SE436129B - Analogiforfarande for framstellning av kinolinkarboxylsyraderivat - Google Patents

Analogiforfarande for framstellning av kinolinkarboxylsyraderivat

Info

Publication number: SE436129B
Authority: SE; Sweden
Prior art keywords: compound; acid; carboxylic acid; concentration; mice
Prior art date: 1977-05-16

Application number

SE7800970A

Other languages

English (en)

Swedish (sv)

Other versions

SE7800970L (sv

Inventor

T Irikura

Original Assignee

Kyorin Seiyaku Kk

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.)

1977-05-16

Filing date

1978-01-26

Publication date

1984-11-12

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=13020985&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SE436129(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1978-01-26 Application filed by Kyorin Seiyaku Kk filed Critical Kyorin Seiyaku Kk

1978-11-17 Publication of SE7800970L publication Critical patent/SE7800970L/xx

1984-11-12 Publication of SE436129B publication Critical patent/SE436129B/sv

Links

238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 7
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 109
239000002253 acid Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 3
150000004677 hydrates Chemical class 0.000 claims description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
241000699670 Mus sp. Species 0.000 description 25
241000700159 Rattus Species 0.000 description 24
JOHZPMXAZQZXHR-UHFFFAOYSA-N pipemidic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCNCC1 JOHZPMXAZQZXHR-UHFFFAOYSA-N 0.000 description 20
229960001732 pipemidic acid Drugs 0.000 description 20
210000002966 serum Anatomy 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical compound C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 description 15
229960000210 nalidixic acid Drugs 0.000 description 15
210000001519 tissue Anatomy 0.000 description 13
208000015181 infectious disease Diseases 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
241000588724 Escherichia coli Species 0.000 description 8
230000000844 anti-bacterial effect Effects 0.000 description 8
210000000941 bile Anatomy 0.000 description 8
238000002474 experimental method Methods 0.000 description 8
210000002700 urine Anatomy 0.000 description 8
241000589517 Pseudomonas aeruginosa Species 0.000 description 7
241000894006 Bacteria Species 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 description 6
229960003669 carbenicillin Drugs 0.000 description 6
210000003734 kidney Anatomy 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000002844 melting Methods 0.000 description 6
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 6
229920001817 Agar Polymers 0.000 description 5
239000008272 agar Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
210000004185 liver Anatomy 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
230000001681 protective effect Effects 0.000 description 5
241000699666 Mus <mouse, genus> Species 0.000 description 4
244000052616 bacterial pathogen Species 0.000 description 4
230000037396 body weight Effects 0.000 description 4
230000029142 excretion Effects 0.000 description 4
238000011081 inoculation Methods 0.000 description 4
238000013048 microbiological method Methods 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
238000007920 subcutaneous administration Methods 0.000 description 4
230000009885 systemic effect Effects 0.000 description 4
-1 1-ethyl Chemical group 0.000 description 3
VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
239000013522 chelant Substances 0.000 description 3
239000000499 gel Substances 0.000 description 3
210000003887 myelocyte Anatomy 0.000 description 3
238000011084 recovery Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
JJWDELPVPRCLQN-UHFFFAOYSA-N 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 JJWDELPVPRCLQN-UHFFFAOYSA-N 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000192125 Firmicutes Species 0.000 description 2
CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 2
229930182566 Gentamicin Natural products 0.000 description 2
206010023424 Kidney infection Diseases 0.000 description 2
241000588653 Neisseria Species 0.000 description 2
206010037596 Pyelonephritis Diseases 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000191967 Staphylococcus aureus Species 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
230000001174 ascending effect Effects 0.000 description 2
238000012742 biochemical analysis Methods 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
210000000349 chromosome Anatomy 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229960002518 gentamicin Drugs 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
229960003506 piperazine hexahydrate Drugs 0.000 description 2
AVRVZRUEXIEGMP-UHFFFAOYSA-N piperazine;hexahydrate Chemical compound O.O.O.O.O.O.C1CNCCN1 AVRVZRUEXIEGMP-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
ITBINNOMHXTMLQ-UHFFFAOYSA-N 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid;hydrate Chemical compound O.C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 ITBINNOMHXTMLQ-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
IKDSIKIBLPIUKA-UHFFFAOYSA-N 6-chloro-1-ethyl-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(Cl)=C1N1CCNCC1 IKDSIKIBLPIUKA-UHFFFAOYSA-N 0.000 description 1
235000002566 Capsicum Nutrition 0.000 description 1
QCDFBFJGMNKBDO-UHFFFAOYSA-N Clioquinol Chemical compound C1=CN=C2C(O)=C(I)C=C(Cl)C2=C1 QCDFBFJGMNKBDO-UHFFFAOYSA-N 0.000 description 1
241000699802 Cricetulus griseus Species 0.000 description 1
206010060891 General symptom Diseases 0.000 description 1
241000588748 Klebsiella Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
239000006002 Pepper Substances 0.000 description 1
235000016761 Piper aduncum Nutrition 0.000 description 1
235000017804 Piper guineense Nutrition 0.000 description 1
244000203593 Piper nigrum Species 0.000 description 1
235000008184 Piper nigrum Nutrition 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000588767 Proteus vulgaris Species 0.000 description 1
208000032536 Pseudomonas Infections Diseases 0.000 description 1
241000607760 Shigella sonnei Species 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
206010043275 Teratogenicity Diseases 0.000 description 1
206010046555 Urinary retention Diseases 0.000 description 1
238000002814 agar dilution Methods 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
229940009976 deoxycholate Drugs 0.000 description 1
KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000001416 effect on chromosomes Effects 0.000 description 1
229960000285 ethambutol Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
229910001447 ferric ion Inorganic materials 0.000 description 1
235000012631 food intake Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002489 hematologic effect Effects 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
239000003978 infusion fluid Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
238000012543 microbiological analysis Methods 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
230000035764 nutrition Effects 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000005305 organ development Effects 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229940115939 shigella sonnei Drugs 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000003390 teratogenic effect Effects 0.000 description 1
231100000211 teratogenicity Toxicity 0.000 description 1
230000003192 teratological effect Effects 0.000 description 1
210000004357 third molar Anatomy 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000041 toxicology testing Toxicity 0.000 description 1
210000001635 urinary tract Anatomy 0.000 description 1
238000005353 urine analysis Methods 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
- 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)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SE7800970A 1977-05-16 1978-01-26 Analogiforfarande for framstellning av kinolinkarboxylsyraderivat SE436129B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP5621977A JPS53141286A (en)	1977-05-16	1977-05-16	Novel substituted quinolinecarboxylic acid

Publications (2)

Publication Number	Publication Date
SE7800970L SE7800970L (sv)	1978-11-17
SE436129B true SE436129B (sv)	1984-11-12

Family

ID=13020985

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7800970A SE436129B (sv)	1977-05-16	1978-01-26	Analogiforfarande for framstellning av kinolinkarboxylsyraderivat

Country Status (11)

Country	Link
US (1)	US4146719A (fr)
JP (1)	JPS53141286A (fr)
AU (1)	AU512940B2 (fr)
BE (1)	BE863429A (fr)
CA (1)	CA1178961A (fr)
DE (1)	DE2804097C3 (fr)
FR (1)	FR2391210A1 (fr)
GB (1)	GB1574285A (fr)
HK (1)	HK10385A (fr)
HU (1)	HU176265B (fr)
SE (1)	SE436129B (fr)

Families Citing this family (76)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4264604A (en) *	1977-07-01	1981-04-28	Ciba-Geigy Corporation	Quinolonecarboxylic acid derivatives as bactericides
SE444566B (sv) *	1977-09-20	1986-04-21	Bellon Labor Sa Roger	7-dialkylamin-6-halogen-4-oxo-1,4-dihydrokinolin-3-karboxylsyra, forfarande for framstellning derav och farmaceutiskt preparat derav
CA1175836A (fr) *	1977-09-20	1984-10-09	Marcel Pesson	Production de derives de l'acide 1,4- dihydroquinoline-3-carboxylique
US4416884A (en) *	1978-04-12	1983-11-22	Otsuka Pharmaceutical Co., Ltd.	Piperazinylbenzoheterocyclic compounds
AR223983A1 (es) *	1978-08-25	1981-10-15	Dainippon Pharmaceutical Co	Un procedimiento para-preparar derivados de acido 6-halogeno-4-oxo-7-(1-piperazinil)-1,8-naftiridin-3-carboxilico
JPS5533453A (en) *	1978-08-31	1980-03-08	Dainippon Pharmaceut Co Ltd	Preventive and remedy for infectious disease of fish
JPS5845426B2 (ja) *	1978-09-29	1983-10-08	杏林製薬株式会社	置換キノリンカルボン酸誘導体
JPS55100364A (en) *	1979-01-26	1980-07-31	Dainippon Pharmaceut Co Ltd	Pyridonecarboxylic acid derivative and its salt
JPS604820B2 (ja) *	1979-02-26	1985-02-06	大塚製薬株式会社	キノリンカルボン酸誘導体
JPS5630964A (en) *	1979-08-22	1981-03-28	Kyorin Pharmaceut Co Ltd	Novel substituted quinolinecarboxylic acid and its preparation
DE3142854A1 (de) *	1981-10-29	1983-05-11	Bayer Ag, 5090 Leverkusen	1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-piperazino-chinolin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
US4670444B1 (en) *	1980-09-03	1999-02-09	Bayer Ag	and-naphthyridine-3-carboxylic acids and antibacte7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-rial agents containing these compounds
JPS5762259A (en) *	1980-09-05	1982-04-15	Kyorin Pharmaceut Co Ltd	Preparation of substituted quinolinecarboxylic acid derivative
IE52125B1 (en) *	1980-10-02	1987-06-24	Fox Charles L Jun	1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quino-line carboxylic acid and metal salts thereof useful in burn therapy
US4522819A (en) *	1980-10-02	1985-06-11	Norwich Eaton Pharmaceuticals, Inc.	1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid and metal salts thereof useful in burn therapy
JPS57106681A (en) *	1980-12-24	1982-07-02	Dainippon Pharmaceut Co Ltd	1,8-naphthyridine derivative and its salt
JPS57134482A (en) *	1981-02-13	1982-08-19	Dainippon Pharmaceut Co Ltd	1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8- naphthyridine-3-carboxylic acid-3/2 hydrate and its preparation
SE440354B (sv) *	1981-02-19	1985-07-29	Kyorin Seiyaku Kk	Kinolinkarboxylsyraderivat
JPS57145862A (en) *	1981-03-06	1982-09-09	Kyorin Pharmaceut Co Ltd	Quinolinecarboxylic acid derivative
US4404197A (en) *	1981-05-15	1983-09-13	Fox Jr Charles L	Antimicrobial compositions containing 1-ethyl-6-fluoro-1,4-dihydro-4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid or metal salts thereof and silver sulfadiazine
JPS57203067A (en) *	1981-06-10	1982-12-13	Kanebo Ltd	Novel quinolinecarboxylic acid derivatives, their preparations, and antibacterial agent comprising them as active ingredient
US4499091A (en) *	1982-03-31	1985-02-12	Sterling Drug Inc.	1-Amino (or substituted amino)-1,4-dihydro-4-oxo-6-fluoro-7-heterylquinoline-3-carboxylic acids and their use as antibacterial agents
ZA832057B (en) *	1982-03-31	1984-06-27	Sterling Drug Inc	New quinolone compounds and preparation thereof
DE3363711D1 (en) *	1982-03-31	1986-07-03	Sterling Drug Inc	New quinolone compounds and preparation thereof
US4665079A (en) *	1984-02-17	1987-05-12	Warner-Lambert Company	Antibacterial agents
JPS59122470A (ja) *	1982-12-27	1984-07-14	Dai Ichi Seiyaku Co Ltd	キノリン−３−カルボン酸誘導体の製造法
DE3248507A1 (de) *	1982-12-29	1984-07-05	Bayer Ag, 5090 Leverkusen	Mikrobizide mittel auf chinoloncarbonsaeure basis
US4730000A (en) *	1984-04-09	1988-03-08	Abbott Laboratories	Quinoline antibacterial compounds
EP0154622A4 (fr) *	1983-09-12	1987-03-16	Research Corp	Compositions antimicrobiennes contenant de l'acide carboxylique de 1-ethyl-6-fluoro-1,4-dihydro-oxo-7-(1-piperazinyl)-3-quinoline ou ses sels metalliques et de la sulfadiazine d'argent.
AU553415B2 (en) *	1983-09-19	1986-07-17	Abbott Japan Co., Ltd.	6-fluoro-1-4-dihydro-4-oxo-7-substituted piperazinyl- quinoline-3-carboxylic acids
US4551456A (en) *	1983-11-14	1985-11-05	Merck & Co., Inc.	Ophthalmic use of norfloxacin and related antibiotics
US4571396A (en) *	1984-04-16	1986-02-18	Warner-Lambert Company	Antibacterial agents
US4698350A (en) *	1984-09-17	1987-10-06	Sterling Drug Inc.	1-ethyl-6-fluoro-1,4-dihydro-7-(2,6-dimethyl-4-pyridinyl)-4-oxo-3-quinolinecarboxylic acid and antibacterial use thereof
EP0181521A1 (fr) *	1984-10-19	1986-05-21	Otsuka Pharmaceutical Co., Ltd.	Composés d'acide 1-phényl substitué-4-oxo-3-quinoléine carboxylique
US4851535A (en) *	1985-01-23	1989-07-25	Toyama Chemical Co., Ltd.	Nicotinic acid derivatives
US4755513A (en) *	1985-01-30	1988-07-05	Otsuka Pharmaceutical Company, Limited	Antimicrobial 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds
HUT40429A (en) *	1985-04-29	1986-12-28	Chinoin Gyogyszer Es Vegyeszet	Process for production of salts of derivatives of kynolin carbonic acid
US4684648A (en) *	1985-05-10	1987-08-04	Otsuka Pharmaceutical Company Limited	Antimicrobial 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds and compositions thereof
GB8512143D0 (en) *	1985-05-14	1985-06-19	Beecham Group Plc	Method of treatment
DE3608745A1 (de) *	1985-07-24	1987-01-29	Bayer Ag	Bakterizide zubereitungen zur anwendung auf dem gebiet der veterinaermedizin
IN166416B (fr) *	1985-09-18	1990-05-05	Pfizer
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1977
- 1977-05-16 JP JP5621977A patent/JPS53141286A/ja active Granted
1978
- 1978-01-25 AU AU32713/78A patent/AU512940B2/en not_active Expired
- 1978-01-26 HU HU78KI755A patent/HU176265B/hu unknown
- 1978-01-26 SE SE7800970A patent/SE436129B/sv not_active IP Right Cessation
- 1978-01-30 BE BE2056647A patent/BE863429A/fr not_active IP Right Cessation
- 1978-01-31 DE DE2804097A patent/DE2804097C3/de not_active Expired
- 1978-01-31 FR FR7802706A patent/FR2391210A1/fr active Granted
- 1978-01-31 CA CA000296108A patent/CA1178961A/fr not_active Expired
- 1978-01-31 GB GB3763/78A patent/GB1574285A/en not_active Expired
- 1978-02-16 US US05/878,600 patent/US4146719A/en not_active Expired - Lifetime
1985
- 1985-02-07 HK HK103/85A patent/HK10385A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE2804097A1 (de)	1978-11-23
CA1178961A (fr)	1984-12-04
JPS5534144B2 (fr)	1980-09-04
AU3271378A (en)	1979-08-02
DE2804097C3 (de)	1980-08-28
DE2804097B2 (de)	1980-01-03
GB1574285A (en)	1980-09-03
FR2391210A1 (fr)	1978-12-15
HU176265B (en)	1981-01-28
BE863429A (fr)	1978-05-16
HK10385A (en)	1985-02-15
US4146719A (en)	1979-03-27
JPS53141286A (en)	1978-12-08
AU512940B2 (en)	1980-11-06
SE7800970L (sv)	1978-11-17
FR2391210B1 (fr)	1981-08-21

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Publication	Publication Date	Title
SE436129B (sv)	1984-11-12	Analogiforfarande for framstellning av kinolinkarboxylsyraderivat
EP0242789A2 (fr)	1987-10-28	Dérivés de quinoléine et procédés pour leur préparation
US4429127A (en)	1984-01-31	Quinoline carboxylic acid derivative
US4472405A (en)	1984-09-18	Antimicrobial 6,7-dihydro-5,8-dimethyl-9 fluoro-1-oxo-1H, 5H-benzo (ij) quinolizine-2-carboxylic acid and derivatives
Peck et al.	1946	Streptomyces antibiotics. IV. Hydrolytic cleavage of streptomycin to streptidine
CA1215713A (fr)	1986-12-23	Derives de substitution de l'acide quinoleine- carboxylique
JPS59176284A (ja)	1984-10-05	８−アルコキシ−６，７−ジヒドロ−５−メチル−９−フルオロ−１−オキソ−１Ｈ，５Ｈ−ベンゾ〔ｉｊ〕キノリジン−２−カルボン酸
EP0312085A2 (fr)	1989-04-19	Dérivés de la quinoléine, procédé de leur préparation et agents antibactériens
EP0038572B1 (fr)	1984-03-21	1-Nitro-9-hydroxyalkylaminoacridines et leurs sels
JPS6399061A (ja)	1988-04-30	ベンジルピリミジン誘導体、その製造方法及びそれを含有する医薬
EP0203559A1 (fr)	1986-12-03	Dérivé de pénicilline contenant de la naphtyridine
US4469691A (en)	1984-09-04	Hexamethylenetetramine-N-acetyl-thiazolidine-4-carboxylate, a process for its preparation and a pharmaceutical composition containing it
SU1029829A3 (ru)	1983-07-15	Способ получени производных 1,8-нафтиридина или их фармацевтически пригодных солей
US4499270A (en)	1985-02-12	Substituted pyridoquinoxaline-6-carboxylic acids and derivatives thereof
US4585868A (en)	1986-04-29	Precursors of 6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid
CA1258073A (fr)	1989-08-01	Complexes antibacteriens d'indium et de 8-hydroxyquinolines halogenees
JPH02231424A (ja)	1990-09-13	抗菌剤
FI89797B (fi)	1993-08-13	Foerfarande foer framstaellning av ett terapeutiskt anvaendbart 7-substituerat 1-cyklopropyl-5,6,8-trifluor-1,4-dihydro-4-oxokinolin-3-karboxylsyraderivat
KR840000522B1 (ko)	1984-04-17	퀴놀린 화합물의 제조방법
KR890000863B1 (ko)	1989-04-11	퀴날딘 유도체
WO2020078205A1 (fr)	2020-04-23	Produit pharmaceutique cristallin de contezolid acéfosamil, son procédé de préparation et ses applications
CS235546B2 (cs)	1985-05-15	Způsob přípravy derivátů 1-ethyl-6-halogen-1,4-dihydro-4-oxo-7-/1-piperazinyl/-1,8-nafthyridinu
IE45029B1 (en)	1982-06-02	Aminoglycosides
ITMI942464A1 (it)	1996-06-06	Sali dell'acido 1-etil-6-fluoro-1,4-diidro-4-oxo-7-(1-piperazinil)-3- chinolicarbossilico
CS195713B2 (cs)	1980-02-29	Způsob výroby nových amfeoglykosidů 2-dsoxystreptaminu