CA1071209A - 8-oxo-2,3,5,8-tetrahydro-furo (2,3-g) quinoline-7-carboxylic acid compounds - Google Patents
8-oxo-2,3,5,8-tetrahydro-furo (2,3-g) quinoline-7-carboxylic acid compoundsInfo
- Publication number
- CA1071209A CA1071209A CA256,253A CA256253A CA1071209A CA 1071209 A CA1071209 A CA 1071209A CA 256253 A CA256253 A CA 256253A CA 1071209 A CA1071209 A CA 1071209A
- Authority
- CA
- Canada
- Prior art keywords
- group
- quinoline
- furo
- process according
- carboxylic acid
- 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.)
- Expired
Links
- YGWDIBNOEHFRGA-UHFFFAOYSA-N 8-oxo-3,5-dihydro-2h-furo[2,3-g]quinoline-7-carboxylic acid Chemical class C1=C2C(=O)C(C(=O)O)=CNC2=CC2=C1OCC2 YGWDIBNOEHFRGA-UHFFFAOYSA-N 0.000 title claims 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 31
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 17
- 239000007795 chemical reaction product Substances 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 14
- -1 allyl ester Chemical class 0.000 claims description 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 150000007529 inorganic bases Chemical class 0.000 claims description 9
- 150000007530 organic bases Chemical class 0.000 claims description 9
- WXXVQWSDMOAHHV-UHFFFAOYSA-N quinoline-7-carboxylic acid Chemical compound C1=CC=NC2=CC(C(=O)O)=CC=C21 WXXVQWSDMOAHHV-UHFFFAOYSA-N 0.000 claims description 7
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims description 5
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims description 4
- USEGQJLHQSTGHW-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene Chemical compound CC(=C)CBr USEGQJLHQSTGHW-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 3
- JTLAIKFGRHDNQM-UHFFFAOYSA-N 1-bromo-2-fluoroethane Chemical compound FCCBr JTLAIKFGRHDNQM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 claims description 3
- 230000008707 rearrangement Effects 0.000 claims description 2
- 125000006017 1-propenyl group Chemical group 0.000 claims 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 239000000376 reactant Substances 0.000 claims 4
- AVMHMVJVHYGDOO-NSCUHMNNSA-N (e)-1-bromobut-2-ene Chemical compound C\C=C\CBr AVMHMVJVHYGDOO-NSCUHMNNSA-N 0.000 claims 3
- 230000003301 hydrolyzing effect Effects 0.000 claims 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 150000001768 cations Chemical class 0.000 claims 2
- 159000000000 sodium salts Chemical class 0.000 claims 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 claims 1
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 claims 1
- SCJCXNFQMAPXEE-UHFFFAOYSA-N 5-(2-methylprop-2-enyl)-8-oxo-2,3-dihydrofuro[2,3-g]quinoline-7-carboxylic acid Chemical compound CC(CN1C=C(C(C=2C=C3C(=CC12)CCO3)=O)C(=O)O)=C SCJCXNFQMAPXEE-UHFFFAOYSA-N 0.000 claims 1
- RMTONOUVVJIQJH-UHFFFAOYSA-N 5-but-1-enyl-8-oxo-2,3-dihydrofuro[2,3-g]quinoline-7-carboxylic acid Chemical compound C(=CCC)N1C=C(C(C=2C=C3C(=CC12)CCO3)=O)C(=O)O RMTONOUVVJIQJH-UHFFFAOYSA-N 0.000 claims 1
- HEMDPIGTOILTGK-UHFFFAOYSA-N 5-but-2-enyl-8-oxo-2,3-dihydrofuro[2,3-g]quinoline-7-carboxylic acid Chemical compound C(C=CC)N1C=C(C(C=2C=C3C(=CC12)CCO3)=O)C(=O)O HEMDPIGTOILTGK-UHFFFAOYSA-N 0.000 claims 1
- ODWRTXNLLQLQJC-UHFFFAOYSA-N 5-ethenyl-8-oxo-2,3-dihydrofuro[2,3-g]quinoline-7-carboxylic acid Chemical compound O=C1C(=CN(C=2C=C3C(=CC12)OCC3)C=C)C(=O)O ODWRTXNLLQLQJC-UHFFFAOYSA-N 0.000 claims 1
- OOINXMDIGUFLAR-UHFFFAOYSA-N 8-oxo-5-prop-1-enyl-2,3-dihydrofuro[2,3-g]quinoline-7-carboxylic acid Chemical compound O=C1C(=CN(C=2C=C3C(=CC12)OCC3)C=CC)C(=O)O OOINXMDIGUFLAR-UHFFFAOYSA-N 0.000 claims 1
- YHDBAQPMINKQEB-UHFFFAOYSA-N 8-oxo-5-prop-2-ynyl-2,3-dihydrofuro[2,3-g]quinoline-7-carboxylic acid Chemical compound O=C1C(=CN(C=2C=C3C(=CC12)OCC3)CC#C)C(=O)O YHDBAQPMINKQEB-UHFFFAOYSA-N 0.000 claims 1
- YNRMPBXICATSSG-UHFFFAOYSA-N O=C1C(=CN(C=2C=C3C(=CC12)OCC3)C=C=C)C(=O)O Chemical compound O=C1C(=CN(C=2C=C3C(=CC12)OCC3)C=C=C)C(=O)O YNRMPBXICATSSG-UHFFFAOYSA-N 0.000 claims 1
- DVQWQNSHEZSKCI-UHFFFAOYSA-N but-2-enyl 5-but-2-enyl-8-oxo-2,3-dihydrofuro[2,3-g]quinoline-7-carboxylate Chemical compound C(C=CC)OC(=O)C1=CN(C=2C=C3C(=CC2C1=O)OCC3)CC=CC DVQWQNSHEZSKCI-UHFFFAOYSA-N 0.000 claims 1
- 239000000083 urinary anti-infective agent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 9
- 239000012265 solid product Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000002168 alkylating agent Substances 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 210000002700 urine Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- IIRVYWCKYUQJCL-UHFFFAOYSA-N 5-ethyl-8-oxo-2,3-dihydrofuro[2,3-g]quinoline-7-carboxylic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC2=C1CCO2 IIRVYWCKYUQJCL-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000004185 ester group Chemical class 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 210000001635 urinary tract Anatomy 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- CUGDYSSBTWBKII-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(dimethylamino)hexane-1,2,3,4,5-pentol Chemical compound CN(C)C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO CUGDYSSBTWBKII-LXGUWJNJSA-N 0.000 description 1
- DZHWBKZPINQYHS-UHFFFAOYSA-N 2,3-dihydrofuro[2,3-g]quinoline-7-carboxylic acid Chemical class O1CCC=2C1=CC=1C=C(C=NC=1C=2)C(=O)O DZHWBKZPINQYHS-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101150107341 RERE gene Proteins 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 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
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752530412 DE2530412A1 (de) | 1975-07-04 | 1975-07-04 | Chinolincarbonsaeurederivate ii |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1071209A true CA1071209A (en) | 1980-02-05 |
Family
ID=5950957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA256,253A Expired CA1071209A (en) | 1975-07-04 | 1976-07-05 | 8-oxo-2,3,5,8-tetrahydro-furo (2,3-g) quinoline-7-carboxylic acid compounds |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5223096A (pt) |
| BE (1) | BE843738A (pt) |
| CA (1) | CA1071209A (pt) |
| CH (1) | CH626894A5 (pt) |
| DE (1) | DE2530412A1 (pt) |
| DK (1) | DK142949C (pt) |
| FR (1) | FR2315932A1 (pt) |
| IE (1) | IE43256B1 (pt) |
| IL (1) | IL49967A0 (pt) |
| LU (1) | LU75294A1 (pt) |
| NL (1) | NL7607417A (pt) |
| PT (1) | PT65299B (pt) |
| SE (1) | SE7607515L (pt) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2030899A1 (de) * | 1970-06-18 | 1971-12-23 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Chinolincarbonsäurederivate |
-
1975
- 1975-07-04 DE DE19752530412 patent/DE2530412A1/de not_active Withdrawn
-
1976
- 1976-06-30 CH CH838876A patent/CH626894A5/de not_active IP Right Cessation
- 1976-06-30 PT PT65299A patent/PT65299B/pt unknown
- 1976-07-01 SE SE7607515A patent/SE7607515L/xx not_active Application Discontinuation
- 1976-07-02 BE BE168601A patent/BE843738A/xx not_active IP Right Cessation
- 1976-07-02 DK DK300076A patent/DK142949C/da not_active IP Right Cessation
- 1976-07-02 LU LU75294A patent/LU75294A1/xx unknown
- 1976-07-04 IL IL49967A patent/IL49967A0/xx unknown
- 1976-07-05 JP JP51079782A patent/JPS5223096A/ja active Pending
- 1976-07-05 NL NL7607417A patent/NL7607417A/xx not_active Application Discontinuation
- 1976-07-05 FR FR7620428A patent/FR2315932A1/fr active Granted
- 1976-07-05 IE IE1476/76A patent/IE43256B1/en unknown
- 1976-07-05 CA CA256,253A patent/CA1071209A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2315932B1 (pt) | 1979-07-20 |
| DK142949C (da) | 1981-10-05 |
| PT65299A (pt) | 1976-07-01 |
| DE2530412A1 (de) | 1977-01-20 |
| JPS5223096A (en) | 1977-02-21 |
| IE43256L (en) | 1977-01-04 |
| FR2315932A1 (fr) | 1977-01-28 |
| IL49967A0 (en) | 1976-09-30 |
| BE843738A (fr) | 1977-01-03 |
| IE43256B1 (en) | 1981-01-14 |
| CH626894A5 (en) | 1981-12-15 |
| NL7607417A (nl) | 1977-01-06 |
| DK142949B (da) | 1981-03-02 |
| SE7607515L (sv) | 1977-01-05 |
| DK300076A (da) | 1977-01-05 |
| LU75294A1 (pt) | 1977-02-23 |
| PT65299B (pt) | 1977-12-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NZ261579A (en) | Imidazopyridine derivatives and pharmaceutical compositions | |
| US3917608A (en) | Substituted 6,7 dihydro-1-oxo N(1H-tetrazol-5-yl)-1H,5H-benzo{8 ij{9 quinolizine carboxamides | |
| US3406168A (en) | Novel 5, 6-dihydro-6-oxo-11h-pyrido [2, 3-b] [1, 4]benzodiazepines | |
| DE2710242A1 (de) | 5-eckige klammer auf 1,1-diphenyl- 3-(5- oder 6-hydroxy-2-azabicyclo eckige klammer auf 2,2,2 eckige klammer zu oct-2-yl)propyl eckige klammer zu -2- alkyl-1,3,4-oxadiazole und verwandte verbindungen | |
| IE48852B1 (en) | Pyrido(2,1-beta)quinazolinone derivatives and their manufacture and use | |
| US4277476A (en) | Derivatives of fluorenes and fluoranthenes and process for their preparation | |
| WO2000062782A1 (en) | Novel synthesis and crystallization of piperazine ring-containing compounds | |
| US3752823A (en) | N alkyl tetrahydrocarbazoles | |
| CA1071209A (en) | 8-oxo-2,3,5,8-tetrahydro-furo (2,3-g) quinoline-7-carboxylic acid compounds | |
| IE46908B1 (en) | Pyridobenzodiazepines | |
| EP0253171A1 (de) | Pyrido [1,8] naphthyridinone, Verfahren zu ihrer Herstellung und ihre Verwendung sowie diese Verbindungen enthaltende Zubereitungen | |
| US6545149B2 (en) | Synthesis and crystallization of piperazine ring-containing compounds | |
| US3705150A (en) | Process for the preparation of 21-deoxy - 21-n-(n'-methylpiperazinyl)-prednisolone and salts thereof | |
| US3917833A (en) | Amino-substituted benzocycloheptenones for inducing sleep | |
| US3407210A (en) | Aminoethyl-benzofurans and derivatives thereof | |
| CA1110249A (en) | Indolopyrones having antiallergic activity | |
| GB1604166A (en) | Process for the preparation of p-hydroxy-alphaamino-benzyl penicillin and intermediates therefor | |
| GB2054556A (en) | Preparation of hydroxy derivatives of 2-isopropylamino-pyrimidine | |
| CA1125762A (en) | Dihydronicotinic acid derivatives and process for the preparation thereof | |
| IE44350B1 (en) | 6 ,17-dihydroxy-7a-(lower alkoxy)carbonyl-3-oxo-17a-pregn-4-ene-21-carboxylic acid -lactones and congeners | |
| US3518269A (en) | 1-oxime substituted quinolizines | |
| US3855406A (en) | Thiaxanthene derivatives useful for treating peptic ulcers | |
| US4179443A (en) | 6-Chloro-1,2,3,4-tetrahydrocarbazole-2-one | |
| DE2237361A1 (de) | (5-indolyloxy)-essigsaeure-derivate und verfahren zur herstellung derselben | |
| US20040176591A1 (en) | Novel synthesis and crystallization of peperazine ring-containing compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |