CA1079736A - Dihydrate cristallin de di-clavulanate de calcium - Google Patents

Dihydrate cristallin de di-clavulanate de calcium

Info

Publication number: CA1079736A
Authority: CA; Canada
Prior art keywords: calcium; salt; clavulanate; solution; resin
Prior art date: 1976-02-26
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

Application number

CA272,740A

Other languages

English (en)

Inventor

John B. Harbridge

Thomas T. Howarth

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.)

Beecham Group PLC

Original Assignee

Beecham Group PLC

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.)

1976-02-26

Filing date

1977-02-25

Publication date

1980-06-17

1977-02-25 Application filed by Beecham Group PLC filed Critical Beecham Group PLC

1980-06-17 Application granted granted Critical

1980-06-17 Publication of CA1079736A publication Critical patent/CA1079736A/fr

Status Expired legal-status Critical Current

Links

OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title claims abstract description 38
239000011575 calcium Substances 0.000 title claims abstract description 35
229910052791 calcium Inorganic materials 0.000 title claims abstract description 35
229940090805 clavulanate Drugs 0.000 title claims abstract description 25
229920005989 resin Polymers 0.000 claims abstract description 32
239000011347 resin Substances 0.000 claims abstract description 32
150000003839 salts Chemical class 0.000 claims abstract description 29
239000000243 solution Substances 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 20
HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 claims abstract description 15
HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 claims abstract description 13
229960003324 clavulanic acid Drugs 0.000 claims abstract description 11
159000000007 calcium salts Chemical class 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims abstract description 9
238000002425 crystallisation Methods 0.000 claims abstract description 8
150000001768 cations Chemical class 0.000 claims abstract description 5
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 3
239000007864 aqueous solution Substances 0.000 claims abstract description 3
239000003729 cation exchange resin Substances 0.000 claims abstract description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
239000013078 crystal Substances 0.000 claims description 12
159000000000 sodium salts Chemical class 0.000 claims description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
229920003053 polystyrene-divinylbenzene Polymers 0.000 claims description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 2
238000005325 percolation Methods 0.000 claims 1
239000002904 solvent Substances 0.000 claims 1
229930182555 Penicillin Natural products 0.000 abstract description 3
229930186147 Cephalosporin Natural products 0.000 abstract description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract description 2
229940124587 cephalosporin Drugs 0.000 abstract description 2
150000001780 cephalosporins Chemical class 0.000 abstract description 2
229940049954 penicillin Drugs 0.000 abstract description 2
239000000825 pharmaceutical preparation Substances 0.000 abstract 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
229940022682 acetone Drugs 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000012153 distilled water Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
238000004132 cross linking Methods 0.000 description 3
150000004683 dihydrates Chemical class 0.000 description 3
239000000463 material Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
-1 sodium clavulanate tetrahydrate Chemical class 0.000 description 3
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000011324 bead Substances 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
238000011068 loading method Methods 0.000 description 2
WOGMLDNCNBLDCA-JSYANWSFSA-M sodium;(2r,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound [Na+].[O-]C(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 WOGMLDNCNBLDCA-JSYANWSFSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241001558496 Talpa caeca Species 0.000 description 1
241000030538 Thecla Species 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
229960003022 amoxicillin Drugs 0.000 description 1
LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 1
229960000723 ampicillin Drugs 0.000 description 1
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
238000011001 backwashing Methods 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
150000001669 calcium Chemical class 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 description 1
229960003669 carbenicillin Drugs 0.000 description 1
RTYJTGSCYUUYAL-YCAHSCEMSA-L carbenicillin disodium Chemical compound [Na+].[Na+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)C(C([O-])=O)C1=CC=CC=C1 RTYJTGSCYUUYAL-YCAHSCEMSA-L 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000005341 cation exchange Methods 0.000 description 1
229940023913 cation exchange resins Drugs 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
JMRXTGCDVQLAFM-JSYANWSFSA-M lithium;(2r,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound [Li+].[O-]C(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 JMRXTGCDVQLAFM-JSYANWSFSA-M 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
ABVRVIZBZKUTMK-JSYANWSFSA-M potassium clavulanate Chemical compound [K+].[O-]C(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 ABVRVIZBZKUTMK-JSYANWSFSA-M 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
150000004685 tetrahydrates Chemical class 0.000 description 1
OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 1
229960004659 ticarcillin Drugs 0.000 description 1
ZBBCUBMBMZNEME-QBGWIPKPSA-L ticarcillin disodium Chemical compound [Na+].[Na+].C=1([C@@H](C([O-])=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C([O-])=O)(C)C)C=CSC=1 ZBBCUBMBMZNEME-QBGWIPKPSA-L 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CA272,740A 1976-02-26 1977-02-25 Dihydrate cristallin de di-clavulanate de calcium Expired CA1079736A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7544/76A GB1561395A (en)	1976-02-26	1976-02-26	-lactam antibiotic

Publications (1)

Publication Number	Publication Date
CA1079736A true CA1079736A (fr)	1980-06-17

Family

ID=9835161

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA272,740A Expired CA1079736A (fr)	1976-02-26	1977-02-25	Dihydrate cristallin de di-clavulanate de calcium

Country Status (13)

Country	Link
JP (1)	JPS52105193A (fr)
AU (1)	AU504721B2 (fr)
BE (1)	BE851872A (fr)
CA (1)	CA1079736A (fr)
CH (1)	CH624957A5 (fr)
DE (1)	DE2708046A1 (fr)
DK (1)	DK86177A (fr)
FR (1)	FR2342289A1 (fr)
GB (1)	GB1561395A (fr)
IE (1)	IE44704B1 (fr)
NL (1)	NL7702036A (fr)
SE (1)	SE7702078L (fr)
ZA (1)	ZA771089B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU600655B2 (en) *	1984-10-27	1990-08-23	Beecham Group Plc	Preparation of clavulanic acid and its salts and esters
AT400033B (de)	1992-03-10	1995-09-25	Biochemie Gmbh	Neues verfahren zur isolierung und reinigung von clavulansäure und zur herstellung von pharmakologisch verträglichen salzen derselben
AT399155B (de) *	1992-03-26	1995-03-27	Lek Tovarna Farmacevtskih	Neue alkylendiammonium-diclavulanat-derivate, verfahren zu deren herstellung sowie deren verwendung
US9433640B2 (en)	2014-12-23	2016-09-06	Ardelyx, Inc.	Compositions and methods for treating hyperkalemia
CA2971725C (fr) *	2014-12-23	2024-05-14	Ardelyx, Inc.	Compositions et methodes de traitement de l'hyperkaliemie

1976
- 1976-02-26 GB GB7544/76A patent/GB1561395A/en not_active Expired
1977
- 1977-02-23 FR FR7705257A patent/FR2342289A1/fr active Granted
- 1977-02-23 ZA ZA00771089A patent/ZA771089B/xx unknown
- 1977-02-24 AU AU22643/77A patent/AU504721B2/en not_active Expired
- 1977-02-24 DE DE19772708046 patent/DE2708046A1/de not_active Withdrawn
- 1977-02-24 SE SE7702078A patent/SE7702078L/xx not_active Application Discontinuation
- 1977-02-25 BE BE175302A patent/BE851872A/fr unknown
- 1977-02-25 CA CA272,740A patent/CA1079736A/fr not_active Expired
- 1977-02-25 CH CH242177A patent/CH624957A5/de not_active IP Right Cessation
- 1977-02-25 NL NL7702036A patent/NL7702036A/xx not_active Application Discontinuation
- 1977-02-25 DK DK86177A patent/DK86177A/da not_active Application Discontinuation
- 1977-02-25 IE IE415/77A patent/IE44704B1/en unknown
- 1977-02-26 JP JP2076577A patent/JPS52105193A/ja active Pending

Also Published As

Publication number	Publication date
IE44704B1 (en)	1982-02-24
DK86177A (da)	1977-08-27
IE44704L (en)	1977-08-26
GB1561395A (en)	1980-02-20
NL7702036A (nl)	1977-08-30
BE851872A (fr)	1977-08-25
ZA771089B (en)	1978-01-25
FR2342289B1 (fr)	1980-02-01
SE7702078L (sv)	1977-08-27
JPS52105193A (en)	1977-09-03
AU504721B2 (en)	1979-10-25
CH624957A5 (en)	1981-08-31
AU2264377A (en)	1978-08-31
DE2708046A1 (de)	1977-09-01
FR2342289A1 (fr)	1977-09-23

Legal Events

Date	Code	Title	Description
1997-06-17	MKEX	Expiry

Publication	Publication Date	Title
US4647659A (en)	1987-03-03	Clavulanic acid amine salts, their preparation and use
JP5184465B2 (ja)	2013-04-17	クラブラン酸カリウムの製造方法
CH622262A5 (fr)	1981-03-31
EP0647229B1 (fr)	1996-07-24	Sels diamine d'acide clavulanique
US4454069A (en)	1984-06-12	Clavulanic acid salts and their preparation from the tertiary butyl amine salt
US4456753A (en)	1984-06-26	Process for the manufacture of highly crystalline sodium cefoperazone
JPS5885893A (ja)	1983-05-23	７−β−〔２−（２−アミノチアゾ−ル−４−イル）−２−シン−メトキシイミノアセトアミド〕−３−（５−カルボキシメチル−４−メチル−１，３−チアゾ−ル−２−イルチオメチル）セフ−３−エム−４−カルボン酸の結晶質水溶性塩およびその製造方法
US3575969A (en)	1971-04-20	Desacetoxycephalosporin antibiotics
CA1272715A (fr)	1990-08-14	Derive antibiotique, et methode d'epuration
GB1561395A (en)	1980-02-20	-lactam antibiotic
PL188634B1 (pl)	2005-03-31	Sposób wytwarzania potasowej soli kwasu klawulanowego
KR920003902B1 (ko)	1992-05-18	페니실린 유도체의 수화물 및 그 제조방법
US3983109A (en)	1976-09-28	Process for recovering cephalosporin C from A fermentation broth as the N-(p-nitrobenzoyl) derivative
US4168376A (en)	1979-09-18	Process for crystalline sodium cefamandole
US3498979A (en)	1970-03-03	Recovery of n-(7-2'-thienylacetamidoceph-3-em-3-ylmethyl) pyridinium - 4-carboxylate from an acid addition salt thereof
EP0051467A1 (fr)	1982-05-12	Dérivés d'hexitol, leur procédé de préparation et compositions pharmaceutiques les contenant
SU833161A3 (ru)	1981-05-23	Способ получени производного 7-метокси-1-оксадетиацефалоспо-РиНА
US5760218A (en)	1998-06-02	Diamine salts of clavulanic acid
KR950013570B1 (ko)	1995-11-09	세포디짐 이나트륨염의 제조방법
JPH02131494A (ja)	1990-05-21	結晶状ｌ−アスコルビン酸−２−リン酸ナトリウム塩の製造法
JPH03153648A (ja)	1991-07-01	光学活性１―メチル―３―フェニルプロピルアミンの製法
IE36089B1 (en)	1976-08-18	Cephem compounds
HK1036621A (en)	2002-01-11	Process for the preparation of potassium clavulanate
IL29529A (en)	1972-02-29	Orally active 7-(4'-(aminoalkyl)phenyl)acetamido cephalosporanic acid derivatives
HK1003245B (en)	1998-10-16	Process for the preparation of potassium clavulanate