FI84072B - Mellanprodukt foer framstaellning av norfloxacin och foerfarande foer dess framstaellning. - Google Patents
Mellanprodukt foer framstaellning av norfloxacin och foerfarande foer dess framstaellning. Download PDFInfo
- Publication number
- FI84072B FI84072B FI873443A FI873443A FI84072B FI 84072 B FI84072 B FI 84072B FI 873443 A FI873443 A FI 873443A FI 873443 A FI873443 A FI 873443A FI 84072 B FI84072 B FI 84072B
- Authority
- FI
- Finland
- Prior art keywords
- carbon atoms
- formula
- halogen
- pct
- ethyl
- Prior art date
Links
- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 title description 2
- 229960001180 norfloxacin Drugs 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 150000001638 boron Chemical class 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 5
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000012450 pharmaceutical intermediate Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- -1 1-ethyl-6-fluoro-7-substituted 4-oxo-1,4-dihydroquinoline-3-carboxylic acids Chemical class 0.000 description 7
- 235000010338 boric acid Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 5
- 239000004327 boric acid Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- NGBZZCXZVDYZQK-UHFFFAOYSA-N ethyl 7-chloro-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylate Chemical compound ClC1=C(F)C=C2C(=O)C(C(=O)OCC)=CN(CC)C2=C1 NGBZZCXZVDYZQK-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- WNNSMMJBBOPPOT-UHFFFAOYSA-N 7-chloro-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(Cl)C=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 WNNSMMJBBOPPOT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- DTYLXDLAOLOTKT-UHFFFAOYSA-N 1,4-dihydroquinoline-3-carboxylic acid Chemical compound C1=CC=C2CC(C(=O)O)=CNC2=C1 DTYLXDLAOLOTKT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005619 boric acid group Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Peptides Or Proteins (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Catalysts (AREA)
- Cephalosporin Compounds (AREA)
- Thin Film Transistor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (4)
1. Föreningar med formeln
5 Rl /R B o xo K A p u> i° YTr^o C2H5 15 väri R och R1 betecknar en alifatisk acyloxigrupp, som har 2-5 kolatomer och som kan vara substituerad med halogen; eller en aromatisk acyloxigrupp med 7-11 kolatomer.
2. Förfarande för framställning av föreningar med formeln 20 R' R B o xo R. p
25 YYVk L JL j %o cK^ijT C2H5 30 väri R och R1 betecknar en alifatisk acyloxigrupp, som har 2-5 kolatomer och som kan vara substituerad med halogen; eller en aromatisk acyloxigrupp med 7-11 kolatomer, kännetecknat därav, att en förening med for-35 meln 9 84072 F\^Ar^C0°R2
5 TXT «m cr^V C2 H5 10 vari R2 betecknar väte eller alkyl med 1-4 kolatomer, om-sätts med ett borderivat med formeln .-OCOR3 B^~-OCOR4 (III) 15 ^^OCOR5 väri R3, R4 och R5 betecknar en alkylgrupp, som har 1-4 kolatomer och som kan vara substituerad med halogen; eller en arylgrupp med 6-10 kolatomer. 20
3. Förfarande enligt patentkravet 2, känne- t e c k n a t därav, att reaktionen av föreningarna med formlerna II och III utförs i närvaro av ett lösningsme-del.
4. Förfarande enligt patentkravet 2, känne-25 tecknat därav, att reaktionen av föreningarna med formlerna II och III utförs vid en temperatur av 0 - 150 °C. 30 35
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU469385 | 1985-12-09 | ||
| HU854693A HU196218B (en) | 1985-12-09 | 1985-12-09 | Process for preparing quinoline carboxylic acid boric acid anhydrides |
| PCT/HU1986/000068 WO1987003595A1 (en) | 1985-12-09 | 1986-12-09 | Norfloxacin intermediate |
| HU8600068 | 1986-12-09 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI873443A FI873443A (fi) | 1987-08-07 |
| FI873443A0 FI873443A0 (fi) | 1987-08-07 |
| FI84072B true FI84072B (fi) | 1991-06-28 |
| FI84072C FI84072C (sv) | 1991-10-10 |
Family
ID=10968688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI873443A FI84072C (sv) | 1985-12-09 | 1987-08-07 | Mellanprodukt för framställning av norfloxacin och förfarande för dess framställning |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4803274A (sv) |
| EP (1) | EP0250535B1 (sv) |
| JP (1) | JPH0742299B2 (sv) |
| KR (1) | KR940009028B1 (sv) |
| AT (1) | ATE53212T1 (sv) |
| CA (1) | CA1284800C (sv) |
| CS (1) | CS265228B2 (sv) |
| DD (1) | DD252608A5 (sv) |
| DE (1) | DE3671628D1 (sv) |
| DK (1) | DK412587A (sv) |
| FI (1) | FI84072C (sv) |
| HR (1) | HRP930558A2 (sv) |
| HU (1) | HU196218B (sv) |
| NO (1) | NO169076C (sv) |
| SI (1) | SI8612108A8 (sv) |
| SU (1) | SU1604156A3 (sv) |
| WO (1) | WO1987003595A1 (sv) |
| YU (1) | YU45388B (sv) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU46451B (sh) * | 1987-04-08 | 1993-10-20 | Chinoin Gyogyszer Es Vegyeszeti Ter Mekek Gyara Rt. | Postupak za dobivanje mešovitih anhidrida hinolin-karboksilne i borne kiseline |
| HU198709B (en) * | 1987-04-08 | 1989-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing quinoline-carboxylic acid derivatives |
| US5380845A (en) * | 1987-06-24 | 1995-01-10 | Chinoin Gyogyszer- Es Vegyeszeti Termekek Gyara Rt. | Process for the preparation of quinoline carboxylic acid derivatives |
| GR910100517A (el) * | 1991-12-30 | 1993-08-31 | Kyorin Seiyaku Kk | Δις(ακυλοξυ-ο) βορικος εστερας του (6,7-υποκατεστημενου-8-αλκοξυ-1- κυκλοπροπυλ-1,4,-διυδρο-4-οξο-3-κινολινοκαρβοξυλικου οξεως-ο3,ο4)και αλας αυτου, και μεθοδος παρασκευης αυτου. |
| ES2077490B1 (es) * | 1992-11-18 | 1996-10-16 | Marga Investigacion | Esteres trimetilsililicos y solvatos de quelatos de acidos quinolin-3-carboxilicos. preparacion y aplicacion al proceso de quinolonas. |
| ES2092963B1 (es) * | 1995-04-12 | 1997-12-16 | Sint Quimica Sa | Procedimiento para la preparacion del acido 1-ciclopropil-6-fluoro-1, 4-dihidro-7-(1s,4s)-5-metil-2,5-diazabiciclo(2.2.1) hept-2-il)-4-oxo-3-quinolincarboxilico y sus sales. |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1195749A (en) * | 1966-12-19 | 1970-06-24 | Lubrizol Corp | Sulfur-Containing Cycloaliphatic Reaction Products and their use in Lubricant Compositions |
| JPS53141286A (en) | 1977-05-16 | 1978-12-08 | Kyorin Seiyaku Kk | Novel substituted quinolinecarboxylic acid |
| SE444566B (sv) | 1977-09-20 | 1986-04-21 | Bellon Labor Sa Roger | 7-dialkylamin-6-halogen-4-oxo-1,4-dihydrokinolin-3-karboxylsyra, forfarande for framstellning derav och farmaceutiskt preparat derav |
| JPS6011913B2 (ja) * | 1977-12-27 | 1985-03-28 | 広栄化学工業株式会社 | １，８−ナフチリジン誘導体ならびにその製造方法 |
| JPS54138582A (en) | 1978-04-19 | 1979-10-27 | Kyorin Seiyaku Kk | Substituted quinolinecarboxylic acid |
| FR2424919B1 (fr) | 1978-05-03 | 1980-10-31 | Kyorin Seiyaku Kk | Acide quinoleinecarboxylique substitue et ses derives et leur utilisation comme agents antibacteriens |
| JPS5533453A (en) | 1978-08-31 | 1980-03-08 | Dainippon Pharmaceut Co Ltd | Preventive and remedy for infectious disease of fish |
| JPS5845426B2 (ja) | 1978-09-29 | 1983-10-08 | 杏林製薬株式会社 | 置換キノリンカルボン酸誘導体 |
| JPS5762259A (en) | 1980-09-05 | 1982-04-15 | Kyorin Pharmaceut Co Ltd | Preparation of substituted quinolinecarboxylic acid derivative |
| JPS59122470A (ja) | 1982-12-27 | 1984-07-14 | Dai Ichi Seiyaku Co Ltd | キノリン−３−カルボン酸誘導体の製造法 |
| JPH0833453B2 (ja) | 1987-05-30 | 1996-03-29 | 大阪瓦斯株式会社 | 金属管の接触位置の検出方法 |
-
1985
- 1985-12-09 HU HU854693A patent/HU196218B/hu not_active IP Right Cessation
-
1986
- 1986-12-08 CA CA000524725A patent/CA1284800C/en not_active Expired - Lifetime
- 1986-12-09 JP JP62500207A patent/JPH0742299B2/ja not_active Expired - Lifetime
- 1986-12-09 US US07/105,298 patent/US4803274A/en not_active Expired - Fee Related
- 1986-12-09 WO PCT/HU1986/000068 patent/WO1987003595A1/en active IP Right Grant
- 1986-12-09 DD DD86297301A patent/DD252608A5/de not_active IP Right Cessation
- 1986-12-09 YU YU2108/86A patent/YU45388B/xx unknown
- 1986-12-09 CS CS869089A patent/CS265228B2/cs unknown
- 1986-12-09 DE DE8787900246T patent/DE3671628D1/de not_active Expired - Fee Related
- 1986-12-09 AT AT87900246T patent/ATE53212T1/de not_active IP Right Cessation
- 1986-12-09 SI SI8612108A patent/SI8612108A8/sl unknown
- 1986-12-09 EP EP87900246A patent/EP0250535B1/en not_active Expired - Lifetime
- 1986-12-09 KR KR1019870700687A patent/KR940009028B1/ko not_active IP Right Cessation
-
1987
- 1987-08-03 NO NO873247A patent/NO169076C/no unknown
- 1987-08-07 DK DK412587A patent/DK412587A/da not_active Application Discontinuation
- 1987-08-07 FI FI873443A patent/FI84072C/sv not_active IP Right Cessation
- 1987-08-07 SU SU874203191A patent/SU1604156A3/ru active
-
1993
- 1993-03-26 HR HR930558A patent/HRP930558A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63501955A (ja) | 1988-08-04 |
| NO169076B (no) | 1992-01-27 |
| FI84072C (sv) | 1991-10-10 |
| DE3671628D1 (de) | 1990-07-05 |
| NO169076C (no) | 1992-05-06 |
| NO873247D0 (no) | 1987-08-03 |
| SI8612108A8 (en) | 1996-10-31 |
| SU1604156A3 (ru) | 1990-10-30 |
| EP0250535A1 (en) | 1988-01-07 |
| NO873247L (no) | 1987-08-03 |
| JPH0742299B2 (ja) | 1995-05-10 |
| WO1987003595A1 (en) | 1987-06-18 |
| HRP930558A2 (en) | 1996-04-30 |
| CS265228B2 (en) | 1989-10-13 |
| HUT44566A (en) | 1988-03-28 |
| FI873443A (fi) | 1987-08-07 |
| DD252608A5 (de) | 1987-12-23 |
| EP0250535B1 (en) | 1990-05-30 |
| CA1284800C (en) | 1991-06-11 |
| DK412587D0 (da) | 1987-08-07 |
| KR880700803A (ko) | 1988-04-12 |
| US4803274A (en) | 1989-02-07 |
| HU196218B (en) | 1988-10-28 |
| DK412587A (da) | 1987-08-07 |
| CS908986A2 (en) | 1988-03-15 |
| KR940009028B1 (ko) | 1994-09-29 |
| YU210886A (en) | 1987-12-31 |
| ATE53212T1 (de) | 1990-06-15 |
| YU45388B (en) | 1992-05-28 |
| FI873443A0 (fi) | 1987-08-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: CHINOIN GYOGUSZER ES VEGYESZETI TERMEKEK |