JPS58103393A - キノリンカルボン酸誘導体 - Google Patents

キノリンカルボン酸誘導体

Info

Publication number: JPS58103393A
Authority: JP; Japan
Prior art keywords: carboxylic acid; quinoline; oxo; fluoro; thiazolo
Prior art date: 1981-12-12
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.): Granted

Application number

JP20067081A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0259152B2 (cs

Inventor

Hiroshi Enomoto

宏榎本

Masahiro Kise

黄瀬　正博

Masakuni Ozaki

尾崎　正邦

Masahiko Kitano

北野　正彦

Iwao Morita

森田　岩男

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nippon Shinyaku Co Ltd

Original Assignee

Nippon Shinyaku Co Ltd

Priority date (The priority date 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 date listed.)

1981-12-12

Filing date

1981-12-12

Publication date

1983-06-20

1981-12-12 Application filed by Nippon Shinyaku Co Ltd filed Critical Nippon Shinyaku Co Ltd

1981-12-12 Priority to JP20067081A priority Critical patent/JPS58103393A/ja

1982-02-11 Priority to DE8282101006T priority patent/DE3267485D1/de

1982-02-11 Priority to EP19820101006 priority patent/EP0058392B1/en

1983-06-20 Publication of JPS58103393A publication Critical patent/JPS58103393A/ja

1990-12-11 Publication of JPH0259152B2 publication Critical patent/JPH0259152B2/ja

Status Granted legal-status Critical Current

Links

LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 title description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
150000003839 salts Chemical class 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
229910052708 sodium Inorganic materials 0.000 claims abstract description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
229910052700 potassium Inorganic materials 0.000 claims abstract description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
229910052744 lithium Inorganic materials 0.000 claims abstract 2
-1 hydroxy, Substituted phenyl Chemical group 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 8
239000011734 sodium Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
239000011591 potassium Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 3
239000000470 constituent Substances 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
239000011575 calcium Chemical group 0.000 claims 1
229910052791 calcium Chemical group 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
125000005633 phthalidyl group Chemical group 0.000 claims 1
229920006395 saturated elastomer Polymers 0.000 claims 1
229930195734 saturated hydrocarbon Natural products 0.000 claims 1
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 1
229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 abstract description 155
150000001875 compounds Chemical class 0.000 abstract description 133
238000000034 method Methods 0.000 abstract description 14
238000010438 heat treatment Methods 0.000 abstract description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 6
229910052794 bromium Inorganic materials 0.000 abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
241000589517 Pseudomonas aeruginosa Species 0.000 abstract description 3
229910052731 fluorine Inorganic materials 0.000 abstract description 3
229910052736 halogen Inorganic materials 0.000 abstract description 3
125000003396 thiol group Chemical group [H]S* 0.000 abstract description 3
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract description 2
241000192125 Firmicutes Species 0.000 abstract description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 2
229910052801 chlorine Inorganic materials 0.000 abstract description 2
239000000463 material Substances 0.000 abstract description 2
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 3
QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical class S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 abstract 2
125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
239000004599 antimicrobial Substances 0.000 abstract 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
125000005843 halogen group Chemical group 0.000 abstract 1
229940117953 phenylisothiocyanate Drugs 0.000 abstract 1
238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 245
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 164
239000013078 crystal Substances 0.000 description 134
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 130
238000000921 elemental analysis Methods 0.000 description 82
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 69
238000002844 melting Methods 0.000 description 67
230000008018 melting Effects 0.000 description 67
238000000862 absorption spectrum Methods 0.000 description 63
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 59
238000001228 spectrum Methods 0.000 description 55
238000000354 decomposition reaction Methods 0.000 description 52
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
238000010992 reflux Methods 0.000 description 44
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 42
238000003756 stirring Methods 0.000 description 42
239000000203 mixture Substances 0.000 description 39
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 35
238000006243 chemical reaction Methods 0.000 description 34
239000000243 solution Substances 0.000 description 29
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 28
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 26
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
229910002091 carbon monoxide Inorganic materials 0.000 description 25
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 20
239000002253 acid Substances 0.000 description 20
229910052799 carbon Inorganic materials 0.000 description 18
238000001816 cooling Methods 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
239000005457 ice water Substances 0.000 description 15
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
239000002904 solvent Substances 0.000 description 14
229910000027 potassium carbonate Inorganic materials 0.000 description 13
FJWYVZDPWAPMGN-UHFFFAOYSA-N ethyl quinoline-4-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)=CC=NC2=C1 FJWYVZDPWAPMGN-UHFFFAOYSA-N 0.000 description 12
238000005259 measurement Methods 0.000 description 11
235000011121 sodium hydroxide Nutrition 0.000 description 11
238000005406 washing Methods 0.000 description 10
230000002378 acidificating effect Effects 0.000 description 9
230000000844 anti-bacterial effect Effects 0.000 description 9
208000015181 infectious disease Diseases 0.000 description 9
239000000047 product Substances 0.000 description 9
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
239000003242 anti bacterial agent Substances 0.000 description 8
238000001035 drying Methods 0.000 description 8
239000000843 powder Substances 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
241000894006 Bacteria Species 0.000 description 7
239000005973 Carvone Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
241000699670 Mus sp. Species 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
239000000126 substance Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
125000000623 heterocyclic group Chemical group 0.000 description 6
239000007924 injection Substances 0.000 description 6
238000002347 injection Methods 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
238000010898 silica gel chromatography Methods 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
VXGYRCVTBHVXMZ-UHFFFAOYSA-N quinoline-6-carboxylic acid Chemical compound N1=CC=CC2=CC(C(=O)O)=CC=C21 VXGYRCVTBHVXMZ-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
230000001225 therapeutic effect Effects 0.000 description 5
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 4
VSXMSYVKRKWKDG-UHFFFAOYSA-N 3-ethyl-1,2-oxazol-5-amine Chemical compound CCC=1C=C(N)ON=1 VSXMSYVKRKWKDG-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
150000001241 acetals Chemical class 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
238000009835 boiling Methods 0.000 description 4
QXFRXARJPDHNTC-UHFFFAOYSA-N ethyl 7-chloro-6-fluoro-4-oxo-2-sulfanyl-1h-quinoline-3-carboxylate Chemical compound ClC1=C(F)C=C2C(=O)C(C(=O)OCC)=C(S)NC2=C1 QXFRXARJPDHNTC-UHFFFAOYSA-N 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
230000037396 body weight Effects 0.000 description 3
238000004364 calculation method Methods 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
239000013256 coordination polymer Substances 0.000 description 3
238000011161 development Methods 0.000 description 3
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
239000007789 gas Substances 0.000 description 3
QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
230000036325 urinary excretion Effects 0.000 description 3
CSVFWMMPUJDVKH-UHFFFAOYSA-N 1,1-dichloropropan-2-one Chemical compound CC(=O)C(Cl)Cl CSVFWMMPUJDVKH-UHFFFAOYSA-N 0.000 description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
238000007605 air drying Methods 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
229910052792 caesium Inorganic materials 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
238000002512 chemotherapy Methods 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 2
QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 2
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
150000003997 cyclic ketones Chemical class 0.000 description 2
229940117389 dichlorobenzene Drugs 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
210000003734 kidney Anatomy 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
238000010899 nucleation Methods 0.000 description 2
239000002674 ointment Substances 0.000 description 2
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
VLCMRTMCMQJSKM-UHFFFAOYSA-N phenyl-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C1=CC=CC=C1 VLCMRTMCMQJSKM-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000011084 recovery Methods 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
208000019206 urinary tract infection Diseases 0.000 description 2
210000002700 urine Anatomy 0.000 description 2
ATWLRNODAYAMQS-UHFFFAOYSA-N 1,1-dibromopropane Chemical compound CCC(Br)Br ATWLRNODAYAMQS-UHFFFAOYSA-N 0.000 description 1
SHKKTLSDGJRCTR-UHFFFAOYSA-N 1,2-dibromoethylbenzene Chemical compound BrCC(Br)C1=CC=CC=C1 SHKKTLSDGJRCTR-UHFFFAOYSA-N 0.000 description 1
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
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Landscapes

Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP20067081A 1981-02-18 1981-12-12 キノリンカルボン酸誘導体 Granted JPS58103393A (ja)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
JP20067081A JPS58103393A (ja)	1981-12-12	1981-12-12	キノリンカルボン酸誘導体
DE8282101006T DE3267485D1 (en)	1981-02-18	1982-02-11	Substituted carboxylic acid derivatives
EP19820101006 EP0058392B1 (en)	1981-02-18	1982-02-11	Substituted carboxylic acid derivatives

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP20067081A JPS58103393A (ja)	1981-12-12	1981-12-12	キノリンカルボン酸誘導体

Publications (2)

Publication Number	Publication Date
JPS58103393A true JPS58103393A (ja)	1983-06-20
JPH0259152B2 JPH0259152B2 (cs)	1990-12-11

Family

ID=16428276

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP20067081A Granted JPS58103393A (ja)	1981-02-18	1981-12-12	キノリンカルボン酸誘導体

Country Status (1)

Country	Link
JP (1)	JPS58103393A (cs)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1992000280A1 (fr) *	1990-06-22	1992-01-09	Nippon Shinyaku Co., Ltd.	Derive de quinoline et production de ce derive
WO1993025532A1 (fr) *	1992-06-16	1993-12-23	Nippon Shinyaku Co., Ltd.	Derive d'acide carboxylique et production de ce derive
WO1994004506A1 (fr) *	1992-08-25	1994-03-03	Nippon Shinyaku Co., Ltd.	Procede de production d'un derive d'acide quinoleine-carboxilique

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6444717A (en) *	1987-08-11	1989-02-17	Riken Plast Kogyo Kk	Apparatus for molding container made of synthetic resin

1981
- 1981-12-12 JP JP20067081A patent/JPS58103393A/ja active Granted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6444717A (en) *	1987-08-11	1989-02-17	Riken Plast Kogyo Kk	Apparatus for molding container made of synthetic resin

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1992000280A1 (fr) *	1990-06-22	1992-01-09	Nippon Shinyaku Co., Ltd.	Derive de quinoline et production de ce derive
WO1993025532A1 (fr) *	1992-06-16	1993-12-23	Nippon Shinyaku Co., Ltd.	Derive d'acide carboxylique et production de ce derive
WO1994004506A1 (fr) *	1992-08-25	1994-03-03	Nippon Shinyaku Co., Ltd.	Procede de production d'un derive d'acide quinoleine-carboxilique

Also Published As

Publication number	Publication date
JPH0259152B2 (cs)	1990-12-11

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KR100226114B1 (ko)	1999-10-15	항증식 작용을 가진 퀴나졸린 화합물
AU668694B2 (en)	1996-05-16	Saccharin derivative proteolytic enzyme inhibitors
AU2019356011B2 (en)	2025-02-06	Fused pyrrolines which act as Ubiquitin-Specific Protease 30 (USP30) inhibitors
DE69628368T2 (de)	2004-03-18	Heterocyclische Verbindungen, ihre Herstellung und Verwendung
KR910002837B1 (ko)	1991-05-06	피롤로[1,2-a]이미다졸 및 이미다조[1,2-a]피리딘 유도체의 제조방법
EP0249043B1 (en)	1993-08-04	Quinolinecarboxylic acid derivatives
Segawa et al.	1992	Studies on pyridonecarboxylic acids. 1. Synthesis and antibacterial evaluation of 7-substituted-6-halo-4-oxo-4H-[1, 3] thiazeto [3, 2-a] quinoline-3-carboxylic acids
JPH0314578A (ja)	1991-01-23	新規抗微生物ラクタム‐キノロン類
JPH0327380A (ja)	1991-02-05	１ｈ―イミダゾ〔４，５―ｃ〕キノリン―４―アミン類
JPS6034967A (ja)	1985-02-22	ナフチリジノン，ピリドンおよびキノロンの融合三環式誘導体ならびに対応するチオン類
HU183087B (en)	1984-04-28	Process for producing substituted pyrano- and thiopyrano-quinolines
AU2004220176A1 (en)	2004-09-23	Novel fused triazolones and the uses thereof
EP0058392B1 (en)	1985-11-21	Substituted carboxylic acid derivatives
AU640300B2 (en)	1993-08-19	Pharmacologically active substituted oxybenzamides
US5488062A (en)	1996-01-30	2-saccharinylmethyl heterocyclic carboxylates useful as proteolytic enzyme inhibitors and compositions and method of use thereof
AU2022412821A1 (en)	2024-08-01	Aromatic heterocyclic compounds, preparation method therefor and uses thereof
CA2048684A1 (en)	1990-10-02	Antiallergy agents
JPH07503248A (ja)	1995-04-06	複素三環式誘導体、それらの製造法およびそれらを含有する医薬組成物
JPS6335574A (ja)	1988-02-16	新規１，４−ベンゾジアゼピン類、それらの製法及び用途
JPS5821681A (ja)	1983-02-08	ペニシリン類、その製造方法及びそれを含有する医薬組成物
JPS5888314A (ja)	1983-05-26	強心剤
US3830813A (en)	1974-08-20	2-(5'-nitro-2'-furyl)-thieno(2,3-d)pyridines and salts thereof
CA1303612C (en)	1992-06-16	Derivatives of quinolinecarboxylic acid
JPH0259152B2 (cs)	1990-12-11

JPS58103393A - キノリンカルボン酸誘導体 - Google Patents

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Priority Applications (3)

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Publications (2)

Family

ID=16428276

Family Applications (1)

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Cited By (3)

Citations (1)

Patent Citations (1)

Cited By (3)

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