HRP20000639A2 - Quinolin-4yl derivatives i - Google Patents

Quinolin-4yl derivatives i Download PDF

Info

Publication number: HRP20000639A2
Authority: HR; Croatia
Prior art keywords: phenyl; quinolin; methoxy; propan; ylamino
Prior art date: 1999-10-01

Application number

HR20000639A

Other languages

English (en)

Croatian (hr)

Inventor

Alexander Alanine

Serge Burner

Bernd Buettelmann

Marie-Paule Heitz Neidhart

Georg Jaeschke

Emmanuel Pinard

Rene Wyler

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

1999-10-01

Filing date

2000-09-28

Publication date

2001-06-30

2000-09-28 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2001-06-30 Publication of HRP20000639A2 publication Critical patent/HRP20000639A2/hr

Links

125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 220
-1 hydroxy, amino Chemical group 0.000 claims description 46
238000000034 method Methods 0.000 claims description 31
150000003839 salts Chemical class 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
230000004770 neurodegeneration Effects 0.000 claims description 11
125000003282 alkyl amino group Chemical group 0.000 claims description 8
102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims description 7
108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
230000001154 acute effect Effects 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
230000001580 bacterial effect Effects 0.000 claims description 4
230000001684 chronic effect Effects 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
230000001225 therapeutic effect Effects 0.000 claims description 4
SLEGUCQUVMBHIC-UHFFFAOYSA-N 1-(2-phenylquinolin-4-yl)oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound N=1C2=CC=CC=C2C(OCC(O)CNC(C)C)=CC=1C1=CC=CC=C1 SLEGUCQUVMBHIC-UHFFFAOYSA-N 0.000 claims description 3
LFPSNZFRCSVPHA-UHFFFAOYSA-N 1-amino-3-[[7-methoxy-2-(4-methylphenyl)quinolin-4-yl]amino]propan-2-ol Chemical compound N=1C2=CC(OC)=CC=C2C(NCC(O)CN)=CC=1C1=CC=C(C)C=C1 LFPSNZFRCSVPHA-UHFFFAOYSA-N 0.000 claims description 3
208000024827 Alzheimer disease Diseases 0.000 claims description 3
208000035143 Bacterial infection Diseases 0.000 claims description 3
208000023105 Huntington disease Diseases 0.000 claims description 3
208000018737 Parkinson disease Diseases 0.000 claims description 3
208000036142 Viral infection Diseases 0.000 claims description 3
208000022362 bacterial infectious disease Diseases 0.000 claims description 3
210000004556 brain Anatomy 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
230000009385 viral infection Effects 0.000 claims description 3
JZVZLICYCUZMOT-ZDUSSCGKSA-N (2s)-1-[[2-(3-chloro-4-methylphenyl)quinolin-4-yl]amino]propan-2-ol Chemical compound N=1C2=CC=CC=C2C(NC[C@@H](O)C)=CC=1C1=CC=C(C)C(Cl)=C1 JZVZLICYCUZMOT-ZDUSSCGKSA-N 0.000 claims description 2
MNXUXICIMVJTRG-AWEZNQCLSA-N (2s)-1-[[2-(4-methoxy-3-methylphenyl)quinolin-4-yl]amino]propan-2-ol Chemical compound C1=C(C)C(OC)=CC=C1C1=CC(NC[C@H](C)O)=C(C=CC=C2)C2=N1 MNXUXICIMVJTRG-AWEZNQCLSA-N 0.000 claims description 2
CRDAHLMJAKVTDA-UHFFFAOYSA-N 1-(7-methoxy-2-phenylquinolin-4-yl)oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound N=1C2=CC(OC)=CC=C2C(OCC(O)CNC(C)C)=CC=1C1=CC=CC=C1 CRDAHLMJAKVTDA-UHFFFAOYSA-N 0.000 claims description 2
NTRCTOSWBGKJJT-UHFFFAOYSA-N 1-(cyclobutylamino)-3-(2-phenylquinolin-4-yl)oxypropan-2-ol Chemical compound C=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1OCC(O)CNC1CCC1 NTRCTOSWBGKJJT-UHFFFAOYSA-N 0.000 claims description 2
ITRQUARAZQAGON-UHFFFAOYSA-N 1-(cyclopentylamino)-3-(2-phenylquinolin-4-yl)oxypropan-2-ol Chemical compound C=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1OCC(O)CNC1CCCC1 ITRQUARAZQAGON-UHFFFAOYSA-N 0.000 claims description 2
HUGMYBRIUBHLLZ-UHFFFAOYSA-N 1-(methylamino)-3-(7-methyl-2-phenylquinolin-4-yl)oxypropan-2-ol Chemical compound N=1C2=CC(C)=CC=C2C(OCC(O)CNC)=CC=1C1=CC=CC=C1 HUGMYBRIUBHLLZ-UHFFFAOYSA-N 0.000 claims description 2
MLNUFIMLFJTBRP-UHFFFAOYSA-N 1-(methylamino)-3-[2-(4-methylphenyl)quinolin-4-yl]oxypropan-2-ol Chemical compound N=1C2=CC=CC=C2C(OCC(O)CNC)=CC=1C1=CC=C(C)C=C1 MLNUFIMLFJTBRP-UHFFFAOYSA-N 0.000 claims description 2
SYDIGZPCXFAHPV-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)-7-methylquinolin-4-yl]oxy-3-(methylamino)propan-2-ol Chemical compound N=1C2=CC(C)=CC=C2C(OCC(O)CNC)=CC=1C1=CC=C(OC)C=C1 SYDIGZPCXFAHPV-UHFFFAOYSA-N 0.000 claims description 2
ZXFFICKRQVKFDH-UHFFFAOYSA-N 1-amino-3-(2-phenylquinolin-4-yl)oxypropan-2-ol Chemical compound N=1C2=CC=CC=C2C(OCC(O)CN)=CC=1C1=CC=CC=C1 ZXFFICKRQVKFDH-UHFFFAOYSA-N 0.000 claims description 2
ZGKKREYJWMDTRZ-UHFFFAOYSA-N 1-amino-3-[[2-(3,4-dihydro-1h-isoquinolin-2-yl)quinolin-4-yl]amino]propan-2-ol Chemical compound C1CC2=CC=CC=C2CN1C1=NC2=CC=CC=C2C(NCC(O)CN)=C1 ZGKKREYJWMDTRZ-UHFFFAOYSA-N 0.000 claims description 2
GEKIARRHTXRYNN-UHFFFAOYSA-N 1-amino-3-[[7-methoxy-2-(4-methoxyphenyl)quinolin-4-yl]amino]propan-2-ol Chemical compound C1=CC(OC)=CC=C1C1=CC(NCC(O)CN)=C(C=CC(OC)=C2)C2=N1 GEKIARRHTXRYNN-UHFFFAOYSA-N 0.000 claims description 2
LXBAEGKBCVHTGA-UHFFFAOYSA-N 2-[[2-(3,4-dihydro-1h-isoquinolin-2-yl)quinolin-4-yl]amino]ethanol Chemical compound C1CC2=CC=CC=C2CN1C1=NC2=CC=CC=C2C(NCCO)=C1 LXBAEGKBCVHTGA-UHFFFAOYSA-N 0.000 claims description 2
PNFBNNDNLLGKLE-UHFFFAOYSA-N 2-[[2-(4-methoxyphenyl)-7-methylquinolin-4-yl]amino]ethanol Chemical compound C1=CC(OC)=CC=C1C1=CC(NCCO)=C(C=CC(C)=C2)C2=N1 PNFBNNDNLLGKLE-UHFFFAOYSA-N 0.000 claims description 2
RVXYSGFHWJGYCX-UHFFFAOYSA-N 2-[[7-methoxy-2-(4-methoxyphenyl)quinolin-4-yl]amino]ethanol Chemical compound C1=CC(OC)=CC=C1C1=CC(NCCO)=C(C=CC(OC)=C2)C2=N1 RVXYSGFHWJGYCX-UHFFFAOYSA-N 0.000 claims description 2
FBJVPWUZWFKALU-UHFFFAOYSA-N 2-[[7-methyl-2-(4-methylphenyl)quinolin-4-yl]amino]ethanol Chemical compound C1=CC(C)=CC=C1C1=CC(NCCO)=C(C=CC(C)=C2)C2=N1 FBJVPWUZWFKALU-UHFFFAOYSA-N 0.000 claims description 2
XPNJWYYAPBKDAQ-UHFFFAOYSA-N 2-amino-1-(6-chloro-2-phenylquinolin-4-yl)butan-1-ol Chemical compound N=1C2=CC=C(Cl)C=C2C(C(O)C(N)CC)=CC=1C1=CC=CC=C1 XPNJWYYAPBKDAQ-UHFFFAOYSA-N 0.000 claims description 2
JJDMFYFYSVVGPI-UHFFFAOYSA-N 2-amino-1-(6-methoxy-2-phenylquinolin-4-yl)butan-1-ol Chemical compound N=1C2=CC=C(OC)C=C2C(C(O)C(N)CC)=CC=1C1=CC=CC=C1 JJDMFYFYSVVGPI-UHFFFAOYSA-N 0.000 claims description 2
YFBMGEUUCADRTG-UHFFFAOYSA-N 2-amino-1-(6-methyl-2-phenylquinolin-4-yl)butan-1-ol Chemical compound N=1C2=CC=C(C)C=C2C(C(O)C(N)CC)=CC=1C1=CC=CC=C1 YFBMGEUUCADRTG-UHFFFAOYSA-N 0.000 claims description 2
VVTQNXBVHXWXIY-UHFFFAOYSA-N 2-amino-1-(8-methoxy-2-phenylquinolin-4-yl)butan-1-ol Chemical compound N=1C2=C(OC)C=CC=C2C(C(O)C(N)CC)=CC=1C1=CC=CC=C1 VVTQNXBVHXWXIY-UHFFFAOYSA-N 0.000 claims description 2
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
GGOIZDJNKGSNQN-UHFFFAOYSA-N 3-[[2-(3,4-dihydro-1h-isoquinolin-2-yl)quinolin-4-yl]amino]propane-1,2-diol Chemical compound C1CC2=CC=CC=C2CN1C1=NC2=CC=CC=C2C(NCC(O)CO)=C1 GGOIZDJNKGSNQN-UHFFFAOYSA-N 0.000 claims description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
208000030886 Traumatic Brain injury Diseases 0.000 claims description 2
125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 4
208000002193 Pain Diseases 0.000 claims 2
208000000094 Chronic Pain Diseases 0.000 claims 1
208000034189 Sclerosis Diseases 0.000 claims 1
208000005298 acute pain Diseases 0.000 claims 1
208000014674 injury Diseases 0.000 claims 1
230000004048 modification Effects 0.000 claims 1
238000012986 modification Methods 0.000 claims 1
230000008733 trauma Effects 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 32
KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 27
238000002360 preparation method Methods 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 21
239000007787 solid Substances 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000000243 solution Substances 0.000 description 18
239000000203 mixture Substances 0.000 description 17
KNDOFJFSHZCKGT-UHFFFAOYSA-N 4-chloroquinoline Chemical compound C1=CC=C2C(Cl)=CC=NC2=C1 KNDOFJFSHZCKGT-UHFFFAOYSA-N 0.000 description 16
229940031098 ethanolamine Drugs 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 description 11
DLFBWXQGVIOCRY-UHFFFAOYSA-N 4-chloro-2-(4-methoxyphenyl)quinoline Chemical compound C1=CC(OC)=CC=C1C1=CC(Cl)=C(C=CC=C2)C2=N1 DLFBWXQGVIOCRY-UHFFFAOYSA-N 0.000 description 10
238000007429 general method Methods 0.000 description 10
HXKKHQJGJAFBHI-VKHMYHEASA-N (2s)-1-aminopropan-2-ol Chemical compound C[C@H](O)CN HXKKHQJGJAFBHI-VKHMYHEASA-N 0.000 description 9
OVSABFHALRRNLF-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-2-phenylquinoline Chemical compound C1OC1COC(C1=CC=CC=C1N=1)=CC=1C1=CC=CC=C1 OVSABFHALRRNLF-UHFFFAOYSA-N 0.000 description 9
239000007832 Na2SO4 Substances 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
239000000872 buffer Substances 0.000 description 8
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238000003756 stirring Methods 0.000 description 7
DEZGFDSJNAWRSM-UHFFFAOYSA-N 4-chloro-2-(3,4-dihydro-1h-isoquinolin-2-yl)quinoline Chemical compound C1CC2=CC=CC=C2CN1C1=NC2=CC=CC=C2C(Cl)=C1 DEZGFDSJNAWRSM-UHFFFAOYSA-N 0.000 description 6
IBKWKEIVRXSSFH-UHFFFAOYSA-N 4-chloro-2-(4-chlorophenyl)quinoline Chemical compound C1=CC(Cl)=CC=C1C1=CC(Cl)=C(C=CC=C2)C2=N1 IBKWKEIVRXSSFH-UHFFFAOYSA-N 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
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PMZDQRJGMBOQBF-UHFFFAOYSA-N 1H-quinolin-4-one Natural products C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 5
PTDZYJPNFDIGTA-UHFFFAOYSA-N 4-chloro-2-(4-methylphenyl)quinoline Chemical compound C1=CC(C)=CC=C1C1=CC(Cl)=C(C=CC=C2)C2=N1 PTDZYJPNFDIGTA-UHFFFAOYSA-N 0.000 description 5
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239000004615 ingredient Substances 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
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235000019198 oils Nutrition 0.000 description 5
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LVFPUONZZHIVEZ-UHFFFAOYSA-N 7-methoxy-4-(oxiran-2-ylmethoxy)-2-phenylquinoline Chemical compound C=1C(C=2C=CC=CC=2)=NC2=CC(OC)=CC=C2C=1OCC1CO1 LVFPUONZZHIVEZ-UHFFFAOYSA-N 0.000 description 4
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238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
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UOWMPESDTCKCRZ-UHFFFAOYSA-N 4-chloro-2-(4-methoxy-3-methylphenyl)quinoline Chemical compound C1=C(C)C(OC)=CC=C1C1=CC(Cl)=C(C=CC=C2)C2=N1 UOWMPESDTCKCRZ-UHFFFAOYSA-N 0.000 description 3
AJKZAFJJETUNKL-UHFFFAOYSA-N 4-chloro-2-(4-methoxyphenyl)-7-methylquinoline Chemical compound C1=CC(OC)=CC=C1C1=CC(Cl)=C(C=CC(C)=C2)C2=N1 AJKZAFJJETUNKL-UHFFFAOYSA-N 0.000 description 3
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PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
230000021617 central nervous system development Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
210000001638 cerebellum Anatomy 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
230000002508 compound effect Effects 0.000 description 1
238000004590 computer program Methods 0.000 description 1
KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 1
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
230000006806 disease prevention Effects 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
MRXFPPLCDBADGB-UHFFFAOYSA-N ethyl 3-oxo-3-(1,2,3,4-tetrahydronaphthalen-2-yl)propanoate Chemical compound C1=CC=C2CC(C(=O)CC(=O)OCC)CCC2=C1 MRXFPPLCDBADGB-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
201000010901 lateral sclerosis Diseases 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
210000001767 medulla oblongata Anatomy 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
208000005264 motor neuron disease Diseases 0.000 description 1
HIDLBJFPRKCUNF-UHFFFAOYSA-N n-[2-hydroxy-3-[(2-phenylquinolin-4-yl)amino]propyl]-2-phenylacetamide Chemical compound C=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1NCC(O)CNC(=O)CC1=CC=CC=C1 HIDLBJFPRKCUNF-UHFFFAOYSA-N 0.000 description 1
230000016273 neuron death Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
239000008213 purified water Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000005060 rubber Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000005504 styryl group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurology (AREA)
Life Sciences & Earth Sciences (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurosurgery (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Psychology (AREA)
Psychiatry (AREA)
Urology & Nephrology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Vascular Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

HR20000639A 1999-10-01 2000-09-28 Quinolin-4yl derivatives i HRP20000639A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP99119539		1999-10-01

Publications (1)

Publication Number	Publication Date
HRP20000639A2 true HRP20000639A2 (en)	2001-06-30

Family

ID=8239107

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR20000639A HRP20000639A2 (en)	1999-10-01	2000-09-28	Quinolin-4yl derivatives i

Country Status (26)

Country	Link
US (1)	US6440995B1 (pt)
JP (1)	JP3523174B2 (pt)
KR (1)	KR100398561B1 (pt)
CN (1)	CN1181059C (pt)
AR (1)	AR025882A1 (pt)
AT (1)	ATE281436T1 (pt)
AU (1)	AU774363B2 (pt)
BR (1)	BR0004548A (pt)
CA (1)	CA2321324A1 (pt)
CO (1)	CO5200789A1 (pt)
CZ (1)	CZ20003575A3 (pt)
DE (1)	DE60015471T2 (pt)
ES (1)	ES2230017T3 (pt)
HR (1)	HRP20000639A2 (pt)
HU (1)	HUP0003861A3 (pt)
ID (1)	ID27525A (pt)
IL (1)	IL138777A0 (pt)
MA (1)	MA26752A1 (pt)
NO (1)	NO20004892L (pt)
NZ (1)	NZ507141A (pt)
PE (1)	PE20010648A1 (pt)
PL (1)	PL342876A1 (pt)
PT (1)	PT1088818E (pt)
SG (1)	SG164268A1 (pt)
TR (1)	TR200002831A3 (pt)
ZA (1)	ZA200005239B (pt)

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Publication number	Priority date	Publication date	Assignee	Title
US6831087B2 (en) *	2001-11-09	2004-12-14	Hoffmann-La Roche Inc.	Pyridine substituted isoquinoline derivatives
KR100618752B1 (ko) *	2002-02-13	2006-08-31	에프. 호프만-라 로슈 아게	신규한 피리딘- 및 퀴놀린-유도체
US7648984B2 (en) *	2004-07-13	2010-01-19	Glaxo Group Limited	Antibacterial agents
EP2573080A1 (en) *	2007-09-27	2013-03-27	The United States of America, as Represented by the Secretary, Department of Health and Human Services	Isoindoline compounds for the treatment of spinal muscular atrophy and other uses
CA2987978C (en) *	2014-06-16	2022-08-16	Fundacion Para La Investigacion Medica Aplicada	Novel compounds as dual inhibitors of histone methyltransferases and dna methyltransferases
US10626094B2 (en)	2014-10-14	2020-04-21	Sanford Burnham Prebys Medical Discovery Institute	Inhibitors of low molecular weight protein tyrosine phosphatase and uses thereof
KR20170074178A (ko) *	2015-12-21	2017-06-29	제이엔씨 주식회사	중합성 액정 화합물, 조성물, 그 액정 중합막류 및 이들의 용도
CN105646462B (zh) *	2016-01-19	2019-04-05	河南大学	芸香宁碱衍生物、其制备方法及应用
WO2018204176A1 (en)	2017-05-01	2018-11-08	Sanford Burnham Prebys Medical Discovery Institute	Inhibitors of low molecular weight protein tyrosine phosphatase (lmptp) and uses thereof

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DE440008C (de)	1924-03-29	1927-05-04	I G Farbenindustrie Akt Ges	Verfahren zur Darstellung von Chinolinderivaten
US4560692A (en)	1984-07-18	1985-12-24	Hoffmann-La Roche Inc.	4-Piperidino-2-phenylquinolines
GB9125515D0 (en)	1991-11-29	1992-01-29	Merck Sharp & Dohme	Therapeutic agents
US5441963A (en)	1991-12-20	1995-08-15	Merrell Dow Pharmaceuticals	Potentiation of NMDA antagonists

2000
- 2000-09-11 US US09/658,934 patent/US6440995B1/en not_active Expired - Fee Related
- 2000-09-26 DE DE60015471T patent/DE60015471T2/de not_active Expired - Fee Related
- 2000-09-26 ES ES00120890T patent/ES2230017T3/es not_active Expired - Lifetime
- 2000-09-26 AT AT00120890T patent/ATE281436T1/de not_active IP Right Cessation
- 2000-09-26 MA MA26068A patent/MA26752A1/fr unknown
- 2000-09-26 PT PT00120890T patent/PT1088818E/pt unknown
- 2000-09-26 NZ NZ507141A patent/NZ507141A/en unknown
- 2000-09-27 CA CA002321324A patent/CA2321324A1/en not_active Abandoned
- 2000-09-27 AU AU61324/00A patent/AU774363B2/en not_active Ceased
- 2000-09-27 SG SG200005551-7A patent/SG164268A1/en unknown
- 2000-09-27 CO CO00073351A patent/CO5200789A1/es not_active Application Discontinuation
- 2000-09-27 CZ CZ20003575A patent/CZ20003575A3/cs unknown
- 2000-09-28 IL IL13877700A patent/IL138777A0/xx unknown
- 2000-09-28 HR HR20000639A patent/HRP20000639A2/hr not_active Application Discontinuation
- 2000-09-28 ZA ZA200005239A patent/ZA200005239B/xx unknown
- 2000-09-28 AR ARP000105102A patent/AR025882A1/es not_active Application Discontinuation
- 2000-09-28 PE PE2000001024A patent/PE20010648A1/es not_active Application Discontinuation
- 2000-09-28 CN CNB001292013A patent/CN1181059C/zh not_active Expired - Fee Related
- 2000-09-29 ID IDP20000849D patent/ID27525A/id unknown
- 2000-09-29 KR KR10-2000-0057259A patent/KR100398561B1/ko not_active IP Right Cessation
- 2000-09-29 TR TR2000/02831A patent/TR200002831A3/tr unknown
- 2000-09-29 PL PL00342876A patent/PL342876A1/xx not_active Application Discontinuation
- 2000-09-29 BR BR0004548-9A patent/BR0004548A/pt not_active IP Right Cessation
- 2000-09-29 JP JP2000298078A patent/JP3523174B2/ja not_active Expired - Fee Related
- 2000-09-29 NO NO20004892A patent/NO20004892L/no unknown
- 2000-09-29 HU HU0003861A patent/HUP0003861A3/hu unknown

Also Published As

Publication number	Publication date
HU0003861D0 (en)	2000-12-28
AU774363B2 (en)	2004-06-24
KR100398561B1 (ko)	2003-09-19
HUP0003861A3 (en)	2002-09-30
ES2230017T3 (es)	2005-05-01
JP2001097952A (ja)	2001-04-10
KR20010050738A (ko)	2001-06-15
HUP0003861A2 (hu)	2001-10-28
DE60015471T2 (de)	2005-10-27
ATE281436T1 (de)	2004-11-15
US6440995B1 (en)	2002-08-27
TR200002831A2 (tr)	2001-04-20
CN1290698A (zh)	2001-04-11
CO5200789A1 (es)	2002-09-27
PT1088818E (pt)	2005-03-31
CA2321324A1 (en)	2001-04-01
NO20004892D0 (no)	2000-09-29
BR0004548A (pt)	2001-05-29
SG164268A1 (en)	2010-09-29
CZ20003575A3 (cs)	2001-11-14
JP3523174B2 (ja)	2004-04-26
AU6132400A (en)	2001-04-05
ID27525A (id)	2001-04-12
CN1181059C (zh)	2004-12-22
NZ507141A (en)	2002-05-31
TR200002831A3 (tr)	2001-04-20
MA26752A1 (fr)	2004-12-20
PL342876A1 (en)	2001-04-09
DE60015471D1 (de)	2004-12-09
AR025882A1 (es)	2002-12-18
ZA200005239B (en)	2001-04-16
IL138777A0 (en)	2001-10-31
NO20004892L (no)	2001-04-02
PE20010648A1 (es)	2001-06-13

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2001-06-30	A1OB	Publication of a patent application
2001-12-05	ARAI	Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application
2008-11-21	OBST	Application withdrawn

Publication	Publication Date	Title
CN100475796C (zh)	2009-04-08	作为***素受体调制剂的噻唑衍生物
Oshiro et al.	2000	3, 4-Dihydro-2 (1 H)-quinolinone as a novel antidepressant drug: synthesis and pharmacology of 1-[3-[4-(3-chlorophenyl)-1-piperazinyl] propyl]-3, 4-dihydro-5-methoxy-2 (1 H)-quinolinone and its derivatives
JP6126233B2 (ja)	2017-05-10	新たなキノリン類の化合物及びその使用
CA2400657A1 (en)	2001-09-07	Derivatives of quinoline as alpha-2 antagonists
MXPA94009601A (es)	2005-02-24	Compuestos de aril y heteroaril quinazolina que inhiben tirozina cinasa del receptor del factor de estimulacion de colonias-1.
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