CA1153374A - Piperazinylbenzoheterocyclic compounds - Google Patents
Piperazinylbenzoheterocyclic compoundsInfo
- Publication number
- CA1153374A CA1153374A CA000325376A CA325376A CA1153374A CA 1153374 A CA1153374 A CA 1153374A CA 000325376 A CA000325376 A CA 000325376A CA 325376 A CA325376 A CA 325376A CA 1153374 A CA1153374 A CA 1153374A
- Authority
- CA
- Canada
- Prior art keywords
- oxo
- dihydro
- carboxylic acid
- methyl
- compound
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 167
- 238000000034 method Methods 0.000 claims abstract description 76
- -1 p-toluene-sulfonyl group Chemical group 0.000 claims abstract description 58
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 125000005843 halogen group Chemical group 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 8
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- KASNWJJVSFNDJM-UHFFFAOYSA-N 1-azatricyclo[7.3.1.05,13]trideca-3,5,7,9(13),10-pentaene-3-carboxylic acid Chemical compound C1=CCN2CC(C(=O)O)=CC3=CC=CC1=C32 KASNWJJVSFNDJM-UHFFFAOYSA-N 0.000 claims description 87
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 64
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 62
- 238000006243 chemical reaction Methods 0.000 claims description 59
- 239000000126 substance Substances 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 22
- 238000006460 hydrolysis reaction Methods 0.000 claims description 16
- 230000007062 hydrolysis Effects 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- RAYMXZBXQCGRGX-UHFFFAOYSA-N quinoline-5-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=N1 RAYMXZBXQCGRGX-UHFFFAOYSA-N 0.000 claims description 13
- 125000005270 trialkylamine group Chemical group 0.000 claims description 10
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 7
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- DWOWONBGQCFTPH-UHFFFAOYSA-N 6-fluoro-2-methyl-5-(4-methylpiperazin-1-yl)-9-oxo-1-azatricyclo[6.3.1.04,12]dodeca-4(12),5,7,10-tetraene-10-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)CC3=C1N1CCN(C)CC1 DWOWONBGQCFTPH-UHFFFAOYSA-N 0.000 claims description 2
- XTZMUAFJCNOPJB-UHFFFAOYSA-N 6-fluoro-5-(4-formylpiperazin-1-yl)-2-methyl-9-oxo-1-azatricyclo[6.3.1.04,12]dodeca-4(12),5,7,10-tetraene-10-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)CC3=C1N1CCN(C=O)CC1 XTZMUAFJCNOPJB-UHFFFAOYSA-N 0.000 claims description 2
- ZUQIMGVUSZQLFX-UHFFFAOYSA-N 6-fluoro-5-iodo-2-methyl-9-oxo-1-azatricyclo[6.3.1.04,12]dodeca-4(12),5,7,10-tetraene-10-carboxylic acid Chemical compound C1C(C)N2C=C(C(O)=O)C(=O)C3=C2C1=C(I)C(F)=C3 ZUQIMGVUSZQLFX-UHFFFAOYSA-N 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- RXPKQZBQCRMCSK-UHFFFAOYSA-N 2-methyl-9-oxo-5-piperazin-1-yl-1-azatricyclo[6.3.1.04,12]dodeca-4,6,8(12),10-tetraene-10-carboxylic acid Chemical compound C1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)CC3=C1N1CCNCC1 RXPKQZBQCRMCSK-UHFFFAOYSA-N 0.000 claims 1
- ZWWBXDVZMPJJBE-UHFFFAOYSA-N 8-(1-piperazinyl)-5-methyl-6,7-dihydro-1-oxo-1h,5h-benzo[ij]quinolizine-2-carboxylic acid Chemical compound C1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)CCC3=C1N1CCNCC1 ZWWBXDVZMPJJBE-UHFFFAOYSA-N 0.000 claims 1
- VSTIIDXCUIAQRQ-UHFFFAOYSA-N 9-oxo-5-piperazin-1-yl-1-azatricyclo[6.3.1.04,12]dodeca-4,6,8(12),10-tetraene-10-carboxylic acid Chemical compound C1=CC(=C23)C(=O)C(C(=O)O)=CN2CCC3=C1N1CCNCC1 VSTIIDXCUIAQRQ-UHFFFAOYSA-N 0.000 claims 1
- 125000005208 trialkylammonium group Chemical group 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 abstract description 13
- 239000013078 crystal Substances 0.000 description 88
- 239000000203 mixture Substances 0.000 description 88
- 235000013350 formula milk Nutrition 0.000 description 77
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- 239000000243 solution Substances 0.000 description 71
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
- 238000002844 melting Methods 0.000 description 62
- 230000008018 melting Effects 0.000 description 61
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 55
- 229910001868 water Inorganic materials 0.000 description 53
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 35
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 238000001914 filtration Methods 0.000 description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 29
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 29
- 239000002904 solvent Substances 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 235000019441 ethanol Nutrition 0.000 description 27
- 239000003921 oil Substances 0.000 description 25
- 235000019198 oils Nutrition 0.000 description 25
- 235000011121 sodium hydroxide Nutrition 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 230000002829 reductive effect Effects 0.000 description 24
- 229940083608 sodium hydroxide Drugs 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 20
- 229960005141 piperazine Drugs 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
- 235000011167 hydrochloric acid Nutrition 0.000 description 19
- 229960000443 hydrochloric acid Drugs 0.000 description 19
- 210000002966 serum Anatomy 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 235000002639 sodium chloride Nutrition 0.000 description 18
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 17
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 16
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 12
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- 239000003826 tablet Substances 0.000 description 11
- 229940086542 triethylamine Drugs 0.000 description 11
- 229920002261 Corn starch Polymers 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- 238000000921 elemental analysis Methods 0.000 description 10
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- 230000002401 inhibitory effect Effects 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 9
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- 229920002472 Starch Polymers 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 125000005605 benzo group Chemical group 0.000 description 7
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- 239000004599 antimicrobial Substances 0.000 description 6
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- AKEKKCGPLHMFCI-UHFFFAOYSA-L potassium sodium hydrogen carbonate Chemical compound [Na+].[K+].OC([O-])=O.OC([O-])=O AKEKKCGPLHMFCI-UHFFFAOYSA-L 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- DASZTFGYDXJWBT-UHFFFAOYSA-N quinoline-2-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC=CC2=NC(C(=O)O)=CC=C21 DASZTFGYDXJWBT-UHFFFAOYSA-N 0.000 description 1
- RAYMXZBXQCGRGX-UHFFFAOYSA-M quinoline-5-carboxylate Chemical compound C1=CC=C2C(C(=O)[O-])=CC=CC2=N1 RAYMXZBXQCGRGX-UHFFFAOYSA-M 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 229940115939 shigella sonnei Drugs 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- QZWYXEBIQWJXAR-UHFFFAOYSA-N spiro[1,3-dihydroindene-2,3'-imidazo[1,2-a]pyridine]-2'-one Chemical compound C1C2=CC=CC=C2CC21N1C=CC=CC1=NC2=O QZWYXEBIQWJXAR-UHFFFAOYSA-N 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 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
- 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
- 229930101283 tetracycline Natural products 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000004954 trialkylamino group Chemical group 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940098232 yersinia enterocolitica Drugs 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Applications Claiming Priority (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP53043624A JPS6034957B2 (ja) | 1978-04-12 | 1978-04-12 | ペニシラン酸誘導体 |
| JP43624/78 | 1978-04-12 | ||
| JP10738778A JPS5576875A (en) | 1978-08-31 | 1978-08-31 | Benzo ij quinolizine-2-carboxylic acid derivative and its preparation |
| JP107387/78 | 1978-08-31 | ||
| JP110464/78 | 1978-09-07 | ||
| JP53110464A JPS6037118B2 (ja) | 1978-09-07 | 1978-09-07 | ペニシラン酸誘導体 |
| JP137157/78 | 1978-11-06 | ||
| JP13715778A JPS5564588A (en) | 1978-11-06 | 1978-11-06 | Pyrrolo (3, 2, 1-ij) quinoline-5-carboxylic acid derivative and its preparation |
| JP53141785A JPS6037119B2 (ja) | 1978-11-16 | 1978-11-16 | ペニシラン酸誘導体 |
| JP141785/78 | 1978-11-16 | ||
| JP142731/78 | 1978-11-17 | ||
| JP14273178A JPS5569583A (en) | 1978-11-17 | 1978-11-17 | Pyrido 3,2,1-jk carbazole derivative |
| JP145638/78 | 1978-11-24 | ||
| JP53145638A JPS5951959B2 (ja) | 1978-11-24 | 1978-11-24 | ペニシラン酸誘導体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1153374A true CA1153374A (en) | 1983-09-06 |
Family
ID=27564567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000325376A Expired CA1153374A (en) | 1978-04-12 | 1979-04-11 | Piperazinylbenzoheterocyclic compounds |
Country Status (8)
| Country | Link |
|---|---|
| AU (1) | AU529330B2 (de) |
| CA (1) | CA1153374A (de) |
| CH (1) | CH640853A5 (de) |
| DE (3) | DE2953974C2 (de) |
| FR (1) | FR2422658A1 (de) |
| GB (2) | GB2020279B (de) |
| IT (1) | IT1196531B (de) |
| NL (1) | NL180664C (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5630964A (en) * | 1979-08-22 | 1981-03-28 | Kyorin Pharmaceut Co Ltd | Novel substituted quinolinecarboxylic acid and its preparation |
| JPS5746986A (en) * | 1980-09-02 | 1982-03-17 | Dai Ichi Seiyaku Co Ltd | Pyrido(1,2,3-de)(1,4)benzoxazine derivative |
| JPS57176987A (en) * | 1981-04-24 | 1982-10-30 | Otsuka Pharmaceut Co Ltd | Pyrrolo(3,2,1-ij)quinoline-5-carboxylic acid derivative |
| NO156828C (no) * | 1980-11-10 | 1987-12-02 | Otsuka Pharma Co Ltd | Analogifremgangsm te for fremstilling av antibakterielt virksomme benzoheterocykliske forbindelser. |
| AT380250B (de) * | 1980-12-18 | 1986-04-25 | Otsuka Pharma Co Ltd | Verfahren zur herstellung benzoheterocyclischer verbindungen |
| PH22140A (en) | 1982-06-29 | 1988-06-01 | Daiichi Seiyaku Co | Tricyclic compounds |
| JPS59137482A (ja) * | 1983-01-26 | 1984-08-07 | Otsuka Pharmaceut Co Ltd | ピロロ〔３，２，１，−ｉｊ〕キノリン−５−カルボン酸誘導体 |
| DE3517709A1 (de) * | 1985-01-05 | 1986-07-10 | Bayer Ag | Basische zubereitungen von chinoloncarbonsaeuren |
| CA1253154A (en) * | 1985-05-24 | 1989-04-25 | Atsushi Takagi | Benzo¬ij|quinolizine-2-carboxylic acid derivatives |
| KR900014383A (ko) * | 1989-03-29 | 1990-10-23 | 원본미기재 | 피롤로퀴놀린 유도체, 이의 제조방법 및 이를 사용한 항균제 |
| EP0443381B2 (de) * | 1990-02-14 | 1997-10-22 | Takeda Chemical Industries, Ltd. | Brausemischung, deren Herstellung sowie Verwendung |
| US6488961B1 (en) | 1996-09-20 | 2002-12-03 | Ethypharm, Inc. | Effervescent granules and methods for their preparation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE793524A (fr) * | 1971-12-30 | 1973-06-29 | Riker Laboratories Inc | Acides benzoquinolizine-carboxyliques et leurs derives |
| US3985882A (en) * | 1972-11-02 | 1976-10-12 | Riker Laboratories, Inc. | Substituted benzo[ij]quinolinzine-2-carboxylic acids and derivatives thereof as bactericidal agents |
-
1979
- 1979-04-09 DE DE2953974A patent/DE2953974C2/de not_active Expired - Fee Related
- 1979-04-09 DE DE19792914258 patent/DE2914258A1/de active Granted
- 1979-04-09 DE DE2953973A patent/DE2953973C2/de not_active Expired
- 1979-04-10 IT IT48690/79A patent/IT1196531B/it active
- 1979-04-11 CH CH343379A patent/CH640853A5/de not_active IP Right Cessation
- 1979-04-11 AU AU46037/79A patent/AU529330B2/en not_active Expired
- 1979-04-11 CA CA000325376A patent/CA1153374A/en not_active Expired
- 1979-04-12 FR FR7909338A patent/FR2422658A1/fr active Granted
- 1979-04-12 GB GB7913040A patent/GB2020279B/en not_active Expired
- 1979-04-12 GB GB7913039A patent/GB2019844B/en not_active Expired
- 1979-04-12 NL NLAANVRAGE7902905,A patent/NL180664C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL180664B (nl) | 1986-11-03 |
| DE2953974C2 (de) | 1992-06-25 |
| DE2914258A1 (de) | 1979-10-25 |
| DE2953973A1 (de) | 1982-08-26 |
| IT1196531B (it) | 1988-11-16 |
| DE2953973C2 (de) | 1989-02-02 |
| GB2019844A (en) | 1979-11-07 |
| IT7948690A0 (it) | 1979-04-10 |
| AU4603779A (en) | 1979-10-18 |
| CH640853A5 (de) | 1984-01-31 |
| NL180664C (nl) | 1987-04-01 |
| NL7902905A (nl) | 1979-10-16 |
| GB2020279A (en) | 1979-11-14 |
| DE2914258C2 (de) | 1989-08-03 |
| FR2422658B1 (de) | 1981-12-31 |
| FR2422658A1 (fr) | 1979-11-09 |
| GB2019844B (en) | 1983-01-19 |
| GB2020279B (en) | 1983-02-02 |
| AU529330B2 (en) | 1983-06-02 |
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| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |