2699285C (en) | 2007-09-10 | 2016-12-13 | Ahmed F. Abdel-Magid | Process for the preparation of compounds useful as inhibitors of sodium-dependent glucose transporter (sglt) |
| CL2008003653A1 (es) | 2008-01-17 | 2010-03-05 | Mitsubishi Tanabe Pharma Corp | Uso de un inhibidor de sglt derivado de glucopiranosilo y un inhibidor de dppiv seleccionado para tratar la diabetes; y composicion farmaceutica. |
| ES2325049B2 (es) * | 2008-02-21 | 2010-03-16 | Universidade De Santiago De Compostela | Deteccion y cuantificacion de iminas ciclicas basada en la union competitiva a receptores nicotinicos de acetilcolina. |
| RS52703B (sr) | 2008-06-20 | 2013-08-30 | Astrazeneca Ab | Derivat dibenzotiazepina i njegova upotreba |
| US9056850B2 (en) | 2008-10-17 | 2015-06-16 | Janssen Pharmaceutica N.V. | Process for the preparation of compounds useful as inhibitors of SGLT |
| TW201031664A (en) | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| US20110009347A1 (en) | 2009-07-08 | 2011-01-13 | Yin Liang | Combination therapy for the treatment of diabetes |
| IN2012DN03299A (enExample) | 2009-10-14 | 2015-10-23 | Janssen Pharmaceutica Nv | |
| SG185525A1 (en) | 2010-05-11 | 2012-12-28 | Janssen Pharmaceutica Nv | Pharmaceutical formulations comprising 1 - (beta-d-glucopyranosyl) - 2 -thienylmethylbenzene derivatives as inhibitors of sglt |
| PT3029039T (pt) | 2010-05-17 | 2017-11-28 | Forum Pharmaceuticals Inc | Formulações farmacêuticas que compreendem formas cristalinas de cloridrato de (r)-7-cloro-n-(quinuclidin-3-il)benzo(b)tiofeno-2-carboxamida mono-hidratado |
| AU2012241897C1 (en) | 2011-04-13 | 2017-05-11 | Janssen Pharmaceutica Nv | Process for the preparation of compounds useful as inhibitors of SGLT2 |
| US9035044B2 (en) | 2011-05-09 | 2015-05-19 | Janssen Pharmaceutica Nv | L-proline and citric acid co-crystals of (2S, 3R, 4R, 5S,6R)-2-(3-((5-(4-fluorophenyl)thiopen-2-yl)methyl)4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol |
| GB201111704D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Novel compounds |
| GB201111705D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Compounds and their use |
| JO3115B1 (ar) | 2011-08-22 | 2017-09-20 | Takeda Pharmaceuticals Co | مركبات بيريدازينون واستخدامها كمثبطات daao |
| EP2846796A4 (en) | 2012-05-08 | 2015-10-21 | Forum Pharmaceuticals Inc | METHODS OF MAINTAINING, PROCESSING OR ENHANCING COGNITIVE FUNCTION |
| GB201209587D0 (en) | 2012-05-30 | 2012-07-11 | Takeda Pharmaceutical | Therapeutic compounds |
| JP6478923B2 (ja) | 2013-02-07 | 2019-03-06 | ヘプタレス セラピューティクス リミテッドＨｅｐｔａｒｅｓ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | ムスカリンｍ４受容体アゴニストとしてのピペリジン−１−イル及びアゼピン−１−イルカルボキシレート |
| EA029430B1 (ru) | 2013-06-21 | 2018-03-30 | Такеда Фармасьютикл Компани Лимитед | Производные 1-сульфонилпиперидина в качестве модуляторов рецепторов прокинетицина |
| GB201314286D0 (en) | 2013-08-08 | 2013-09-25 | Takeda Pharmaceutical | Therapeutic Compounds |
| GB201318222D0 (en) | 2013-10-15 | 2013-11-27 | Takeda Pharmaceutical | Novel compounds |
| GB201320905D0 (en) | 2013-11-27 | 2014-01-08 | Takeda Pharmaceutical | Therapeutic compounds |
| TW201613864A (en) | 2014-02-20 | 2016-04-16 | Takeda Pharmaceutical | Novel compounds |
| US20170071970A1 (en) | 2015-09-15 | 2017-03-16 | Janssen Pharmaceutica Nv | Co-therapy comprising canagliflozin and phentermine for the treatment of obesity and obesity related disorders |
| GB201616839D0 (en) | 2016-10-04 | 2016-11-16 | Takeda Pharmaceutical Company Limited | Therapeutic compounds |
| GB201619514D0 (en) | 2016-11-18 | 2017-01-04 | Takeda Pharmaceuticals Co | Novel compounds |
| JP2021138648A (ja) | 2020-03-04 | 2021-09-16 | 武田薬品工業株式会社 | 経口固形製剤 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR013184A1 (es) * | 1997-07-18 | 2000-12-13 | Astrazeneca Ab | Aminas heterociclicas espiroazobiciclicas, composicion farmaceutica, uso de dichas aminas para preparar medicamentos y metodo de tratamiento o profilaxis |
| SE9900100D0 (sv) * | 1999-01-15 | 1999-01-15 | Astra Ab | New compounds |
| FR2788982B1 (fr) | 1999-02-02 | 2002-08-02 | Synthelabo | Compositions pharmaceutiques contenant de la nicotine et leur application dans le sevrage tabagique |
| US6569865B2 (en) | 2001-06-01 | 2003-05-27 | Astrazeneca Ab | Spiro 1-azabicyclo[2.2.2]octane-3,2′(3′h)-furo[2,3-b]pyridine |
| CN1294136C (zh) | 2001-06-01 | 2007-01-10 | 阿斯特拉曾尼卡有限公司 | 用于治疗的烟碱乙酰胆碱受体新型配体 |
-
2003
- 2003-04-15 MX MXPA04010190A patent/MXPA04010190A/es active IP Right Grant
- 2003-04-15 BR BR0309345-0A patent/BR0309345A/pt not_active IP Right Cessation
- 2003-04-15 CA CA002482313A patent/CA2482313A1/en not_active Abandoned
- 2003-04-15 DE DE60328010T patent/DE60328010D1/de not_active Expired - Lifetime
- 2003-04-15 JP JP2003584060A patent/JP4523775B2/ja not_active Expired - Fee Related
- 2003-04-15 EP EP03721209A patent/EP1499616B1/en not_active Expired - Lifetime
- 2003-04-15 US US10/511,525 patent/US7417050B2/en not_active Expired - Fee Related
- 2003-04-15 AT AT03721209T patent/ATE433981T1/de not_active IP Right Cessation
- 2003-04-15 ES ES03721209T patent/ES2326638T3/es not_active Expired - Lifetime
- 2003-04-15 NZ NZ561993A patent/NZ561993A/en unknown
- 2003-04-15 CN CNB038139014A patent/CN1325501C/zh not_active Expired - Fee Related
- 2003-04-15 WO PCT/SE2003/000615 patent/WO2003087104A1/en not_active Ceased
- 2003-04-15 AU AU2003224546A patent/AU2003224546B2/en not_active Ceased
- 2003-04-15 KR KR10-2004-7016545A patent/KR20040099446A/ko not_active Ceased
- 2003-04-15 HK HK06100288.5A patent/HK1080470B/zh not_active IP Right Cessation
-
2004
- 2004-10-11 IL IL16451104A patent/IL164511A0/xx unknown
- 2004-11-17 NO NO20044995A patent/NO20044995L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1499616A1 (en) | 2005-01-26 |
| HK1080470A1 (zh) | 2006-04-28 |
| IL164511A0 (en) | 2005-12-18 |
| US7417050B2 (en) | 2008-08-26 |
| KR20040099446A (ko) | 2004-11-26 |
| NZ561993A (en) | 2008-09-26 |
| JP2005534624A (ja) | 2005-11-17 |
| WO2003087104A1 (en) | 2003-10-23 |
| CN1325501C (zh) | 2007-07-11 |
| CN1662542A (zh) | 2005-08-31 |
| CA2482313A1 (en) | 2003-10-23 |
| JP4523775B2 (ja) | 2010-08-11 |
| EP1499616B1 (en) | 2009-06-17 |
| AU2003224546B2 (en) | 2008-11-06 |
| NO20044995L (no) | 2005-01-18 |
| BR0309345A (pt) | 2005-02-15 |
| HK1080470B (zh) | 2008-03-07 |
| MXPA04010190A (es) | 2005-02-03 |
| DE60328010D1 (de) | 2009-07-30 |
| ATE433981T1 (de) | 2009-07-15 |
| AU2003224546A1 (en) | 2003-10-27 |
| US20050131003A1 (en) | 2005-06-16 |
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