NO317601B1 - Kinolinderivater - Google Patents
Kinolinderivater Download PDFInfo
- Publication number
- NO317601B1 NO317601B1 NO20010211A NO20010211A NO317601B1 NO 317601 B1 NO317601 B1 NO 317601B1 NO 20010211 A NO20010211 A NO 20010211A NO 20010211 A NO20010211 A NO 20010211A NO 317601 B1 NO317601 B1 NO 317601B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- quinoline
- dihydro
- oxo
- carboxamide
- Prior art date
Links
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000460 chlorine Substances 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 10
- 239000011737 fluorine Substances 0.000 claims abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 6
- -1 methylenedioxy Chemical group 0.000 claims abstract description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001767 cationic compounds Chemical class 0.000 claims abstract description 4
- 150000002892 organic cations Chemical class 0.000 claims abstract description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 3
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical group CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000003937 drug carrier Substances 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 238000010168 coupling process Methods 0.000 claims description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
- 230000008878 coupling Effects 0.000 claims description 12
- 238000005859 coupling reaction Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 7
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims description 5
- ODHLTMOBLGQWPW-UHFFFAOYSA-N 5-chloro-n-(2,4-difluorophenyl)-4-hydroxy-n,1-dimethyl-2-oxoquinoline-3-carboxamide Chemical compound OC=1C2=C(Cl)C=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=CC=C(F)C=C1F ODHLTMOBLGQWPW-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 230000037396 body weight Effects 0.000 claims description 4
- ONDYALNGTUAJDX-UHFFFAOYSA-N tasquinimod Chemical compound OC=1C=2C(OC)=CC=CC=2N(C)C(=O)C=1C(=O)N(C)C1=CC=C(C(F)(F)F)C=C1 ONDYALNGTUAJDX-UHFFFAOYSA-N 0.000 claims description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 3
- FUDWAPGUYBYXQF-UHFFFAOYSA-N 5-chloro-n-(2,5-difluorophenyl)-4-hydroxy-n,1-dimethyl-2-oxoquinoline-3-carboxamide Chemical compound OC=1C2=C(Cl)C=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=CC(F)=CC=C1F FUDWAPGUYBYXQF-UHFFFAOYSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- GUSDWFSFDMALPX-UHFFFAOYSA-N n-(2,4-difluorophenyl)-9-hydroxy-n,6-dimethyl-7-oxo-[1,3]dioxolo[4,5-f]quinoline-8-carboxamide Chemical compound OC=1C2=C3OCOC3=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=CC=C(F)C=C1F GUSDWFSFDMALPX-UHFFFAOYSA-N 0.000 claims description 3
- MJEGPKLIGUTZKB-UHFFFAOYSA-N n-(2,5-difluorophenyl)-4-hydroxy-5-methoxy-n,1-dimethyl-2-oxoquinoline-3-carboxamide Chemical compound OC=1C=2C(OC)=CC=CC=2N(C)C(=O)C=1C(=O)N(C)C1=CC(F)=CC=C1F MJEGPKLIGUTZKB-UHFFFAOYSA-N 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- NBBLDIJJFFEJGC-UHFFFAOYSA-N 5-chloro-n-ethyl-n-(3-fluorophenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide Chemical compound OC=1C2=C(Cl)C=CC=C2N(C)C(=O)C=1C(=O)N(CC)C1=CC=CC(F)=C1 NBBLDIJJFFEJGC-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910001411 inorganic cation Inorganic materials 0.000 claims description 2
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 13
- 201000010099 disease Diseases 0.000 abstract description 12
- 206010061218 Inflammation Diseases 0.000 abstract description 5
- 230000004054 inflammatory process Effects 0.000 abstract description 5
- 230000005784 autoimmunity Effects 0.000 abstract description 4
- 230000001575 pathological effect Effects 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 241000124008 Mammalia Species 0.000 abstract 2
- 239000000203 mixture Substances 0.000 description 27
- 238000011282 treatment Methods 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- SGOOQMRIPALTEL-UHFFFAOYSA-N 4-hydroxy-N,1-dimethyl-2-oxo-N-phenyl-3-quinolinecarboxamide Chemical compound OC=1C2=CC=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=CC=CC=C1 SGOOQMRIPALTEL-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- 238000002101 electrospray ionisation tandem mass spectrometry Methods 0.000 description 18
- 239000012634 fragment Substances 0.000 description 18
- 201000006417 multiple sclerosis Diseases 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- 229960003522 roquinimex Drugs 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 241000699670 Mus sp. Species 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
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- 108010058846 Ovalbumin Proteins 0.000 description 8
- 229940092253 ovalbumin Drugs 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 description 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- BLTDCIWCFCUQCB-UHFFFAOYSA-N quinoline-3-carboxamide Chemical class C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 description 5
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
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- 238000001816 cooling Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 210000003979 eosinophil Anatomy 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
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- 150000003248 quinolines Chemical class 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
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- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
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- 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
- C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms
-
- 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
- C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9802549A SE9802549D0 (sv) | 1998-07-15 | 1998-07-15 | Quinoline derivatives |
| PCT/SE1999/001270 WO2000003991A1 (en) | 1998-07-15 | 1999-07-14 | Quinoline derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20010211D0 NO20010211D0 (no) | 2001-01-12 |
| NO20010211L NO20010211L (no) | 2001-03-15 |
| NO317601B1 true NO317601B1 (no) | 2004-11-22 |
Family
ID=20412093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20010211A NO317601B1 (no) | 1998-07-15 | 2001-01-12 | Kinolinderivater |
Country Status (32)
| Country | Link |
|---|---|
| EP (1) | EP1095021B1 (is) |
| JP (1) | JP4045070B2 (is) |
| KR (1) | KR100516382B1 (is) |
| CN (1) | CN1157378C (is) |
| AP (1) | AP1366A (is) |
| AT (1) | ATE250036T1 (is) |
| AU (1) | AU751103B2 (is) |
| BR (1) | BR9912109B1 (is) |
| CA (1) | CA2336968C (is) |
| CZ (1) | CZ300229B6 (is) |
| DE (1) | DE69911415T2 (is) |
| DK (1) | DK1095021T3 (is) |
| EE (1) | EE04673B1 (is) |
| ES (1) | ES2205854T3 (is) |
| HR (1) | HRP20010039B1 (is) |
| HU (1) | HU229427B1 (is) |
| ID (1) | ID27423A (is) |
| IL (2) | IL140346A0 (is) |
| IS (1) | IS2208B (is) |
| ME (1) | MEP57408A (is) |
| NO (1) | NO317601B1 (is) |
| NZ (1) | NZ508923A (is) |
| OA (1) | OA11906A (is) |
| PL (1) | PL199783B1 (is) |
| PT (1) | PT1095021E (is) |
| RS (1) | RS50128B (is) |
| RU (1) | RU2213733C2 (is) |
| SE (1) | SE9802549D0 (is) |
| TR (1) | TR200100087T2 (is) |
| UA (1) | UA64791C2 (is) |
| WO (1) | WO2000003991A1 (is) |
| ZA (1) | ZA200007593B (is) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100390148C (zh) * | 1999-10-25 | 2008-05-28 | 活跃生物技术有限公司 | 用于治疗恶性肿瘤的药物 |
| SE0002320D0 (sv) * | 1999-10-25 | 2000-06-21 | Active Biotech Ab | Malignant tumors |
| EA009523B1 (ru) * | 2002-06-05 | 2008-02-28 | Инститьют Оф Медисинал Молекьюлар Дизайн. Инк. | Ингибиторы в отношении активации ар-1 и nfat |
| WO2003103656A1 (ja) | 2002-06-06 | 2003-12-18 | 株式会社医薬分子設計研究所 | Ｏ−置換ヒドロキシアリール誘導体 |
| EA011707B1 (ru) * | 2002-06-11 | 2009-04-28 | Инститьют Оф Медисинал Молекьюлар Дизайн. Инк. | Лекарственное средство для лечения нейродегенеративных заболеваний |
| SE0400235D0 (sv) | 2004-02-06 | 2004-02-06 | Active Biotech Ab | New composition containing quinoline compounds |
| US8314124B2 (en) | 2004-02-06 | 2012-11-20 | Active Biotech Ab | Crystalline salts of quinoline compounds and methods for preparing them |
| MY134672A (en) * | 2004-05-20 | 2007-12-31 | Japan Tobacco Inc | Stable crystal of 4-oxoquinoline compound |
| SE0401578D0 (sv) * | 2004-06-18 | 2004-06-18 | Active Biotech Ab | Novel compounds |
| PT1937642E (pt) | 2005-10-19 | 2014-11-25 | Teva Pharma | Cristais de sódio de laquinimod, e processos para o fabrico dos mesmos |
| KR20140091778A (ko) | 2006-06-12 | 2014-07-22 | 테바 파마슈티컬 인더스트리즈 리미티드 | 안정한 라퀴니모드 제제 |
| WO2008113006A1 (en) * | 2007-03-14 | 2008-09-18 | Xenon Pharmaceuticals Inc. | Methods of using quinolinone compounds in treating sodium channel-mediated diseases or conditions |
| PL2234485T3 (pl) | 2007-12-20 | 2014-06-30 | Teva Pharma | Stabilne preparaty lakwinimodu |
| KR20110048571A (ko) | 2008-09-03 | 2011-05-11 | 테바 파마슈티컬 인더스트리즈 리미티드 | 면역 기능을 지닌 ２―옥소―１,２―다이하이드로―퀴놀린 조절제 |
| DE102010048788A1 (de) | 2009-02-13 | 2011-05-19 | Amw Gmbh | Transdermales System mit Immunmodulator |
| DE102009008851A1 (de) | 2009-02-13 | 2010-08-19 | Amw Gmbh | Transdermales System mit Immunmodulator |
| KR20160148050A (ko) | 2009-07-30 | 2016-12-23 | 테바 파마슈티컬 인더스트리즈 리미티드 | 라퀴니모드를 이용한 크론병의 치료 |
| US9585878B2 (en) | 2009-08-10 | 2017-03-07 | Teva Pharmaceutical Industries, Ltd. | Treatment of BDNF-related disorders using laquinimod |
| DE102010026879A1 (de) | 2010-02-11 | 2011-08-11 | AMW GmbH, 83627 | Transdermales System mit Immunmodulator |
| PH12012501740A1 (en) | 2010-03-03 | 2012-11-12 | Teva Pharma | Treatment of rheumatoid arthritis with a combination of laquinimod and methotrexate |
| KR20160129093A (ko) | 2010-03-03 | 2016-11-08 | 테바 파마슈티컬 인더스트리즈 리미티드 | 라퀴니모드를 이용한 루푸스 신장염의 치료 |
| WO2012006538A1 (en) | 2010-07-09 | 2012-01-12 | Teva Pharmaceutical Industries Ltd. | Deuterated n-ethyl-n-phenyl-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoquinoline-3-carboxamide, salts and uses thereof |
| JP5837934B2 (ja) * | 2010-08-27 | 2015-12-24 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | Ｋｃｎｑ２／３調節因子としての置換２−オキソ−および２−チオキソ−ジヒドロキノリン−３−カルボキサミド |
| WO2012050500A1 (en) * | 2010-10-14 | 2012-04-19 | Lars Pettersson | 1,2-dihydro-4-hydroxy-2-oxo-quinoline-3-carboxanilides as ahr activators. |
| EP2537517A1 (en) | 2011-06-22 | 2012-12-26 | Active Biotech AB | Deuterium-enriched 4-hydroxy-5-methoxy-n,1-dimethyl-2-oxo-n-[(4-trifluoro-methyl)phenyl]-1,2-dihydroquinoline-3-carboxamide |
| WO2013055907A1 (en) | 2011-10-12 | 2013-04-18 | Teva Pharmaceutical Industries Ltd. | Treatment of multiple sclerosis with combination of laquinimod and fingolimod |
| CN104093310A (zh) | 2012-02-03 | 2014-10-08 | 泰华制药工业有限公司 | 拉喹莫德用于治疗一线抗TNFα疗法失败的克罗恩氏病患者的用途 |
| US9284276B2 (en) | 2012-02-16 | 2016-03-15 | Teva Pharmaceutical Industries, Ltd. | N-ethyl-N-phenyl-1,2-dihydro-4,5-di-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide, preparation and uses thereof |
| TW201350467A (zh) | 2012-05-08 | 2013-12-16 | Teva Pharma | Ｎ－乙基－４－羥基－１－甲基－５－（甲基（２，３，４，５，６－五羥基己基）胺基）－２－側氧－ｎ－苯基－１，２－二氫喹啉－３－甲醯胺 |
| TW201400117A (zh) | 2012-06-05 | 2014-01-01 | Teva Pharma | 使用拉喹莫德治療眼發炎疾病 |
| TW201410244A (zh) | 2012-08-13 | 2014-03-16 | Teva Pharma | 用於治療ｇａｂａ媒介之疾病之拉喹莫德（ｌａｑｕｉｎｉｍｏｄ） |
| US8975279B2 (en) | 2012-11-07 | 2015-03-10 | Teva Pharmaceutical Industries, Ltd. | Amine salts of laquinimod |
| JP5868839B2 (ja) | 2012-12-27 | 2016-02-24 | 三菱重工業株式会社 | チャー払出管 |
| WO2014153145A2 (en) | 2013-03-14 | 2014-09-25 | Teva Pharmaceutical Industries Ltd. | Crystals of laquinimod sodium and improved process for the manufacture thereof |
| HK1231413A1 (zh) | 2014-04-29 | 2017-12-22 | Teva Pharmaceutical Industries Ltd. | 用於治疗具有高残疾状况的复发-缓解型多发性硬化症(rrms)的患者的拉喹莫德 |
| CN108358842A (zh) * | 2014-08-28 | 2018-08-03 | 杭州普晒医药科技有限公司 | 他喹莫德的晶型及其制备方法、其药物组合物和用途 |
| ES2631194T3 (es) | 2014-09-23 | 2017-08-29 | Active Biotech Ab | Quinolincarboxamidas para usar en el tratamiento del mieloma múltiple |
| WO2016078921A1 (en) | 2014-11-19 | 2016-05-26 | Active Biotech Ab | Quinoline carboxamides for use in the treatment of leukemia |
| EP3067062A1 (en) | 2015-03-13 | 2016-09-14 | Ipsen Pharma S.A.S. | Combination of tasquinimod or a pharmaceutically acceptable salt thereof and a pd1 and/or pdl1 inhibitor, for use as a medicament |
| WO2018105943A1 (ko) * | 2016-12-07 | 2018-06-14 | 순천향대학교 산학협력단 | 폐섬유증 또는 천식의 치료 또는 완화용 약학 조성물 |
| MX2022010327A (es) | 2020-03-03 | 2022-11-09 | Active Biotech Ab | Tasquinimod o una sal farmaceuticamente aceptable del mismo para el uso en una terapia combinada. |
| AU2021313388A1 (en) | 2020-07-23 | 2023-01-19 | Erasmus University Medical Center Rotterdam (Erasmus Mc) | S100 proteins as novel therapeutic targets in myeloproliferative neoplasms |
| JP2024503372A (ja) | 2021-01-18 | 2024-01-25 | アクティブ バイオテック エイビー | 骨髄異形成症候群の処置における使用のためのタスキニモドまたはその薬学的に許容される塩 |
| CA3218977A1 (en) | 2021-05-25 | 2022-12-01 | Hans Wannman | A plurality of tasquinimod particles and use thereof |
| WO2023275248A1 (en) | 2021-07-02 | 2023-01-05 | Active Biotech Ab | A pharmaceutical product containing tasquinimod and a method for assessing the purity of said product |
| AR126963A1 (es) * | 2021-09-13 | 2023-12-06 | Lilly Co Eli | Agonistas de ahr |
| TWI838849B (zh) * | 2021-09-13 | 2024-04-11 | 美商美國禮來大藥廠 | Ahr促效劑 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE52670B1 (en) * | 1981-03-03 | 1988-01-20 | Leo Ab | Heterocyclic carboxamides,compositions containing such compounds,and processes for their preparation |
| GB9108547D0 (en) * | 1991-04-22 | 1991-06-05 | Fujisawa Pharmaceutical Co | Quinoline derivatives |
| DE4120646A1 (de) * | 1991-06-22 | 1992-12-24 | Bayer Ag | 7-isoindolinyl-chinolon- und naphthyridoncarbonsaeure-derivate |
| SE469368B (sv) * | 1991-10-09 | 1993-06-28 | Kabi Pharmacia Ab | Ny anvaendning av linomide foer tillverkning av laekemedel foer behandling av multiple sclerosis (ms) |
| SE9201076L (sv) * | 1992-04-06 | 1993-10-07 | Shimon Slavin | Användningen av gamla läkemedel för behandling av diabetes |
| JPH07224040A (ja) * | 1994-02-07 | 1995-08-22 | Fujisawa Pharmaceut Co Ltd | キノリン誘導体 |
| GB9404378D0 (en) * | 1994-03-07 | 1994-04-20 | Fujisawa Pharmaceutical Co | Quinoline derivatives |
| SE9400810D0 (sv) * | 1994-03-10 | 1994-03-10 | Pharmacia Ab | New use of Quinoline-3-carboxamide compounds |
| SE9400809D0 (sv) * | 1994-03-10 | 1994-03-10 | Pharmacia Ab | New use of quinoline-3-carboxamide compounds |
| GB2290786A (en) * | 1994-06-30 | 1996-01-10 | Fujisawa Pharmaceutical Co | Quinoline derivatives |
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1998
- 1998-07-15 SE SE9802549A patent/SE9802549D0/xx unknown
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1999
- 1999-07-14 JP JP2000560098A patent/JP4045070B2/ja not_active Expired - Fee Related
- 1999-07-14 AU AU49504/99A patent/AU751103B2/en not_active Ceased
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- 1999-07-14 HR HR20010039A patent/HRP20010039B1/xx not_active IP Right Cessation
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- 1999-07-14 EE EEP200100010A patent/EE04673B1/xx unknown
- 1999-07-14 WO PCT/SE1999/001270 patent/WO2000003991A1/en not_active Ceased
- 1999-07-14 CZ CZ20010094A patent/CZ300229B6/cs not_active IP Right Cessation
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- 1999-07-14 CN CNB998085987A patent/CN1157378C/zh not_active Expired - Fee Related
- 1999-07-14 AT AT99933452T patent/ATE250036T1/de active
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