HRP960352A2 - Novel coumarin quinoline carboxylic acids - Google Patents

Novel coumarin quinoline carboxylic acids Download PDF

Info

Publication number: HRP960352A2
Authority: HR; Croatia
Prior art keywords: nhch; general formula; compound; co2c2h5; chnh
Prior art date: 1996-07-26

Application number

HR960352A

Other languages

English (en)

Croatian (hr)

Inventor

Mladen Trkovnik

Zrinka Ivezic

Zeljko Kelneric

Ljerka Polak

Original Assignee

Pliva Pharm & Chem Works

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.)

1996-07-26

Filing date

1996-07-26

Publication date

1998-08-31

1996-07-26 Application filed by Pliva Pharm & Chem Works filed Critical Pliva Pharm & Chem Works

1996-07-26 Priority to HR960352A priority Critical patent/HRP960352A2/hr

1997-07-18 Priority to US08/897,057 priority patent/US5908933A/en

1997-07-23 Priority to SI9700197A priority patent/SI9700197B/sl

1997-07-24 Priority to PT97112743T priority patent/PT820998E/pt

1997-07-24 Priority to EP97112743A priority patent/EP0820998B1/de

1997-07-24 Priority to SK1016-97A priority patent/SK101697A3/sk

1997-07-24 Priority to CA002210448A priority patent/CA2210448A1/en

1997-07-24 Priority to ES97112743T priority patent/ES2163694T3/es

1997-07-24 Priority to PL97321308A priority patent/PL321308A1/xx

1997-07-24 Priority to JP9198505A priority patent/JPH1087668A/ja

1997-07-24 Priority to DE69706487T priority patent/DE69706487T2/de

1997-07-24 Priority to AT97112743T priority patent/ATE205211T1/de

1997-07-25 Priority to UA97073970A priority patent/UA45383C2/uk

1997-07-25 Priority to CN97117456A priority patent/CN1075500C/zh

1997-07-25 Priority to BG101796A priority patent/BG63085B1/bg

1997-07-25 Priority to HU9701298A priority patent/HUP9701298A3/hu

1997-07-25 Priority to RU97113254/04A priority patent/RU2166504C2/ru

1997-07-25 Priority to CZ972382A priority patent/CZ238297A3/cs

1998-08-31 Publication of HRP960352A2 publication Critical patent/HRP960352A2/hr

Links

POJLYDQQQIUQNS-UHFFFAOYSA-N N1=C(C=CC2=CC=CC=C12)C(=O)O.O1C(=O)C=CC2=CC=CC=C12 Chemical class N1=C(C=CC2=CC=CC=C12)C(=O)O.O1C(=O)C=CC2=CC=CC=C12 POJLYDQQQIUQNS-UHFFFAOYSA-N 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 18
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 5
229960000956 coumarin Drugs 0.000 claims abstract description 3
235000001671 coumarin Nutrition 0.000 claims abstract description 3
LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims abstract description 3
238000002360 preparation method Methods 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 25
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 9
230000000259 anti-tumor effect Effects 0.000 claims description 3
230000004071 biological effect Effects 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
230000000845 anti-microbial effect Effects 0.000 claims 1
230000000840 anti-viral effect Effects 0.000 claims 1
OUQXVSSHSMCKQD-UHFFFAOYSA-N chromen-2-one;1h-quinolin-2-one Chemical class C1=CC=C2NC(=O)C=CC2=C1.C1=CC=C2OC(=O)C=CC2=C1 OUQXVSSHSMCKQD-UHFFFAOYSA-N 0.000 claims 1
AEEFWKGWOPFEDT-UHFFFAOYSA-N chromen-2-one 2-oxo-1H-quinoline-3-carboxylic acid Chemical class C1=CC=C2OC(=O)C=CC2=C1.C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 AEEFWKGWOPFEDT-UHFFFAOYSA-N 0.000 abstract 2
230000031018 biological processes and functions Effects 0.000 abstract 1
125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 abstract 1
238000005160 1H NMR spectroscopy Methods 0.000 description 17
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 17
238000004458 analytical method Methods 0.000 description 16
238000002844 melting Methods 0.000 description 15
230000008018 melting Effects 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 8
125000000896 monocarboxylic acid group Chemical group 0.000 description 8
SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
239000000243 solution Substances 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 description 6
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 5
235000001968 nicotinic acid Nutrition 0.000 description 5
239000011664 nicotinic acid Substances 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
HMXVDNOGULOYGE-UHFFFAOYSA-N (4-methoxycarbonylphenyl) 4-nitrobenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OC(=O)C1=CC=C([N+]([O-])=O)C=C1 HMXVDNOGULOYGE-UHFFFAOYSA-N 0.000 description 3
241000588724 Escherichia coli Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
KNAPZAUWFKJYGM-UHFFFAOYSA-N ethyl 9-nitro-1,5-dioxo-4h-chromeno[3,4-b]pyridine-2-carboxylate Chemical compound [O-][N+](=O)C1=CC=C2OC(=O)C(NC=C(C3=O)C(=O)OCC)=C3C2=C1 KNAPZAUWFKJYGM-UHFFFAOYSA-N 0.000 description 3
FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 3
210000002950 fibroblast Anatomy 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
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 2
244000063299 Bacillus subtilis Species 0.000 description 2
235000014469 Bacillus subtilis Nutrition 0.000 description 2
206010006187 Breast cancer Diseases 0.000 description 2
208000026310 Breast neoplasm Diseases 0.000 description 2
206010008342 Cervix carcinoma Diseases 0.000 description 2
241000194032 Enterococcus faecalis Species 0.000 description 2
206010023825 Laryngeal cancer Diseases 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
206010061902 Pancreatic neoplasm Diseases 0.000 description 2
241000193996 Streptococcus pyogenes Species 0.000 description 2
208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 2
201000010881 cervical cancer Diseases 0.000 description 2
OQYNXVQXCSVEPP-UHFFFAOYSA-N ethyl 3-hydroxy-4,7-dioxo-2,6-dihydropyrano[2,3-g]quinoline-3-carboxylate Chemical compound C1=CC(=O)NC2=C1C=C1OCC(C(=O)OCC)(O)C(=O)C1=C2 OQYNXVQXCSVEPP-UHFFFAOYSA-N 0.000 description 2
MNLARMGWWCGCLU-UHFFFAOYSA-N ethyl 7-fluoro-1,5-dioxo-4h-chromeno[3,4-b]pyridine-2-carboxylate Chemical compound C1=CC(F)=C2OC(=O)C(NC=C(C3=O)C(=O)OCC)=C3C2=C1 MNLARMGWWCGCLU-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
206010023841 laryngeal neoplasm Diseases 0.000 description 2
208000015486 malignant pancreatic neoplasm Diseases 0.000 description 2
201000002528 pancreatic cancer Diseases 0.000 description 2
208000008443 pancreatic carcinoma Diseases 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
MOZYQMRRCLGEIX-UHFFFAOYSA-N 7-fluoro-1,5-dioxo-4h-chromeno[3,4-b]pyridine-2-carboxylic acid Chemical compound C1=CC(F)=C2OC(=O)C(NC=C(C3=O)C(=O)O)=C3C2=C1 MOZYQMRRCLGEIX-UHFFFAOYSA-N 0.000 description 1
HFFYTAGPNFMIDU-UHFFFAOYSA-N 7-fluoro-1,5-dioxo-4h-chromeno[3,4-b]pyridine-3-carboxylic acid Chemical compound C12=CC=CC(F)=C2OC(=O)C2=C1C(=O)C=C(C(=O)O)N2 HFFYTAGPNFMIDU-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
241000943303 Enterococcus faecalis ATCC 29212 Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000515012 Micrococcus flavus Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
241001148137 Salmonella enterica subsp. enterica serovar Panama Species 0.000 description 1
241001051049 Sporobolus pumilus Species 0.000 description 1
241000676491 Sporobolus subtilis Species 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
ONJZRBLUIQDRLI-UHFFFAOYSA-N chromen-2-one propanedioic acid Chemical class OC(=O)CC(O)=O.C1=CC=C2OC(=O)C=CC2=C1 ONJZRBLUIQDRLI-UHFFFAOYSA-N 0.000 description 1
-1 coumarin malonate ester Chemical class 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
210000002615 epidermis Anatomy 0.000 description 1
ZQVMCLBNBIBRGM-UHFFFAOYSA-N ethyl 1,5-dioxo-4h-chromeno[3,4-b]pyridine-2-carboxylate Chemical compound C1=CC=C2OC(=O)C(NC=C(C3=O)C(=O)OCC)=C3C2=C1 ZQVMCLBNBIBRGM-UHFFFAOYSA-N 0.000 description 1
BZCSJNPIUJVOQF-UHFFFAOYSA-N ethyl 9-amino-1,5-dioxo-4h-chromeno[3,4-b]pyridine-2-carboxylate Chemical compound NC1=CC=C2OC(=O)C(NC=C(C3=O)C(=O)OCC)=C3C2=C1 BZCSJNPIUJVOQF-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
201000004962 larynx cancer Diseases 0.000 description 1
244000005700 microbiome Species 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 1
229960001180 norfloxacin Drugs 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- 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
- 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
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- C07D491/12—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 three hetero rings
- C07D491/14—Ortho-condensed systems

Landscapes

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

HR960352A 1996-07-26 1996-07-26 Novel coumarin quinoline carboxylic acids HRP960352A2 (en)

Priority Applications (18)

Application Number	Priority Date	Filing Date	Title
HR960352A HRP960352A2 (en)	1996-07-26	1996-07-26	Novel coumarin quinoline carboxylic acids
US08/897,057 US5908933A (en)	1996-07-26	1997-07-18	Certain 4H- 1!benzopyrano 3,4-b!pyridine derivatives and their corresponding 6,7-b! and 7,8-b! ring isomers
SI9700197A SI9700197B (sl)	1996-07-26	1997-07-23	Nove kumarin-kinolonske karboksilne kisline in postopki za njihovo pripravo
PT97112743T PT820998E (pt)	1996-07-26	1997-07-24	Novos acidos carboxilicos de benzopiranopiridona e processos para a sua preparacao
EP97112743A EP0820998B1 (de)	1996-07-26	1997-07-24	Benzopyranopyridoncarbonsäuren und Verfahren zu ihrer Herstellung
SK1016-97A SK101697A3 (en)	1996-07-26	1997-07-24	Novel coumarin quinolone carboxylic acids and processes for the preparation thereof
CA002210448A CA2210448A1 (en)	1996-07-26	1997-07-24	Novel coumarin quinolone carboxylic acids and processes for the preparation thereof
ES97112743T ES2163694T3 (es)	1996-07-26	1997-07-24	Acidos benzopiranopiridona carboxilicos y procedimiento para su preparacion.
PL97321308A PL321308A1 (en)	1996-07-26	1997-07-24	Novel coumarin-quinolone carboxylic acids and method of obtaining them
JP9198505A JPH1087668A (ja)	1996-07-26	1997-07-24	新規なクマリンキノロン・カルボン酸及びその製造方法
DE69706487T DE69706487T2 (de)	1996-07-26	1997-07-24	Benzopyranopyridoncarbonsäuren und Verfahren zu ihrer Herstellung
AT97112743T ATE205211T1 (de)	1996-07-26	1997-07-24	Benzopyranopyridoncarbonsäuren und verfahren zu ihrer herstellung
UA97073970A UA45383C2 (uk)	1996-07-26	1997-07-25	Кумаринохінолонкарбонові кислоти та спосіб їх одержання
CN97117456A CN1075500C (zh)	1996-07-26	1997-07-25	香豆素喹诺酮羧酸及其制备方法和用途
BG101796A BG63085B1 (bg)	1996-07-26	1997-07-25	Нови кумаринови хинолонкарбонови киселини и методи за тяхното получаване
HU9701298A HUP9701298A3 (en)	1996-07-26	1997-07-25	Coumarin quinolone carboxylic acids, process for preparation thereof and their use
RU97113254/04A RU2166504C2 (ru)	1996-07-26	1997-07-25	Кумаринхинолонкарбоновые кислоты и способ их получения
CZ972382A CZ238297A3 (cs)	1996-07-26	1997-07-25	Nové kumarin quinolonové karboxylové kyseliny a způsob jejich přípravy

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HR960352A HRP960352A2 (en)	1996-07-26	1996-07-26	Novel coumarin quinoline carboxylic acids

Publications (1)

Publication Number	Publication Date
HRP960352A2 true HRP960352A2 (en)	1998-08-31

Family

ID=10946437

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR960352A HRP960352A2 (en)	1996-07-26	1996-07-26	Novel coumarin quinoline carboxylic acids

Country Status (18)

Country	Link
US (1)	US5908933A (de)
EP (1)	EP0820998B1 (de)
JP (1)	JPH1087668A (de)
CN (1)	CN1075500C (de)
AT (1)	ATE205211T1 (de)
BG (1)	BG63085B1 (de)
CA (1)	CA2210448A1 (de)
CZ (1)	CZ238297A3 (de)
DE (1)	DE69706487T2 (de)
ES (1)	ES2163694T3 (de)
HR (1)	HRP960352A2 (de)
HU (1)	HUP9701298A3 (de)
PL (1)	PL321308A1 (de)
PT (1)	PT820998E (de)
RU (1)	RU2166504C2 (de)
SI (1)	SI9700197B (de)
SK (1)	SK101697A3 (de)
UA (1)	UA45383C2 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HRP960308A2 (en) *	1996-07-02	1998-08-31	Ljerka Poljak	New coumarine derivatives, process for the preparation thereof and their use
WO2000042045A2 (en) *	1999-01-13	2000-07-20	Warner-Lambert Company	Functionalized heterocycles as chemokine receptor modulators
AU779232B2 (en) *	2001-06-28	2005-01-13	Activus Pharma Co., Ltd	Benzopyran derivative and antiallergic agent
FR2827864B1 (fr) *	2001-07-25	2005-09-16	Servier Lab	Nouveaux derives de benzo[b]pyrano[3,2-h]acridin-7-one, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
WO2009152210A2 (en) *	2008-06-12	2009-12-17	National Health Research Institutes	Coumarin compounds and their use for treating cancer
CN105218531B (zh) *	2015-10-14	2018-03-16	西南大学	香豆素喹诺酮杂合体或其可药用盐及其制备方法和应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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1996
- 1996-07-26 HR HR960352A patent/HRP960352A2/hr not_active Application Discontinuation
1997
- 1997-07-18 US US08/897,057 patent/US5908933A/en not_active Expired - Fee Related
- 1997-07-23 SI SI9700197A patent/SI9700197B/sl unknown
- 1997-07-24 SK SK1016-97A patent/SK101697A3/sk unknown
- 1997-07-24 AT AT97112743T patent/ATE205211T1/de not_active IP Right Cessation
- 1997-07-24 DE DE69706487T patent/DE69706487T2/de not_active Expired - Fee Related
- 1997-07-24 ES ES97112743T patent/ES2163694T3/es not_active Expired - Lifetime
- 1997-07-24 PL PL97321308A patent/PL321308A1/xx unknown
- 1997-07-24 CA CA002210448A patent/CA2210448A1/en not_active Abandoned
- 1997-07-24 EP EP97112743A patent/EP0820998B1/de not_active Expired - Lifetime
- 1997-07-24 JP JP9198505A patent/JPH1087668A/ja active Pending
- 1997-07-24 PT PT97112743T patent/PT820998E/pt unknown
- 1997-07-25 CZ CZ972382A patent/CZ238297A3/cs unknown
- 1997-07-25 CN CN97117456A patent/CN1075500C/zh not_active Expired - Fee Related
- 1997-07-25 UA UA97073970A patent/UA45383C2/uk unknown
- 1997-07-25 RU RU97113254/04A patent/RU2166504C2/ru active
- 1997-07-25 BG BG101796A patent/BG63085B1/bg unknown
- 1997-07-25 HU HU9701298A patent/HUP9701298A3/hu unknown

Also Published As

Publication number	Publication date
PL321308A1 (en)	1998-02-02
DE69706487T2 (de)	2002-05-08
US5908933A (en)	1999-06-01
EP0820998A3 (de)	1998-04-29
EP0820998B1 (de)	2001-09-05
HU9701298D0 (en)	1997-09-29
SK101697A3 (en)	1998-05-06
HUP9701298A2 (hu)	1999-06-28
ATE205211T1 (de)	2001-09-15
PT820998E (pt)	2002-02-28
BG101796A (en)	1998-10-30
BG63085B1 (bg)	2001-03-30
HUP9701298A3 (en)	1999-07-28
UA45383C2 (uk)	2002-04-15
CZ238297A3 (cs)	1998-03-18
SI9700197A (sl)	1998-02-28
ES2163694T3 (es)	2002-02-01
CN1075500C (zh)	2001-11-28
DE69706487D1 (de)	2001-10-11
JPH1087668A (ja)	1998-04-07
CN1176252A (zh)	1998-03-18
SI9700197B (sl)	2002-02-28
RU2166504C2 (ru)	2001-05-10
CA2210448A1 (en)	1998-01-26
EP0820998A2 (de)	1998-01-28

Legal Events

Date	Code	Title
1998-08-31	A1OB	Publication of a patent application
1998-09-11	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2002-05-03	ODBC	Application rejected

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SU1635898A3 (ru)	1991-03-15	Способ получени производных хинолина или их фармацевтически приемлемых сложных эфиров, или фармацевтически приемлемых солей указанных производных или сложных эфиров
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RU2166504C2 (ru)	2001-05-10	Кумаринхинолонкарбоновые кислоты и способ их получения
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Dammak et al.	2017	Synthesis and antibacterial activity of 2-amino chromenes arising cyanoiminocoumarins and β-naphthol
El-Gazzar et al.	2008	A Simple Synthesis and Antimicrobial Activity of Sulfur-containing Poly-condensed Heterocyclic Derivatives from 1, 3-benzothiazole.
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HRP960308A2 (en)	1998-08-31	New coumarine derivatives, process for the preparation thereof and their use
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TW319766B (de)	1997-11-11
KR0145181B1 (ko)	1998-07-15	신규 벤조 [1,8] 나프티리딘 유도체 및 그의 제법
FI105400B (fi)	2000-08-15	Uudet 3-karboksyylihappo-fluorikinoliinijohdannaiset, niiden valmistus ja niiden käyttö bentsonaftyridiinijohdannaisten valmistukseen
AU705938B2 (en)	1999-06-03	Pyridazino quinoline compounds
SU888823A3 (ru)	1981-12-07	Способ получени производных пиридо (3,4- )-асимм-триазина или их солей