MXPA06012323A - Derivado de quinolina fusionada y uso del mismo. - Google Patents
Derivado de quinolina fusionada y uso del mismo.Info
- Publication number
- MXPA06012323A MXPA06012323A MXPA06012323A MXPA06012323A MXPA06012323A MX PA06012323 A MXPA06012323 A MX PA06012323A MX PA06012323 A MXPA06012323 A MX PA06012323A MX PA06012323 A MXPA06012323 A MX PA06012323A MX PA06012323 A MXPA06012323 A MX PA06012323A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- optionally
- substituent
- alkyl
- group
- Prior art date
Links
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 749
- 125000001424 substituent group Chemical group 0.000 claims abstract description 370
- 150000001875 compounds Chemical class 0.000 claims abstract description 340
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 91
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 81
- 150000002367 halogens Chemical class 0.000 claims abstract description 81
- 150000003839 salts Chemical class 0.000 claims abstract description 59
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 10
- -1 carbamoylcarbonylamino Chemical group 0.000 claims description 491
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 205
- 125000000623 heterocyclic group Chemical group 0.000 claims description 137
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 124
- 125000000217 alkyl group Chemical group 0.000 claims description 112
- 125000003545 alkoxy group Chemical group 0.000 claims description 86
- 125000003118 aryl group Chemical group 0.000 claims description 80
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 71
- 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 63
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 61
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 47
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 43
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 38
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 34
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 34
- 125000001188 haloalkyl group Chemical group 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 26
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 25
- 239000007787 solid Substances 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 239000004202 carbamide Substances 0.000 claims description 22
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 108010040722 Neurokinin-2 Receptors Proteins 0.000 claims description 19
- 102100037342 Substance-K receptor Human genes 0.000 claims description 19
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 18
- 150000002430 hydrocarbons Chemical group 0.000 claims description 18
- 125000006239 protecting group Chemical group 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 15
- 229940002612 prodrug Drugs 0.000 claims description 15
- 239000000651 prodrug Substances 0.000 claims description 15
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 13
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 12
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 239000008177 pharmaceutical agent Substances 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- 238000011321 prophylaxis Methods 0.000 claims description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 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
- 239000002464 receptor antagonist Substances 0.000 claims description 9
- 229940044551 receptor antagonist Drugs 0.000 claims description 9
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 claims description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
- 239000005557 antagonist Substances 0.000 claims description 7
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 7
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims description 7
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 7
- 230000002496 gastric effect Effects 0.000 claims description 7
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 7
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 7
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 7
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 7
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 6
- 201000006549 dyspepsia Diseases 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 5
- 125000005091 alkenylcarbonylamino group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 238000006482 condensation reaction Methods 0.000 claims description 3
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000036961 partial effect Effects 0.000 claims description 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- 230000003042 antagnostic effect Effects 0.000 abstract description 8
- 101000831616 Homo sapiens Protachykinin-1 Proteins 0.000 abstract 2
- 102100024304 Protachykinin-1 Human genes 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 237
- 239000000203 mixture Substances 0.000 description 195
- 230000002829 reductive effect Effects 0.000 description 112
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- 239000002904 solvent Substances 0.000 description 93
- 239000011541 reaction mixture Substances 0.000 description 79
- 239000000243 solution Substances 0.000 description 69
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 57
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
- 101150041968 CDC13 gene Proteins 0.000 description 55
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 49
- 239000000741 silica gel Substances 0.000 description 47
- 229910002027 silica gel Inorganic materials 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 238000004440 column chromatography Methods 0.000 description 45
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 239000003814 drug Substances 0.000 description 39
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 35
- 239000007864 aqueous solution Substances 0.000 description 34
- 229940079593 drug Drugs 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
- 238000001816 cooling Methods 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
- 235000013877 carbamide Nutrition 0.000 description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 20
- 239000013078 crystal Substances 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 229910052740 iodine Inorganic materials 0.000 description 16
- 239000011630 iodine Substances 0.000 description 16
- 238000010898 silica gel chromatography Methods 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- 239000012230 colorless oil Substances 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 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
- 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
- 229910052731 fluorine Inorganic materials 0.000 description 14
- 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 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- 239000011737 fluorine Substances 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 230000037396 body weight Effects 0.000 description 12
- 125000002950 monocyclic group Chemical group 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 11
- 239000003112 inhibitor Substances 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 230000032050 esterification Effects 0.000 description 10
- 238000005886 esterification reaction Methods 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 239000000047 product Substances 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229950010765 pivalate Drugs 0.000 description 9
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 239000012298 atmosphere Substances 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
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 8
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 8
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 8
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- 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 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000007832 Na2SO4 Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 230000009471 action Effects 0.000 description 7
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 7
- ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 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
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 125000001544 thienyl group Chemical group 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-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
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| PCT/JP2005/008558 WO2005105802A1 (en) | 2004-04-28 | 2005-04-28 | Fused quinoline derivative and use thereof |
Publications (1)
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Family
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Family Applications (1)
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| RS (1) | RS50756B (enExample) |
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| WO (1) | WO2005105802A1 (enExample) |
| ZA (1) | ZA200609261B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1740584B9 (en) * | 2004-04-28 | 2010-06-09 | Takeda Pharmaceutical Company Limited | Fused quinoline derivative and use thereof |
| MXPA06014909A (es) | 2004-06-18 | 2007-02-28 | Chiron Corp | Derivados de n-(1-(1-bencil -4-fenil-1h -imidazol -2-il)-2, 2-dimetilpropil) benzamida y compuestos relacionados como inhibidores de proteina de huso de cinesina (ksp) para el tratamiento del cancer. |
| NZ554555A (en) | 2004-10-20 | 2011-09-30 | Univ California | Cyclohexyl-urea derivatives as improved inhibitors for the soluble epoxide hydrolase |
| DE102005027170A1 (de) * | 2005-06-13 | 2006-12-14 | Merck Patent Gmbh | Substituierte Tetrahydrochinoline |
| GB0522715D0 (en) | 2005-11-08 | 2005-12-14 | Helperby Therapeutics Ltd | New use |
| WO2007074491A1 (en) * | 2005-12-28 | 2007-07-05 | Universita Degli Studi Di Siena | HETEROTRICYCLIC AMIDE DERIVATIVES AS NEUROKININ-l (NKl) RECEPTOR LIGANDS |
| JP4509080B2 (ja) * | 2006-09-28 | 2010-07-21 | 信越化学工業株式会社 | シルセスキオキサン系化合物混合物及び加水分解性シラン化合物、その製造方法及びそれを用いたレジスト組成物並びにパターン形成方法及び基板の加工方法 |
| WO2008070994A1 (en) | 2006-12-14 | 2008-06-19 | Nps Pharmaceuticals, Inc. | Use of d-serine derivatives for the treatment of anxiety disorders |
| CA2680366C (en) | 2007-03-09 | 2016-06-21 | University Health Network | Inhibitors of carnitine palmitoyltransferase and treating cancer |
| DE102007013856A1 (de) | 2007-03-20 | 2008-09-25 | Merck Patent Gmbh | Substituierte Tetrahydropyrrolochinoline |
| WO2008153027A1 (ja) * | 2007-06-11 | 2008-12-18 | Takeda Pharmaceutical Company Limited | ピロロキノリン誘導体およびその用途 |
| 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 |
| TWI498115B (zh) | 2007-12-27 | 2015-09-01 | Daiichi Sankyo Co Ltd | 咪唑羰基化合物 |
| USRE48334E1 (en) | 2008-09-19 | 2020-12-01 | Takeda Pharmaceutical Company Limited | Nitrogen-containing heterocyclic compound and use of same |
| WO2010038434A1 (ja) * | 2008-09-30 | 2010-04-08 | 武田薬品工業株式会社 | 光学活性なヘキサヒドロピロロキノリン類の製造法およびその中間体 |
| JP2011256110A (ja) * | 2008-09-30 | 2011-12-22 | Takeda Chem Ind Ltd | ヘキサヒドロピロロキノリンの製造法 |
| 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 |
| EP2647638A1 (en) * | 2012-04-02 | 2013-10-09 | Almirall, S.A. | Substituted tricyclic compounds with activity towards ep1 receptors |
| CN105017266B (zh) * | 2015-07-17 | 2017-07-18 | 安徽农业大学 | 手性2‑芳基‑1,2,3,4‑四氢喹啉类化合物及其合成方法 |
| 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 |
| AU2020394131A1 (en) * | 2019-11-27 | 2022-07-14 | Sumitomo Pharma Co., Ltd. | Cycloalkyl urea derivative |
| US11352357B2 (en) | 2019-11-27 | 2022-06-07 | Sumitomo Dainippon Pharma Co., Ltd. | Cycloalkylurea derivative |
| US11530218B2 (en) | 2020-01-20 | 2022-12-20 | Incyte Corporation | Spiro compounds as inhibitors of KRAS |
| US11739102B2 (en) | 2020-05-13 | 2023-08-29 | Incyte Corporation | Fused pyrimidine compounds as KRAS inhibitors |
| WO2022047093A1 (en) | 2020-08-28 | 2022-03-03 | Incyte Corporation | Vinyl imidazole compounds as inhibitors of kras |
| 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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| US5288725A (en) * | 1992-10-15 | 1994-02-22 | Merck & Co., Inc. | Pyrroloquinoline Bradykinin antagonist |
| 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 |
| US20040082589A1 (en) | 2000-11-13 | 2004-04-29 | Carlo Farina | Quinoline derivatives as nk-3 and nk-2 antagonists |
| 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 |
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2005
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- 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
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2009
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- 2009-06-23 JP JP2009149204A patent/JP2009256362A/ja not_active Abandoned
- 2009-07-07 US US12/498,629 patent/US20090275568A1/en not_active Abandoned
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