CA1097340A - Derives de la cephalosporine, leur preparation et les compositions qui les contiennent - Google Patents

Derives de la cephalosporine, leur preparation et les compositions qui les contiennent

Info

Publication number: CA1097340A
Authority: CA; Canada
Prior art keywords: formula; radical; acid; carboxy; product
Prior art date: 1977-06-09
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

CA305,063A

Other languages

English (en)

French (fr)

Inventor

Christian Berger

Dominique Deprez

Daniel Farge

Claude Moutonnier

Gerard Wolff

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.)

Rhone Poulenc Industries SA

Original Assignee

Rhone Poulenc Industries SA

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.)

1977-06-09

Filing date

1978-06-08

Publication date

1981-03-10

1978-06-08 Application filed by Rhone Poulenc Industries SA filed Critical Rhone Poulenc Industries SA

1981-03-10 Application granted granted Critical

1981-03-10 Publication of CA1097340A publication Critical patent/CA1097340A/fr

Status Expired legal-status Critical Current

Links

239000002253 acid Substances 0.000 claims abstract description 78
239000000203 mixture Substances 0.000 claims abstract description 44
150000003839 salts Chemical class 0.000 claims abstract description 28
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims abstract description 13
229930186147 Cephalosporin Natural products 0.000 claims abstract description 10
229940124587 cephalosporin Drugs 0.000 claims abstract description 10
150000001780 cephalosporins Chemical class 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
150000007513 acids Chemical class 0.000 claims abstract description 7
229910052751 metal Inorganic materials 0.000 claims abstract description 7
239000002184 metal Substances 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 24
125000006239 protecting group Chemical group 0.000 claims description 17
150000001412 amines Chemical class 0.000 claims description 16
-1 salt tertiary amine Chemical class 0.000 claims description 7
150000001413 amino acids Chemical class 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 5
239000002585 base Substances 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
230000002255 enzymatic effect Effects 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
239000011253 protective coating Substances 0.000 claims description 2
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239000000654 additive Chemical class 0.000 claims 1
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230000001580 bacterial effect Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
125000006630 butoxycarbonylamino group Chemical group 0.000 description 1
LGUHADBEXWHGIZ-UHFFFAOYSA-N butyl n-diazocarbamate Chemical group CCCCOC(=O)N=[N+]=[N-] LGUHADBEXWHGIZ-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000006198 deformylation Effects 0.000 description 1
238000006344 deformylation reaction Methods 0.000 description 1
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
239000000686 essence Substances 0.000 description 1
FPULFENIJDPZBX-UHFFFAOYSA-N ethyl 2-isocyanoacetate Chemical compound CCOC(=O)C[N+]#[C-] FPULFENIJDPZBX-UHFFFAOYSA-N 0.000 description 1
IYPSSPPKMLXXRN-UHFFFAOYSA-N ethyl 2-isothiocyanatoacetate Chemical compound CCOC(=O)CN=C=S IYPSSPPKMLXXRN-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000727 fraction Substances 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
OKXGHXHZNCJMSV-UHFFFAOYSA-N nitro phenyl carbonate Chemical compound [O-][N+](=O)OC(=O)OC1=CC=CC=C1 OKXGHXHZNCJMSV-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient 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
238000000053 physical method Methods 0.000 description 1
238000011197 physicochemical method Methods 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000013589 supplement Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000011800 void material Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
- 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)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA305,063A 1977-06-09 1978-06-08 Derives de la cephalosporine, leur preparation et les compositions qui les contiennent Expired CA1097340A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR777717663A FR2393806A1 (fr)	1977-06-09	1977-06-09	Nouveaux derives de la cephalosporine, leur preparation et les compositions qui les contiennent
FR7717663		1977-06-09

Publications (1)

Publication Number	Publication Date
CA1097340A true CA1097340A (fr)	1981-03-10

Family

ID=9191876

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA305,063A Expired CA1097340A (fr)	1977-06-09	1978-06-08	Derives de la cephalosporine, leur preparation et les compositions qui les contiennent

Country Status (22)

Country	Link
JP (1)	JPS545993A (pt)
AT (1)	AT357678B (pt)
AU (1)	AU3695778A (pt)
BE (1)	BE867957A (pt)
CA (1)	CA1097340A (pt)
DE (1)	DE2825427A1 (pt)
DK (1)	DK254478A (pt)
ES (1)	ES470670A1 (pt)
FI (1)	FI781850A7 (pt)
FR (1)	FR2393806A1 (pt)
GB (1)	GB1600728A (pt)
GR (1)	GR64145B (pt)
HU (1)	HU178715B (pt)
IL (1)	IL54877A0 (pt)
IT (1)	IT1098320B (pt)
LU (1)	LU79788A1 (pt)
NL (1)	NL7806004A (pt)
NO (1)	NO782001L (pt)
PL (1)	PL207238A1 (pt)
PT (1)	PT68151A (pt)
SE (1)	SE7806689L (pt)
ZA (1)	ZA783271B (pt)

1977
- 1977-06-09 FR FR777717663A patent/FR2393806A1/fr active Granted
1978
- 1978-01-27 GB GB44606/76A patent/GB1600728A/en not_active Expired
- 1978-05-31 PL PL20723878A patent/PL207238A1/xx unknown
- 1978-06-01 NL NL7806004A patent/NL7806004A/xx not_active Application Discontinuation
- 1978-06-07 ZA ZA00783271A patent/ZA783271B/xx unknown
- 1978-06-07 JP JP6787278A patent/JPS545993A/ja active Pending
- 1978-06-07 HU HU78RO985A patent/HU178715B/hu unknown
- 1978-06-08 BE BE188442A patent/BE867957A/xx unknown
- 1978-06-08 SE SE7806689A patent/SE7806689L/xx unknown
- 1978-06-08 AU AU36957/78A patent/AU3695778A/en active Pending
- 1978-06-08 GR GR56463A patent/GR64145B/el unknown
- 1978-06-08 NO NO782001A patent/NO782001L/no unknown
- 1978-06-08 LU LU79788A patent/LU79788A1/xx unknown
- 1978-06-08 PT PT68151A patent/PT68151A/pt unknown
- 1978-06-08 DK DK254478A patent/DK254478A/da unknown
- 1978-06-08 IL IL7854877A patent/IL54877A0/xx unknown
- 1978-06-08 CA CA305,063A patent/CA1097340A/fr not_active Expired
- 1978-06-09 ES ES470670A patent/ES470670A1/es not_active Expired
- 1978-06-09 IT IT24385/78A patent/IT1098320B/it active
- 1978-06-09 FI FI781850A patent/FI781850A7/fi not_active Application Discontinuation
- 1978-06-09 AT AT420178A patent/AT357678B/de active
- 1978-06-09 DE DE19782825427 patent/DE2825427A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
JPS545993A (en)	1979-01-17
FR2393806A1 (fr)	1979-01-05
IT1098320B (it)	1985-09-07
ES470670A1 (es)	1979-02-01
DK254478A (da)	1978-12-10
NO782001L (no)	1978-12-12
ZA783271B (en)	1979-06-27
PL207238A1 (pl)	1979-05-21
AT357678B (de)	1980-07-25
LU79788A1 (fr)	1979-02-02
AU3695778A (en)	1979-12-13
FR2393806B1 (pt)	1980-02-01
DE2825427A1 (de)	1978-12-21
HU178715B (en)	1982-06-28
IL54877A0 (en)	1978-08-31
GB1600728A (en)	1981-10-21
GR64145B (en)	1980-01-31
FI781850A7 (fi)	1978-12-10
BE867957A (fr)	1978-12-08
PT68151A (fr)	1978-07-01
ATA420178A (de)	1979-12-15
SE7806689L (sv)	1978-12-10
NL7806004A (nl)	1978-12-12
IT7824385A0 (it)	1978-06-09

Legal Events

Date	Code	Title	Description
1998-03-10	MKEX	Expiry

Publication	Publication Date	Title
EP0036812B1 (fr)	1985-01-30	Nouveaux dérivés des céphalosporines, leur procédé de préparation et les médicaments utilisables comme antibiotiques qui contiennent lesdits dérivés
EP0586486A1 (fr)	1994-03-16	Derives du thiopyranopyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent
EP0060745B1 (fr)	1986-03-05	Nouveaux dérivés antibiotiques dérivés des céphalosporines
FR2496654A1 (fr)	1982-06-25	Nouveaux tri-, tetra- et pentapeptides, leur preparation et les medicaments qui les contiennent
EP0178980B1 (fr)	1989-03-29	Dérivés de céphalosporines, procédé d'obtention et leur application à titre d'antibiotiques
CA1251000A (fr)	1989-03-07	Dipeptides, leur preparation et les medicaments qui les contiennent
EP0127543B1 (fr)	1989-09-13	Nouveaux composés antibiotiques dérivés des céphalosporines, procédé d'obtention et compositions pharmaceutiques les contenant
CH629815A5 (en)	1982-05-14	Oximes derived from 7-(aminothiazolylacetamido)cephalosporanic acid, process of preparation and pharmaceutical compositions
EP0533827B1 (fr)	1994-08-24	Nouveaux derives de l'oxazole, leur preparation et les compositions pharmaceutiques qui les contiennent
EP0072755B1 (fr)	1985-08-21	Nouveaux derivés de la cephalosporine, leur préparation et les médicaments qui les contiennent
CA1097340A (fr)	1981-03-10	Derives de la cephalosporine, leur preparation et les compositions qui les contiennent
EP0080944B1 (fr)	1985-08-28	Nouveaux dérivés de céphalosporines substitués en position 3 par un groupe hétérocycle thiométhyl, procédé de préparation desdits composés et compositions pharmaceutiques en contenant
EP0044238B1 (fr)	1984-02-01	Dérivés de céphalosporines sulfoxydes, procédé de préparation et compositions pharmaceutiques en contenant
EP0099297B1 (fr)	1988-04-06	Nouveaux dérivés des céphalosporines, leur procédé de préparation et médicaments antibiotiques contenant lesdits dérivés
CA1038374A (fr)	1978-09-12	Derives de la cephalosporine, leur preparation et les compositions qui les contiennent
EP0539460B1 (fr)	1994-10-05	Sels derives de la dialcoylaminoalcoylsulfonyl-26 pristinamycine ii b
FR2468608A1 (fr)	1981-05-08	Derives de la 1-oxadethiacephalosporine, leur procede de production et compositions anti-bacteriennes les contenant
EP0102291A1 (fr)	1984-03-07	Nouveaux dérivés de la céphalosporine, leur préparation et les médicaments qui les contiennent
EP0133096A1 (fr)	1985-02-13	Nouveaux dérivés de synergistines, leur préparation et les compositions pharmaceutiques qui les contiennent
EP0269512B1 (fr)	1991-09-11	Dérivés des céphalosporines à pharmacocinétique améliorée, procédé pour leur préparation et compositions pharmaceutiques les contenant
FR2485540A1 (fr)	1981-12-31	Nouveaux derives antibiotiques des cephalosporines, leur procede de preparation et les medicaments en contenant
KR810001669B1 (ko)	1981-10-27	세팔로스포린 유도체의 제조방법
US4178290A (en)	1979-12-11	Dithiinoacetic acid and its preparation
FR2621589A1 (fr)	1989-04-14	Derives des cephalosporines a pharmacocinetique amelioree, procede pour leur preparation et compositions pharmaceutiques les contenant
FR2801591A1 (fr)	2001-06-01	Derives macrocycliques de l'acide hydroxamique, leur preparation et les compositions qui les contiennent