CS265228B2 - Making of intermediate for norfloxacine production - Google Patents

Making of intermediate for norfloxacine production Download PDF

Info

Publication number: CS265228B2
Authority: CS; Czechoslovakia
Prior art keywords: carbon atoms; iii; formula; pct; ethyl
Prior art date: 1985-12-09

Application number

CS869089A

Other languages

Czech (cs)

English (en)

Other versions

CS908986A2 (en

Inventor

Istvan Dr Hermezc

Geza Kereszturi

Lelle Vasvar

Agnes Dr Horvath

Maria Dr Balogh

Gabor Dr Kovacs

Zoltan Dr Meszaros

Peter Ritli

Judit Sipos

Aniko Pajor

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

Priority date (The priority date 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 date listed.)

1985-12-09

Filing date

1986-12-09

Publication date

1989-10-13

1986-12-09 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1988-03-15 Publication of CS908986A2 publication Critical patent/CS908986A2/cs

1989-10-13 Publication of CS265228B2 publication Critical patent/CS265228B2/cs

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 claims description 4
229960001180 norfloxacin Drugs 0.000 title claims description 4
238000004519 manufacturing process Methods 0.000 title description 3
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
238000000034 method Methods 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 6
150000001638 boron Chemical class 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
238000006243 chemical reaction Methods 0.000 claims description 7
150000008064 anhydrides Chemical class 0.000 claims description 5
239000000543 intermediate Substances 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims 1
125000004423 acyloxy group Chemical group 0.000 abstract description 4
125000005843 halogen group Chemical group 0.000 abstract description 4
125000000217 alkyl group Chemical group 0.000 abstract description 3
125000003118 aryl group Chemical group 0.000 abstract description 3
229910052736 halogen Inorganic materials 0.000 abstract 2
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
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 6
239000004327 boric acid Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
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 5
-1 1-ethyl-6-fluoro-7-substituted-4-oxo-1,4-dihydroquinoline-3-carboxylic acids Chemical class 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000000354 decomposition reaction Methods 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
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
125000003277 amino group Chemical group 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000000203 mixture Substances 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product 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
ZBFDBJYOOUAQSA-UHFFFAOYSA-N C(CC)(=O)OOBOOC(CC)=O Chemical compound C(CC)(=O)OOBOOC(CC)=O ZBFDBJYOOUAQSA-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 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
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000000994 depressogenic effect Effects 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
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 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
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
150000003462 sulfoxides Chemical class 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

Chemical & Material Sciences (AREA)
Organic Chemistry (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)
Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Thin Film Transistor (AREA)
Cephalosporin Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CS869089A 1985-12-09 1986-12-09 Making of intermediate for norfloxacine production CS265228B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU854693A HU196218B (en)	1985-12-09	1985-12-09	Process for preparing quinoline carboxylic acid boric acid anhydrides

Publications (2)

Publication Number	Publication Date
CS908986A2 CS908986A2 (en)	1988-03-15
CS265228B2 true CS265228B2 (en)	1989-10-13

Family

ID=10968688

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS869089A CS265228B2 (en)	1985-12-09	1986-12-09	Making of intermediate for norfloxacine production

Country Status (18)

Country	Link
US (1)	US4803274A (ko)
EP (1)	EP0250535B1 (ko)
JP (1)	JPH0742299B2 (ko)
KR (1)	KR940009028B1 (ko)
AT (1)	ATE53212T1 (ko)
CA (1)	CA1284800C (ko)
CS (1)	CS265228B2 (ko)
DD (1)	DD252608A5 (ko)
DE (1)	DE3671628D1 (ko)
DK (1)	DK412587A (ko)
FI (1)	FI84072C (ko)
HR (1)	HRP930558A2 (ko)
HU (1)	HU196218B (ko)
NO (1)	NO169076C (ko)
SI (1)	SI8612108A8 (ko)
SU (1)	SU1604156A3 (ko)
WO (1)	WO1987003595A1 (ko)
YU (1)	YU45388B (ko)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SI8810667A8 (en) *	1987-04-08	1996-04-30	Chinoin Gyogyszer Es Vegyeszet	Anhydride of quinoline carboxylic acid of boron acid and process for their production.
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)

* Cited by examiner, † Cited by third party
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 SI SI8612108A patent/SI8612108A8/sl unknown
- 1986-12-09 YU YU2108/86A patent/YU45388B/xx unknown
- 1986-12-09 US US07/105,298 patent/US4803274A/en not_active Expired - Fee Related
- 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
- 1986-12-09 JP JP62500207A patent/JPH0742299B2/ja not_active Expired - Lifetime
- 1986-12-09 CS CS869089A patent/CS265228B2/cs unknown
- 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 DE DE8787900246T patent/DE3671628D1/de not_active Expired - Fee Related
- 1986-12-09 AT AT87900246T patent/ATE53212T1/de 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/fi 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
FI873443A0 (fi)	1987-08-07
NO169076C (no)	1992-05-06
NO873247D0 (no)	1987-08-03
EP0250535B1 (en)	1990-05-30
FI873443A (fi)	1987-08-07
NO873247L (no)	1987-08-03
EP0250535A1 (en)	1988-01-07
HRP930558A2 (en)	1996-04-30
US4803274A (en)	1989-02-07
FI84072C (fi)	1991-10-10
CS908986A2 (en)	1988-03-15
CA1284800C (en)	1991-06-11
DK412587D0 (da)	1987-08-07
JPS63501955A (ja)	1988-08-04
KR880700803A (ko)	1988-04-12
SU1604156A3 (ru)	1990-10-30
JPH0742299B2 (ja)	1995-05-10
YU45388B (en)	1992-05-28
KR940009028B1 (ko)	1994-09-29
HU196218B (en)	1988-10-28
SI8612108A8 (en)	1996-10-31
YU210886A (en)	1987-12-31
ATE53212T1 (de)	1990-06-15
DK412587A (da)	1987-08-07
NO169076B (no)	1992-01-27
HUT44566A (en)	1988-03-28
DE3671628D1 (de)	1990-07-05
DD252608A5 (de)	1987-12-23
WO1987003595A1 (en)	1987-06-18
FI84072B (fi)	1991-06-28

Publication	Publication Date	Title
JPH0778065B2 (ja)	1995-08-23	（６，７―置換―８―アルコキシ―１―シクロプロピル―１，４―ジヒドロ―４―オキソ―３―キノリンカルボン酸―ｏ▲上３▼，ｏ▲上４▼）ビス（アシルオキシ―ｏ）ホウ素化合物及びその塩並びにその製造方法
EP0310647B1 (en)	1992-12-09	Quinoline carboxylic acid boric acid anhydrides and process for the preparation thereof
EP0351889B1 (en)	1994-06-29	Process for the preparation of a quinoline carboxylic acid
CS265228B2 (en)	1989-10-13	Making of intermediate for norfloxacine production
EP0329719A1 (en)	1989-08-30	Process for the preparation of quinoline carboxylic acid derivatives
HU198709B (en)	1989-11-28	Process for producing quinoline-carboxylic acid derivatives
JPS63179856A (ja)	1988-07-23	キノロンカルボン酸誘導体の製造方法並びにその中間体
EP0248876B1 (en)	1995-03-15	Process for the preparation of 1-methylamino-quinoline-carboxylic acid derivatives
EP0370686B1 (en)	1993-12-29	A process for preparing quinolone carboxylic acid intermediates
EP0248072B1 (en)	1992-03-18	Amifloxacine intermediate
KR830002721B1 (ko)	1983-12-09	퀴놀린 카복실산 유도체의 제조방법
KR950001013B1 (ko)	1995-02-07	퀴놀론 유도체의 제조방법
KR890002639B1 (ko)	1989-07-21	퀴놀린 유도체의 제조 방법
RU2049783C1 (ru)	1995-12-10	Способ получения производных хинолинкарбоновых кислот или их фармацевтически приемлемых солей
KR900000554B1 (ko)	1990-01-31	퀴놀린카르복실산 유도체의 제조방법
HU198728B (hu)	1989-11-28	Eljárás kinolinkarbonsavszármazékok előállítására
KR900002041B1 (ko)	1990-03-31	퀴놀론 유도체의 제조방법
HUT67395A (en)	1995-04-28	Method for the n-cyclopropylation of primary and secondary aromatic amines
JPS61143362A (ja)	1986-07-01	キノリンカルボン酸誘導体