CH527855A - Verfahren zur Herstellung neuer Derivate der 7-Amino-cephalosporansäure - Google Patents

Verfahren zur Herstellung neuer Derivate der 7-Amino-cephalosporansäure

Info

Publication number: CH527855A
Authority: CH; Switzerland
Prior art keywords: formula; amino; group; acylated; compound
Prior art date: 1968-12-12

Application number

CH4471A

Other languages

German (de)

English (en)

Inventor

Hans Dr Bickel

Johannes Dr Mueller

Rolf Dr Bosshardt

Heinrich Dr Peter

Bruno Dr Fechtig

Original Assignee

Ciba Geigy Ag

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.)

1968-12-12

Filing date

1968-12-12

Publication date

1972-09-15

1968-12-12 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1968-12-12 Priority to CH4471A priority Critical patent/CH527855A/de

1972-09-15 Publication of CH527855A publication Critical patent/CH527855A/de

Links

HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 title claims abstract description 8
239000003242 anti bacterial agent Substances 0.000 title abstract 2
229940088710 antibiotic agent Drugs 0.000 title abstract 2
241001465754 Metazoa Species 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 11
-1 carbamoyloxy Chemical group 0.000 claims abstract description 10
238000000034 method Methods 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000012948 isocyanate Substances 0.000 claims description 2
150000002513 isocyanates Chemical class 0.000 claims description 2
150000002540 isothiocyanates Chemical class 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 abstract 1
125000003277 amino group Chemical group 0.000 abstract 1
235000019730 animal feed additive Nutrition 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
159000000000 sodium salts Chemical class 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
239000000872 buffer Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
BLDFSDCBQJUWFG-UHFFFAOYSA-N 2-(methylamino)-1,2-diphenylethanol Chemical compound C=1C=CC=CC=1C(NC)C(O)C1=CC=CC=C1 BLDFSDCBQJUWFG-UHFFFAOYSA-N 0.000 description 1
JVSMPWHQUPKRNV-UHFFFAOYSA-N 2h-tetrazol-5-amine;hydrate Chemical compound O.NC=1N=NNN=1 JVSMPWHQUPKRNV-UHFFFAOYSA-N 0.000 description 1
108010013043 Acetylesterase Proteins 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229930186147 Cephalosporin Natural products 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000588747 Klebsiella pneumoniae Species 0.000 description 1
102100036617 Monoacylglycerol lipase ABHD2 Human genes 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
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 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000003674 animal food additive Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
239000002585 base Substances 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
238000007865 diluting Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
LKHYFCSSVZVVNF-UHFFFAOYSA-N ethyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OCC LKHYFCSSVZVVNF-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000000203 mixture Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000004321 preservation Methods 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings

Landscapes

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

CH4471A 1968-12-12 1968-12-12 Verfahren zur Herstellung neuer Derivate der 7-Amino-cephalosporansäure CH527855A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH4471A CH527855A (de)	1968-12-12	1968-12-12	Verfahren zur Herstellung neuer Derivate der 7-Amino-cephalosporansäure

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH1851668A CH507985A (de)	1968-12-12	1968-12-12	Verfahren zur Herstellung neuer Derivate der 7-Aminocephalosporansäure
CH4471A CH527855A (de)	1968-12-12	1968-12-12	Verfahren zur Herstellung neuer Derivate der 7-Amino-cephalosporansäure

Publications (1)

Publication Number	Publication Date
CH527855A true CH527855A (de)	1972-09-15

Family

ID=4433518

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH4471A CH527855A (de)	1968-12-12	1968-12-12	Verfahren zur Herstellung neuer Derivate der 7-Amino-cephalosporansäure
CH1851668A CH507985A (de)	1968-12-12	1968-12-12	Verfahren zur Herstellung neuer Derivate der 7-Aminocephalosporansäure

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH1851668A CH507985A (de)	1968-12-12	1968-12-12	Verfahren zur Herstellung neuer Derivate der 7-Aminocephalosporansäure

Country Status (5)

Country	Link
AT (2)	AT301031B (cs)
BR (1)	BR6915033D0 (cs)
CH (2)	CH527855A (cs)
CS (2)	CS156462B2 (cs)
SU (2)	SU400106A3 (cs)

1968
- 1968-12-12 CH CH4471A patent/CH527855A/de not_active IP Right Cessation
- 1968-12-12 CH CH1851668A patent/CH507985A/de not_active IP Right Cessation
1969
- 1969-11-10 CS CS739269A patent/CS156462B2/cs unknown
- 1969-11-10 CS CS238673*1A patent/CS156463B2/cs unknown
- 1969-12-08 SU SU1670625A patent/SU400106A3/ru active
- 1969-12-08 SU SU1382754A patent/SU410590A3/ru active
- 1969-12-11 AT AT427271A patent/AT301031B/de not_active IP Right Cessation
- 1969-12-11 AT AT1155169A patent/AT297924B/de not_active IP Right Cessation
- 1969-12-12 BR BR215033/69A patent/BR6915033D0/pt unknown

Also Published As

Publication number	Publication date
SU400106A3 (cs)	1973-10-03
CH507985A (de)	1971-05-31
BR6915033D0 (pt)	1973-05-24
CS156462B2 (cs)	1974-07-24
CS156463B2 (cs)	1974-07-24
AT301031B (de)	1972-08-25
AT297924B (de)	1972-04-10
SU410590A3 (cs)	1974-01-05

Legal Events

Date	Code	Title	Description
1976-07-15	PL	Patent ceased

Publication	Publication Date	Title
DE2304226B2 (de)	1979-07-19	Verfahren zur Herstellung von Penicillinen und Cephalosporinen
DE1670324B2 (de)	1977-03-10	7-cyanacetylamino-cephalosporansaeurederivate
DE2514020A1 (de)	1975-10-02	Acylureidocephalosporine
CH648561A5 (cs)	1985-03-29
DE2203653A1 (de)	1972-08-10	Cephalosporincarbamate und Verfahren zu deren Herstellung
DE2715038A1 (de)	1977-11-24	Neue antibakterielle verbindungen
CH527855A (de)	1972-09-15	Verfahren zur Herstellung neuer Derivate der 7-Amino-cephalosporansäure
EP0553792B1 (de)	1999-05-26	Verfahren zur Herstellung von Ceftriaxon-dinatriumsalzhemiheptahydrat
DE3851449T2 (de)	1995-03-16	Cephalosporinderivate, Verfahren zu ihrer Herstellung und antibakterielle Mittel.
CH524634A (de)	1972-06-30	Verfahren zur Herstellung neuer Derivate der 7-Aminocephalosporansäure
DE2236422C2 (de)	1981-12-10	Cephalosporinverbindungen und Verfahren zu deren Herstellung
DE1960643A1 (de)	1970-07-02	Verfahren zur Herstellung neuer Derivate der 7-Aminocephalosporansaeure
EP0054677B1 (de)	1985-05-29	Neue Cephalosporine, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
CH593924A5 (en)	1977-12-30	Cephalosporin carbamates - from alcohols and isocyanates
AT337365B (de)	1977-06-27	Verfahren zur herstellung von neuen derivaten des cephalosporins und von ihren salzen
CH634326A5 (de)	1983-01-31	2-hydroxyiminoacetamido-cephemcarbonsaeuren und ihre herstellung.
CH528540A (de)	1972-09-30	Verfahren zur Herstellung neuer Derivate der 7-Aminocephalosporansäure
CH545815A (en)	1974-02-15	Acylated 7-amino cephalosporanic acid - derivs as antibiotics and animal feed addtvs
AT301756B (de)	1972-09-25	Verfahren zur Herstellung neuer Derivate der 7-Amino-cephalosporansäure
AT337366B (de)	1977-06-27	Verfahren zur herstellung von neuen derivaten des cephalosporins und von ihren salzen
DE1670324C3 (de)	1977-10-20	7-Cyanacetylamino-cephalosporansäurederivate
CH535257A (de)	1973-03-31	Verfahren zur Herstellung neuer Derivate der 7-Aminocephalosporansäure
CH545814A (en)	1974-02-15	7-amino cephalosporanic acid derivatives, antibacterials - feed additives
AT367062B (de)	1982-05-25	Verfahren zur herstellung von neuen 7alphamethoxy-cephalosporansaeurederivaten
CH505146A (de)	1971-03-31	Verfahren zur Herstellung neuer Derivate der 7-Aminocephalosporansäure