CA1326239C - Preparation de la ciprofloxacine - Google Patents

Preparation de la ciprofloxacine

Info

Publication number: CA1326239C
Authority: CA; Canada
Prior art keywords: formula; compound; quinoline; ciprofloxacin; piperazino
Prior art date: 1988-01-12
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 - Fee Related

Application number

CA 556352

Other languages

English (en)

Inventor

Veronica Scherrer-Pangka

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Torcan Chemical Ltd

Original Assignee

Torcan Chemical Ltd

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.)

1988-01-12

Filing date

1988-01-12

Publication date

1994-01-18

1988-01-12 Application filed by Torcan Chemical Ltd filed Critical Torcan Chemical Ltd

1988-01-12 Priority to CA 556352 priority Critical patent/CA1326239C/fr

1994-01-18 Application granted granted Critical

1994-01-18 Publication of CA1326239C publication Critical patent/CA1326239C/fr

2011-01-18 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 title abstract description 39
229960003405 ciprofloxacin Drugs 0.000 title abstract description 20
238000002360 preparation method Methods 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 14
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 13
150000004885 piperazines Chemical class 0.000 claims abstract description 8
239000012429 reaction media Substances 0.000 claims abstract description 6
238000000034 method Methods 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
230000008569 process Effects 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
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 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
150000004677 hydrates Chemical class 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000002516 radical scavenger Substances 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims description 2
239000007788 liquid Substances 0.000 claims 3
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 2
238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
239000012458 free base Substances 0.000 abstract description 6
-1 piperazino Chemical group 0.000 abstract description 5
239000007858 starting material Substances 0.000 abstract description 5
239000002244 precipitate Substances 0.000 abstract description 4
239000003242 anti bacterial agent Substances 0.000 abstract description 3
239000003674 animal food additive Substances 0.000 abstract description 2
238000007039 two-step reaction Methods 0.000 abstract 1
239000000047 product Substances 0.000 description 11
238000010992 reflux Methods 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
238000000746 purification Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
239000003513 alkali Substances 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
SIZQHYOHXHCYHI-UHFFFAOYSA-N 1-cyclopropyl-7-(4-ethoxycarbonylpiperazin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(C(=O)OCC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 SIZQHYOHXHCYHI-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000002585 base Substances 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000000463 material Substances 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
ISPVACVJFUIDPD-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 ISPVACVJFUIDPD-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical class CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
DIOIOSKKIYDRIQ-UHFFFAOYSA-N ciprofloxacin hydrochloride Chemical compound Cl.C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 DIOIOSKKIYDRIQ-UHFFFAOYSA-N 0.000 description 1
229960001229 ciprofloxacin hydrochloride Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
ZPJZSEHCMJYUPI-UHFFFAOYSA-N methyl piperazine-1-carboxylate Chemical compound COC(=O)N1CCNCC1 ZPJZSEHCMJYUPI-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
IGXBNWXKQPCCCJ-UHFFFAOYSA-N propyl piperazine-1-carboxylate Chemical compound CCCOC(=O)N1CCNCC1 IGXBNWXKQPCCCJ-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 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

Classifications

- 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
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Quinoline Compounds (AREA)

CA 556352 1988-01-12 1988-01-12 Preparation de la ciprofloxacine Expired - Fee Related CA1326239C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 556352 CA1326239C (fr)	1988-01-12	1988-01-12	Preparation de la ciprofloxacine

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 556352 CA1326239C (fr)	1988-01-12	1988-01-12	Preparation de la ciprofloxacine

Publications (1)

Publication Number	Publication Date
CA1326239C true CA1326239C (fr)	1994-01-18

Family

ID=4137237

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 556352 Expired - Fee Related CA1326239C (fr)	1988-01-12	1988-01-12	Preparation de la ciprofloxacine

Country Status (1)

Country	Link
CA (1)	CA1326239C (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2005075430A1 (fr) *	2004-02-02	2005-08-18	Krka, Tovarna Zdravil, D.D., Novo Mesto	Procede de preparation de ciprofloxacine purifiee

1988
- 1988-01-12 CA CA 556352 patent/CA1326239C/fr not_active Expired - Fee Related

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2005075430A1 (fr) *	2004-02-02	2005-08-18	Krka, Tovarna Zdravil, D.D., Novo Mesto	Procede de preparation de ciprofloxacine purifiee

Legal Events

Date	Code	Title	Description
2005-01-18	MKLA	Lapsed

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US6576764B2 (en)	2003-06-10	Synthesis and crystallization of piperazine ring-containing compounds
EP0449172B1 (fr)	1996-06-05	Méthode de réduction d'une acridine contenant un groupe carbonyle
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US4301289A (en)	1981-11-17	Process for 6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo(ij)quinolizine-2-carboxylic acid
IL93393A (en)	1994-10-07	Process for the preparation of omicron-carboxypyridyl and omicron-carboxyquinolyl- imidazolinones
US2773064A (en)	1956-12-04	Y-substituted amino-benz
JPS60181058A (ja)	1985-09-14	シアノメチル‐（２‐シアノ‐エチル）‐（３‐ヒドロキシ‐プロピル）‐アミン及びその製法、及び１‐（３‐ヒドロキシ‐プロピル）‐１，４‐ジアゼパン及び１，４‐ビス‐〔３‐（３，４，５‐トリメトキシ‐ベンゾイルオキシ）‐プロピル〕‐ジアゼパンの製法
CA1044239A (fr)	1978-12-12	Acides alkoxy-6 hydroxyquinoline-7 carboxyliques-3 et leurs derives
US4709026A (en)	1987-11-24	Ketosultams
US4758679A (en)	1988-07-19	Preparation of 7-(3-(propylamino)-2-hydroxypropoxy)flavone
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US4301291A (en)	1981-11-17	Intermediates for 6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo(ij)quinolizine-2-carboxylic acid

CA1326239C - Preparation de la ciprofloxacine - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4137237

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

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