JPH0148910B2 - - Google Patents
Info
- Publication number
- JPH0148910B2 JPH0148910B2 JP14191981A JP14191981A JPH0148910B2 JP H0148910 B2 JPH0148910 B2 JP H0148910B2 JP 14191981 A JP14191981 A JP 14191981A JP 14191981 A JP14191981 A JP 14191981A JP H0148910 B2 JPH0148910 B2 JP H0148910B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- benzoxazine
- dihydro
- pyrido
- oxo
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 22
- 238000000354 decomposition reaction Methods 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 4
- QDEJGQKJMKXYLM-UHFFFAOYSA-N 2h-pyrido[2,3-h][1,2]benzoxazine Chemical class C1=CC2=NC=CC=C2C2=C1C=CNO2 QDEJGQKJMKXYLM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000004885 piperazines Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000013522 chelant Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000013078 crystal Substances 0.000 description 19
- 238000001914 filtration Methods 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 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 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- NVKWWNNJFKZNJO-UHFFFAOYSA-N 82419-35-0 Chemical compound O1CC(C)N2C=C(C(O)=O)C(=O)C3=C2C1=C(F)C(F)=C3 NVKWWNNJFKZNJO-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- 229940113088 dimethylacetamide Drugs 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- DUGFZRFLUQJFOO-UHFFFAOYSA-N 4-oxa-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13),11-pentaene-11-carboxylic acid Chemical compound C1=COC2=CC=CC3=C2N1C=C(C(=O)O)C3 DUGFZRFLUQJFOO-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 description 2
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- YILGXIZRZUDENO-UHFFFAOYSA-N 10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13),11-tetraene-11-carboxylic acid Chemical compound C1COC2=CC=CC3=C2N1C=C(C(=O)O)C3=O YILGXIZRZUDENO-UHFFFAOYSA-N 0.000 description 1
- CFLBIADORGSMCX-UHFFFAOYSA-N 2h-1,4-benzoxazine-6-carboxylic acid Chemical compound O1CC=NC2=CC(C(=O)O)=CC=C21 CFLBIADORGSMCX-UHFFFAOYSA-N 0.000 description 1
- BVHSAZFNVBBGNX-UHFFFAOYSA-N 7,8-difluoro-3-methyl-3,4-dihydro-2h-1,4-benzoxazine Chemical compound C1=CC(F)=C(F)C2=C1NC(C)CO2 BVHSAZFNVBBGNX-UHFFFAOYSA-N 0.000 description 1
- WKRSSAPQZDHYRV-UHFFFAOYSA-N 82419-52-1 Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCNCC1 WKRSSAPQZDHYRV-UHFFFAOYSA-N 0.000 description 1
- OYHNLEGFMGVEHA-UHFFFAOYSA-N 9-chloro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7h-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid Chemical compound ClC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 OYHNLEGFMGVEHA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000005973 Carvone Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- -1 etc. Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- CHNLPLHJUPMEOI-UHFFFAOYSA-N oxolane;trifluoroborane Chemical compound FB(F)F.C1CCOC1 CHNLPLHJUPMEOI-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14191981A JPS5843977A (ja) | 1981-09-09 | 1981-09-09 | ピリドベンズオキサジン誘導体の製法 |
| FI823024A FI76345C (fi) | 1981-09-09 | 1982-09-01 | Foerfarande foer framstaellning av pyridobensoxazinderivat. |
| AR29051082A AR230451A1 (es) | 1981-09-09 | 1982-09-01 | Procedimiento para preparar derivados del acido pirido(1,3-de)1,4-benzoxacin-6-carboxilico |
| PT7552382A PT75523B (en) | 1981-09-09 | 1982-09-07 | Process for preparing pyridobenzoxazine derivatives |
| DK399782A DK158268C (da) | 1981-09-09 | 1982-09-07 | Fremgangsmaade til fremstilling af pyridobenzoxazin-derivater |
| SI8212021A SI8212021A8 (sl) | 1981-09-09 | 1982-09-07 | Postopek za pripravo derivatov pirido/1,2,3-de//1,4/-benzoksazin-6-karboksilne kisline |
| YU202182A YU43922B (en) | 1981-09-09 | 1982-09-07 | Process for preparing pyrido (1,2,3-de)(1,4)-benzoxazine-6-carboxylic acid derivatives |
| PL23817782A PL130881B1 (en) | 1981-09-09 | 1982-09-08 | Process for preparing novel derivatives of pyrido /1,2,3-de/-/1,4/-benzoxazin-6-carboxylic acid |
| DD24311682A DD203719A5 (de) | 1981-09-09 | 1982-09-08 | Verfahren zur herstellung neuer, antibakteriell wirkender pyrido (1,2,3-de)(1,4)benzoxazin-5-carbonsaeure-derivate |
| MX787982A MX155044A (es) | 1981-09-09 | 1982-09-08 | Procedimiento para preparar derivados de piridobenzo-xazina |
| ES515608A ES8400432A1 (es) | 1981-09-09 | 1982-09-09 | Un procedimiento para la preparacion de derivados del acido pirido-1,2,3-1,4 benzoxazin-6-carboxilico. |
| FI881403A FI80463C (fi) | 1981-09-09 | 1988-03-24 | Pyrido/1,2,3-de//1,4/benzoxazin-6- karboxylsyra-bf2-kelatderivat och foerfarande foer deras framstaellning. |
| DK173588A DK173588A (da) | 1981-09-09 | 1988-03-29 | Fremgangsmaade til fremstilliing af pyrido(1,2,3-de)(1,4)benzoxazin-6-carboxylsyre-bf2-chelatforbindelser |
| SI8810746A SI8810746A8 (sl) | 1981-09-09 | 1988-04-14 | Postopek za pripravo bf2-kelatne spojine pirido/1,2,3-de//1,4/ benzoksazin-6-karboksilne kisline |
| YU74688A YU46542B (sh) | 1981-09-09 | 1988-04-14 | Postopek za pripravo bf2-kelatne spojine pirido/1,2,3-de//1,4/benzoksazin-6-karboksilne kisline |
| HR930085A HRP930085B1 (en) | 1981-09-09 | 1993-02-01 | PROCESS FOR THE PREPARATION OF BF2-KETONIC COMPOUND PYRIDOL (1,2,3-de)(1,4) BENZOXAZYNE-6-CARBOXYLIC ACID |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14191981A JPS5843977A (ja) | 1981-09-09 | 1981-09-09 | ピリドベンズオキサジン誘導体の製法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62234466A Division JPS63119487A (ja) | 1987-09-18 | 1987-09-18 | ピリドベンズオキサジン誘導体の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5843977A JPS5843977A (ja) | 1983-03-14 |
| JPH0148910B2 true JPH0148910B2 (fr) | 1989-10-20 |
Family
ID=15303207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14191981A Granted JPS5843977A (ja) | 1981-09-09 | 1981-09-09 | ピリドベンズオキサジン誘導体の製法 |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5843977A (fr) |
| AR (1) | AR230451A1 (fr) |
| DD (1) | DD203719A5 (fr) |
| DK (2) | DK158268C (fr) |
| ES (1) | ES8400432A1 (fr) |
| FI (1) | FI76345C (fr) |
| PL (1) | PL130881B1 (fr) |
| PT (1) | PT75523B (fr) |
| YU (2) | YU43922B (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1267413A (fr) * | 1984-04-26 | 1990-04-03 | Abbott Laboratories | Composes antibacteriens de quino-benoxazine |
| CA1306750C (fr) | 1985-12-09 | 1992-08-25 | Istvan Hermecz | Procede pour la preparation d'acides quinoline carboxyliques |
| TW208013B (fr) * | 1990-03-01 | 1993-06-21 | Daiichi Co Ltd |
-
1981
- 1981-09-09 JP JP14191981A patent/JPS5843977A/ja active Granted
-
1982
- 1982-09-01 FI FI823024A patent/FI76345C/fi not_active IP Right Cessation
- 1982-09-01 AR AR29051082A patent/AR230451A1/es active
- 1982-09-07 PT PT7552382A patent/PT75523B/pt unknown
- 1982-09-07 DK DK399782A patent/DK158268C/da not_active IP Right Cessation
- 1982-09-07 YU YU202182A patent/YU43922B/xx unknown
- 1982-09-08 DD DD24311682A patent/DD203719A5/de unknown
- 1982-09-08 PL PL23817782A patent/PL130881B1/pl unknown
- 1982-09-09 ES ES515608A patent/ES8400432A1/es not_active Expired
-
1988
- 1988-03-29 DK DK173588A patent/DK173588A/da active IP Right Grant
- 1988-04-14 YU YU74688A patent/YU46542B/sh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK399782A (da) | 1983-03-10 |
| DK173588D0 (da) | 1988-03-29 |
| DK173588A (da) | 1988-03-29 |
| FI76345C (fi) | 1988-10-10 |
| DK158268B (da) | 1990-04-23 |
| FI76345B (fi) | 1988-06-30 |
| PT75523B (en) | 1984-12-12 |
| PT75523A (en) | 1982-10-01 |
| DK158268C (da) | 1990-10-15 |
| YU43922B (en) | 1989-12-31 |
| FI823024A0 (fi) | 1982-09-01 |
| AR230451A1 (es) | 1984-04-30 |
| ES515608A0 (es) | 1983-11-01 |
| YU46542B (sh) | 1993-11-16 |
| FI823024L (fi) | 1983-03-10 |
| PL238177A1 (en) | 1983-05-09 |
| YU74688A (en) | 1989-12-31 |
| DD203719A5 (de) | 1983-11-02 |
| YU202182A (en) | 1984-12-31 |
| PL130881B1 (en) | 1984-09-29 |
| JPS5843977A (ja) | 1983-03-14 |
| ES8400432A1 (es) | 1983-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |