FI73213B - Foerfarande foer framstaellning av 6,7-dihydro-5,8-dimetyl-9-fluor-1-oxo-1h,5h-benzo/i,j/kinolizin-2 -karboxyl-syra och mellanprodukter foer anvaendning vid foerfarandet. - Google Patents
Foerfarande foer framstaellning av 6,7-dihydro-5,8-dimetyl-9-fluor-1-oxo-1h,5h-benzo/i,j/kinolizin-2 -karboxyl-syra och mellanprodukter foer anvaendning vid foerfarandet. Download PDFInfo
- Publication number
- FI73213B FI73213B FI834147A FI834147A FI73213B FI 73213 B FI73213 B FI 73213B FI 834147 A FI834147 A FI 834147A FI 834147 A FI834147 A FI 834147A FI 73213 B FI73213 B FI 73213B
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- Finland
- Prior art keywords
- fluoro
- dihydro
- formula
- oxo
- compounds
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- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
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- UUDMRWQDWVOXFN-UHFFFAOYSA-N benzo[j]quinolizine-2-carboxylic acid Chemical compound C1=CC=CC2=CC=CN3C21C=C(C(=O)O)C=C3 UUDMRWQDWVOXFN-UHFFFAOYSA-N 0.000 description 1
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- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
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- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- 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
-
- 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
- C07D215/18—Halogen atoms or nitro radicals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Quinoline Compounds (AREA)
Claims (8)
1. Föreningen 5-karboxyl-6-fluorkinaldin med formeln 5 ΓΥΝΥΗ3 COOH
2. Föreningen 6-fluor-5-metyl-l,2,3,4-tetrahydro-10 kinaldin med formeln H XX
15 CH3
3. Föreningen 1,2-dihydro-6-fluor-5-hydroximetylkin-aldin med formeln H N'YCH3 20 i ch2oh
4. Föreningen dietyl-2-ZJl- (6-fluor-5-metyl-l, 2,3,4-tetrahydrokinaldinyl)_7metylenmalonat med formeln 25 h=c(co2c2h5)2 CH, 30 3
5. Förfarande för framställning av 6,7-dihydro-5,8-dime ty 1-9- f luor-l-oxo-lH, 5H-bensc/ i, j/kinolizin-2-karboxyl-syra, vilken har antimikrobiell inverkan och vilken har formeln 7321 3 O COOH CH^V'^N^ och dess karboxylatsalter, kännetecknat därav, att förfarandet omfattar följande steg: a) 5-amino-2-fluorbensoesyra med formeln 10 r^VNH2 ,u COOH 15 omsätts med krotonaldehyd CH3CH=CHCO eller dess prekursor, b) den erhällna 5-karboxi-6-fluorkinaldinen med formeln nV-ch3 20 COOH reduceras för erhällande av 6-fluor-5-metyl-l,2,3,4-tetra-hydrokinaldin med formeln 25 H ^νΝνΗ3 { ί 30 c) den erhällna 6-fluor-5-metyl-l,2,3,4-tetrahydro- kinaldinen kondenseras med en alkoximetylenmalonsyradiester med formeln CO-R1 / 2 alk-0-CH=C C oc \ i
35 C02R
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/441,245 US4472405A (en) | 1982-11-12 | 1982-11-12 | Antimicrobial 6,7-dihydro-5,8-dimethyl-9 fluoro-1-oxo-1H, 5H-benzo (ij) quinolizine-2-carboxylic acid and derivatives |
| US44124582 | 1982-11-12 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI834147A0 FI834147A0 (fi) | 1983-11-11 |
| FI834147A FI834147A (fi) | 1984-05-13 |
| FI73213B true FI73213B (fi) | 1987-05-29 |
| FI73213C FI73213C (sv) | 1987-09-10 |
Family
ID=23752110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI834147A FI73213C (sv) | 1982-11-12 | 1983-11-11 | Förfarande för framställning av 6,7-dihydro-5,8-dimetyl-9-fluor-1-oxo- 1H,5H-benzo/i,j/kinolizin-2 -karboxyl-syra och mellanprodukter för an vändning vid förfarandet. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4472405A (sv) |
| EP (1) | EP0109284B1 (sv) |
| JP (1) | JPH0826017B2 (sv) |
| KR (1) | KR890000864B1 (sv) |
| AT (1) | ATE39926T1 (sv) |
| AU (1) | AU568319B2 (sv) |
| CA (2) | CA1254568A (sv) |
| CS (1) | CS390391A3 (sv) |
| DE (1) | DE3378912D1 (sv) |
| EG (1) | EG16492A (sv) |
| ES (1) | ES527163A0 (sv) |
| FI (1) | FI73213C (sv) |
| GR (1) | GR79402B (sv) |
| IE (1) | IE56232B1 (sv) |
| IL (1) | IL70198A (sv) |
| IN (1) | IN161391B (sv) |
| MX (1) | MX7314E (sv) |
| NO (1) | NO160782C (sv) |
| NZ (1) | NZ206233A (sv) |
| OA (1) | OA07586A (sv) |
| PT (1) | PT77649B (sv) |
| ZA (1) | ZA838436B (sv) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3519926A1 (de) * | 1985-06-04 | 1986-12-04 | Bayer Ag | Indolinderivate, verfahren zu ihrer herstellung und diese indolinderivate enthaltende kosmetische lichtschutzmittel |
| CA1302413C (en) * | 1986-01-22 | 1992-06-02 | Bruce E. Williams | Process for 6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo- 1h,5h-benzo[ij]quinolizine-2-carboxylic acid |
| US4898945A (en) * | 1986-01-22 | 1990-02-06 | Minnesota Mining And Manufacturing Company | Process for 6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid |
| GB9827865D0 (en) * | 1998-12-18 | 1999-02-10 | Woodcock Fiona | Medicament |
| DE10312346A1 (de) * | 2003-03-20 | 2004-09-30 | Bayer Healthcare Ag | Kontrolliertes Freisetzungssystem |
| DE10351448A1 (de) | 2003-11-04 | 2005-06-09 | Bayer Healthcare Ag | Geschmackstoffhaltige Arzneimittelformulierungen mit verbesserten pharmazeutischen Eigenschaften |
| DE102005055385A1 (de) * | 2004-12-09 | 2006-06-14 | Bayer Healthcare Ag | Arzneimittel zur hygienischen Applikation im Ohr |
| DE102006010643A1 (de) | 2006-03-08 | 2007-09-13 | Bayer Healthcare Aktiengesellschaft | Arzneimittel enthaltend Fluorchinolone |
| DE102006010642A1 (de) * | 2006-03-08 | 2007-09-27 | Bayer Healthcare Aktiengesellschaft | Arzneimittelformulierungen, enthaltend Fluorchinolone |
| DE102007026550A1 (de) * | 2007-06-08 | 2008-12-11 | Bayer Healthcare Ag | Extrudate mit verbesserter Geschmacksmaskierung |
| DE102007055341A1 (de) | 2007-11-19 | 2009-05-20 | Bayer Animal Health Gmbh | Stabilisierung öliger Suspensionen enthaltend hydrophobe Kieselsäuren |
| CA2814082A1 (en) | 2010-10-12 | 2012-04-19 | Bayer Intellectual Property Gmbh | Non-starch based soft chewables |
| CA2895254C (en) | 2012-12-19 | 2021-01-26 | Bayer Animal Health Gmbh | Tablets with improved acceptance and good storage stability |
| MD4291C1 (ro) * | 2013-12-27 | 2015-02-28 | Государственный Медицинский И Фармацевтический Университет "Nicolae Testemitanu" Республики Молдова | Preparat medicamentos pentru tratamentul otitelor |
| US20210068425A1 (en) * | 2019-09-06 | 2021-03-11 | Bayer Healthcare Llc | Palatable granular veterinary compositions |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE793524A (fr) * | 1971-12-30 | 1973-06-29 | Riker Laboratories Inc | Acides benzoquinolizine-carboxyliques et leurs derives |
| ZA728444B (en) * | 1971-12-30 | 1973-10-31 | Riker Laboratories Inc | Substituted benzo(ij)quinolizine-2-carboxylic acids and derivatives thereof |
| JPS5630964A (en) * | 1979-08-22 | 1981-03-28 | Kyorin Pharmaceut Co Ltd | Novel substituted quinolinecarboxylic acid and its preparation |
| JPS5655388A (en) | 1979-10-11 | 1981-05-15 | Otsuka Pharmaceut Co Ltd | Benzo ij quinolidine-2-carboxylic acid derivative, and its preparation |
| US4301289A (en) * | 1980-02-19 | 1981-11-17 | Minnesota Mining And Manufacturing Company | Process for 6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo(ij)quinolizine-2-carboxylic acid |
| JPS59155381A (ja) * | 1983-02-22 | 1984-09-04 | Kyorin Pharmaceut Co Ltd | ベンゾキノリジンカルボン酸誘導体及びその製造法 |
-
1982
- 1982-11-12 US US06/441,245 patent/US4472405A/en not_active Expired - Lifetime
-
1983
- 1983-10-27 CA CA000439826A patent/CA1254568A/en not_active Expired
- 1983-11-09 NO NO834093A patent/NO160782C/no unknown
- 1983-11-10 ES ES527163A patent/ES527163A0/es active Granted
- 1983-11-10 OA OA58156A patent/OA07586A/xx unknown
- 1983-11-11 IL IL70198A patent/IL70198A/xx not_active IP Right Cessation
- 1983-11-11 JP JP58212306A patent/JPH0826017B2/ja not_active Expired - Lifetime
- 1983-11-11 AT AT83306908T patent/ATE39926T1/de not_active IP Right Cessation
- 1983-11-11 PT PT77649A patent/PT77649B/pt not_active IP Right Cessation
- 1983-11-11 IN IN1382/CAL/83A patent/IN161391B/en unknown
- 1983-11-11 DE DE8383306908T patent/DE3378912D1/de not_active Expired
- 1983-11-11 GR GR72947A patent/GR79402B/el unknown
- 1983-11-11 NZ NZ206233A patent/NZ206233A/en unknown
- 1983-11-11 EP EP83306908A patent/EP0109284B1/en not_active Expired
- 1983-11-11 MX MX8310883U patent/MX7314E/es unknown
- 1983-11-11 FI FI834147A patent/FI73213C/sv not_active IP Right Cessation
- 1983-11-11 AU AU21181/83A patent/AU568319B2/en not_active Ceased
- 1983-11-11 ZA ZA838436A patent/ZA838436B/xx unknown
- 1983-11-11 IE IE2639/83A patent/IE56232B1/en not_active IP Right Cessation
- 1983-11-12 KR KR1019830005376A patent/KR890000864B1/ko not_active IP Right Cessation
- 1983-11-12 EG EG70383A patent/EG16492A/xx active
-
1988
- 1988-08-05 CA CA000574069A patent/CA1280755C/en not_active Expired - Fee Related
-
1991
- 1991-12-19 CS CS913903A patent/CS390391A3/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI834147A0 (fi) | 1983-11-11 |
| DE3378912D1 (de) | 1989-02-16 |
| FI73213C (sv) | 1987-09-10 |
| FI834147A (fi) | 1984-05-13 |
| IE56232B1 (en) | 1991-05-22 |
| CA1254568A (en) | 1989-05-23 |
| CA1280755C (en) | 1991-02-26 |
| ATE39926T1 (de) | 1989-01-15 |
| NO160782B (no) | 1989-02-20 |
| EP0109284B1 (en) | 1989-01-11 |
| GR79402B (sv) | 1984-10-22 |
| OA07586A (fr) | 1985-03-31 |
| PT77649B (en) | 1986-03-19 |
| EP0109284A1 (en) | 1984-05-23 |
| ES8504727A1 (es) | 1985-05-01 |
| IL70198A (en) | 1988-11-15 |
| EG16492A (en) | 1994-11-30 |
| AU568319B2 (en) | 1987-12-24 |
| KR840006659A (ko) | 1984-12-01 |
| IE832639L (en) | 1984-05-12 |
| KR890000864B1 (ko) | 1989-04-11 |
| NO160782C (no) | 1989-05-31 |
| PT77649A (en) | 1983-12-01 |
| IN161391B (sv) | 1987-11-28 |
| JPS59112969A (ja) | 1984-06-29 |
| ZA838436B (en) | 1985-06-26 |
| JPH0826017B2 (ja) | 1996-03-13 |
| ES527163A0 (es) | 1985-05-01 |
| AU2118183A (en) | 1984-05-17 |
| NZ206233A (en) | 1986-10-08 |
| US4472405A (en) | 1984-09-18 |
| CS390391A3 (en) | 1992-09-16 |
| IL70198A0 (en) | 1984-02-29 |
| NO834093L (no) | 1984-05-14 |
| MX7314E (es) | 1988-05-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: RIKER LABORATORIES, INC. |