CA1077939A - Acide 1-difluomethyl-6,7-methylenedioxy-1,4-dihydro-4-oxo-3-quinolinecarboxylique et ses esters comme agents antibacteriens - Google Patents

Acide 1-difluomethyl-6,7-methylenedioxy-1,4-dihydro-4-oxo-3-quinolinecarboxylique et ses esters comme agents antibacteriens

Info

Publication number: CA1077939A
Authority: CA; Canada
Prior art keywords: compound; acid; oxo; formula; dihydro
Prior art date: 1976-02-23
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

Application number

CA272,396A

Other languages

English (en)

Inventor

Kyu T. Lee

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.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

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.)

1976-02-23

Filing date

1977-02-21

Publication date

1980-05-20

1977-01-14 Priority claimed from US05/758,331 external-priority patent/US4147788A/en

1977-02-21 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1980-05-20 Application granted granted Critical

1980-05-20 Publication of CA1077939A publication Critical patent/CA1077939A/fr

Status Expired legal-status Critical Current

Links

JYJKFMPCGBLLHN-UHFFFAOYSA-N 5-(difluoromethyl)-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid Chemical compound C1=C2C(=O)C(C(=O)O)=CN(C(F)F)C2=CC2=C1OCO2 JYJKFMPCGBLLHN-UHFFFAOYSA-N 0.000 title abstract 2
150000002148 esters Chemical class 0.000 title description 8
230000000844 anti-bacterial effect Effects 0.000 title description 5
229940088710 antibiotic agent Drugs 0.000 title description 2
238000000034 method Methods 0.000 claims description 26
150000001875 compounds Chemical class 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
239000000010 aprotic solvent Substances 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
230000003301 hydrolyzing effect Effects 0.000 claims 2
239000012442 inert solvent Substances 0.000 claims 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 1
241000124008 Mammalia Species 0.000 abstract description 4
208000035143 Bacterial infection Diseases 0.000 abstract 1
125000000278 alkyl amino alkyl group Chemical group 0.000 abstract 1
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238000012360 testing method Methods 0.000 description 11
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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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 description 4
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
KYGZCKSPAKDVKC-UHFFFAOYSA-N Oxolinic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 KYGZCKSPAKDVKC-UHFFFAOYSA-N 0.000 description 4
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
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LXCFILQKKLGQFO-UHFFFAOYSA-N p-hydroxybenzoic acid methyl ester Natural products COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
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QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
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MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
NAMDIHYPBYVYAP-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOCCOC.COCCOCCOC NAMDIHYPBYVYAP-UHFFFAOYSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
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QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
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FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
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QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
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ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
231100000645 Reed–Muench method Toxicity 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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239000007864 aqueous solution Substances 0.000 description 1
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
238000000576 coating method Methods 0.000 description 1
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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
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150000002334 glycols Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
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235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
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230000037023 motor activity Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
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239000002674 ointment Substances 0.000 description 1
235000019629 palatability Nutrition 0.000 description 1
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HTYIXCKSEQQCJO-UHFFFAOYSA-N phenaglycodol Chemical compound CC(C)(O)C(C)(O)C1=CC=C(Cl)C=C1 HTYIXCKSEQQCJO-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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239000011591 potassium Substances 0.000 description 1
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239000000843 powder Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
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LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
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235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
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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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA272,396A 1976-02-23 1977-02-21 Acide 1-difluomethyl-6,7-methylenedioxy-1,4-dihydro-4-oxo-3-quinolinecarboxylique et ses esters comme agents antibacteriens Expired CA1077939A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US66085276A	1976-02-23	1976-02-23
US05/758,331 US4147788A (en)	1976-02-23	1977-01-14	Antibacterials: 1-difluoromethyl-6,7-methylenedioxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and its esters

Publications (1)

Publication Number	Publication Date
CA1077939A true CA1077939A (fr)	1980-05-20

Family

ID=27098199

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA272,396A Expired CA1077939A (fr)	1976-02-23	1977-02-21	Acide 1-difluomethyl-6,7-methylenedioxy-1,4-dihydro-4-oxo-3-quinolinecarboxylique et ses esters comme agents antibacteriens

Country Status (24)

Country	Link
JP (1)	JPS52118496A (fr)
AR (1)	AR212613A1 (fr)
AU (1)	AU510359B2 (fr)
CA (1)	CA1077939A (fr)
CH (1)	CH631986A5 (fr)
DD (1)	DD129450A5 (fr)
DE (1)	DE2706781A1 (fr)
DK (1)	DK76077A (fr)
ES (2)	ES456162A1 (fr)
FI (1)	FI66175C (fr)
FR (2)	FR2341580A1 (fr)
GB (1)	GB1517674A (fr)
GR (1)	GR62469B (fr)
IE (1)	IE44701B1 (fr)
IL (1)	IL51518A (fr)
LU (1)	LU76818A1 (fr)
MX (1)	MX4877E (fr)
NL (1)	NL7701884A (fr)
NO (2)	NO147069C (fr)
PH (1)	PH13084A (fr)
PT (1)	PT66219B (fr)
SE (1)	SE434400B (fr)
SU (1)	SU626700A3 (fr)
YU (2)	YU49277A (fr)

1977
- 1977-01-27 SE SE7700871A patent/SE434400B/xx unknown
- 1977-02-17 DE DE19772706781 patent/DE2706781A1/de not_active Withdrawn
- 1977-02-21 PT PT66219A patent/PT66219B/pt unknown
- 1977-02-21 AR AR266624A patent/AR212613A1/es active
- 1977-02-21 AU AU22488/77A patent/AU510359B2/en not_active Expired
- 1977-02-21 CA CA272,396A patent/CA1077939A/fr not_active Expired
- 1977-02-22 NL NL7701884A patent/NL7701884A/xx not_active Application Discontinuation
- 1977-02-22 IL IL51518A patent/IL51518A/xx unknown
- 1977-02-22 GR GR52825A patent/GR62469B/el unknown
- 1977-02-22 MX MX775452U patent/MX4877E/es unknown
- 1977-02-22 FI FI770567A patent/FI66175C/fi not_active IP Right Cessation
- 1977-02-22 NO NO770580A patent/NO147069C/no unknown
- 1977-02-22 DK DK76077A patent/DK76077A/da not_active Application Discontinuation
- 1977-02-22 FR FR7705060A patent/FR2341580A1/fr active Granted
- 1977-02-22 DD DD7700197500A patent/DD129450A5/xx unknown
- 1977-02-22 PH PH19479A patent/PH13084A/en unknown
- 1977-02-22 LU LU76818A patent/LU76818A1/xx unknown
- 1977-02-22 SU SU772455503A patent/SU626700A3/ru active
- 1977-02-22 ES ES456162A patent/ES456162A1/es not_active Expired
- 1977-02-22 GB GB7417/77A patent/GB1517674A/en not_active Expired
- 1977-02-22 YU YU00492/77A patent/YU49277A/xx unknown
- 1977-02-23 JP JP1974977A patent/JPS52118496A/ja active Pending
- 1977-02-23 CH CH226677A patent/CH631986A5/de not_active IP Right Cessation
- 1977-02-23 IE IE380/77A patent/IE44701B1/en unknown
1978
- 1978-02-27 ES ES467360A patent/ES467360A1/es not_active Expired
- 1978-05-03 FR FR7813145A patent/FR2378034A1/fr active Granted
1982
- 1982-05-06 NO NO821500A patent/NO149138C/no unknown
- 1982-06-30 YU YU01419/82A patent/YU141982A/xx unknown

Also Published As

Publication number	Publication date
CH631986A5 (en)	1982-09-15
IE44701L (en)	1977-08-23
NO147069B (no)	1982-10-18
IE44701B1 (en)	1982-02-24
NO770580L (no)	1977-08-24
FR2378034A1 (fr)	1978-08-18
FR2378034B1 (fr)	1981-01-30
FR2341580B1 (fr)	1979-08-03
ES467360A1 (es)	1979-10-16
AR212613A1 (es)	1978-08-15
FI66175B (fi)	1984-05-31
AU2248877A (en)	1978-08-31
FI770567A7 (fr)	1977-08-24
DK76077A (da)	1977-08-24
FR2341580A1 (fr)	1977-09-16
ES456162A1 (es)	1978-05-01
SE7700871L (sv)	1977-08-24
YU141982A (en)	1982-10-31
NO147069C (no)	1983-01-26
NO821500L (no)	1977-08-24
FI66175C (fi)	1984-09-10
IL51518A0 (en)	1977-04-29
DE2706781A1 (de)	1977-09-01
DD129450A5 (de)	1978-01-18
JPS52118496A (en)	1977-10-04
PT66219B (en)	1978-07-14
GR62469B (en)	1979-04-13
IL51518A (en)	1980-10-26
YU49277A (en)	1982-10-31
PH13084A (en)	1979-11-23
MX4877E (es)	1982-11-26
NO149138C (no)	1984-02-29
AU510359B2 (en)	1980-06-19
SE434400B (sv)	1984-07-23
NO149138B (no)	1983-11-14
GB1517674A (en)	1978-07-12
PT66219A (en)	1977-03-01
LU76818A1 (fr)	1978-04-13
SU626700A3 (ru)	1978-09-30
NL7701884A (nl)	1977-08-25

Legal Events

Date	Code	Title	Description
1997-05-20	MKEX	Expiry

Publication	Publication Date	Title
US3287458A (en)	1966-11-22	1, 4-dihydro-1-lower alkyl-6, 7-methylene-dioxy-4-oxo-3-quinoline-carboxylic acid
DE2560549C2 (fr)	1990-08-16
SU1598873A3 (ru)	1990-10-07	Способ получени производных хинолина или их фармацевтически приемлемых сложных эфиров или фармацевтически приемлемых аддитивных солей кислоты
JPH0316344B2 (fr)	1991-03-05
US3506667A (en)	1970-04-14	Furo quinoline carboxylates
EP0723544A1 (fr)	1996-07-31	CARBAMATES D'ALCOXYALKYLE OBTENUS A PARTIR D'IMIDAZOL(1,2-a)PYRIDINES
HK10491A (en)	1991-02-13	7-(pyrrol-1-yl)-1-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and 7-(pyrrol-1-yl)-1-ethyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid derivatives, their preparation and use as medicaments
DE2362553A1 (de)	1974-06-20	Neue piperazinderivate
EP0090424A1 (fr)	1983-10-05	Dérivés de la quinolone et leur préparation
CA1077939A (fr)	1980-05-20	Acide 1-difluomethyl-6,7-methylenedioxy-1,4-dihydro-4-oxo-3-quinolinecarboxylique et ses esters comme agents antibacteriens
DE3153221C2 (fr)	1991-07-04
RU1776257C (ru)	1992-11-15	Способ получени ацилоксипропаноламинов
EP0061056A1 (fr)	1982-09-29	5,6-Diméthylpyrrolo (2,3-b) pyridines, procédé pour leur préparation et leur utilisation comme médicament
US2772280A (en)	1956-11-27	Synthesis of 4-amino-3-isoxazolidone and its derivatives
US4496566A (en)	1985-01-29	Naphthyridine derivatives
CA1218659A (fr)	1987-03-03	Composes a base de 1,3-dioxolo¬4,5-g\|quinoline
DE1795151B2 (de)	1974-08-29	7- eckige Klammer auf D-alpha-Amino-(3-actamidophenylacetamido) eckige Klammer zu -cephalosporansäure
CA1066706A (fr)	1979-11-20	Derives de la 14,15-dihydroeburnamenine
DE69222818T2 (de)	1998-02-19	Kondensierte Naphthyridinderivate
US3503952A (en)	1970-03-31	Azoxybis(2-phenylacrylic acid,3-tropanyl esters)
US4147788A (en)	1979-04-03	Antibacterials: 1-difluoromethyl-6,7-methylenedioxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and its esters
US3673177A (en)	1972-06-27	Substituted 4-(anilinomethylene)-3-galanthamaninones
FR2465733A1 (fr)	1981-03-27	Nouveaux derives imidazolylethoxymethyliques de 1,3-dioxoloquinoleines utiles notamment comme medicaments antibacteriens et antifongiques, leur procede de preparation et compositions therapeutiques et formes pharmaceutiques les contenant
US4216324A (en)	1980-08-05	1-Difluoromethyl-6,7-methylenedioxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
US3287459A (en)	1966-11-22	Carbostyrils, coumarines and thiocoumarines