GB2049420A - Veterinary medicament based on benxoquinolizine carboxylic acids and their derivatives - Google Patents
Veterinary medicament based on benxoquinolizine carboxylic acids and their derivatives Download PDFInfo
- Publication number
- GB2049420A GB2049420A GB8011882A GB8011882A GB2049420A GB 2049420 A GB2049420 A GB 2049420A GB 8011882 A GB8011882 A GB 8011882A GB 8011882 A GB8011882 A GB 8011882A GB 2049420 A GB2049420 A GB 2049420A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxo
- benzo
- dihydro
- quinolizine
- methyl
- Prior art date
- 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.)
- Withdrawn
Links
- 239000003814 drug Substances 0.000 title description 8
- 150000001735 carboxylic acids Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- -1 halegeno Chemical group 0.000 claims abstract description 8
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical group F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 208000015181 infectious disease Diseases 0.000 claims abstract description 5
- 150000003254 radicals Chemical group 0.000 claims abstract description 5
- SWWBKIRNVOWLRS-UHFFFAOYSA-N 4h-benzo[a]quinolizine-1-carboxylic acid Chemical class C1=CC=C2C3=C(C(=O)O)C=CCN3C=CC2=C1 SWWBKIRNVOWLRS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 230000001079 digestive effect Effects 0.000 claims abstract description 3
- 210000002249 digestive system Anatomy 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 210000002345 respiratory system Anatomy 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 230000000813 microbial effect Effects 0.000 claims abstract 2
- DPSPPJIUMHPXMA-UHFFFAOYSA-N 9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid Chemical compound C1CC(C)N2C=C(C(O)=O)C(=O)C3=C2C1=CC(F)=C3 DPSPPJIUMHPXMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims description 3
- UBAPLOXHNASCBG-UHFFFAOYSA-N 6,12-dimethyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylic acid Chemical compound C1CC(C)N2C=C(C(O)=O)C(=O)C3=C2C1=CC=C3C UBAPLOXHNASCBG-UHFFFAOYSA-N 0.000 claims description 2
- RMUSBGNTSLJXFW-UHFFFAOYSA-N 6,7-dihydro-8-methoxy-5-methyl-1-oxo-1h,5h-benzo[ij]quinolizine-2-carboxylic acid Chemical compound C1CC(C)N2C=C(C(O)=O)C(=O)C3=CC=C(OC)C1=C23 RMUSBGNTSLJXFW-UHFFFAOYSA-N 0.000 claims description 2
- PPWSMSAQXQFEMG-UHFFFAOYSA-N 6,8,12-trimethyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylic acid Chemical compound C1CC(C)N2C=C(C(O)=O)C(=O)C3=C2C1=C(C)C=C3C PPWSMSAQXQFEMG-UHFFFAOYSA-N 0.000 claims description 2
- SBXQDPQZLFXMSA-UHFFFAOYSA-N 7-fluoro-10,12-dimethyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5(13),6,8-tetraene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)C2=CC(F)=CC3=C2N1C(C)CC3C SBXQDPQZLFXMSA-UHFFFAOYSA-N 0.000 claims description 2
- XJXILAMYZXODBV-UHFFFAOYSA-N 7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxamide Chemical compound C1CC(C)N2C=C(C(N)=O)C(=O)C3=C2C1=CC(F)=C3 XJXILAMYZXODBV-UHFFFAOYSA-N 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- ZOUSZSYEPIAUBH-UHFFFAOYSA-N 6,7-dihydro-9-fluoro-1-oxo-5-trifluoromethyl-1h,5h-benzo[ij]quinolizine-2-carboxylic acid Chemical compound FC(F)(F)C1CCC2=CC(F)=CC3=C2N1C=C(C(=O)O)C3=O ZOUSZSYEPIAUBH-UHFFFAOYSA-N 0.000 claims 1
- LMZQMBQTJLWVBS-UHFFFAOYSA-N 8,12-dimethyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5(13),6,8-tetraene-3-carboxylic acid Chemical compound C1CC(C)N2C=C(C(O)=O)C(=O)C3=C2C1=C(C)C=C3 LMZQMBQTJLWVBS-UHFFFAOYSA-N 0.000 claims 1
- XMLKZFJCWUKBGF-UHFFFAOYSA-N 8-chloro-5-methyl-6,7-dihydro-1-oxo-1h,5h-benzo-[ij]quinolizine-2-carboxylic acid Chemical compound C1CC(C)N2C=C(C(O)=O)C(=O)C3=C2C1=C(Cl)C=C3 XMLKZFJCWUKBGF-UHFFFAOYSA-N 0.000 claims 1
- MPBKXLYEVJVZEX-UHFFFAOYSA-M sodium 7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylate Chemical compound [Na+].C1CC(C)N2C=C(C([O-])=O)C(=O)C3=C2C1=CC(F)=C3 MPBKXLYEVJVZEX-UHFFFAOYSA-M 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 208000035475 disorder Diseases 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 241000282887 Suidae Species 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 230000002485 urinary effect Effects 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 3
- 241000283707 Capra Species 0.000 description 3
- 241001494479 Pecora Species 0.000 description 3
- 241000288906 Primates Species 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 230000001575 pathological effect Effects 0.000 description 3
- 244000144977 poultry Species 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- KASNWJJVSFNDJM-UHFFFAOYSA-N 1-azatricyclo[7.3.1.05,13]trideca-3,5,7,9(13),10-pentaene-3-carboxylic acid Chemical compound C1=CCN2CC(C(=O)O)=CC3=CC=CC1=C32 KASNWJJVSFNDJM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000192125 Firmicutes Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000002685 pulmonary effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- 125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 description 2
- 208000019206 urinary tract infection Diseases 0.000 description 2
- PSZAEHPBBUYICS-UHFFFAOYSA-N 2-methylidenepropanedioic acid Chemical group OC(=O)C(=C)C(O)=O PSZAEHPBBUYICS-UHFFFAOYSA-N 0.000 description 1
- XMZFEGSYODZXFT-UHFFFAOYSA-N 6h-quinolizine-4-carboxylic acid Chemical compound C1=CCN2C(C(=O)O)=CC=CC2=C1 XMZFEGSYODZXFT-UHFFFAOYSA-N 0.000 description 1
- 241000607534 Aeromonas Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241001415288 Coccidae Species 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 241000588914 Enterobacter Species 0.000 description 1
- 241000588724 Escherichia coli Species 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
- 241000588748 Klebsiella Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001443706 Papio papio Species 0.000 description 1
- 241001504519 Papio ursinus Species 0.000 description 1
- 241000606860 Pasteurella Species 0.000 description 1
- 206010034107 Pasteurella infections Diseases 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 206010039438 Salmonella Infections Diseases 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000025087 Yersinia pseudotuberculosis infectious disease Diseases 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 210000002257 embryonic structure Anatomy 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000005075 mammary gland Anatomy 0.000 description 1
- OFWHOYXPLWWGSA-UHFFFAOYSA-N methyl 7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylate Chemical compound CC1CCC2=CC(F)=CC3=C2N1C=C(C(=O)OC)C3=O OFWHOYXPLWWGSA-UHFFFAOYSA-N 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940041667 oral paste Drugs 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000001635 urinary tract Anatomy 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
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21723/79A IT1111918B (it) | 1979-04-10 | 1979-04-10 | Medicamento veterinario a base di acidi benzochinolizin carbossilici e loro derivati |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2049420A true GB2049420A (en) | 1980-12-31 |
Family
ID=11185937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8011882A Withdrawn GB2049420A (en) | 1979-04-10 | 1980-04-10 | Veterinary medicament based on benxoquinolizine carboxylic acids and their derivatives |
Country Status (7)
| Country | Link |
|---|---|
| AU (1) | AU5728280A (cg-RX-API-DMAC7.html) |
| FR (1) | FR2453647A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB2049420A (cg-RX-API-DMAC7.html) |
| IE (1) | IE52296B1 (cg-RX-API-DMAC7.html) |
| IT (1) | IT1111918B (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ193374A (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA802088B (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992016209A1 (en) * | 1991-03-14 | 1992-10-01 | Reanal Finomvegyszergyár | Granules and veterinary compositions comprising a water-soluble complex of flumequine |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4380543A (en) * | 1981-11-06 | 1983-04-19 | Riker Laboratories, Inc. | Antimicrobial 8-cyano-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acids |
| HUP9601362A3 (en) * | 1996-05-21 | 1999-04-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing optically active compounds |
| HUP9601361A3 (en) * | 1996-05-21 | 1999-04-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing optically active compounds |
-
1979
- 1979-04-10 IT IT21723/79A patent/IT1111918B/it active
-
1980
- 1980-04-09 ZA ZA00802088A patent/ZA802088B/xx unknown
- 1980-04-09 AU AU57282/80A patent/AU5728280A/en not_active Withdrawn
- 1980-04-09 IE IE712/80A patent/IE52296B1/en not_active IP Right Cessation
- 1980-04-09 NZ NZ193374A patent/NZ193374A/xx unknown
- 1980-04-10 FR FR8008061A patent/FR2453647A1/fr active Granted
- 1980-04-10 GB GB8011882A patent/GB2049420A/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992016209A1 (en) * | 1991-03-14 | 1992-10-01 | Reanal Finomvegyszergyár | Granules and veterinary compositions comprising a water-soluble complex of flumequine |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ193374A (en) | 1982-12-07 |
| AU5728280A (en) | 1980-10-16 |
| IT1111918B (it) | 1986-01-13 |
| FR2453647B1 (cg-RX-API-DMAC7.html) | 1983-12-23 |
| FR2453647A1 (fr) | 1980-11-07 |
| IE800712L (en) | 1980-10-10 |
| IT7921723A0 (it) | 1979-04-10 |
| IE52296B1 (en) | 1987-09-02 |
| ZA802088B (en) | 1981-08-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |