LU82411A1 - Epimere d du sel de diammonium d'un antibiotique d'oxa-b-lac-tame - Google Patents

Epimere d du sel de diammonium d'un antibiotique d'oxa-b-lac-tame Download PDF

Info

Publication number: LU82411A1
Authority: LU; Luxembourg
Prior art keywords: epimer; solution; diammonium salt; salt; oxa
Prior art date: 1979-05-01

Application number

LU82411A

Other languages

English (en)

French (fr)

Inventor

K Yang

Original Assignee

Lilly Co Eli

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.)

1979-05-01

Filing date

1980-04-29

Publication date

1980-07-31

1980-04-29 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1980-07-31 Publication of LU82411A1 publication Critical patent/LU82411A1/fr

Links

150000003839 salts Chemical class 0.000 title claims description 80
230000003115 biocidal effect Effects 0.000 title claims description 7
239000000243 solution Substances 0.000 claims description 36
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 33
238000000034 method Methods 0.000 claims description 27
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 14
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 10
239000000908 ammonium hydroxide Substances 0.000 claims description 10
239000007864 aqueous solution Substances 0.000 claims description 10
239000003960 organic solvent Substances 0.000 claims description 8
239000003782 beta lactam antibiotic agent Substances 0.000 claims description 7
239000002132 β-lactam antibiotic Substances 0.000 claims description 7
229940124586 β-lactam antibiotics Drugs 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 3
238000004811 liquid chromatography Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
238000002425 crystallisation Methods 0.000 description 9
230000008025 crystallization Effects 0.000 description 9
238000006345 epimerization reaction Methods 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
-1 amine salts Chemical class 0.000 description 3
239000013078 crystal Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
239000011549 crystallization solution Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
150000004685 tetrahydrates Chemical group 0.000 description 2
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
229930186147 Cephalosporin Natural products 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
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 description 1
229930182555 Penicillin Natural products 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
239000008351 acetate buffer Substances 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000000634 powder X-ray diffraction Methods 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
238000004448 titration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; 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)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Cephalosporin Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

LU82411A 1979-05-01 1980-04-29 Epimere d du sel de diammonium d'un antibiotique d'oxa-b-lac-tame LU82411A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US3503779		1979-05-01
US06/035,037 US4252953A (en)	1979-05-01	1979-05-01	Antibiotic crystalline epimer

Publications (1)

Publication Number	Publication Date
LU82411A1 true LU82411A1 (fr)	1980-07-31

Family

ID=21880235

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU82411A LU82411A1 (fr)	1979-05-01	1980-04-29	Epimere d du sel de diammonium d'un antibiotique d'oxa-b-lac-tame

Country Status (34)

Country	Link
US (1)	US4252953A (cs)
EP (1)	EP0018811B1 (cs)
JP (1)	JPS55153788A (cs)
KR (1)	KR840000078B1 (cs)
AR (1)	AR230450A1 (cs)
AT (1)	AT370108B (cs)
AU (1)	AU538283B2 (cs)
BE (1)	BE882980A (cs)
BG (1)	BG34905A3 (cs)
CA (1)	CA1138867A (cs)
CH (1)	CH646434A5 (cs)
CS (1)	CS226013B2 (cs)
DD (1)	DD150352A5 (cs)
DE (1)	DE3061751D1 (cs)
DK (1)	DK177980A (cs)
EG (1)	EG14719A (cs)
ES (1)	ES8105316A1 (cs)
FI (1)	FI801345A7 (cs)
FR (1)	FR2455605A1 (cs)
GB (1)	GB2047707B (cs)
GR (1)	GR68202B (cs)
HU (1)	HU184750B (cs)
IE (1)	IE49775B1 (cs)
IL (1)	IL59912A (cs)
IT (1)	IT1141935B (cs)
LU (1)	LU82411A1 (cs)
MY (1)	MY8500601A (cs)
NZ (1)	NZ193528A (cs)
PH (1)	PH15596A (cs)
PL (1)	PL125579B1 (cs)
PT (1)	PT71140A (cs)
RO (1)	RO79684A (cs)
SU (1)	SU860705A3 (cs)
ZA (1)	ZA802475B (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS597193A (ja) *	1982-07-02	1984-01-14	Shionogi & Co Ltd	マロニルメチル基の異性化方法
DE102004049398A1 (de) *	2003-10-08	2005-07-07	Behr Gmbh & Co. Kg	Verfahren und Vorrichtung zur Herstellung eines Bauteils, insbesondere eines Hybridbauteils für einen Querträger eines Fahrzeugs sowie Bauteil und Verwendung eines Bauteils
ATE464196T1 (de) *	2003-10-08	2010-04-15	Behr Gmbh & Co Kg	Bauteil, insbesondere hybridträger für ein fahrzeug, und verwendung eines derartigen bauteils

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE443143B (sv) *	1976-03-25	1986-02-17	Shionogi & Co	Forfarande for framstellning av arylmalonamido-1-oxadetiacefalosporiner
CA1085392A (en) *	1976-03-25	1980-09-09	Masayuki Narisada	Arylmalonamido-1-oxadethiacephalosporins
US4124762A (en) *	1977-11-07	1978-11-07	Yeda Research And Development Co., Ltd.	7-[(Pyridylthiomethyl)phenyl]acetamido-cephalosporin derivatives
US4148997A (en) *	1977-11-07	1979-04-10	Yeda Research And Development Co., Ltd.	7-[Sulfomethyl)phenyl]acetamidocephalosporin derivatives
US4125715A (en) *	1977-11-25	1978-11-14	Yeda Research And Development Co. Ltd.	7-[(Substituted-isothioureamethyl)phenyl]-acetamidocephalosporin derivatives

1979
- 1979-05-01 US US06/035,037 patent/US4252953A/en not_active Expired - Lifetime
1980
- 1980-04-21 PH PH23927A patent/PH15596A/en unknown
- 1980-04-24 ZA ZA00802475A patent/ZA802475B/xx unknown
- 1980-04-24 FR FR8009241A patent/FR2455605A1/fr active Granted
- 1980-04-24 IL IL59912A patent/IL59912A/xx not_active IP Right Cessation
- 1980-04-24 NZ NZ193528A patent/NZ193528A/xx unknown
- 1980-04-24 PT PT71140A patent/PT71140A/pt unknown
- 1980-04-24 CA CA000350600A patent/CA1138867A/en not_active Expired
- 1980-04-24 AT AT0220980A patent/AT370108B/de not_active IP Right Cessation
- 1980-04-25 FI FI801345A patent/FI801345A7/fi not_active Application Discontinuation
- 1980-04-25 PL PL1980223753A patent/PL125579B1/pl unknown
- 1980-04-25 HU HU801040A patent/HU184750B/hu not_active IP Right Cessation
- 1980-04-25 DK DK177980A patent/DK177980A/da not_active Application Discontinuation
- 1980-04-25 BE BE1/9799A patent/BE882980A/fr not_active IP Right Cessation
- 1980-04-25 JP JP5611080A patent/JPS55153788A/ja active Granted
- 1980-04-26 RO RO80100971A patent/RO79684A/ro unknown
- 1980-04-28 GB GB8013972A patent/GB2047707B/en not_active Expired
- 1980-04-28 EP EP80301392A patent/EP0018811B1/en not_active Expired
- 1980-04-28 DE DE8080301392T patent/DE3061751D1/de not_active Expired
- 1980-04-29 GR GR61808A patent/GR68202B/el unknown
- 1980-04-29 SU SU802913905A patent/SU860705A3/ru active
- 1980-04-29 AR AR280840A patent/AR230450A1/es active
- 1980-04-29 LU LU82411A patent/LU82411A1/fr unknown
- 1980-04-29 IT IT21697/80A patent/IT1141935B/it active
- 1980-04-30 BG BG047588A patent/BG34905A3/xx unknown
- 1980-04-30 ES ES491085A patent/ES8105316A1/es not_active Expired
- 1980-04-30 CH CH335480A patent/CH646434A5/fr not_active IP Right Cessation
- 1980-04-30 AU AU57914/80A patent/AU538283B2/en not_active Ceased
- 1980-04-30 DD DD80220809A patent/DD150352A5/de unknown
- 1980-04-30 IE IE882/80A patent/IE49775B1/en not_active IP Right Cessation
- 1980-04-30 EG EG268/80A patent/EG14719A/xx active
- 1980-04-30 CS CS803045A patent/CS226013B2/cs unknown
- 1980-05-01 KR KR1019800001756A patent/KR840000078B1/ko not_active Expired
1985
- 1985-12-30 MY MY601/85A patent/MY8500601A/xx unknown

Also Published As

Publication number	Publication date
HU184750B (en)	1984-10-29
SU860705A3 (ru)	1981-08-30
AT370108B (de)	1983-03-10
CH646434A5 (fr)	1984-11-30
IE49775B1 (en)	1985-12-11
JPH0118077B2 (cs)	1989-04-03
KR830002779A (ko)	1983-05-30
NZ193528A (en)	1982-03-23
ZA802475B (en)	1981-12-30
CA1138867A (en)	1983-01-04
KR840000078B1 (ko)	1984-02-08
DE3061751D1 (en)	1983-03-03
GB2047707A (en)	1980-12-03
DK177980A (da)	1980-11-02
ATA220980A (de)	1982-07-15
FR2455605A1 (fr)	1980-11-28
GR68202B (cs)	1981-11-10
PL223753A1 (cs)	1981-02-13
IT8021697A0 (it)	1980-04-29
AR230450A1 (es)	1984-04-30
MY8500601A (en)	1985-12-31
EG14719A (en)	1985-06-30
IT1141935B (it)	1986-10-08
DD150352A5 (de)	1981-08-26
IL59912A (en)	1984-02-29
BG34905A3 (bg)	1983-12-15
JPS55153788A (en)	1980-11-29
BE882980A (fr)	1980-10-27
EP0018811A1 (en)	1980-11-12
PH15596A (en)	1983-02-28
RO79684A (ro)	1982-08-17
AU538283B2 (en)	1984-08-09
ES491085A0 (es)	1981-05-16
PL125579B1 (en)	1983-05-31
IE800882L (en)	1980-11-01
AU5791480A (en)	1980-11-06
US4252953A (en)	1981-02-24
FI801345A7 (fi)	1980-11-02
GB2047707B (en)	1983-05-18
PT71140A (en)	1980-05-01
CS226013B2 (en)	1984-03-19
FR2455605B1 (cs)	1983-05-27
EP0018811B1 (en)	1983-01-26
ES8105316A1 (es)	1981-05-16

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