NO313590B1 - Nye dihydro- og tetrahydrokinolinforbindelser og farmasöytiske sammensetninger inneholdende dem - Google Patents
Nye dihydro- og tetrahydrokinolinforbindelser og farmasöytiske sammensetninger inneholdende dem Download PDFInfo
- Publication number
- NO313590B1 NO313590B1 NO19995175A NO995175A NO313590B1 NO 313590 B1 NO313590 B1 NO 313590B1 NO 19995175 A NO19995175 A NO 19995175A NO 995175 A NO995175 A NO 995175A NO 313590 B1 NO313590 B1 NO 313590B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- optionally substituted
- group
- cycloalkyl
- formula
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 title abstract description 6
- 125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 44
- -1 1-6C perhaloalkyl Chemical group 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 110
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 230000032683 aging Effects 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 3
- 201000006474 Brain Ischemia Diseases 0.000 claims description 3
- 208000002177 Cataract Diseases 0.000 claims description 3
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 3
- 210000004227 basal ganglia Anatomy 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 206010008118 cerebral infarction Diseases 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 2
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 208000010877 cognitive disease Diseases 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- ORKLLXITKSXYBP-UHFFFAOYSA-N 6-ethoxy-2,2,5,7,8-pentamethyl-3,4-dihydro-1h-quinoline Chemical group N1C(C)(C)CCC2=C(C)C(OCC)=C(C)C(C)=C21 ORKLLXITKSXYBP-UHFFFAOYSA-N 0.000 claims 1
- MKWBZCHWGSOVOD-UHFFFAOYSA-N 6-ethoxyspiro[1h-quinoline-2,1'-cyclohexane] Chemical compound C1=CC2=CC(OCC)=CC=C2NC21CCCCC2 MKWBZCHWGSOVOD-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 14
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 125000003118 aryl group Chemical group 0.000 abstract 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 8
- 125000001072 heteroaryl group Chemical group 0.000 abstract 7
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 125000004446 heteroarylalkyl group Chemical group 0.000 abstract 4
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 3
- 125000000304 alkynyl group Chemical group 0.000 abstract 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 3
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 125000003107 substituted aryl group Chemical group 0.000 abstract 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- DDVIUSBRMFDHGP-UHFFFAOYSA-N 7-methoxy-2,2-diphenyl-1h-quinoline Chemical compound N1C2=CC(OC)=CC=C2C=CC1(C=1C=CC=CC=1)C1=CC=CC=C1 DDVIUSBRMFDHGP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004450 alkenylene group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000004419 alkynylene group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 109
- 239000000243 solution Substances 0.000 description 55
- 239000000047 product Substances 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 238000000034 method Methods 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- 239000000203 mixture Substances 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 27
- 239000012074 organic phase Substances 0.000 description 19
- 238000004452 microanalysis Methods 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 14
- 239000003480 eluent Substances 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 238000007912 intraperitoneal administration Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 230000016273 neuron death Effects 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
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- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 5
- 230000004224 protection Effects 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- GBHYSRYVIVDDHC-UHFFFAOYSA-N 1-chloro-1-ethynylcyclohexane Chemical compound C#CC1(Cl)CCCCC1 GBHYSRYVIVDDHC-UHFFFAOYSA-N 0.000 description 4
- QSILYWCNPOLKPN-UHFFFAOYSA-N 3-chloro-3-methylbut-1-yne Chemical compound CC(C)(Cl)C#C QSILYWCNPOLKPN-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000011785 NMRI mouse Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- 230000000971 hippocampal effect Effects 0.000 description 4
- 231100000225 lethality Toxicity 0.000 description 4
- 210000002569 neuron Anatomy 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 3
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 3
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- ALRLHJOTKVZEEQ-UHFFFAOYSA-N 6-ethoxy-2,2,5,7-tetramethyl-3,4-dihydro-1h-quinoline;hydrochloride Chemical compound Cl.N1C(C)(C)CCC2=C(C)C(OCC)=C(C)C=C21 ALRLHJOTKVZEEQ-UHFFFAOYSA-N 0.000 description 2
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- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 210000002385 vertebral artery Anatomy 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 238000005406 washing Methods 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
- C07D215/04—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/12—Ophthalmic agents for cataracts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D215/20—Oxygen 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Ophthalmology & Optometry (AREA)
- Vascular Medicine (AREA)
- Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
- Materials For Medical Uses (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9813306A FR2784988B1 (fr) | 1998-10-23 | 1998-10-23 | Nouveaux composes dihydro et tetrahydroquinoleiniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO995175D0 NO995175D0 (no) | 1999-10-22 |
| NO995175L NO995175L (no) | 2000-04-25 |
| NO313590B1 true NO313590B1 (no) | 2002-10-28 |
Family
ID=9531911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19995175A NO313590B1 (no) | 1998-10-23 | 1999-10-22 | Nye dihydro- og tetrahydrokinolinforbindelser og farmasöytiske sammensetninger inneholdende dem |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6350759B1 (de) |
| EP (1) | EP0995743B1 (de) |
| JP (1) | JP3159971B2 (de) |
| KR (1) | KR100421074B1 (de) |
| CN (1) | CN1255493A (de) |
| AT (1) | ATE236129T1 (de) |
| AU (1) | AU753044B2 (de) |
| BR (1) | BR9905587A (de) |
| CA (1) | CA2287046C (de) |
| DE (1) | DE69906445T2 (de) |
| DK (1) | DK0995743T3 (de) |
| EA (1) | EA003272B1 (de) |
| ES (1) | ES2196742T3 (de) |
| FR (1) | FR2784988B1 (de) |
| NO (1) | NO313590B1 (de) |
| NZ (1) | NZ500574A (de) |
| PL (1) | PL336139A1 (de) |
| PT (1) | PT995743E (de) |
| SI (1) | SI0995743T1 (de) |
| ZA (1) | ZA996667B (de) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6703384B2 (en) | 1998-09-23 | 2004-03-09 | Research Development Foundation | Tocopherols, tocotrienols, other chroman and side chain derivatives and uses thereof |
| JP2004504268A (ja) * | 2000-02-11 | 2004-02-12 | リサーチ ディベロップメント ファンデーション | トコフェロール、トコトリエノール、その他のクロマン、及びそれらの側鎖誘導体とその利用法 |
| AU4322802A (en) * | 2000-11-16 | 2002-06-24 | Univ California | Marine actinomycete taxon for drug and fermentation product dicovery |
| KR100488444B1 (ko) * | 2001-12-31 | 2005-05-11 | 한국과학기술연구원 | 퀴놀론 유도체 및 그 제조 방법 |
| US7176232B2 (en) | 2002-06-24 | 2007-02-13 | The Regents Of The University Of California | Salinosporamides and methods for use thereof |
| KR101184374B1 (ko) * | 2002-08-02 | 2012-09-20 | 니리어스 파마슈티컬즈, 인코퍼레이션 | 데하이드로페닐아히스틴 및 그의 동족체, 및 이들의 합성 방법 |
| US7935704B2 (en) * | 2003-08-01 | 2011-05-03 | Nereus Pharmaceuticals, Inc. | Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof |
| US7919497B2 (en) | 2002-08-02 | 2011-04-05 | Nereus Pharmaceuticals, Inc. | Analogs of dehydrophenylahistins and their therapeutic use |
| AU2003296908A1 (en) * | 2002-09-27 | 2004-05-04 | Nereus Pharmaceuticals, Inc. | Macrocyclic lactams |
| AU2004226876A1 (en) * | 2003-04-03 | 2004-10-14 | Prana Biotechnology Ltd | Treatment of neurological conditions |
| ZA200600473B (en) * | 2003-06-20 | 2007-04-25 | Univ California | Salinosporamides and methods for use thereof |
| NZ544588A (en) * | 2003-06-20 | 2010-06-25 | Nereus Pharmaceuticals Inc | Use of salinosporamide A and analogs thereof for the treatment of cancer, inflammation and infectious diseases |
| EP1711486B1 (de) | 2004-01-23 | 2011-05-11 | Nereus Pharmaceuticals, Inc. | Als antimikrobielle mittel geeignete bisindolpyrrole |
| US7579371B2 (en) | 2004-04-30 | 2009-08-25 | Nereus Pharmaceuticals, Inc. | Methods of using [3.2.0] heterocyclic compounds and analogs thereof |
| EP1812443A2 (de) | 2004-04-30 | 2007-08-01 | Nereus Pharmaceuticals, Inc. | [3,2,0]-heterocyclische verbindungen und verfahren zu ihrer verwendung |
| US20070225350A1 (en) * | 2004-12-03 | 2007-09-27 | Anderson Kenneth C | Compositions and methods for treating neoplastic diseases |
| BRPI0519013A2 (pt) * | 2004-12-13 | 2009-11-03 | Lilly Co Eli | composto ou esteroisÈmeros únicos, misturas de esteroisÈmeros, sais, tautÈmeros ou pró-drogas destes farmaceuticamente aceitáveis, composição farmacêutica, e, uso de um composto |
| NZ596653A (en) | 2006-04-06 | 2012-10-26 | Nereus Pharmaceuticals Inc | Total synthesis of salinosporamide a and analogs thereof |
| US8129527B2 (en) * | 2006-11-03 | 2012-03-06 | Nereus Pharmacuticals, Inc. | Analogs of dehydrophenylahistins and their therapeutic use |
| WO2008095195A2 (en) * | 2007-02-02 | 2008-08-07 | Nereus Pharmaceuticals, Inc. | Lyophilized formulations of salinosporamide a |
| TWI366565B (en) * | 2007-06-06 | 2012-06-21 | Otsuka Pharma Co Ltd | Quinolone compound and pharmaceutical composition |
| US8394816B2 (en) * | 2007-12-07 | 2013-03-12 | Irene Ghobrial | Methods of using [3.2.0] heterocyclic compounds and analogs thereof in treating Waldenstrom's Macroglobulinemia |
| MX2010012341A (es) * | 2008-05-12 | 2010-12-06 | Nereus Pharmaceuticals Inc | Derivados de salinosporamida como inhibidores de proteasoma. |
| JP5247667B2 (ja) * | 2008-12-05 | 2013-07-24 | 大塚製薬株式会社 | 医薬 |
| KR101053329B1 (ko) | 2009-07-09 | 2011-08-01 | 삼성전기주식회사 | 세라믹 전자부품 |
| CN102958919A (zh) * | 2010-07-02 | 2013-03-06 | 霍夫曼-拉罗奇有限公司 | 新的四氢喹啉衍生物 |
| CN103159676B (zh) * | 2011-12-16 | 2015-07-15 | 卢忠林 | 一种式i化合物的制备方法 |
| US8835643B2 (en) | 2012-02-23 | 2014-09-16 | Empire Technology Development Llc | Molecules, compositions, and methods for light absorption |
| RU2020116666A (ru) | 2014-09-14 | 2020-07-31 | Аванир Фармасьютикалз, Инк. | Фармацевтические композиции, содержащие декстрометорфановое соединение и хинидин для лечения возбуждения при деменции |
| US10076518B2 (en) | 2015-03-06 | 2018-09-18 | Beyondspring Pharmaceuticals, Inc. | Method of treating a brain tumor |
| US10238650B2 (en) | 2015-03-06 | 2019-03-26 | Beyondspring Pharmaceuticals, Inc. | Method of treating cancer associated with a RAS mutation |
| AU2016291708B2 (en) | 2015-07-13 | 2020-12-24 | Beyondspring Pharmaceuticals, Inc | Plinabulin compositions |
| SG11201806583XA (en) | 2016-02-08 | 2018-09-27 | Beyondspring Pharmaceuticals Inc | Compositions containing tucaresol or its analogs |
| CN107304184A (zh) * | 2016-04-18 | 2017-10-31 | 诺华丝国际股份有限公司 | 用于从取代的1,2‑二氢喹啉除去污染物的方法 |
| CN109475524A (zh) | 2016-06-06 | 2019-03-15 | 万春药业公司 | 用于减少中性粒细胞减少症的组合物和方法 |
| CN110431135A (zh) | 2017-01-06 | 2019-11-08 | 大连万春布林医药有限公司 | 微管蛋白结合化合物及其治疗用途 |
| KR20190109479A (ko) | 2017-02-01 | 2019-09-25 | 비욘드스프링 파마수티컬스, 인코포레이티드. | 호중구감소증의 감소 방법 |
| CN109553575B (zh) * | 2017-09-27 | 2022-06-03 | 泰兴瑞泰化工有限公司 | 一种高纯乙氧基喹啉的吸附除杂方法 |
| US11786523B2 (en) | 2018-01-24 | 2023-10-17 | Beyondspring Pharmaceuticals, Inc. | Composition and method for reducing thrombocytopenia |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3331846A (en) * | 1963-08-28 | 1967-07-18 | Lilly Co Eli | Metal catalyst process for converting alpha-amino-acetylenes to dihydroquinoline |
| IL51342A (en) * | 1977-01-27 | 1980-11-30 | Abic Ltd | Ethoxyquin derivatives,their preparation and pharmaceutical and veterinary compositions comprising them |
| GB8816269D0 (en) * | 1988-07-08 | 1988-08-10 | Int Assn Of Fish Meal Manufact | Compounds for use as anti-oxidants in fish meal/fish oil |
| US5688808A (en) * | 1994-12-22 | 1997-11-18 | Ligand Pharmaceuticals Incorporated | Steroid receptor modulator compounds and methods |
| JPH09301953A (ja) * | 1996-03-12 | 1997-11-25 | Sanwa Kagaku Kenkyusho Co Ltd | マロン酸ジアミド誘導体及びその用途 |
-
1998
- 1998-10-23 FR FR9813306A patent/FR2784988B1/fr not_active Expired - Fee Related
-
1999
- 1999-10-20 CA CA002287046A patent/CA2287046C/fr not_active Expired - Fee Related
- 1999-10-21 JP JP29930399A patent/JP3159971B2/ja not_active Expired - Fee Related
- 1999-10-21 PL PL99336139A patent/PL336139A1/xx not_active Application Discontinuation
- 1999-10-22 EA EA199900865A patent/EA003272B1/ru not_active IP Right Cessation
- 1999-10-22 ZA ZA9906667A patent/ZA996667B/xx unknown
- 1999-10-22 EP EP99402624A patent/EP0995743B1/de not_active Expired - Lifetime
- 1999-10-22 NZ NZ500574A patent/NZ500574A/en unknown
- 1999-10-22 ES ES99402624T patent/ES2196742T3/es not_active Expired - Lifetime
- 1999-10-22 AU AU56009/99A patent/AU753044B2/en not_active Ceased
- 1999-10-22 DK DK99402624T patent/DK0995743T3/da active
- 1999-10-22 BR BR9905587-2A patent/BR9905587A/pt not_active IP Right Cessation
- 1999-10-22 CN CN99125591A patent/CN1255493A/zh active Pending
- 1999-10-22 SI SI9930251T patent/SI0995743T1/xx unknown
- 1999-10-22 DE DE69906445T patent/DE69906445T2/de not_active Expired - Fee Related
- 1999-10-22 PT PT99402624T patent/PT995743E/pt unknown
- 1999-10-22 AT AT99402624T patent/ATE236129T1/de not_active IP Right Cessation
- 1999-10-22 US US09/425,267 patent/US6350759B1/en not_active Expired - Fee Related
- 1999-10-22 NO NO19995175A patent/NO313590B1/no not_active IP Right Cessation
- 1999-10-23 KR KR10-1999-0046162A patent/KR100421074B1/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20000029268A (ko) | 2000-05-25 |
| EA199900865A2 (ru) | 2000-04-24 |
| US6350759B1 (en) | 2002-02-26 |
| DE69906445D1 (de) | 2003-05-08 |
| EA003272B1 (ru) | 2003-02-27 |
| NO995175D0 (no) | 1999-10-22 |
| CA2287046C (fr) | 2003-12-02 |
| CA2287046A1 (fr) | 2000-04-23 |
| DK0995743T3 (da) | 2003-07-21 |
| AU753044B2 (en) | 2002-10-03 |
| ES2196742T3 (es) | 2003-12-16 |
| FR2784988B1 (fr) | 2002-09-20 |
| AU5600999A (en) | 2000-05-04 |
| NZ500574A (en) | 2000-08-25 |
| EA199900865A3 (ru) | 2000-10-30 |
| ATE236129T1 (de) | 2003-04-15 |
| JP2000128865A (ja) | 2000-05-09 |
| EP0995743B1 (de) | 2003-04-02 |
| SI0995743T1 (en) | 2003-08-31 |
| DE69906445T2 (de) | 2004-04-08 |
| NO995175L (no) | 2000-04-25 |
| JP3159971B2 (ja) | 2001-04-23 |
| PL336139A1 (en) | 2000-04-25 |
| CN1255493A (zh) | 2000-06-07 |
| PT995743E (pt) | 2003-07-31 |
| ZA996667B (en) | 2000-05-02 |
| FR2784988A1 (fr) | 2000-04-28 |
| KR100421074B1 (ko) | 2004-03-04 |
| BR9905587A (pt) | 2001-12-11 |
| EP0995743A1 (de) | 2000-04-26 |
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