SU1731055A3 - Способ получени азетидиновых производных 1,4-дигидро-4-оксохинолин-3-карбоновых кислот - Google Patents
Способ получени азетидиновых производных 1,4-дигидро-4-оксохинолин-3-карбоновых кислот Download PDFInfo
- Publication number
- SU1731055A3 SU1731055A3 SU884613206A SU4613206A SU1731055A3 SU 1731055 A3 SU1731055 A3 SU 1731055A3 SU 884613206 A SU884613206 A SU 884613206A SU 4613206 A SU4613206 A SU 4613206A SU 1731055 A3 SU1731055 A3 SU 1731055A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- atcc
- dihydro
- hydrogen
- oxoquinoline
- acetamidoalkyl
- Prior art date
Links
- 150000001539 azetidines Chemical class 0.000 title claims abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title description 3
- -1 hydroxy, amino Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 3
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract 2
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 241000256215 Spongomorpha aeruginosa Species 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 241000193755 Bacillus cereus Species 0.000 claims 1
- 244000063299 Bacillus subtilis Species 0.000 claims 1
- 235000014469 Bacillus subtilis Nutrition 0.000 claims 1
- 241000588724 Escherichia coli Species 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 241000607768 Shigella Species 0.000 claims 1
- 241001467018 Typhis Species 0.000 claims 1
- 239000011737 fluorine Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 230000000845 anti-microbial effect Effects 0.000 abstract description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 229920001817 Agar Polymers 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000008272 agar Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000002609 medium Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- 239000008121 dextrose Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KNEXGVPHPGXAGF-UHFFFAOYSA-N 1-cyclopropyl-6,7-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 KNEXGVPHPGXAGF-UHFFFAOYSA-N 0.000 description 2
- CTJMNBROBOZHAP-UHFFFAOYSA-N 7-(3-aminoazetidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 CTJMNBROBOZHAP-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000002255 vaccination Methods 0.000 description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- BVGDAZBTIVRTGO-UONOGXRCSA-N 3-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[4-methoxy-6-[(2s)-2-methylpiperazin-1-yl]pyridin-3-yl]pyridin-2-amine Chemical compound C1([C@@H](C)OC=2C(N)=NC=C(C=2)C2=CN=C(C=C2OC)N2[C@H](CNCC2)C)=C(Cl)C=CC(F)=C1Cl BVGDAZBTIVRTGO-UONOGXRCSA-N 0.000 description 1
- UNCFNIZANBZRHN-UHFFFAOYSA-N Cl.FC(C(=O)NN1CCC1)(F)F Chemical compound Cl.FC(C(=O)NN1CCC1)(F)F UNCFNIZANBZRHN-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- BMUIAEREBKVJQG-UHFFFAOYSA-N n,n-dimethylazetidin-3-amine;hydrochloride Chemical compound Cl.CN(C)C1CNC1 BMUIAEREBKVJQG-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8718289A FR2625200A1 (en) | 1987-12-29 | 1987-12-29 | 7-(1-Azetidinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid derivatives, their preparation and their application as medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1731055A3 true SU1731055A3 (ru) | 1992-04-30 |
Family
ID=9358387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU884613206A SU1731055A3 (ru) | 1987-12-29 | 1988-12-28 | Способ получени азетидиновых производных 1,4-дигидро-4-оксохинолин-3-карбоновых кислот |
Country Status (4)
| Country | Link |
|---|---|
| DD (1) | DD283385A5 (enrdf_load_stackoverflow) |
| FR (1) | FR2625200A1 (enrdf_load_stackoverflow) |
| SU (1) | SU1731055A3 (enrdf_load_stackoverflow) |
| ZA (1) | ZA889705B (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2161154C2 (ru) * | 1992-12-30 | 2000-12-27 | Чейл Фудз энд Кемикал, Инк. | Новые производные пиридоновых карбоновых кислот, способ и промежуточные для их получения, фармацевтическая композиция и способ лечения инфекционных заболеваний |
| RU2193558C2 (ru) * | 1997-09-15 | 2002-11-27 | Дзе Проктер Энд Гэмбл Компани | Производные хинолона и фармацевтическая композиция на их основе |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005026146A1 (en) * | 2003-09-12 | 2005-03-24 | Warner-Lambert Company Llc | Azetidinyl quinolones as antibacterial agents |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5746986A (en) * | 1980-09-02 | 1982-03-17 | Dai Ichi Seiyaku Co Ltd | Pyrido(1,2,3-de)(1,4)benzoxazine derivative |
| IE55898B1 (en) * | 1982-09-09 | 1991-02-14 | Warner Lambert Co | Antibacterial agents |
| US4617308A (en) * | 1985-01-25 | 1986-10-14 | Warner-Lambert Company | 7-substituted amino-1-aryl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids and derivatives thereof as antibacterial agents |
| CN1019114B (zh) * | 1986-03-31 | 1992-11-18 | 三共株式会社 | 喹啉-3-羟酸衍生物的制备方法 |
-
1987
- 1987-12-29 FR FR8718289A patent/FR2625200A1/fr active Granted
-
1988
- 1988-12-28 SU SU884613206A patent/SU1731055A3/ru active
- 1988-12-28 DD DD88324257A patent/DD283385A5/de not_active IP Right Cessation
- 1988-12-29 ZA ZA889705A patent/ZA889705B/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| ЕР Ь 0106489, кл. С 07 D 401/04, 1984. ЕР № 0153163, кл. С 07 D 401/04, 1985. * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2161154C2 (ru) * | 1992-12-30 | 2000-12-27 | Чейл Фудз энд Кемикал, Инк. | Новые производные пиридоновых карбоновых кислот, способ и промежуточные для их получения, фармацевтическая композиция и способ лечения инфекционных заболеваний |
| RU2193558C2 (ru) * | 1997-09-15 | 2002-11-27 | Дзе Проктер Энд Гэмбл Компани | Производные хинолона и фармацевтическая композиция на их основе |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2625200B1 (enrdf_load_stackoverflow) | 1991-04-12 |
| ZA889705B (en) | 1989-10-25 |
| FR2625200A1 (en) | 1989-06-30 |
| DD283385A5 (de) | 1990-10-10 |
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