HRP931485A2 - Process for the preparation of 1-supst.-fluoro-4-oxo-7-(1-piperazinyl)-1,4-hydroquinoline-3-carbonic acid, new rmediate, used in that process and a process for the aration of that intermediate - Google Patents

Process for the preparation of 1-supst.-fluoro-4-oxo-7-(1-piperazinyl)-1,4-hydroquinoline-3-carbonic acid, new rmediate, used in that process and a process for the aration of that intermediate Download PDF

Info

Publication number: HRP931485A2
Authority: HR; Croatia
Prior art keywords: oxo; fluoro; piperazinyl; general formula; dihydroquinoline
Prior art date: 1992-12-11

Application number

Other languages

English (en)

Croatian (hr)

Inventor

I Nata A Zupan

Martin Barbo

Boris Ket

Pavel Zupet

Original Assignee

Zupan~I~, Nata{A

Martin Barbo

[Ket, Boris

Pavel Zupet

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.)

1992-12-11

Filing date

1993-12-10

Publication date

1995-04-30

1993-12-10 Application filed by Zupan~I~, Nata{A, Martin Barbo, [Ket, Boris, Pavel Zupet filed Critical Zupan~I~, Nata{A

1995-04-30 Publication of HRP931485A2 publication Critical patent/HRP931485A2/hr

Links

238000000034 method Methods 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 10
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 6
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
229910052796 boron Inorganic materials 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
238000010534 nucleophilic substitution reaction Methods 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 3
-1 1-substituted piperazine Chemical class 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
KPVRJEIPIYNFNT-UHFFFAOYSA-L [B+2].CC([O-])=O.CC([O-])=O Chemical compound [B+2].CC([O-])=O.CC([O-])=O KPVRJEIPIYNFNT-UHFFFAOYSA-L 0.000 claims 1
239000012736 aqueous medium Substances 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000006467 substitution reaction Methods 0.000 description 5
230000000975 bioactive effect Effects 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
DGLCLBGXXHVMDM-UHFFFAOYSA-K C(C)(=O)[O-].C(C)(=O)[O-].[B+3].C(C)N1C=C(C(C2=CC(=C(C=C12)N1CCN(CC1)C(=O)OCC)F)=O)C(=O)[O-] Chemical compound C(C)(=O)[O-].C(C)(=O)[O-].[B+3].C(C)N1C=C(C(C2=CC(=C(C=C12)N1CCN(CC1)C(=O)OCC)F)=O)C(=O)[O-] DGLCLBGXXHVMDM-UHFFFAOYSA-K 0.000 description 3
OMWSMXOINRZRFS-UHFFFAOYSA-K C(C)(=O)[O-].C(C)(=O)[O-].[B+3].C1(CC1)N1C=C(C(C2=CC(=C(C=C12)N1CCN(CC1)C(=O)OCC)F)=O)C(=O)[O-] Chemical compound C(C)(=O)[O-].C(C)(=O)[O-].[B+3].C1(CC1)N1C=C(C(C2=CC(=C(C=C12)N1CCN(CC1)C(=O)OCC)F)=O)C(=O)[O-] OMWSMXOINRZRFS-UHFFFAOYSA-K 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
125000004193 piperazinyl group Chemical group 0.000 description 3
239000007858 starting material Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
ARPUHYJMCVWYCZ-UHFFFAOYSA-N ciprofloxacin hydrochloride hydrate Chemical compound O.Cl.C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 ARPUHYJMCVWYCZ-UHFFFAOYSA-N 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
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 description 2
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
238000004611 spectroscopical analysis Methods 0.000 description 2
241000894006 Bacteria Species 0.000 description 1
CQHKERVHCZAOQI-UHFFFAOYSA-K C(C)(=O)[O-].C(C)(=O)[O-].[B+3].C(C)N1C=C(C(C2=CC(=C(C=C12)Cl)F)=O)C(=O)[O-] Chemical compound C(C)(=O)[O-].C(C)(=O)[O-].[B+3].C(C)N1C=C(C(C2=CC(=C(C=C12)Cl)F)=O)C(=O)[O-] CQHKERVHCZAOQI-UHFFFAOYSA-K 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
HOPSUUQSCYMEJR-UHFFFAOYSA-K [B+3].CC([O-])=O.CC([O-])=O.C12=CC(Cl)=C(F)C=C2C(=O)C(C(=O)[O-])=CN1C1CC1 Chemical compound [B+3].CC([O-])=O.CC([O-])=O.C12=CC(Cl)=C(F)C=C2C(=O)C(C(=O)[O-])=CN1C1CC1 HOPSUUQSCYMEJR-UHFFFAOYSA-K 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001638 boron Chemical class 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Quinoline Compounds (AREA)

HRP931485 1992-12-11 1993-12-10 Process for the preparation of 1-supst.-fluoro-4-oxo-7-(1-piperazinyl)-1,4-hydroquinoline-3-carbonic acid, new rmediate, used in that process and a process for the aration of that intermediate HRP931485A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SI9200377A SI9200377A (en)	1992-12-11	1992-12-11	Process for the preparation of 1-substituted 6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxilic acid, novel intermediate used in this process and process for its preparation

Publications (1)

Publication Number	Publication Date
HRP931485A2 true HRP931485A2 (en)	1995-04-30

Family

ID=20431064

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HRP931485 HRP931485A2 (en)	1992-12-11	1993-12-10	Process for the preparation of 1-supst.-fluoro-4-oxo-7-(1-piperazinyl)-1,4-hydroquinoline-3-carbonic acid, new rmediate, used in that process and a process for the aration of that intermediate

Country Status (13)

Country	Link
AT (1)	AT401648B (de)
CA (1)	CA2111181A1 (de)
CZ (1)	CZ284715B6 (de)
EE (1)	EE9400277A (de)
HR (1)	HRP931485A2 (de)
HU (1)	HUT75319A (de)
LT (1)	LT3084B (de)
LV (1)	LV10863B (de)
PL (1)	PL173784B1 (de)
RU (1)	RU2127270C1 (de)
SI (1)	SI9200377A (de)
SK (1)	SK140093A3 (de)
YU (1)	YU76593A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BRPI0308696B8 (pt) *	2002-03-27	2021-05-25	Axovant Sciences Gmbh	composto derivado de quinolina, seu processo de preparação, sua composição farmacêutica e seus usos

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
DE2747357A1 (de)	1977-10-21	1979-04-26	Bayer Ag	Substituierte pyrimidinyl(thiono) (thiol)phosphor (phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
JPS5533453A (en)	1978-08-31	1980-03-08	Dainippon Pharmaceut Co Ltd	Preventive and remedy for infectious disease of fish
JPS5762259A (en)	1980-09-05	1982-04-15	Kyorin Pharmaceut Co Ltd	Preparation of substituted quinolinecarboxylic acid derivative
DE3308909A1 (de)	1983-03-12	1984-09-13	Bayer Ag, 5090 Leverkusen	Bakterizide mittel auf chinoloncarbonsaeure-basis
HU198709B (en) *	1987-04-08	1989-11-28	Chinoin Gyogyszer Es Vegyeszet	Process for producing quinoline-carboxylic acid derivatives
SI8712447A8 (en) *	1987-12-31	1995-12-31	Krka Tovarna Zdravil	Process for preparing 1-substituted 6-fluoro-4-oxo-7-(1-piperazinyl) -1,4-dihydroquinoline-3-carboxylic acid and new intermediate used in this process
DE8812756U1 (de)	1988-09-22	1988-12-01	Weinschlauch Hemü Weinhandel GmbH, 4000 Düsseldorf	Zapfschrank

1992
- 1992-12-11 SI SI9200377A patent/SI9200377A/sl unknown
1993
- 1993-10-18 HU HU9302940A patent/HUT75319A/hu unknown
- 1993-11-12 PL PL93301045A patent/PL173784B1/pl unknown
- 1993-12-06 CZ CZ932643A patent/CZ284715B6/cs not_active IP Right Cessation
- 1993-12-07 LT LTIP1558A patent/LT3084B/lt not_active IP Right Cessation
- 1993-12-10 RU RU93054527A patent/RU2127270C1/ru active
- 1993-12-10 SK SK140093A patent/SK140093A3/sk unknown
- 1993-12-10 CA CA 2111181 patent/CA2111181A1/en not_active Abandoned
- 1993-12-10 HR HRP931485 patent/HRP931485A2/hr not_active Application Discontinuation
- 1993-12-10 YU YU76593A patent/YU76593A/sh unknown
- 1993-12-10 AT AT249793A patent/AT401648B/de not_active IP Right Cessation
- 1993-12-10 LV LVP-93-1317A patent/LV10863B/en unknown
1994
- 1994-11-17 EE EE9400277A patent/EE9400277A/xx unknown

Also Published As

Publication number	Publication date
HUT75319A (en)	1997-05-28
CZ284715B6 (cs)	1999-02-17
CZ264393A3 (en)	1994-07-13
ATA249793A (de)	1996-03-15
RU2127270C1 (ru)	1999-03-10
PL301045A1 (en)	1994-06-13
LT3084B (en)	1994-11-25
CA2111181A1 (en)	1994-06-12
EE9400277A (et)	1996-04-15
SK140093A3 (en)	1994-11-09
LV10863B (en)	1996-08-20
YU76593A (sh)	1996-07-24
PL173784B1 (pl)	1998-04-30
LV10863A (lv)	1995-10-20
HU9302940D0 (en)	1993-12-28
SI9200377A (en)	1994-06-30
AT401648B (de)	1996-10-25
LTIP1558A (en)	1994-06-15

Legal Events

Date	Code	Title
1995-04-30	A1OB	Publication of a patent application
1995-10-27	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2000-06-15	ODBC	Application rejected

Publication	Publication Date	Title
CA1340285C (en)	1998-12-22	Novel quinolonecarboxylic acid derivatives having at 7-position a piperidin-1-yl substituent
KR940007305B1 (ko)	1994-08-12	8-위치에서 치환된 퀴놀론카복실산 유도체, 이의 제조방법 및 이를 함유하는 약제학적 조성물
HU203339B (en)	1991-07-29	Process for producing new 8-alkoxy-quinolone-carboxylic acid derivatives
JPH0244827B2 (de)	1990-10-05
JPH05239051A (ja)	1993-09-17	７−イソインドリニル−キノロン−および−ナフチリドンカルボン酸誘導体
US6136823A (en)	2000-10-24	Pyridonecarboxylic acid derivatives or salts thereof and drugs containing the same as the active ingredient
JPH0637490B2 (ja)	1994-05-18	キノロンカルボン酸誘導体
JPWO1998023592A1 (ja)	2000-03-28	新規ピリドンカルボン酸誘導体又はその塩及びこれを有効成分とする医薬
UA56286C2 (uk)	2003-05-15	Спосіб одержання похідних 8-метокси-3-хінолонкарбонової кислоти
JPH0653741B2 (ja)	1994-07-20	６，７―二置換された１―シクロプロピル―１，４―ジヒドロ―４―オキソ―１，８―ナフチリジン―３―カルボン酸類
JPS61205258A (ja)	1986-09-11	キノロンカルボン酸誘導体及びその製造方法
HU187356B (en)	1985-12-28	Process for producing quinoline-carboxylic acid derivatives
HRP931485A2 (en)	1995-04-30	Process for the preparation of 1-supst.-fluoro-4-oxo-7-(1-piperazinyl)-1,4-hydroquinoline-3-carbonic acid, new rmediate, used in that process and a process for the aration of that intermediate
JPS6324991B2 (de)	1988-05-23
HRP930558A2 (en)	1996-04-30	Process for the preparation of norfloxacine intermediates
KR930003611B1 (ko)	1993-05-08	퀴놀론 카복실산 유도체의 제조방법
JPWO1997040036A1 (ja)	1999-05-25	新規ピリドンカルボン酸誘導体又はその塩並びに該物質を有効成分とする抗菌剤
EP0221541A2 (de)	1987-05-13	Chinolincarbonsäurederivate und ihre Herstellung
JPH0219377A (ja)	1990-01-23	８‐メチルキノロンカルボン酸誘導体
US4946844A (en)	1990-08-07	Optically active benzoquinolizine compounds, process for preparing same, and antibacterial preparation containing same as active ingredient
WO1997040036A1 (en)	1997-10-30	Novel pyridonecarboxylic acid derivatives or salts thereof and antibacterial agents containing the same as the active ingredient
AU2019260015B2 (en)	2024-07-11	Process for the hydrolysis of quinolone carboxylic esters
EP0216245A1 (de)	1987-04-01	Chinoloncarbonsäurederivate und Verfahren zu ihrer Herstellung
LT3274B (en)	1995-05-25	Process for preparing 1-substituted 6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid
SI9300192A (sl)	1994-12-31	Postopek za pripravo 1-subst.-6-fluoro-4-okso-7-(1-piperazinil ali 4-subst.-1-piperazinil)- 1.4-dihidrokinolin-3-karboksilne kisline, nov intermediat, uporaben v tem postopku, in postopek za pripravo tega intermediata