IL28540A - 4-hydroxy quinoline-3-carboxylic acid ester derivatives - Google Patents

4-hydroxy quinoline-3-carboxylic acid ester derivatives

Info

Publication number: IL28540A
Authority: IL; Israel
Prior art keywords: radical; stands; parts; quinoline; allyloxy
Prior art date: 1966-09-19

Application number

IL28540A

Other languages

English (en)

Original Assignee

Ici 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.)

1966-09-19

Filing date

1967-08-22

Publication date

1971-10-20

1967-08-22 Application filed by Ici Ltd filed Critical Ici Ltd

1971-10-20 Publication of IL28540A publication Critical patent/IL28540A/en

Links

ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 title description 2
-1 alkyl radical Chemical class 0.000 claims description 50
239000000203 mixture Substances 0.000 claims description 32
150000003248 quinolines Chemical class 0.000 claims description 23
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical group ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 10
239000004480 active ingredient Substances 0.000 claims description 8
244000144977 poultry Species 0.000 claims description 8
241001465754 Metazoa Species 0.000 claims description 6
125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 6
235000013305 food Nutrition 0.000 claims description 6
230000003993 interaction Effects 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
208000003495 Coccidiosis Diseases 0.000 claims description 4
206010023076 Isosporiasis Diseases 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
230000032050 esterification Effects 0.000 claims description 4
238000005886 esterification reaction Methods 0.000 claims description 4
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 4
150000003254 radicals Chemical class 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
239000011574 phosphorus Substances 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
239000003377 acid catalyst Substances 0.000 claims description 2
230000000507 anthelmentic effect Effects 0.000 claims description 2
229940124339 anthelmintic agent Drugs 0.000 claims description 2
239000000921 anthelmintic agent Substances 0.000 claims description 2
230000000844 anti-bacterial effect Effects 0.000 claims description 2
239000003224 coccidiostatic agent Substances 0.000 claims description 2
239000003701 inert diluent Substances 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
238000011321 prophylaxis Methods 0.000 claims description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 1
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
150000007942 carboxylates Chemical class 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
239000007952 growth promoter Substances 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
238000010992 reflux Methods 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
240000008042 Zea mays Species 0.000 description 5
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
235000002017 Zea mays subsp mays Nutrition 0.000 description 5
235000005822 corn Nutrition 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
125000005336 allyloxy group Chemical group 0.000 description 3
150000001448 anilines Chemical class 0.000 description 3
UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000007858 starting material Substances 0.000 description 3
PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 2
241000237502 Ostreidae Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
IXWIAFSBWGYQOE-UHFFFAOYSA-M aluminum;magnesium;oxygen(2-);silicon(4+);hydroxide;tetrahydrate Chemical compound O.O.O.O.[OH-].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Mg+2].[Al+3].[Si+4].[Si+4].[Si+4].[Si+4] IXWIAFSBWGYQOE-UHFFFAOYSA-M 0.000 description 2
MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 2
230000001165 anti-coccidial effect Effects 0.000 description 2
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
LQAWZEZWVLAIHL-UHFFFAOYSA-N diethyl 2-(methoxymethylidene)propanedioate Chemical compound CCOC(=O)C(=COC)C(=O)OCC LQAWZEZWVLAIHL-UHFFFAOYSA-N 0.000 description 2
RHFZTBSULNJWEI-UHFFFAOYSA-N dimethyl 2-(methoxymethylidene)propanedioate Chemical compound COC=C(C(=O)OC)C(=O)OC RHFZTBSULNJWEI-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
235000020636 oyster Nutrition 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000000069 prophylactic effect Effects 0.000 description 2
239000001117 sulphuric acid Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
MMYKTRPLXXWLBC-UHFFFAOYSA-N 1-bromo-2-ethoxyethane Chemical compound CCOCCBr MMYKTRPLXXWLBC-UHFFFAOYSA-N 0.000 description 1
VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
IRSVDHPYXFLLDS-UHFFFAOYSA-N 2,4-dichloro-1-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1Cl IRSVDHPYXFLLDS-UHFFFAOYSA-N 0.000 description 1
ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 1
YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
RSSAOYGNGJHIPY-UHFFFAOYSA-N 2-anilino-1,3-dioxane-4,6-dione Chemical compound O1C(=O)CC(=O)OC1NC1=CC=CC=C1 RSSAOYGNGJHIPY-UHFFFAOYSA-N 0.000 description 1
JJFOBACUIRKUPN-UHFFFAOYSA-N 2-bromoethoxybenzene Chemical compound BrCCOC1=CC=CC=C1 JJFOBACUIRKUPN-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
229940093475 2-ethoxyethanol Drugs 0.000 description 1
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
SDEBYHVDMCQKNZ-UHFFFAOYSA-N 4-methoxy-6-piperazin-1-ylpyrimidine;hydrochloride Chemical compound Cl.C1=NC(OC)=CC(N2CCNCC2)=N1 SDEBYHVDMCQKNZ-UHFFFAOYSA-N 0.000 description 1
STAAMFWKDIAVEO-UHFFFAOYSA-N 4-nitro-2-phenylmethoxyphenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1OCC1=CC=CC=C1 STAAMFWKDIAVEO-UHFFFAOYSA-N 0.000 description 1
XJNPNXSISMKQEX-UHFFFAOYSA-N 4-nitrocatechol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1O XJNPNXSISMKQEX-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 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
241000499566 Eimeria brunetti Species 0.000 description 1
241000499563 Eimeria necatrix Species 0.000 description 1
241000223932 Eimeria tenella Species 0.000 description 1
241000209140 Triticum Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
MMCPOSDMTGQNKG-UJZMCJRSSA-N aniline;hydrochloride Chemical compound Cl.N[14C]1=[14CH][14CH]=[14CH][14CH]=[14CH]1 MMCPOSDMTGQNKG-UJZMCJRSSA-N 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229940124536 anticoccidial agent Drugs 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
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 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000011973 solid acid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
- 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Quinoline Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

IL28540A 1966-09-19 1967-08-22 4-hydroxy quinoline-3-carboxylic acid ester derivatives IL28540A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB41718/66A GB1138540A (en)	1966-09-19	1966-09-19	Quinoline derivatives

Publications (1)

Publication Number	Publication Date
IL28540A true IL28540A (en)	1971-10-20

Family

ID=10421042

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL28540A IL28540A (en)	1966-09-19	1967-08-22	4-hydroxy quinoline-3-carboxylic acid ester derivatives

Country Status (10)

Country	Link
US (1)	US3534043A (da)
BE (1)	BE704062A (da)
CH (1)	CH494225A (da)
DE (1)	DE1695285A1 (da)
DK (1)	DK120132B (da)
FR (1)	FR1560273A (da)
GB (1)	GB1138540A (da)
IL (1)	IL28540A (da)
NL (1)	NL6712788A (da)
SE (1)	SE330696B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5729564A (en) *	1996-07-31	1998-03-17	Visx, Incorporated	Electrostatic precipitator for a gas discharge laser
WO2014158916A1 (en) *	2013-03-14	2014-10-02	Dart Neuroscience, Llc	Substituted naphthyridine and quinoline compounds as mao inhibitors

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1505313A (fr) *	1962-04-09	1967-12-15	Norwich Pharma Co	Esters d'alkyle inférieur des acides 6, 7-dialkoxy (inférieur)-4-hydroxy-3-quinoléine carboxyliques et leur procédé de préparation
US3414576A (en) *	1965-02-19	1968-12-03	Ici Ltd	7-n-dodecyloxy and 7-benzyloxy-4-hydroxy-3-carbalkoxy quinolines

1966
- 1966-09-19 GB GB41718/66A patent/GB1138540A/en not_active Expired
1967
- 1967-08-17 US US661234A patent/US3534043A/en not_active Expired - Lifetime
- 1967-08-21 DE DE19671695285 patent/DE1695285A1/de active Pending
- 1967-08-22 IL IL28540A patent/IL28540A/en unknown
- 1967-08-31 SE SE12104/67A patent/SE330696B/xx unknown
- 1967-09-12 DK DK457267AA patent/DK120132B/da unknown
- 1967-09-19 BE BE704062D patent/BE704062A/xx unknown
- 1967-09-19 CH CH1308367A patent/CH494225A/de not_active IP Right Cessation
- 1967-09-19 FR FR1560273D patent/FR1560273A/fr not_active Expired
- 1967-09-19 NL NL6712788A patent/NL6712788A/xx unknown

Also Published As

Publication number	Publication date
GB1138540A (en)	1969-01-01
DK120132B (da)	1971-04-13
BE704062A (da)	1968-03-19
US3534043A (en)	1970-10-13
CH494225A (de)	1970-07-31
SE330696B (da)	1970-11-30
FR1560273A (da)	1969-03-21
NL6712788A (da)	1968-03-20
DE1695285A1 (de)	1971-03-18

Publication	Publication Date	Title
US3472859A (en)	1969-10-14	1-alkyl-1,4-dihydro-4-oxo-3 quinoline-carboxylic acids and esters
EP0167763B1 (de)	1988-08-03	7-Amino-1-cyclopropyl-6,8-dihalogen-1,4-dihydro-4-oxo-3-chinolincarbonsäuren, Verfahren zur ihrer Herstellung sowie diese enthaltende antibakterielle Mittel
US4620007A (en)	1986-10-28	6-fluoro-7-chloro-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
US4559341A (en)	1985-12-17	Quinolonecarboxylic acids and antibacterial agents containing these compounds
EP0126355A1 (de)	1984-11-28	7-Amino-1-cyclopropyl-6,8-difluor-1,4-dihydro-4-oxo-3-chinolincarbonsäuren, Verfahren zu ihrer Herstellung sowie diese enthaltende antibakterielle Mittel
DK157997B (da)	1990-03-12	6-fluor-1,4-dihydro-4-oxo-7-substituerede piperazinylquinolin-3-carboxylsyrederivater og deres farmakologisk acceptable salte samt farmaceutiske sammensaetninger til brug ved behandling af bakterielle sygdomme
HU199821B (en)	1990-03-28	Process for production of derivatives of in 8 position substituated quinoline carbonic acid and medical compositions containing them
US3351525A (en)	1967-11-07	Coccidiostatic compositions and methods of using same
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