CA1057739A - Derives de type pyridinylthiomethyl de cyanomethylthioacetylcephalosporines - Google Patents

Derives de type pyridinylthiomethyl de cyanomethylthioacetylcephalosporines

Info

Publication number: CA1057739A
Authority: CA; Canada
Prior art keywords: formula; acid; lower alkyl; salt; compound
Prior art date: 1974-08-21
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

CA229,637A

Other languages

English (en)

Other versions

CA229637S (en

Inventor

Hermann Breuer

Uwe D. Treuner

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.)

ER Squibb and Sons LLC

Original Assignee

ER Squibb and Sons LLC

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.)

1974-08-21

Filing date

1975-06-18

Publication date

1979-07-03

1975-06-18 Application filed by ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC

1979-07-03 Application granted granted Critical

1979-07-03 Publication of CA1057739A publication Critical patent/CA1057739A/fr

Status Expired legal-status Critical Current

Links

-1 Pyridinylthiomethyl Chemical class 0.000 title abstract description 25
229940124587 cephalosporin Drugs 0.000 title description 3
229930186147 Cephalosporin Natural products 0.000 title description 2
150000003839 salts Chemical class 0.000 claims abstract description 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
239000001257 hydrogen Substances 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims description 20
150000001875 compounds Chemical class 0.000 claims description 16
238000000034 method Methods 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 6
150000001340 alkali metals Chemical class 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
150000001342 alkaline earth metals Chemical class 0.000 claims 2
FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 15
150000002431 hydrogen Chemical group 0.000 abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
239000003242 anti bacterial agent Substances 0.000 abstract description 2
125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
125000000446 sulfanediyl group Chemical group *S* 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
239000011591 potassium Substances 0.000 description 5
229940086542 triethylamine Drugs 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical group 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
239000000047 product Substances 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000004423 acyloxy group Chemical group 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-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
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
229960000443 hydrochloric acid Drugs 0.000 description 2
235000011167 hydrochloric acid Nutrition 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JRRFRAHROZUYJH-UHFFFAOYSA-N 2-(cyanomethylsulfanyl)acetic acid Chemical class OC(=O)CSCC#N JRRFRAHROZUYJH-UHFFFAOYSA-N 0.000 description 1
JRGRABSYRWMJPN-UHFFFAOYSA-N 2-(cyanomethylsulfanyl)acetyl chloride Chemical compound ClC(=O)CSCC#N JRGRABSYRWMJPN-UHFFFAOYSA-N 0.000 description 1
YJVXEQJVAOGXKM-UHFFFAOYSA-N 2-ethoxy-2h-quinoline-1-carboxylic acid Chemical compound C1=CC=C2N(C(O)=O)C(OCC)C=CC2=C1 YJVXEQJVAOGXKM-UHFFFAOYSA-N 0.000 description 1
CRPFKUKPDCBUIX-UHFFFAOYSA-N 2-ethyl-5-phenyl-1,2-oxazol-2-ium-3-sulfonate Chemical compound [O-]S(=O)(=O)C1=[N+](CC)OC(C=2C=CC=CC=2)=C1 CRPFKUKPDCBUIX-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000588729 Hafnia alvei Species 0.000 description 1
101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
DTOZRCOCJVVION-UHFFFAOYSA-N O-methyl ethanethioate Chemical compound COC(C)=S DTOZRCOCJVVION-UHFFFAOYSA-N 0.000 description 1
101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
241000588767 Proteus vulgaris Species 0.000 description 1
241000588777 Providencia rettgeri Species 0.000 description 1
OATSQCXMYKYFQO-UHFFFAOYSA-N S-methyl ethanethioic acid ester Natural products CSC(C)=O OATSQCXMYKYFQO-UHFFFAOYSA-N 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
125000005042 acyloxymethyl group Chemical group 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
150000001447 alkali salts Chemical group 0.000 description 1
229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
150000001727 carbonic acid monoesters Chemical class 0.000 description 1
229960002588 cefradine Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
RDLPVSKMFDYCOR-UEKVPHQBSA-N cephradine Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CCC=CC1 RDLPVSKMFDYCOR-UEKVPHQBSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
SLFUXNFVAANERW-UHFFFAOYSA-N ethyl hexanoate;potassium Chemical compound [K].CCCCCC(=O)OCC SLFUXNFVAANERW-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
KCKPYKDFOFPQTB-UHFFFAOYSA-N methyl 2-(cyanomethylsulfanyl)acetate Chemical compound COC(=O)CSCC#N KCKPYKDFOFPQTB-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
JSXUVPOJUSIVDQ-UHFFFAOYSA-M potassium;2-(cyanomethylsulfanyl)acetate Chemical compound [K+].[O-]C(=O)CSCC#N JSXUVPOJUSIVDQ-UHFFFAOYSA-M 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000007614 solvation Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—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, cefaclor, or cephalexine

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (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)

CA229,637A 1974-08-21 1975-06-18 Derives de type pyridinylthiomethyl de cyanomethylthioacetylcephalosporines Expired CA1057739A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US49935474A	1974-08-21	1974-08-21

Publications (1)

Publication Number	Publication Date
CA1057739A true CA1057739A (fr)	1979-07-03

Family

ID=23984947

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA229,637A Expired CA1057739A (fr)	1974-08-21	1975-06-18	Derives de type pyridinylthiomethyl de cyanomethylthioacetylcephalosporines

Country Status (9)

Country	Link
JP (1)	JPS5143795A (fr)
AU (1)	AU497282B2 (fr)
BE (1)	BE832615A (fr)
CA (1)	CA1057739A (fr)
CH (1)	CH608240A5 (fr)
DE (1)	DE2537280A1 (fr)
FR (1)	FR2282274A1 (fr)
GB (1)	GB1507925A (fr)
NL (1)	NL7508109A (fr)

1975
- 1975-05-19 GB GB2125475A patent/GB1507925A/en not_active Expired
- 1975-06-16 AU AU82257/75A patent/AU497282B2/en not_active Expired
- 1975-06-18 CA CA229,637A patent/CA1057739A/fr not_active Expired
- 1975-07-08 NL NL7508109A patent/NL7508109A/xx not_active Application Discontinuation
- 1975-08-07 CH CH1032075A patent/CH608240A5/xx not_active IP Right Cessation
- 1975-08-19 FR FR7525670A patent/FR2282274A1/fr not_active Withdrawn
- 1975-08-21 JP JP10198075A patent/JPS5143795A/ja active Pending
- 1975-08-21 DE DE19752537280 patent/DE2537280A1/de not_active Withdrawn
- 1975-08-21 BE BE159353A patent/BE832615A/fr unknown

Also Published As

Publication number	Publication date
NL7508109A (nl)	1976-02-24
AU497282B2 (en)	1978-12-07
GB1507925A (en)	1978-04-19
JPS5143795A (ja)	1976-04-14
DE2537280A1 (de)	1976-03-04
AU8225775A (en)	1976-12-23
BE832615A (fr)	1975-12-16
FR2282274A1 (fr)	1976-03-19
CH608240A5 (en)	1978-12-29

Publication	Publication Date	Title
JPH0313237B2 (fr)	1991-02-22
NO763601L (fr)	1977-04-26
JPS6153359B2 (fr)	1986-11-17
US3701775A (en)	1972-10-31	Esters of mandeloylaminocephalosporanic acids
CA1057739A (fr)	1979-07-03	Derives de type pyridinylthiomethyl de cyanomethylthioacetylcephalosporines
US3855212A (en)	1974-12-17	Cyanomethylth ioacetylcephalosporins
US3919208A (en)	1975-11-11	7-(Cyanomethylaryl)acetamide-cephalosporin derivatives
US4005081A (en)	1977-01-25	3-Heterothiomethyl-7α-methoxy-7β-tetrazolylmethylthioacetamido-3-cephem derivatives
US3956287A (en)	1976-05-11	7-[(2-Oxo-1-pyridinyl)acylamino]cephalosporin derivatives
US4051129A (en)	1977-09-27	Process for preparing 7-methoxycephalosporin compounds
US3991051A (en)	1976-11-09	[(Oxyalkyl)thioacetyl]cephalosporin derivatives
US3994889A (en)	1976-11-30	3-Heterothio derivatives of (α-thiocarbonylaminol)-7α-methoxy-cephalosporins
US3944546A (en)	1976-03-16	Cyanomethylthioacetylcephalosporins
NO752217L (fr)	1975-12-30
US4219648A (en)	1980-08-26	7-[[Amino(1,3-dihydrobenzo[c]thienyl)acetyl]amino]cephalosporin derivatives
US4150224A (en)	1979-04-17	7[[(1-Pyrrollyl)7 acetyl]amino]cephalosporin derivatives
CS195680B2 (en)	1980-02-29	Process for preparing derivatives of 7-/substituted phenylglycinamido/-3-substituted-3-cephem-4-carboxylic acid
US3996216A (en)	1976-12-07	3-Heterothio derivatives of (formylamino)acetylamino-7-alpha-methoxy cephalosporins
GB2045233A (en)	1980-10-29	Unsaturated 3-heterocyclyl- thiomethyl-7???-methoxy-7???- acylamido-3-cephem-4- carboxylic acid derivatives
US4180660A (en)	1979-12-25	Cephalosporin derivatives
US4122260A (en)	1978-10-24	Cephalosporin derivatives
US4111978A (en)	1978-09-05	Cyanomethylthioacetylcephalosporin intermediates
US3978050A (en)	1976-08-31	3-Tetrazolyl and other derivatives of [[(alkoxy)thiocarbonyl]oxy]acetyl cephalosporins
US3929778A (en)	1975-12-30	{8 (Acylcarbamoyl) thioacetyl{9 {0 cephalosporin derivatives
US3720665A (en)	1973-03-13	Acyloxymethyl esters of alpha-preidocyclo-hexadienylalkylene-penicillins