JPS5818361A - キノリンの新誘導体及びその塩、それらの製造法、それらの薬剤としての使用並びにこれらを含む組成物 - Google Patents
キノリンの新誘導体及びその塩、それらの製造法、それらの薬剤としての使用並びにこれらを含む組成物Info
- Publication number
- JPS5818361A JPS5818361A JP57122246A JP12224682A JPS5818361A JP S5818361 A JPS5818361 A JP S5818361A JP 57122246 A JP57122246 A JP 57122246A JP 12224682 A JP12224682 A JP 12224682A JP S5818361 A JPS5818361 A JP S5818361A
- Authority
- JP
- Japan
- Prior art keywords
- quinoline
- carbon atoms
- hydroxy
- group
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 29
- 239000003814 drug Substances 0.000 title claims description 12
- 229940079593 drug Drugs 0.000 title claims description 6
- 239000000203 mixture Substances 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 21
- -1 4-hydroxy-N-(5-methoxyphenyl)-6- Quinoline carboxamides Chemical class 0.000 claims description 11
- 150000007524 organic acids Chemical class 0.000 claims description 11
- 235000005985 organic acids Nutrition 0.000 claims description 11
- 150000003248 quinolines Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 150000007522 mineralic acids Chemical class 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- ZPQZHSSSPISMGY-UHFFFAOYSA-N n-(4-hydroxyphenyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=CC(O)=CC=C1NC(=O)C1=CN=C(C=CC=C2)C2=C1O ZPQZHSSSPISMGY-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims 1
- IFHUTOBHWBPFEE-UHFFFAOYSA-N n-hexyl-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=CC=CC2=C(O)C(C(=O)NCCCCCC)=CN=C21 IFHUTOBHWBPFEE-UHFFFAOYSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 3
- 208000027534 Emotional disease Diseases 0.000 abstract description 2
- 230000000949 anxiolytic effect Effects 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 230000003467 diminishing effect Effects 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 230000003236 psychic effect Effects 0.000 abstract 1
- BLTDCIWCFCUQCB-UHFFFAOYSA-N quinoline-3-carboxamide Chemical class C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 abstract 1
- 125000002653 sulfanylmethyl group Chemical group [H]SC([H])([H])[*] 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 208000019901 Anxiety disease Diseases 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 3
- 229960003529 diazepam Drugs 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 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 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000007891 compressed tablet Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- OYCRVKCENBPOHN-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carbonyl chloride Chemical compound C1=CC=C2C(=O)C(C(=O)Cl)=CNC2=C1 OYCRVKCENBPOHN-UHFFFAOYSA-N 0.000 description 1
- DDHLWCQHLAFXJM-UHFFFAOYSA-N 4-oxo-n-propyl-1h-quinoline-3-carboxamide Chemical compound C1=CC=CC2=C(O)C(C(=O)NCCC)=CN=C21 DDHLWCQHLAFXJM-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 206010043268 Tension Diseases 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
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- FXCTZFMSAHZQTR-KAMYIIQDSA-N cpccoet Chemical compound O\N=C/1C2=CC=CC=C2OC2(C(=O)OCC)C\1C2 FXCTZFMSAHZQTR-KAMYIIQDSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
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- 230000009429 distress Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- ZNPJEEKRBNYZQQ-UHFFFAOYSA-N ethyl quinoline-5-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)=CC=CC2=N1 ZNPJEEKRBNYZQQ-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000000968 medical method and process Methods 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- UFDILRBQIHLZHV-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CNC2=CC=CC=C2C1=O UFDILRBQIHLZHV-UHFFFAOYSA-N 0.000 description 1
- APQQTNAPJVSBEI-UHFFFAOYSA-N n-butyl-4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=CC=C2C(=O)C(C(=O)NCCCC)=CNC2=C1 APQQTNAPJVSBEI-UHFFFAOYSA-N 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 description 1
- YMNAJWHTELQUJU-UHFFFAOYSA-N quinoline-6-carboxamide Chemical class N1=CC=CC2=CC(C(=O)N)=CC=C21 YMNAJWHTELQUJU-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Anesthesiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8113957 | 1981-07-17 | ||
| FR8113957A FR2509728A1 (fr) | 1981-07-17 | 1981-07-17 | Nouveaux derives de la quinoleine, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5818361A true JPS5818361A (ja) | 1983-02-02 |
Family
ID=9260604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57122246A Pending JPS5818361A (ja) | 1981-07-17 | 1982-07-15 | キノリンの新誘導体及びその塩、それらの製造法、それらの薬剤としての使用並びにこれらを含む組成物 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4450167A (enExample) |
| EP (1) | EP0070767B1 (enExample) |
| JP (1) | JPS5818361A (enExample) |
| KR (1) | KR880002232B1 (enExample) |
| AT (1) | ATE12635T1 (enExample) |
| AU (1) | AU552147B2 (enExample) |
| CA (1) | CA1204441A (enExample) |
| DE (1) | DE3262985D1 (enExample) |
| ES (1) | ES8305335A1 (enExample) |
| FI (1) | FI77654C (enExample) |
| FR (1) | FR2509728A1 (enExample) |
| HU (1) | HU186561B (enExample) |
| ZA (1) | ZA824746B (enExample) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008504291A (ja) * | 2004-06-24 | 2008-02-14 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ａｔｐ結合カセットトランスポーターのモジュレーター |
| JP2013536212A (ja) * | 2010-08-27 | 2013-09-19 | 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キノリン−３−カルボキサミド |
| US9670163B2 (en) | 2005-12-28 | 2017-06-06 | Vertex Pharmaceuticals Incorporated | Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| US9701639B2 (en) | 2014-10-07 | 2017-07-11 | Vertex Pharmaceuticals Incorporated | Co-crystals of modulators of cystic fibrosis transmembrane conductance regulator |
| US9751839B2 (en) | 2009-03-20 | 2017-09-05 | Vertex Pharmaceuticals Incorporated | Process for making modulators of cystic fibrosis transmembrane conductance regulator |
| US10272046B2 (en) | 2012-02-27 | 2019-04-30 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| US10646481B2 (en) | 2008-08-13 | 2020-05-12 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| US12458635B2 (en) | 2008-08-13 | 2025-11-04 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2564832B1 (fr) * | 1984-05-23 | 1987-05-15 | Panmedica Sa | Nouveaux n-acyl derives d'amino-acides et leurs esters, leur procede de preparation et medicaments les contenant |
| ZA854556B (en) * | 1984-06-25 | 1986-08-27 | Roussel Uclaf | Derivatives of isoxazoloquinolinone,process and intermediates for preparation,use as medicaments,and compositions containing them |
| FR2566405B1 (fr) * | 1984-06-25 | 1986-09-26 | Roussel Uclaf | Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2 par une fonction aminee, leur preparation, leur application comme medicaments, les compositions les renfermant et les intermediaires nouveaux obtenus |
| US4602014A (en) * | 1984-07-09 | 1986-07-22 | Ciba-Geigy Corporation | Ring-fused pyrazolo[3,4-d]-pyridin-3-one derivatives as benzodiazepine receptor modulators |
| EP0172004B1 (en) * | 1984-08-15 | 1990-03-21 | The Boots Company PLC | Quinolinones, process for their preparation and pharmaceutical compositions containing them |
| FR2585356B1 (fr) * | 1985-07-25 | 1987-10-23 | Roussel Uclaf | Nouveaux derives de l'acide 4-oh quinoleine carboxylique substitues en 2 par deux fonctions hydroxyle eventuellement etherifiees ou esterifiees, leurs procedes de preparation, les nouveaux intermediaires obtenus, leur application comme medicaments et les compositions les renfermant |
| FR2593810B1 (fr) * | 1986-01-24 | 1988-04-22 | Sanofi Sa | Derives de la quinoleine, leur procede de preparation, leur application a titre de medicaments et les compositions les renfermant |
| FR2593811B1 (fr) * | 1986-01-24 | 1989-03-31 | Sanofi Sa | Derives alcoyl-1 oxo-4 dihydro-1,4 quinoleine carboxamide-3, leur procede de preparation, leur application a titre de medicaments et les compositions les renfermant |
| GB8610980D0 (en) * | 1986-05-06 | 1986-06-11 | Ici America Inc | Heterocyclic fused tricyclic compounds |
| GB8610981D0 (en) * | 1986-05-06 | 1986-06-11 | Ici America Inc | Quinoline amides |
| US5235054A (en) * | 1992-07-15 | 1993-08-10 | Pfizer Inc. | 3-carboxaldehyde substituted quinolines and naphthyridines |
| KR20000022040A (ko) | 1996-06-20 | 2000-04-25 | 보오드 오브 리젠츠, 더 유니버시티 오브 텍사스 시스템 | 약학적 활성 제제를 제공하기 위한 화합물, 방법 및 그의 용도 |
| DE19738616A1 (de) * | 1997-09-04 | 1999-03-11 | Clariant Gmbh | 4-Hydroxychinolin-3-carbonsäure-Derivate als Lichtschutzmittel |
| CN1158264C (zh) * | 1997-11-21 | 2004-07-21 | Nps药物有限公司 | 用于治疗中枢神经系统疾病的代谢性谷氨酸受体拮抗剂 |
| US6429207B1 (en) * | 1997-11-21 | 2002-08-06 | Nps Pharmaceuticals, Inc. | Metabotropic glutamate receptor antagonists and their use for treating central nervous system diseases |
| AU736232B2 (en) * | 1997-12-03 | 2001-07-26 | Nihon Nohyaku Co., Ltd. | 1,2-dihydro-2-oxoquinoline derivatives |
| NZ505362A (en) * | 1997-12-22 | 2004-12-24 | Upjohn Co | 4-hydroxyquinoline-3-carboxamides and -hydrazides useful as antiviral agents |
| US6194427B1 (en) | 1998-02-26 | 2001-02-27 | Neurogen Corporation | Substituted cycloalkyl-4-Oxonicotinic carboxamides; gaba brain receptor ligands |
| ATE289593T1 (de) * | 1999-05-06 | 2005-03-15 | Neurogen Corp | Substituierte 4-oxo-chinolin-3-carboxamide als gaba gehirnrezeptorliganden |
| US8354427B2 (en) | 2004-06-24 | 2013-01-15 | Vertex Pharmaceutical Incorporated | Modulators of ATP-binding cassette transporters |
| US20090105272A1 (en) * | 2005-12-24 | 2009-04-23 | Grootenhuis Peter D J | Prodrugs of modulators of ABC transporters |
| AR074060A1 (es) | 2008-10-23 | 2010-12-22 | Vertex Pharma | Moduladores del regulador de conductancia transmembrana de la fibrosis quistica |
| PE20140214A1 (es) | 2010-08-27 | 2014-02-19 | Gruenenthal Chemie | 2-oxo- y 2-tioxo-dihidroquinolina-3-carboxamidas sustituidos como moduladores kcnq2/3 |
| AR082733A1 (es) | 2010-08-27 | 2012-12-26 | Gruenenthal Gmbh | 2-amino-quinolina-3-carboxamidas sustituidas como moduladores de kcnq2/3 |
| BR112013004562A2 (pt) | 2010-08-27 | 2016-09-06 | Gruenenthal Gmbh | 2-óxi-quinolina-3-carboxamidas substituídas como moduladores kcnq2/3 |
| AU2011297937B2 (en) | 2010-09-01 | 2015-10-01 | Grunenthal Gmbh | Substituted 1-oxo-dihydroisoquinoline-3-carboxamides as KCNQ2/3 modulators |
| US8802700B2 (en) | 2010-12-10 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| JP2020529432A (ja) * | 2017-08-04 | 2020-10-08 | アキシャル バイオセラピューティクス, インク.Axial Biotherapeutics, Inc. | 微生物により誘発されるアミロイドの阻害剤 |
| GB202016245D0 (en) * | 2020-10-13 | 2020-11-25 | Univ College Cardiff Consultants Ltd | Compounds |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5141366A (en) * | 1974-08-13 | 1976-04-07 | Roussel Uclaf | 33 kinorinkarubonsannoshinkina judotainoseizoho |
| JPS5291876A (en) * | 1976-01-27 | 1977-08-02 | Roussel Uclaf | Novel derivatives of 33quinolinecarboxylic acid and medicine comprising same |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR960299A (enExample) * | 1950-04-15 | |||
| DE540697C (de) * | 1925-08-11 | 1933-01-28 | Chemische Ind Ges | Verfahren zur Darstellung einseitig acylierter Diamine |
| US2504896A (en) * | 1945-06-04 | 1950-04-18 | Us Sec War | Method of preparing intermediates suitable for conversion into nuclear substituted heterocyclic compounds |
| US2504875A (en) * | 1945-06-04 | 1950-04-18 | Us Sec War | Method for producing 4-hydroxyquinolines |
| US2614121A (en) * | 1946-03-01 | 1952-10-14 | Charles C Price | Process for making intermediates for producing basic compounds |
| US2798070A (en) * | 1954-02-04 | 1957-07-02 | Mcneilab Inc | Quaternary quinoline carboxamide salts and method of preparing same |
| DE1908548A1 (de) * | 1968-02-29 | 1970-11-05 | Warner Lambert Co | Chinolinderivate |
| US3755332A (en) * | 1971-07-01 | 1973-08-28 | Ciba Geigy Corp | Substituted 4 indazolaminoquinolines |
| GB1433774A (en) * | 1973-02-26 | 1976-04-28 | Allen & Hanburys Ltd | Heterocyclic compounds apparatus for conveying articles |
| FR2221126B2 (enExample) * | 1973-03-12 | 1977-01-28 | Roussel Uclaf | |
| CA1034124A (en) * | 1973-05-11 | 1978-07-04 | Ciba-Geigy Ag | Process for the manufacture of new quinolines |
| 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 |
| 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 |
| DE2730061A1 (de) * | 1977-07-02 | 1979-01-18 | Bayer Ag | Verfahren zur herstellung von chinolin-derivaten |
| FR2443467A1 (fr) * | 1978-12-08 | 1980-07-04 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
| DE2854190C2 (de) * | 1978-12-15 | 1980-11-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von lasierenden Pigmentformen des Indanthrens und des chlorierten Indanthrone |
-
1981
- 1981-07-17 FR FR8113957A patent/FR2509728A1/fr active Granted
-
1982
- 1982-07-02 ZA ZA824746A patent/ZA824746B/xx unknown
- 1982-07-12 AT AT82401317T patent/ATE12635T1/de not_active IP Right Cessation
- 1982-07-12 EP EP82401317A patent/EP0070767B1/fr not_active Expired
- 1982-07-12 DE DE8282401317T patent/DE3262985D1/de not_active Expired
- 1982-07-14 KR KR8203141A patent/KR880002232B1/ko not_active Expired
- 1982-07-14 FI FI822509A patent/FI77654C/fi not_active IP Right Cessation
- 1982-07-15 JP JP57122246A patent/JPS5818361A/ja active Pending
- 1982-07-15 US US06/398,575 patent/US4450167A/en not_active Expired - Fee Related
- 1982-07-16 AU AU86118/82A patent/AU552147B2/en not_active Ceased
- 1982-07-16 ES ES514053A patent/ES8305335A1/es not_active Expired
- 1982-07-16 CA CA000407411A patent/CA1204441A/fr not_active Expired
- 1982-07-16 HU HU822323A patent/HU186561B/hu unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5141366A (en) * | 1974-08-13 | 1976-04-07 | Roussel Uclaf | 33 kinorinkarubonsannoshinkina judotainoseizoho |
| JPS5291876A (en) * | 1976-01-27 | 1977-08-02 | Roussel Uclaf | Novel derivatives of 33quinolinecarboxylic acid and medicine comprising same |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10662192B2 (en) | 2004-06-24 | 2020-05-26 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| JP2012056963A (ja) * | 2004-06-24 | 2012-03-22 | Vertex Pharmaceuticals Inc | Ａｔｐ結合カセットトランスポーターのモジュレーター |
| JP2012062319A (ja) * | 2004-06-24 | 2012-03-29 | Vertex Pharmaceuticals Inc | Ａｔｐ結合カセットトランスポーターのモジュレーター |
| JP2012107069A (ja) * | 2004-06-24 | 2012-06-07 | Vertex Pharmaceuticals Inc | Ａｔｐ結合カセットトランスポーターのモジュレーター |
| JP2008504291A (ja) * | 2004-06-24 | 2008-02-14 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ａｔｐ結合カセットトランスポーターのモジュレーター |
| JP2014156468A (ja) * | 2004-06-24 | 2014-08-28 | Vertex Pharmaceuticals Inc | Ａｔｐ結合カセットトランスポーターのモジュレーター |
| US11291662B2 (en) | 2005-12-28 | 2022-04-05 | Vertex Pharmaceuticals Incorporated | Solid forms of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| US10537565B2 (en) | 2005-12-28 | 2020-01-21 | Vertex Pharmaceuticals Incorporated | Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| US9670163B2 (en) | 2005-12-28 | 2017-06-06 | Vertex Pharmaceuticals Incorporated | Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| US9931334B2 (en) | 2005-12-28 | 2018-04-03 | Vertex Pharmaceuticals Incorporated | Solid forms of N[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| US11564916B2 (en) | 2008-08-13 | 2023-01-31 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| US10646481B2 (en) | 2008-08-13 | 2020-05-12 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| US12458635B2 (en) | 2008-08-13 | 2025-11-04 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| US9751839B2 (en) | 2009-03-20 | 2017-09-05 | Vertex Pharmaceuticals Incorporated | Process for making modulators of cystic fibrosis transmembrane conductance regulator |
| JP2013536212A (ja) * | 2010-08-27 | 2013-09-19 | 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キノリン−３−カルボキサミド |
| US10272046B2 (en) | 2012-02-27 | 2019-04-30 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| US11147770B2 (en) | 2012-02-27 | 2021-10-19 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| US11752106B2 (en) | 2012-02-27 | 2023-09-12 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| US12214083B2 (en) | 2012-02-27 | 2025-02-04 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| US9701639B2 (en) | 2014-10-07 | 2017-07-11 | Vertex Pharmaceuticals Incorporated | Co-crystals of modulators of cystic fibrosis transmembrane conductance regulator |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0070767B1 (fr) | 1985-04-10 |
| FI77654C (fi) | 1989-04-10 |
| FR2509728A1 (fr) | 1983-01-21 |
| FI822509A0 (fi) | 1982-07-14 |
| AU8611882A (en) | 1983-01-20 |
| FR2509728B1 (enExample) | 1985-03-01 |
| ES514053A0 (es) | 1983-04-01 |
| FI77654B (fi) | 1988-12-30 |
| EP0070767A1 (fr) | 1983-01-26 |
| ES8305335A1 (es) | 1983-04-01 |
| FI822509L (fi) | 1983-01-18 |
| DE3262985D1 (en) | 1985-05-15 |
| HU186561B (en) | 1985-08-28 |
| CA1204441A (fr) | 1986-05-13 |
| AU552147B2 (en) | 1986-05-22 |
| ZA824746B (en) | 1983-04-27 |
| KR880002232B1 (ko) | 1988-10-20 |
| US4450167A (en) | 1984-05-22 |
| ATE12635T1 (de) | 1985-04-15 |
| KR840000501A (ko) | 1984-02-22 |
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