DK175302B1 - Anvendelse af ofloxacin eller et salt deraf til fremstilling af et topisk præparat til behandling af otopati - Google Patents

Anvendelse af ofloxacin eller et salt deraf til fremstilling af et topisk præparat til behandling af otopati Download PDF

Info

Publication number: DK175302B1
Authority: DK; Denmark
Prior art keywords: ofloxacin; group; otopathy; solution; treatment
Prior art date: 1988-04-08

Application number

DK198901681A

Other languages

Danish (da)

English (en)

Other versions

DK168189D0 (da

DK168189A (da

Inventor

Kiichi Sato

Akira Handa

Takeji Kitahara

Original Assignee

Daiichi Seiyaku 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.)

1988-04-08

Filing date

1989-04-07

Publication date

2004-08-16

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=13885215&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DK175302(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1989-04-07 Application filed by Daiichi Seiyaku Co filed Critical Daiichi Seiyaku Co

1989-04-07 Publication of DK168189D0 publication Critical patent/DK168189D0/da

1989-10-09 Publication of DK168189A publication Critical patent/DK168189A/da

2004-08-16 Application granted granted Critical

2004-08-16 Publication of DK175302B1 publication Critical patent/DK175302B1/da

Links

GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 title claims abstract description 46
229960001699 ofloxacin Drugs 0.000 title claims abstract description 32
230000000699 topical effect Effects 0.000 title claims abstract description 9
150000003839 salts Chemical class 0.000 title claims abstract description 8
238000002360 preparation method Methods 0.000 title claims abstract description 7
239000000203 mixture Substances 0.000 title claims description 11
GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 claims description 4
239000000243 solution Substances 0.000 description 24
210000000959 ear middle Anatomy 0.000 description 12
210000004877 mucosa Anatomy 0.000 description 11
210000001519 tissue Anatomy 0.000 description 9
MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 8
239000002504 physiological saline solution Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 7
239000003814 drug Substances 0.000 description 6
239000007924 injection Substances 0.000 description 6
238000002347 injection Methods 0.000 description 6
229940079593 drug Drugs 0.000 description 5
210000002768 hair cell Anatomy 0.000 description 5
241001465754 Metazoa Species 0.000 description 4
210000005013 brain tissue Anatomy 0.000 description 4
230000008859 change Effects 0.000 description 4
229960003405 ciprofloxacin Drugs 0.000 description 4
206010033072 otitis externa Diseases 0.000 description 4
230000009467 reduction Effects 0.000 description 4
230000004044 response Effects 0.000 description 4
210000002966 serum Anatomy 0.000 description 4
206010033078 Otitis media Diseases 0.000 description 3
210000003477 cochlea Anatomy 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
238000000034 method Methods 0.000 description 3
210000004049 perilymph Anatomy 0.000 description 3
210000003454 tympanic membrane Anatomy 0.000 description 3
241000894006 Bacteria Species 0.000 description 2
208000035143 Bacterial infection Diseases 0.000 description 2
241000700198 Cavia Species 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
229930182566 Gentamicin Natural products 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
WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical compound C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
208000005141 Otitis Diseases 0.000 description 2
206010033109 Ototoxicity Diseases 0.000 description 2
201000002014 Suppurative Otitis Media Diseases 0.000 description 2
239000002253 acid Chemical class 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
208000022362 bacterial infectious disease Diseases 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
210000000613 ear canal Anatomy 0.000 description 2
208000019258 ear infection Diseases 0.000 description 2
210000005069 ears Anatomy 0.000 description 2
230000000694 effects Effects 0.000 description 2
229960002518 gentamicin Drugs 0.000 description 2
239000011521 glass Substances 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
238000005259 measurement Methods 0.000 description 2
244000005700 microbiome Species 0.000 description 2
231100001098 no ototoxicity Toxicity 0.000 description 2
231100000262 ototoxicity Toxicity 0.000 description 2
239000012188 paraffin wax Substances 0.000 description 2
239000008055 phosphate buffer solution Substances 0.000 description 2
238000001878 scanning electron micrograph Methods 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
XNIVKSPSCYJKBL-UHFFFAOYSA-N 2h-1,2-benzoxazine-6-carboxylic acid Chemical compound O1NC=CC2=CC(C(=O)O)=CC=C21 XNIVKSPSCYJKBL-UHFFFAOYSA-N 0.000 description 1
244000063299 Bacillus subtilis Species 0.000 description 1
241000197194 Bulla Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 1
241000699670 Mus sp. Species 0.000 description 1
208000006735 Periostitis Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000002421 anti-septic effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229940064004 antiseptic throat preparations Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
210000003030 auditory receptor cell Anatomy 0.000 description 1
239000002585 base Substances 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
208000002352 blister Diseases 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
210000000133 brain stem Anatomy 0.000 description 1
239000000872 buffer Substances 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229960005091 chloramphenicol Drugs 0.000 description 1
WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000013461 design Methods 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003221 ear drop Substances 0.000 description 1
229940047652 ear drops Drugs 0.000 description 1
YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
PGBHMTALBVVCIT-VCIWKGPPSA-N framycetin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO PGBHMTALBVVCIT-VCIWKGPPSA-N 0.000 description 1
238000002695 general anesthesia Methods 0.000 description 1
239000002271 gyrase inhibitor Substances 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000008595 infiltration Effects 0.000 description 1
238000001764 infiltration Methods 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
210000000067 inner hair cell Anatomy 0.000 description 1
QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
229960000318 kanamycin Drugs 0.000 description 1
229930027917 kanamycin Natural products 0.000 description 1
SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 1
229930182823 kanamycin A Natural products 0.000 description 1
229940039412 ketalar Drugs 0.000 description 1
VCMGMSHEPQENPE-UHFFFAOYSA-N ketamine hydrochloride Chemical compound [Cl-].C=1C=CC=C(Cl)C=1C1([NH2+]C)CCCCC1=O VCMGMSHEPQENPE-UHFFFAOYSA-N 0.000 description 1
230000003902 lesion Effects 0.000 description 1
210000002751 lymph Anatomy 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000000877 morphologic effect Effects 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229940126701 oral medication Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
230000021962 pH elevation Effects 0.000 description 1
210000003460 periosteum Anatomy 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
-1 platinum ions Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229940072132 quinolone antibacterials Drugs 0.000 description 1
230000011514 reflex Effects 0.000 description 1
238000005070 sampling Methods 0.000 description 1
210000000582 semen Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000004544 sputter deposition Methods 0.000 description 1
238000010998 test method Methods 0.000 description 1
230000008719 thickening Effects 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
210000001364 upper extremity Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
229960001600 xylazine Drugs 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals

Landscapes

Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicinal Preparation (AREA)
Orthopedics, Nursing, And Contraception (AREA)

DK198901681A 1988-04-08 1989-04-07 Anvendelse af ofloxacin eller et salt deraf til fremstilling af et topisk præparat til behandling af otopati DK175302B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP8637888		1988-04-08
JP63086378A JPH01258620A (ja)	1988-04-08	1988-04-08	耳疾患用局所製剤

Publications (3)

Publication Number	Publication Date
DK168189D0 DK168189D0 (da)	1989-04-07
DK168189A DK168189A (da)	1989-10-09
DK175302B1 true DK175302B1 (da)	2004-08-16

Family

ID=13885215

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK198901681A DK175302B1 (da)	1988-04-08	1989-04-07	Anvendelse af ofloxacin eller et salt deraf til fremstilling af et topisk præparat til behandling af otopati

Country Status (16)

Country	Link
US (1)	US5401741A (fr)
EP (1)	EP0337328B1 (fr)
JP (2)	JPH01258620A (fr)
KR (1)	KR0126471B1 (fr)
AT (1)	ATE109350T1 (fr)
AU (1)	AU614349B2 (fr)
CA (1)	CA1330946C (fr)
DE (1)	DE68917186T2 (fr)
DK (1)	DK175302B1 (fr)
HK (1)	HK196596A (fr)
HU (1)	HU00407A9 (fr)
IE (1)	IE65859B1 (fr)
IL (1)	IL89807A (fr)
NZ (1)	NZ228632A (fr)
PH (1)	PH26367A (fr)
ZA (1)	ZA892449B (fr)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5686095A (en) *	1995-10-23	1997-11-11	Price, Jr.; Francis W.	Method of treating canker sores
US5753269A (en) *	1995-12-27	1998-05-19	Bayer Corporation	Otic microbial combinations
US5972358A (en) *	1998-01-20	1999-10-26	Ethicon, Inc.	Low tack lotion, gels and creams
US6022551A (en) *	1998-01-20	2000-02-08	Ethicon, Inc.	Antimicrobial composition
US5997893A (en) *	1998-01-20	1999-12-07	Ethicon, Inc.	Alcohol based anti-microbial compositions with cosmetic appearance
US6248343B1 (en)	1998-01-20	2001-06-19	Ethicon, Inc.	Therapeutic antimicrobial compositions
US6017912A (en) *	1998-02-27	2000-01-25	Bussell; Letantia	Topical fluoroquinolone antibiotics in an alcohol and acetone vehicle
US5912255A (en) *	1998-02-27	1999-06-15	Bussell; Letantia	Topical fluoroquinolone antibiotics combined with benzoyl peroxide
KR100595956B1 (ko) *	1998-08-21	2006-07-03	센주 세이야꾸 가부시키가이샤	수성액 제약학적 조성물
DE19937116A1 (de) *	1999-08-06	2001-02-08	Bayer Ag	Moxifloxacin Kochsalzformulierung
US6156294A (en) *	1999-11-28	2000-12-05	Scientific Development And Research, Inc.	Composition and method for treatment of otitis media
US7064132B2 (en) *	1999-11-28	2006-06-20	Scientific Development And Research, Inc.	Composition and method for treatment of otitis external
US6676930B2 (en)	1999-11-28	2004-01-13	Scientific Development And Research, Inc.	Composition and method for treatment of otitis media
EP1331945A2 (fr)	2000-09-25	2003-08-06	Bayer Healthcare, LLC	Combinaisons microbiennes pour l'oreille destinees au traitement d'animaux dont la membrane du tympan est dechiree
US20090215735A1 (en) *	2002-02-25	2009-08-27	Alcon, Inc.	Topical solution formulations containing a corticosteroid and a cyclodextrin
US8940321B2 (en)	2003-12-12	2015-01-27	Otic Pharma Ltd.	Compositions for treatment of ear disorders and methods of use thereof
CA2548892C (fr) *	2003-12-12	2015-10-27	Eran Eilat	Compositions pour le traitement de troubles auriculaires et procedes d'utilisation de ces compositions
US8318817B2 (en)	2008-07-21	2012-11-27	Otonomy, Inc.	Controlled release antimicrobial compositions and methods for the treatment of otic disorders
JP2016534121A (ja)	2013-08-27	2016-11-04	オトノミ—，インク．	小児の耳の病気の処置
EP3512513A4 (fr)	2016-09-16	2020-04-15	Otonomy, Inc.	Formulations de gel otique pour le traitement de l'otite externe

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4260416A (en) *	1979-09-04	1981-04-07	Allied Chemical Corporation	Amorphous metal alloy for structural reinforcement
JPS5746986A (en) *	1980-09-02	1982-03-17	Dai Ichi Seiyaku Co Ltd	Pyrido(1,2,3-de)(1,4)benzoxazine derivative
US4551456A (en) *	1983-11-14	1985-11-05	Merck & Co., Inc.	Ophthalmic use of norfloxacin and related antibiotics
JPS638333A (ja) *	1986-06-30	1988-01-14	Dai Ichi Seiyaku Co Ltd	外用剤
JP2558107B2 (ja) *	1986-12-18	1996-11-27	第一製薬株式会社	外用剤
CA1309024C (fr) *	1986-12-19	1992-10-20	Hiromitsu Seki	Composition pharmaceutique aqueuse renfermant de l'acide s-(-)-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl -7-oxo-2,3-dihydro-7h-pyridole[1,2,3,-de][1,4]benzoxazine -6-carboxylique

1988
- 1988-04-08 JP JP63086378A patent/JPH01258620A/ja active Pending
1989
- 1989-03-30 IL IL89807A patent/IL89807A/xx unknown
- 1989-03-30 CA CA000595126A patent/CA1330946C/fr not_active Expired - Lifetime
- 1989-04-03 ZA ZA892449A patent/ZA892449B/xx unknown
- 1989-04-06 NZ NZ228632A patent/NZ228632A/xx unknown
- 1989-04-06 PH PH38446A patent/PH26367A/en unknown
- 1989-04-06 KR KR1019890004498A patent/KR0126471B1/ko not_active Ceased
- 1989-04-07 AU AU32567/89A patent/AU614349B2/en not_active Expired
- 1989-04-07 DK DK198901681A patent/DK175302B1/da not_active IP Right Cessation
- 1989-04-07 EP EP89106215A patent/EP0337328B1/fr not_active Expired - Lifetime
- 1989-04-07 DE DE68917186T patent/DE68917186T2/de not_active Expired - Lifetime
- 1989-04-07 IE IE111889A patent/IE65859B1/en not_active IP Right Cessation
- 1989-04-07 AT AT89106215T patent/ATE109350T1/de not_active IP Right Cessation
- 1989-04-07 JP JP1089379A patent/JP2573351B2/ja not_active Expired - Lifetime
1993
- 1993-04-12 US US08/048,959 patent/US5401741A/en not_active Expired - Lifetime
1995
- 1995-06-22 HU HU95P/P00407P patent/HU00407A9/hu unknown
1996
- 1996-10-24 HK HK196596A patent/HK196596A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE68917186T2 (de)	1995-01-05
US5401741A (en)	1995-03-28
DK168189D0 (da)	1989-04-07
IE65859B1 (en)	1995-11-29
PH26367A (en)	1992-06-01
CA1330946C (fr)	1994-07-26
JPH01258620A (ja)	1989-10-16
AU3256789A (en)	1989-10-12
DK168189A (da)	1989-10-09
EP0337328A2 (fr)	1989-10-18
IE891118L (en)	1989-10-08
HU00407A9 (en)	1995-09-28
ATE109350T1 (de)	1994-08-15
DE68917186D1 (de)	1994-09-08
JP2573351B2 (ja)	1997-01-22
ZA892449B (en)	1989-12-27
HK196596A (en)	1996-11-01
JPH0334925A (ja)	1991-02-14
KR890015742A (ko)	1989-11-25
IL89807A (en)	1993-08-18
EP0337328B1 (fr)	1994-08-03
EP0337328A3 (fr)	1991-12-27
KR0126471B1 (ko)	1997-12-24
AU614349B2 (en)	1991-08-29
NZ228632A (en)	1991-10-25

Legal Events

Date	Code	Title	Description
1994-02-28	B1	Patent granted (law 1993)
2009-04-27	PUP	Patent expired

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Esposito et al.	1990	Topical and oral treatment of chronic otitis media with ciprofloxacin: a preliminary study
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