JP5042028B2 - キノリノン−カルボキサミド化合物 - Google Patents
キノリノン−カルボキサミド化合物 Download PDFInfo
- Publication number
- JP5042028B2 JP5042028B2 JP2007539375A JP2007539375A JP5042028B2 JP 5042028 B2 JP5042028 B2 JP 5042028B2 JP 2007539375 A JP2007539375 A JP 2007539375A JP 2007539375 A JP2007539375 A JP 2007539375A JP 5042028 B2 JP5042028 B2 JP 5042028B2
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- JP
- Japan
- Prior art keywords
- alkyl
- compound
- hydrogen
- hydroxy
- formula
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims abstract description 202
- 238000000034 method Methods 0.000 claims abstract description 77
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 32
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 31
- 230000000694 effects Effects 0.000 claims abstract description 23
- 230000008569 process Effects 0.000 claims abstract description 11
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 132
- 125000000217 alkyl group Chemical group 0.000 claims description 120
- -1 1,1-dioxo isothiazolidinyl Chemical group 0.000 claims description 101
- 229910052739 hydrogen Inorganic materials 0.000 claims description 100
- 239000001257 hydrogen Substances 0.000 claims description 96
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 50
- 150000002431 hydrogen Chemical class 0.000 claims description 46
- 102000005962 receptors Human genes 0.000 claims description 44
- 108020003175 receptors Proteins 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 42
- UUCJNYSXZJNSLE-UHFFFAOYSA-N 2-oxo-1-propan-2-ylquinoline-3-carboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(=O)N(C(C)C)C2=C1 UUCJNYSXZJNSLE-UHFFFAOYSA-N 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 27
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 27
- 125000005466 alkylenyl group Chemical group 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 20
- 241000124008 Mammalia Species 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
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- 239000003937 drug carrier Substances 0.000 claims description 10
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 10
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 8
- 230000001684 chronic effect Effects 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 201000006549 dyspepsia Diseases 0.000 claims description 8
- 230000002496 gastric effect Effects 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 208000007542 Paresis Diseases 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 claims description 6
- 206010052105 Gastrointestinal hypomotility Diseases 0.000 claims description 5
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 206010021518 Impaired gastric emptying Diseases 0.000 claims description 3
- 208000003243 intestinal obstruction Diseases 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 230000002980 postoperative effect Effects 0.000 claims description 3
- 201000005081 Intestinal Pseudo-Obstruction Diseases 0.000 claims description 2
- 206010033799 Paralysis Diseases 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- DIZXBSHARPXAAZ-UHFFFAOYSA-N aminomethyl carbamate Chemical compound NCOC(N)=O DIZXBSHARPXAAZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 19
- 125000001475 halogen functional group Chemical group 0.000 claims 9
- 239000000543 intermediate Substances 0.000 abstract description 68
- 239000000018 receptor agonist Substances 0.000 abstract description 16
- 229940044601 receptor agonist Drugs 0.000 abstract description 16
- 201000010099 disease Diseases 0.000 abstract description 12
- 108091005482 5-HT4 receptors Proteins 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
- 238000006243 chemical reaction Methods 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 210000004027 cell Anatomy 0.000 description 51
- 239000000243 solution Substances 0.000 description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 35
- 239000011541 reaction mixture Substances 0.000 description 35
- 239000007787 solid Substances 0.000 description 34
- 238000003556 assay Methods 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 26
- 238000012360 testing method Methods 0.000 description 24
- 238000004128 high performance liquid chromatography Methods 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 230000014759 maintenance of location Effects 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 16
- 239000002585 base Substances 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- 125000005843 halogen group Chemical group 0.000 description 15
- 239000012528 membrane Substances 0.000 description 15
- 239000002775 capsule Substances 0.000 description 14
- 125000006239 protecting group Chemical group 0.000 description 14
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 13
- 239000003826 tablet Substances 0.000 description 13
- 229960000583 acetic acid Drugs 0.000 description 12
- 238000009739 binding Methods 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- 239000007995 HEPES buffer Substances 0.000 description 11
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 230000027455 binding Effects 0.000 description 10
- 239000004615 ingredient Substances 0.000 description 10
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- 238000003653 radioligand binding assay Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- 239000003701 inert diluent Substances 0.000 description 9
- 238000002953 preparative HPLC Methods 0.000 description 9
- 208000035475 disorder Diseases 0.000 description 8
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- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 7
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- CCNJXCAILFDYJZ-UHFFFAOYSA-N CNS(=O)=O.C1CNCCN1 Chemical compound CNS(=O)=O.C1CNCCN1 CCNJXCAILFDYJZ-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 6
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
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- 239000013543 active substance Substances 0.000 description 6
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
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- 229940098773 bovine serum albumin Drugs 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
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- 150000003335 secondary amines Chemical class 0.000 description 6
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- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 6
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 6
- FHPZUVVXVRYZAS-SFYZADRCSA-N (1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-5-amine Chemical compound C1CC[C@@]2(N)CC[C@]1([H])N2C FHPZUVVXVRYZAS-SFYZADRCSA-N 0.000 description 5
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 5
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- MOZPSIXKYJUTKI-RLXJOQACSA-N [1-[2-(methanesulfonamido)ethyl]piperidin-4-yl]methyl 1-(tritritiomethyl)indole-3-carboxylate Chemical compound C12=CC=CC=C2N(C([3H])([3H])[3H])C=C1C(=O)OCC1CCN(CCNS(C)(=O)=O)CC1 MOZPSIXKYJUTKI-RLXJOQACSA-N 0.000 description 5
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- 239000003446 ligand Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
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- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OVRJVKCZJCNSOW-UHFFFAOYSA-N thian-4-one Chemical compound O=C1CCSCC1 OVRJVKCZJCNSOW-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- XOFLBQFBSOEHOG-UUOKFMHZSA-N γS-GTP Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=S)[C@@H](O)[C@H]1O XOFLBQFBSOEHOG-UUOKFMHZSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62523304P | 2004-11-05 | 2004-11-05 | |
| US60/625,233 | 2004-11-05 | ||
| PCT/US2005/040292 WO2006052889A2 (en) | 2004-11-05 | 2005-11-04 | Quinolinone-carboxamide compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008518975A JP2008518975A (ja) | 2008-06-05 |
| JP2008518975A5 JP2008518975A5 (cg-RX-API-DMAC10.html) | 2008-12-04 |
| JP5042028B2 true JP5042028B2 (ja) | 2012-10-03 |
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| JP2007539375A Expired - Fee Related JP5042028B2 (ja) | 2004-11-05 | 2005-11-04 | キノリノン−カルボキサミド化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7396933B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP1807423B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP5042028B2 (cg-RX-API-DMAC10.html) |
| AT (1) | ATE431824T1 (cg-RX-API-DMAC10.html) |
| DE (1) | DE602005014566D1 (cg-RX-API-DMAC10.html) |
| ES (1) | ES2327142T3 (cg-RX-API-DMAC10.html) |
| WO (1) | WO2006052889A2 (cg-RX-API-DMAC10.html) |
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| TWI351282B (en) | 2004-04-07 | 2011-11-01 | Theravance Inc | Quinolinone-carboxamide compounds as 5-ht4 recepto |
| US8309575B2 (en) | 2004-04-07 | 2012-11-13 | Theravance, Inc. | Quinolinone-carboxamide compounds as 5-HT4 receptor agonists |
| DE602005014566D1 (de) * | 2004-11-05 | 2009-07-02 | Theravance Inc | Chinolinon-carboxamid-verbindungen |
| DE602005016446D1 (de) * | 2004-11-05 | 2009-10-15 | Theravance Inc | 5-HT4-Rezeptoragonistenverbindungen |
| ATE469897T1 (de) * | 2004-12-22 | 2010-06-15 | Theravance Inc | Indazolcarbonsäureamidverbindungen |
| BRPI0608392A2 (pt) * | 2005-03-02 | 2009-12-29 | Theravance Inc | compostos de quinolinona como agonistas do receptor 5-ht4 |
| TWI377206B (en) * | 2005-04-06 | 2012-11-21 | Theravance Inc | Crystalline form of a quinolinone-carboxamide compound |
| US7317022B2 (en) * | 2005-06-07 | 2008-01-08 | Theravance, Inc. | Benzoimidazolone-carboxamide compounds as 5-HT4 receptors agonists |
| MY143574A (en) * | 2005-11-22 | 2011-05-31 | Theravance Inc | Carbamate compounds as 5-ht4 receptor agonists |
| GB0525068D0 (en) | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
| US7671198B2 (en) * | 2006-02-16 | 2010-03-02 | Theravance, Inc. | Process for preparing intermediates to 5-HT4 receptor agonist compounds |
| FR2911874B1 (fr) * | 2007-01-25 | 2009-03-06 | Sanofi Aventis Sa | Derives d'urees de tropane, leur preparation et leur application en therapeutique |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| CN102762572A (zh) | 2010-02-01 | 2012-10-31 | 诺瓦提斯公司 | 作为CRF-1受体拮抗剂的吡唑并[5,1b]*唑衍生物 |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| EP2531490B1 (en) | 2010-02-02 | 2014-10-15 | Novartis AG | Cyclohexyl amide derivatives as crf receptor antagonists |
| UY34094A (es) | 2011-05-27 | 2013-01-03 | Novartis Ag | Derivados de la piperidina 3-espirocíclica como agonistas de receptores de la ghrelina |
| WO2013164790A1 (en) | 2012-05-03 | 2013-11-07 | Novartis Ag | L-malate salt of 2, 7 - diaza - spiro [4.5 ] dec- 7 - yle derivatives and crystalline forms thereof as ghrelin receptor agonists |
| CN104491640A (zh) * | 2014-12-26 | 2015-04-08 | 广东聚智诚科技有限公司 | 一种治疗功能性消化不良的药物组合物 |
| CA3245086A1 (en) | 2022-01-11 | 2023-07-20 | Suven Life Sciences Limited | PYRROLO[1,2-B]-2-PYRIDAZINONE COMPOUNDS AS 5-HT4 RECEPTOR AGONISTS |
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-
2005
- 2005-11-04 DE DE602005014566T patent/DE602005014566D1/de not_active Expired - Lifetime
- 2005-11-04 EP EP05824243A patent/EP1807423B1/en not_active Expired - Lifetime
- 2005-11-04 JP JP2007539375A patent/JP5042028B2/ja not_active Expired - Fee Related
- 2005-11-04 US US11/267,720 patent/US7396933B2/en not_active Expired - Lifetime
- 2005-11-04 WO PCT/US2005/040292 patent/WO2006052889A2/en not_active Ceased
- 2005-11-04 ES ES05824243T patent/ES2327142T3/es not_active Expired - Lifetime
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2008
- 2008-03-13 US US12/075,740 patent/US7498442B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1807423A2 (en) | 2007-07-18 |
| US7396933B2 (en) | 2008-07-08 |
| US20080167295A1 (en) | 2008-07-10 |
| JP2008518975A (ja) | 2008-06-05 |
| US7498442B2 (en) | 2009-03-03 |
| EP1807423B1 (en) | 2009-05-20 |
| WO2006052889A3 (en) | 2006-06-29 |
| ATE431824T1 (de) | 2009-06-15 |
| ES2327142T3 (es) | 2009-10-26 |
| DE602005014566D1 (de) | 2009-07-02 |
| WO2006052889A2 (en) | 2006-05-18 |
| US20060100426A1 (en) | 2006-05-11 |
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