HU186909B - Process for producing heterocyclic carboxamides - Google Patents
Process for producing heterocyclic carboxamides Download PDFInfo
- Publication number
- HU186909B HU186909B HU82638A HU63882A HU186909B HU 186909 B HU186909 B HU 186909B HU 82638 A HU82638 A HU 82638A HU 63882 A HU63882 A HU 63882A HU 186909 B HU186909 B HU 186909B
- Authority
- HU
- Hungary
- Prior art keywords
- methyl
- hydroxy
- dihydro
- carboxamide
- formula
- Prior art date
Links
- -1 heterocyclic carboxamides Chemical class 0.000 title claims abstract description 71
- 238000000034 method Methods 0.000 title claims abstract description 45
- 230000008569 process Effects 0.000 title claims description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 139
- 238000002360 preparation method Methods 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 239000007858 starting material Substances 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001767 cationic compounds Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 229910001411 inorganic cation Inorganic materials 0.000 claims description 6
- 150000002892 organic cations Chemical class 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052757 nitrogen Chemical group 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- TXJUTRJFNRYTHH-UHFFFAOYSA-N 1h-3,1-benzoxazine-2,4-dione Chemical class C1=CC=C2C(=O)OC(=O)NC2=C1 TXJUTRJFNRYTHH-UHFFFAOYSA-N 0.000 claims description 3
- SAVFUICZNSANQU-UHFFFAOYSA-N 4-amino-n,1-dimethyl-2-oxo-n-(1,3-thiazol-2-yl)quinoline-3-carboxamide Chemical compound NC=1C2=CC=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=NC=CS1 SAVFUICZNSANQU-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- NFPVOQNNDIVHCT-UHFFFAOYSA-N 4-hydroxy-n,1-dimethyl-2-oxo-n-pyrazin-2-ylquinoline-3-carboxamide Chemical compound OC=1C2=CC=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=CN=CC=N1 NFPVOQNNDIVHCT-UHFFFAOYSA-N 0.000 claims description 3
- BKZYJVCYFHUGNV-UHFFFAOYSA-N 4-hydroxy-n-(1h-imidazol-2-yl)-n,1-dimethyl-2-oxoquinoline-3-carboxamide Chemical compound OC=1C2=CC=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=NC=CN1 BKZYJVCYFHUGNV-UHFFFAOYSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- RJSDDIAVJYVXSC-UHFFFAOYSA-N 4-amino-n,1-dimethyl-2-oxo-n-phenylquinoline-3-carboxamide Chemical compound NC=1C2=CC=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=CC=CC=C1 RJSDDIAVJYVXSC-UHFFFAOYSA-N 0.000 claims description 2
- SIYLKKMGJDFLGI-UHFFFAOYSA-N 4-hydroxy-n-(4-methoxyphenyl)-n,1-dimethyl-2-oxoquinoline-3-carboxamide Chemical compound C1=CC(OC)=CC=C1N(C)C(=O)C1=C(O)C2=CC=CC=C2N(C)C1=O SIYLKKMGJDFLGI-UHFFFAOYSA-N 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- IOVIGMVIEPJACK-UHFFFAOYSA-N N=C1N(C)C2=CC=CC=C2C(O)=C1C(=O)NC1=CC=CC=C1 Chemical compound N=C1N(C)C2=CC=CC=C2C(O)=C1C(=O)NC1=CC=CC=C1 IOVIGMVIEPJACK-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- PHXXBOPXWCTFGU-UHFFFAOYSA-N n-(4-chlorophenyl)-4-hydroxy-n,1-dimethyl-2-oxoquinoline-3-carboxamide Chemical compound OC=1C2=CC=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=CC=C(Cl)C=C1 PHXXBOPXWCTFGU-UHFFFAOYSA-N 0.000 claims 1
- 125000006501 nitrophenyl group Chemical group 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- BLTDCIWCFCUQCB-UHFFFAOYSA-N quionoline-3-carboxamide Natural products C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 14
- 210000000987 immune system Anatomy 0.000 abstract description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000012360 testing method Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 241000700159 Rattus Species 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 230000007969 cellular immunity Effects 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 206010030113 Oedema Diseases 0.000 description 12
- 235000010418 carrageenan Nutrition 0.000 description 12
- 229920001525 carrageenan Polymers 0.000 description 12
- SCIYKTDXFNBCIV-UHFFFAOYSA-N 4-hydroxy-1-methyl-2-oxo-n-phenylquinoline-3-carboxamide Chemical compound O=C1N(C)C2=CC=CC=C2C(O)=C1C(=O)NC1=CC=CC=C1 SCIYKTDXFNBCIV-UHFFFAOYSA-N 0.000 description 11
- 239000000679 carrageenan Substances 0.000 description 10
- 229940113118 carrageenan Drugs 0.000 description 10
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 208000009386 Experimental Arthritis Diseases 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229960001614 levamisole Drugs 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 201000005702 Pertussis Diseases 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229920000609 methyl cellulose Polymers 0.000 description 5
- 239000001923 methylcellulose Substances 0.000 description 5
- 235000010981 methylcellulose Nutrition 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
- 206010020751 Hypersensitivity Diseases 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 230000002708 enhancing effect Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 210000000548 hind-foot Anatomy 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 210000003141 lower extremity Anatomy 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- AXNDSVUDUQXRKG-UHFFFAOYSA-N 4-methoxy-1-methyl-2-oxo-n-phenylquinoline-3-carboxamide Chemical compound O=C1N(C)C2=CC=CC=C2C(OC)=C1C(=O)NC1=CC=CC=C1 AXNDSVUDUQXRKG-UHFFFAOYSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 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 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000003304 gavage Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229960001639 penicillamine Drugs 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 208000027930 type IV hypersensitivity disease Diseases 0.000 description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical compound COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- GLGXBPBPRWWXJA-UHFFFAOYSA-N 4-chloro-1-methyl-2-oxoquinoline-3-carboxylic acid Chemical compound C1=CC=C2C(Cl)=C(C(O)=O)C(=O)N(C)C2=C1 GLGXBPBPRWWXJA-UHFFFAOYSA-N 0.000 description 2
- OMFYMMCGJVONAP-UHFFFAOYSA-N 4-hydroxy-n-(4-hydroxyphenyl)-1-methyl-2-oxoquinoline-3-carboxamide Chemical compound O=C1N(C)C2=CC=CC=C2C(O)=C1C(=O)NC1=CC=C(O)C=C1 OMFYMMCGJVONAP-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- KJMRWDHBVCNLTQ-UHFFFAOYSA-N N-methylisatoic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)N(C)C2=C1 KJMRWDHBVCNLTQ-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- 210000004224 pleura Anatomy 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- AGZPNUZBDCYTBB-UHFFFAOYSA-N triethyl methanetricarboxylate Chemical compound CCOC(=O)C(C(=O)OCC)C(=O)OCC AGZPNUZBDCYTBB-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
-
- 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
-
- 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
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
-
- 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
- C07D471/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8106594 | 1981-03-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU186909B true HU186909B (en) | 1985-10-28 |
Family
ID=10520089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU82638A HU186909B (en) | 1981-03-03 | 1982-03-02 | Process for producing heterocyclic carboxamides |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US4547511A (OSRAM) |
| EP (1) | EP0059698B1 (OSRAM) |
| JP (1) | JPS57171975A (OSRAM) |
| KR (1) | KR860001876B1 (OSRAM) |
| AT (1) | ATE15798T1 (OSRAM) |
| AU (1) | AU547849B2 (OSRAM) |
| CA (1) | CA1182455A (OSRAM) |
| DE (1) | DE3266464D1 (OSRAM) |
| DK (1) | DK157859C (OSRAM) |
| ES (1) | ES510042A0 (OSRAM) |
| FI (1) | FI79532C (OSRAM) |
| GR (1) | GR76073B (OSRAM) |
| HK (1) | HK38689A (OSRAM) |
| HU (1) | HU186909B (OSRAM) |
| IE (1) | IE52670B1 (OSRAM) |
| IL (1) | IL65028A (OSRAM) |
| NO (1) | NO163130C (OSRAM) |
| NZ (1) | NZ199888A (OSRAM) |
| PH (1) | PH18520A (OSRAM) |
| PT (1) | PT74512B (OSRAM) |
| ZA (1) | ZA821210B (OSRAM) |
Families Citing this family (98)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3269753A (en) * | 1964-08-31 | 1966-08-30 | Data Man Inc | Bookkeeping unit |
| IE52670B1 (en) * | 1981-03-03 | 1988-01-20 | Leo Ab | Heterocyclic carboxamides,compositions containing such compounds,and processes for their preparation |
| US4400017A (en) * | 1981-03-04 | 1983-08-23 | Pendergrass Russell G | Integrated budget and check record book |
| US4650804A (en) * | 1984-03-30 | 1987-03-17 | Fujisawa Pharmaceutical Co., Ltd. | Quinolizinone compounds and pharmaceutical composition comprising the same, useful as anti-ulcerative and anti-allergic agents |
| DE3420116A1 (de) * | 1984-05-30 | 1985-12-05 | Bayer Ag, 5090 Leverkusen | Immunstimulierende mittel |
| US4786644A (en) * | 1987-11-27 | 1988-11-22 | Hoechst-Roussel Pharmaceuticals Inc. | 1-aryl-3-quinolinecarboxamide |
| IT1228293B (it) * | 1989-02-06 | 1991-06-07 | Angeli Inst Spa | Benzoderivati di composti eterociclici contenenti azoto. |
| US5310913A (en) * | 1989-06-09 | 1994-05-10 | Kabi Pharmacia Aktiebolag | Derivatives of quinoline-3-carboxanilide |
| SE8902076D0 (sv) * | 1989-06-09 | 1989-06-09 | Pharmacia Ab | Derivatives of quinoline-3-carboxanilide |
| US5691350A (en) * | 1990-02-22 | 1997-11-25 | Kabi Pharmacia Ab | Use of linomide for treatment of retrovirus infections specifically HIV infections |
| SE9000624D0 (sv) * | 1990-02-22 | 1990-02-22 | Pharmacia Ab | New use |
| US5504092A (en) * | 1990-03-27 | 1996-04-02 | Pharmacia Ab | Use of Linomide to increase hemopoietic cell precursors |
| SE9001111D0 (sv) * | 1990-03-27 | 1990-03-27 | Pharmacia Ab | Supportive use |
| WO1992004327A1 (en) * | 1990-09-07 | 1992-03-19 | Schering Corporation | Antiviral compounds and antihypertensive compounds |
| CA2091171A1 (en) * | 1990-09-07 | 1992-03-08 | Adriano Afonso | Antiviral compounds |
| CA2091173A1 (en) * | 1990-09-07 | 1992-03-08 | Adriano Afonso | Antiviral compounds and antihypertensive compounds |
| US5219864A (en) * | 1991-03-12 | 1993-06-15 | Kyowa Hakko Kogyo Co., Ltd. | Thienopyridine derivatives |
| GB9108547D0 (en) * | 1991-04-22 | 1991-06-05 | Fujisawa Pharmaceutical Co | Quinoline derivatives |
| 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) |
| TW222276B (OSRAM) * | 1992-01-27 | 1994-04-11 | Fujisawa Pharmaceutical Co | |
| SE9201076L (sv) * | 1992-04-06 | 1993-10-07 | Shimon Slavin | Användningen av gamla läkemedel för behandling av diabetes |
| GB9311562D0 (en) * | 1993-06-04 | 1993-07-21 | Fujisawa Pharmaceutical Co | Heterocyclic derivatives |
| SE9302490D0 (sv) * | 1993-07-26 | 1993-07-26 | Kabi Pharmacia Ab | New use of old drugs |
| 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 |
| CA2222471A1 (en) * | 1996-03-27 | 1997-10-02 | Toray Industries, Inc. | Ketone derivatives and medical application thereof |
| US5912349A (en) * | 1997-01-31 | 1999-06-15 | Pharmacia & Upjohn Company | Process for the preparation of roquinimex |
| JPH1171351A (ja) * | 1997-08-29 | 1999-03-16 | Ss Pharmaceut Co Ltd | 置換キノロン誘導体及びこれを含有する医薬 |
| SE9801474D0 (sv) * | 1998-04-27 | 1998-04-27 | Active Biotech Ab | Quinoline Derivatives |
| US6077851A (en) * | 1998-04-27 | 2000-06-20 | Active Biotech Ab | Quinoline derivatives |
| SE9802550D0 (sv) * | 1998-07-15 | 1998-07-15 | Active Biotech Ab | Quinoline derivatives |
| SE9802549D0 (sv) * | 1998-07-15 | 1998-07-15 | Active Biotech Ab | Quinoline derivatives |
| US6121287A (en) * | 1998-07-15 | 2000-09-19 | Active Biotech Ab | Quinoline derivatives |
| US6133285A (en) * | 1998-07-15 | 2000-10-17 | Active Biotech Ab | Quinoline derivatives |
| JP2000044561A (ja) * | 1998-07-31 | 2000-02-15 | Kyorin Pharmaceut Co Ltd | ピロロキノリン誘導体及びその製造方法 |
| JP2000044560A (ja) * | 1998-07-31 | 2000-02-15 | Kyorin Pharmaceut Co Ltd | ベンゾキノリジン誘導体及びその製造方法 |
| JP2000256323A (ja) | 1999-01-08 | 2000-09-19 | Japan Tobacco Inc | ２−オキソキノリン化合物及びその医薬用途 |
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| RU2240313C2 (ru) * | 1999-10-25 | 2004-11-20 | Эктив Байотек Аб | Лекарственные средства для лечения злокачественных опухолей |
| SE0002320D0 (sv) * | 1999-10-25 | 2000-06-21 | Active Biotech Ab | Malignant tumors |
| WO2001034570A1 (en) * | 1999-11-08 | 2001-05-17 | Sankyo Company, Limited | Nitrogenous heterocycle derivatives |
| US6525049B2 (en) | 2000-07-05 | 2003-02-25 | Pharmacia & Upjohn Company | Pyrroloquinolones as antiviral agents |
| JP2003012667A (ja) * | 2001-06-26 | 2003-01-15 | Rrf Kenkyusho:Kk | キノリンカルボキサミド骨格を有する抗菌剤 |
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| US6875869B2 (en) * | 2002-06-12 | 2005-04-05 | Active Biotech Ab | Process for the manufacture of quinoline derivatives |
| US7560557B2 (en) * | 2002-06-12 | 2009-07-14 | Active Biotech Ag | Process for the manufacture of quinoline derivatives |
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| AU2006326662B2 (en) * | 2005-12-09 | 2011-07-28 | Amgen Inc. | Quinolone based compounds exhibiting prolyl hydroxylase inhibitory activity, and compositions, and uses thereof |
| WO2007124617A1 (fr) * | 2006-04-28 | 2007-11-08 | Institute Of Mataria Medica, Chinese Academy Of Medical Sciences | Dérivés de coumarine, leurs procédés de préparation, compositions pharmaceutiques et utilisations |
| US7989473B2 (en) | 2006-06-12 | 2011-08-02 | Teva Pharmaceutical Industries, Ltd. | Stable laquinimod preparations |
| US8178127B2 (en) * | 2007-12-20 | 2012-05-15 | Teva Pharmaceuticals Industries, Ltd. | Stable laquinimod preparations |
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| WO2018075598A1 (en) | 2016-10-19 | 2018-04-26 | Constellation Pharmaceuticals, Inc. | Synthesis of inhibitors of ezh2 |
| GB202006390D0 (en) * | 2020-04-30 | 2020-06-17 | Aqilion Ab | Novel treatments |
| WO2021237112A1 (en) * | 2020-05-21 | 2021-11-25 | Stemsynergy Therapeutics, Inc. | Notch inhibitors and uses thereof |
| CN111732540B (zh) * | 2020-07-20 | 2020-11-13 | 湖南速博生物技术有限公司 | 一种罗喹美克的制备方法 |
| 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 |
| WO2024097606A1 (en) | 2022-10-31 | 2024-05-10 | Eli Lilly And Company | Ahr agonists |
| US20240199608A1 (en) * | 2022-11-15 | 2024-06-20 | Eli Lilly And Company | Ahr agonists |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH471784A (de) * | 1966-01-26 | 1969-04-30 | Bayer Ag | Verfahren zur Herstellung von Carbostyrilderivaten |
| US3524858A (en) * | 1967-05-18 | 1970-08-18 | Warner Lambert Pharmaceutical | 1,4 - dihydro-1-substituted alkyl-6,7-methylenedioxy - 4 - oxoquinoline-3-carboxylic acid |
| CA1034124A (en) * | 1973-05-11 | 1978-07-04 | Ciba-Geigy Ag | Process for the manufacture of new quinolines |
| CH578535A5 (en) | 1973-05-11 | 1976-08-13 | Ciba Geigy Ag | Quinoline-3-carboxylic acid derivs - with e.g. analgesic, antinociceptive, antiinflammatory and antiallergic props |
| CH578537A5 (en) | 1973-05-11 | 1976-08-13 | Ciba Geigy Ag | Quinoline-3-carboxylic acid derivs - with e.g. analgesic, antinociceptive, antiinflammatory and antiallergic props |
| CH578534A5 (en) | 1973-05-11 | 1976-08-13 | Ciba Geigy Ag | Quinoline-3-carboxylic acid derivs - with e.g. analgesic, antinociceptive, antiinflammatory and antiallergic props |
| CH578536A5 (en) | 1973-05-11 | 1976-08-13 | Ciba Geigy Ag | Quinoline-3-carboxylic acid derivs - with e.g. analgesic, antinociceptive, antiinflammatory and antiallergic props |
| US3917609A (en) * | 1973-06-27 | 1975-11-04 | Minnesota Mining & Mfg | Pyrroloquinoline carboxylic acids and derivatives |
| FR2281761A1 (fr) * | 1974-08-13 | 1976-03-12 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
| FR2340735A1 (fr) | 1976-02-11 | 1977-09-09 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
| FR2482596A1 (fr) * | 1980-05-19 | 1981-11-20 | Roussel Uclaf | Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2, leur procede de preparation et leur application comme medicament |
| IE52670B1 (en) * | 1981-03-03 | 1988-01-20 | Leo Ab | Heterocyclic carboxamides,compositions containing such compounds,and processes for their preparation |
-
1982
- 1982-02-12 IE IE314/82A patent/IE52670B1/en not_active IP Right Cessation
- 1982-02-16 IL IL65028A patent/IL65028A/xx unknown
- 1982-02-22 US US06/350,890 patent/US4547511A/en not_active Expired - Lifetime
- 1982-02-22 DE DE8282850032T patent/DE3266464D1/de not_active Expired
- 1982-02-22 AT AT82850032T patent/ATE15798T1/de not_active IP Right Cessation
- 1982-02-22 EP EP82850032A patent/EP0059698B1/en not_active Expired
- 1982-02-24 DK DK081282A patent/DK157859C/da not_active IP Right Cessation
- 1982-02-24 ZA ZA821210A patent/ZA821210B/xx unknown
- 1982-03-01 FI FI820728A patent/FI79532C/fi not_active IP Right Cessation
- 1982-03-01 NO NO820642A patent/NO163130C/no unknown
- 1982-03-02 PH PH26933A patent/PH18520A/en unknown
- 1982-03-02 NZ NZ199888A patent/NZ199888A/en unknown
- 1982-03-02 PT PT74512A patent/PT74512B/pt not_active IP Right Cessation
- 1982-03-02 GR GR67454A patent/GR76073B/el unknown
- 1982-03-02 HU HU82638A patent/HU186909B/hu unknown
- 1982-03-02 CA CA000397413A patent/CA1182455A/en not_active Expired
- 1982-03-02 ES ES510042A patent/ES510042A0/es active Granted
- 1982-03-03 KR KR8200910A patent/KR860001876B1/ko not_active Expired
- 1982-03-03 JP JP57033722A patent/JPS57171975A/ja active Granted
- 1982-03-03 AU AU81076/82A patent/AU547849B2/en not_active Expired
-
1985
- 1985-04-16 US US06/723,746 patent/US4738971A/en not_active Expired - Lifetime
-
1989
- 1989-05-11 HK HK386/89A patent/HK38689A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA821210B (en) | 1983-01-26 |
| AU547849B2 (en) | 1985-11-07 |
| PH18520A (en) | 1985-08-02 |
| EP0059698B1 (en) | 1985-09-25 |
| ES8400409A1 (es) | 1983-10-16 |
| NO163130C (no) | 1990-04-11 |
| CA1182455A (en) | 1985-02-12 |
| FI820728L (fi) | 1982-09-04 |
| HK38689A (en) | 1989-05-19 |
| IL65028A0 (en) | 1982-04-30 |
| DK157859C (da) | 1990-07-30 |
| GR76073B (OSRAM) | 1984-08-03 |
| DE3266464D1 (en) | 1985-10-31 |
| AU8107682A (en) | 1982-09-09 |
| US4738971A (en) | 1988-04-19 |
| KR830009037A (ko) | 1983-12-17 |
| JPH049786B2 (OSRAM) | 1992-02-21 |
| IE52670B1 (en) | 1988-01-20 |
| DK81282A (da) | 1982-09-04 |
| ES510042A0 (es) | 1983-10-16 |
| NZ199888A (en) | 1985-07-31 |
| ATE15798T1 (de) | 1985-10-15 |
| FI79532B (fi) | 1989-09-29 |
| KR860001876B1 (ko) | 1986-10-24 |
| IL65028A (en) | 1986-11-30 |
| NO820642L (no) | 1982-09-06 |
| US4547511A (en) | 1985-10-15 |
| PT74512A (en) | 1982-04-01 |
| IE820314L (en) | 1982-09-03 |
| EP0059698A1 (en) | 1982-09-08 |
| DK157859B (da) | 1990-02-26 |
| NO163130B (no) | 1990-01-02 |
| PT74512B (en) | 1983-11-08 |
| FI79532C (fi) | 1990-01-10 |
| JPS57171975A (en) | 1982-10-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HPC4 | Succession in title of patentee |
Owner name: ACTIVE BIOTECH AB, SE |