AU2005238388B2 - Fused quinoline derivative and use thereof - Google Patents
Fused quinoline derivative and use thereof Download PDFInfo
- Publication number
- AU2005238388B2 AU2005238388B2 AU2005238388A AU2005238388A AU2005238388B2 AU 2005238388 B2 AU2005238388 B2 AU 2005238388B2 AU 2005238388 A AU2005238388 A AU 2005238388A AU 2005238388 A AU2005238388 A AU 2005238388A AU 2005238388 B2 AU2005238388 B2 AU 2005238388B2
- Authority
- AU
- Australia
- Prior art keywords
- optionally
- carbonyl
- alkyl
- substituent
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 371
- 150000001875 compounds Chemical class 0.000 claims abstract description 370
- 150000002367 halogens Chemical class 0.000 claims abstract description 125
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 113
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 96
- 150000003839 salts Chemical class 0.000 claims abstract description 72
- 230000003042 antagnostic effect Effects 0.000 claims abstract description 10
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- -1 carbamoylcarbonylamino Chemical group 0.000 claims description 371
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 221
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 203
- 125000000217 alkyl group Chemical group 0.000 claims description 143
- 125000000623 heterocyclic group Chemical group 0.000 claims description 102
- 125000003545 alkoxy group Chemical group 0.000 claims description 82
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 80
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 77
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 44
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 43
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 239000004202 carbamide Substances 0.000 claims description 41
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 36
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 35
- 239000003795 chemical substances by application Substances 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 26
- 125000003282 alkyl amino group Chemical group 0.000 claims description 25
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 18
- 150000002430 hydrocarbons Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000006239 protecting group Chemical group 0.000 claims description 18
- 108010040722 Neurokinin-2 Receptors Proteins 0.000 claims description 17
- 102100037342 Substance-K receptor Human genes 0.000 claims description 17
- 229940002612 prodrug Drugs 0.000 claims description 17
- 239000000651 prodrug Substances 0.000 claims description 17
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 14
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 14
- 239000008177 pharmaceutical agent Substances 0.000 claims description 14
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 13
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 13
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 12
- 238000011321 prophylaxis Methods 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229940044551 receptor antagonist Drugs 0.000 claims description 10
- 239000002464 receptor antagonist Substances 0.000 claims description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 9
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 8
- 208000014540 Functional gastrointestinal disease Diseases 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000005281 alkyl ureido group Chemical group 0.000 claims description 7
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 7
- 125000005544 phthalimido group Chemical group 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 6
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims description 6
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
- 201000006549 dyspepsia Diseases 0.000 claims description 6
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000005091 alkenylcarbonylamino group Chemical group 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 4
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- ZLHOMSKRRPRXOD-WXGGYGAESA-N n-[(1r,2s)-2-[(3ar,4r,9br)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydropyrrolo[3,2-c]quinoline-1-carbonyl]cyclohexyl]-4-(1h-imidazol-2-yl)benzamide Chemical compound N([C@@H]1CCCC[C@@H]1C(=O)N1CC[C@H]2[C@@H]1C1=CC=CC=C1N[C@H]2COC)C(=O)C(C=C1)=CC=C1C1=NC=CN1 ZLHOMSKRRPRXOD-WXGGYGAESA-N 0.000 claims description 2
- 229940044601 receptor agonist Drugs 0.000 claims description 2
- 239000000018 receptor agonist Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 1
- KOFHYLXEWKAQSR-RMNHWBOMSA-N n-[(1r,2s)-2-[(3ar,4r,9br)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydropyrrolo[3,2-c]quinoline-1-carbonyl]cyclohexyl]-4-(trifluoromethyl)benzamide Chemical compound N([C@@H]1CCCC[C@@H]1C(=O)N1CC[C@H]2[C@@H]1C1=CC=CC=C1N[C@H]2COC)C(=O)C1=CC=C(C(F)(F)F)C=C1 KOFHYLXEWKAQSR-RMNHWBOMSA-N 0.000 claims 1
- 102100024304 Protachykinin-1 Human genes 0.000 abstract description 6
- 101000831616 Homo sapiens Protachykinin-1 Proteins 0.000 abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 279
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 270
- 239000000203 mixture Substances 0.000 description 219
- 230000002829 reductive effect Effects 0.000 description 123
- 239000000243 solution Substances 0.000 description 114
- 239000002904 solvent Substances 0.000 description 103
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 90
- 239000011541 reaction mixture Substances 0.000 description 86
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- 238000005160 1H NMR spectroscopy Methods 0.000 description 56
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 54
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 49
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
- 239000000741 silica gel Substances 0.000 description 47
- 229910002027 silica gel Inorganic materials 0.000 description 47
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 44
- 238000004440 column chromatography Methods 0.000 description 43
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 38
- 239000003814 drug Substances 0.000 description 36
- 238000001816 cooling Methods 0.000 description 34
- 229940079593 drug Drugs 0.000 description 32
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 29
- 229920006395 saturated elastomer Polymers 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 27
- 235000017557 sodium bicarbonate Nutrition 0.000 description 27
- 238000010898 silica gel chromatography Methods 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000011734 sodium Substances 0.000 description 23
- 239000000460 chlorine Substances 0.000 description 22
- 239000007787 solid Substances 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 19
- 239000013078 crystal Substances 0.000 description 19
- 239000003921 oil Substances 0.000 description 18
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 239000012230 colorless oil Substances 0.000 description 16
- 229910052740 iodine Inorganic materials 0.000 description 16
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- 239000011630 iodine Substances 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 14
- 229910052794 bromium Inorganic materials 0.000 description 14
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
- 229910052801 chlorine Inorganic materials 0.000 description 14
- 239000011737 fluorine Substances 0.000 description 14
- 229910052731 fluorine Inorganic materials 0.000 description 14
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- 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 description 13
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 13
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 11
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- 230000037396 body weight Effects 0.000 description 10
- 238000005886 esterification reaction Methods 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 10
- 239000012312 sodium hydride Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 8
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 7
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 7
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 7
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 7
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 7
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 7
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 7
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 7
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 6
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 125000006251 butylcarbonyl group Chemical group 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
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 5
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| DE102007013856A1 (de) | 2007-03-20 | 2008-09-25 | Merck Patent Gmbh | Substituierte Tetrahydropyrrolochinoline |
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| US8680282B2 (en) | 2007-08-01 | 2014-03-25 | University Health Network | Cyclic inhibitors of carnitine palmitoyltransferase and treating cancer |
| PE20091093A1 (es) | 2007-12-03 | 2009-08-25 | Takeda Pharmaceutical | Compuesto heterociclico que contiene nitrogeno y su uso |
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| AR075158A1 (es) | 2009-01-27 | 2011-03-16 | Takeda Pharmaceutical | Derivados de pirrolopirimidinas, composiciones farmaceuticas y usos. |
| JP2013053070A (ja) * | 2009-11-06 | 2013-03-21 | Takeda Chem Ind Ltd | ジヒドロピロロキノリン誘導体 |
| EP2521545B1 (en) | 2010-01-07 | 2019-11-27 | Alkermes Pharma Ireland Limited | Prodrugs of heteroaromatic compounds |
| FR2974729B1 (fr) * | 2011-05-02 | 2013-04-19 | Servier Lab | Nouvelle association entre le 4-{3-[cis-hexahydrocyclopenta[c]pyrrol-2(1h)-yl]propoxy}benzamide et un inhibiteur de l'acetylcholinesterase et les compositions pharmaceutiques qui la contiennent |
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| SG11201806416XA (en) | 2016-02-12 | 2018-08-30 | Astellas Pharma Inc | Tetrahydroisoquinoline derivatives |
| US11787795B2 (en) | 2016-11-01 | 2023-10-17 | President And Fellows Of Harvard College | Inhibitors of RNA guided nucleases and uses thereof |
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| US11739102B2 (en) | 2020-05-13 | 2023-08-29 | Incyte Corporation | Fused pyrimidine compounds as KRAS inhibitors |
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| WO2022072783A1 (en) | 2020-10-02 | 2022-04-07 | Incyte Corporation | Bicyclic dione compounds as inhibitors of kras |
| WO2022204112A1 (en) | 2021-03-22 | 2022-09-29 | Incyte Corporation | Imidazole and triazole kras inhibitors |
| WO2023283213A1 (en) | 2021-07-07 | 2023-01-12 | Incyte Corporation | Tricyclic compounds as inhibitors of kras |
| US11738021B2 (en) * | 2021-08-23 | 2023-08-29 | Ckp Therapeutics, Inc. | Composition and method for preventing, alleviating or treating cancer |
| US12441742B2 (en) | 2021-08-31 | 2025-10-14 | Incyte Corporation | Naphthyridine compounds as inhibitors of KRAS |
| US12030883B2 (en) | 2021-09-21 | 2024-07-09 | Incyte Corporation | Hetero-tricyclic compounds as inhibitors of KRAS |
| JP2024537824A (ja) | 2021-10-01 | 2024-10-16 | インサイト・コーポレイション | ピラゾロキノリンｋｒａｓ阻害剤 |
| MX2024004444A (es) | 2021-10-14 | 2024-05-08 | Incyte Corp | Compuestos de quinolina como inhibidores de la proteina del virus de sarcoma de rata kirsten (kras). |
| CN114524811B (zh) * | 2022-03-16 | 2025-01-24 | 中国人民解放军军事科学院军事医学研究院 | Lxh0307、lxh0308作为基因编辑的小分子抑制剂及其应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2145606C1 (ru) * | 1994-05-24 | 2000-02-20 | Ф.Хоффманн-Ля Рош Аг | Трициклические дикарбонильные производные и лекарственный препарат на их основе |
| IT1283171B1 (it) | 1996-03-01 | 1998-04-16 | Interdipartimentale Di Ricerca | Composti solubili antagonisti delle tachichinine loro preparazione e loro uso in composizioni farmaceutiche |
| GB0027701D0 (en) | 2000-11-13 | 2000-12-27 | Smithkline Beecham Spa | Novel compounds |
| ES2254688T3 (es) | 2001-04-11 | 2006-06-16 | Glaxosmithkline S.P.A. | Derivados de quinolina-4-carboxamida como antagonistas de los receptores nk-3 y nk-2. |
| JP2004134705A (ja) | 2002-10-15 | 2004-04-30 | Jiaotong Univ | 金属酸化膜半導体電界効果トランジスタおよびそのゲート構造 |
| EP1740584B9 (en) * | 2004-04-28 | 2010-06-09 | Takeda Pharmaceutical Company Limited | Fused quinoline derivative and use thereof |
-
2005
- 2005-04-28 EP EP05738868A patent/EP1740584B9/en not_active Expired - Lifetime
- 2005-04-28 KR KR1020067024809A patent/KR20070015598A/ko not_active Ceased
- 2005-04-28 MY MYPI20051875A patent/MY143370A/en unknown
- 2005-04-28 US US11/587,788 patent/US7592453B2/en not_active Expired - Fee Related
- 2005-04-28 TW TW094113637A patent/TW200540155A/zh unknown
- 2005-04-28 RU RU2006141842/04A patent/RU2384571C2/ru not_active IP Right Cessation
- 2005-04-28 WO PCT/JP2005/008558 patent/WO2005105802A1/en not_active Ceased
- 2005-04-28 RS RSP-2009/0085A patent/RS50756B/sr unknown
- 2005-04-28 ES ES05738868T patent/ES2318483T4/es not_active Expired - Lifetime
- 2005-04-28 JP JP2006540061A patent/JP4361566B2/ja not_active Expired - Fee Related
- 2005-04-28 AT AT05738868T patent/ATE416176T1/de active
- 2005-04-28 PL PL05738868T patent/PL1740584T3/pl unknown
- 2005-04-28 DK DK05738868.8T patent/DK1740584T5/da active
- 2005-04-28 BR BRPI0510365-7A patent/BRPI0510365A/pt not_active IP Right Cessation
- 2005-04-28 EP EP08020921A patent/EP2080760A1/en not_active Withdrawn
- 2005-04-28 MX MXPA06012323A patent/MXPA06012323A/es active IP Right Grant
- 2005-04-28 ZA ZA200609261A patent/ZA200609261B/xx unknown
- 2005-04-28 SI SI200530595T patent/SI1740584T1/sl unknown
- 2005-04-28 PT PT05738868T patent/PT1740584E/pt unknown
- 2005-04-28 NZ NZ550983A patent/NZ550983A/en unknown
- 2005-04-28 AU AU2005238388A patent/AU2005238388B2/en not_active Expired - Fee Related
- 2005-04-28 CA CA002565018A patent/CA2565018A1/en not_active Abandoned
- 2005-04-28 HR HR20090121T patent/HRP20090121T5/hr unknown
- 2005-04-28 DE DE602005011424T patent/DE602005011424D1/de not_active Expired - Lifetime
- 2005-04-28 CN CNA200580021496XA patent/CN1976932A/zh active Pending
-
2006
- 2006-11-17 CR CR8755A patent/CR8755A/es not_active Application Discontinuation
- 2006-11-28 NO NO20065494A patent/NO20065494L/no not_active Application Discontinuation
-
2009
- 2009-02-27 CY CY20091100236T patent/CY1109222T1/el unknown
- 2009-06-02 US US12/476,626 patent/US7943770B2/en not_active Expired - Fee Related
- 2009-06-02 US US12/476,619 patent/US7973163B2/en not_active Expired - Fee Related
- 2009-06-23 JP JP2009149204A patent/JP2009256362A/ja not_active Abandoned
- 2009-07-07 US US12/498,629 patent/US20090275568A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994009001A1 (en) * | 1992-10-15 | 1994-04-28 | Merck & Co., Inc. | Pyrroloquinoline bradykinin antagonist |
| WO2002038547A1 (en) * | 2000-11-13 | 2002-05-16 | Glaxosmithkline Spa | Quinoline derivatives as nk-3 and nk-2 antagonists |
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