US3890311A - 7-(2-(1-(phenylsulfonyl)-2-pyrrolidinylthio)acetamino)cephalosporanic acids - Google Patents
7-(2-(1-(phenylsulfonyl)-2-pyrrolidinylthio)acetamino)cephalosporanic acids Download PDFInfo
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- US3890311A US3890311A US452011A US45201174A US3890311A US 3890311 A US3890311 A US 3890311A US 452011 A US452011 A US 452011A US 45201174 A US45201174 A US 45201174A US 3890311 A US3890311 A US 3890311A
- Authority
- US
- United States
- Prior art keywords
- pyrrolidinylthio
- phenylsulfonyl
- group
- acid
- acetamino
- Prior art date
- 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 - Lifetime
Links
- 239000002253 acid Substances 0.000 title description 6
- 150000007513 acids Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 13
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000003242 anti bacterial agent Substances 0.000 abstract description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 229930186147 Cephalosporin Natural products 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 229940124587 cephalosporin Drugs 0.000 description 5
- 150000001780 cephalosporins Chemical class 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
- -1 alkali metal Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 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 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
- 229930182555 Penicillin Natural products 0.000 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 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 229930185482 poranic acid Natural products 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229920001817 Agar Polymers 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
- 208000035143 Bacterial infection Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- OIPLVYQFDZAYCB-UHFFFAOYSA-N n-(4,4-diethoxybutyl)benzenesulfonamide Chemical compound CCOC(OCC)CCCNS(=O)(=O)C1=CC=CC=C1 OIPLVYQFDZAYCB-UHFFFAOYSA-N 0.000 description 1
- HNAMACAPDOPVBC-UHFFFAOYSA-N n-[4-(4,4-diethoxybutylsulfamoyl)phenyl]acetamide Chemical compound CCOC(OCC)CCCNS(=O)(=O)C1=CC=C(NC(C)=O)C=C1 HNAMACAPDOPVBC-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
Definitions
- YRR LID R is a member selected from the group consisting of PORANIC ACIDS -H, alkyl of l to 3 carbon atoms, halo, nitro, al- 5 kanoylamido of 2 to 6 carbon atoms and trifluorometh l.
- the intermediate carboxylic acid is coupled with the R is a member selected from the group consisting of 7-amino cephalosporanic acid derivative by either the alkyl 0f 1 t0 3 Carbon atoms, halo, Him), dehydrative coupling or mixed anhydride technique kanoylamido of 2 to 6 carbon atoms, and trifluorocommonly employed in the production of amide linkmethyl; ages as in the field of polypeptide production.
- the free R is a member selected from the group consisting of carboxyl group of the 7-amino cephalosporanic acid H and alkyl of l to 3 carbon atoms; derivative may be converted to a salt (e.g. alkali metal, is 11 member Selected mm the group ccmsisting of ammonium or trialkylamine) before or after the coulk n yl xy 0f 2 t0 6 carbon atOmS, pling reaction by techniques well known in the art.
- a salt e.g. alkali metal, is 11 member Selected mm the group ccmsisting of ammonium or trialkylamine
- M is a member selected from the group consisting of
- the preferred anti-bacterial agents of this invention an alk "16ml 11nd from the standpoint of production economies are those
- this invention provides intermediate of the formula: compounds for the production of the cephalosporin derivatives described in the foregoing paragraph.
- the intermediate [l-(ph'enyl and substituted phenyl- R 2 sulfonyl)Lpyrrolidinylthiolacctic acids present the structural formula scacdiiii 8 t l r R (C 2 s l I y I 002'.”
- R is a member selected from the group consisting of Cl, Br and NO- R is a member selected from the group consisting of -H and acetoxy; and M is a member selected from the group consisting of H, sodium and potassium.
- cephalosporin derivatives of this invention have been found to be active anti-bacterial agents effective against gram-positive and gram-negative test organisms as well as penicillin resistant staphlococcus, in the well known and scientifically accepted agar serial dilution testing procedure.
- the cephalosporin derivatives of this invention are useful in the fields of comparative pharmacology and in microbiology and for the treatment of bacterial infections amenable to treatment with penicillin and cephalosporin derivatives.
- the intermediate carboxylic acids of this invention are useful for the preparation of the disclosed anti-bacterial ceph- 2O alosporin derivatives.
- the following examples illustrate the preparation of representative intermediate carboxylic acids and representative cephalosporanic acid derivatives of those carboxylie acid reactants.
- the cephalosporanic acid alkali metal salts were recovered in each instance, the free carboxylic acids being readily produced by known methods.
- the small amount of residual solvent present in some of the products exemplified is readily removed, if desired by vacuum stripping.
- the activity of each of the cephalosporin derivatives is provided for the specific bacterial strains against which the compound exemplified was active at or below 250 micrograms per milliliter.
- the representative nature of the bacterial strains employed to demonstrate anti-bacterial activity are indicative of the broader applicability of the compounds of this invention in the control of bacterial infestations other than those specifically referred to in each of the following examples:
- the title compound (m.p. l-l38C. from benzene) was prepared by a similar procedure to that described in Example I except that p-nitro-N-(4,4-die thoxybutyl)benzenc sulfonamide was utilized at room temperature.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
The invention relates to 7-(2-(1-(phenyl or substituted phenylsulfonyl)-2-pyrrolidinylthio)-acetamido)cephalosporanic acids as anti-bacterial agents and the intermediate (1-(phenyl- or substituted phenyl-sulfonyl)-2-pyrrolidinylthio)acetic acids employed in their production.
Description
United States Patent 11 1 Wei et al.
[ 7-(2-[l-(PHENYLSULFONYLl-Z- PYRROLIDINYLTHIOlACETAMlNO)CEPH- ALOSPORANIC ACIDS [75] Inventors: Peter H. L. Wei, Springfield; Carl Gochman, Philadelphia. both of Pa.
[73] Assignee: American Home Products Corporation, New York, NY.
221 Filed: Mar. 18, 1974 1211 Appl. N0.: 452,011
[52] US. Cl 260/243 C; 260/239.6; 260/239.7;
260/326.42; 260/326.47; 424/246 [51] Int. Cl C07d 99/24 [58] Field of Search 260/243 C [56] References Cited UNITED STATES PATENTS 3.658.799 4/1972 Eardley et al 260/243 C June 17, 1975 Primary ExaminerDonald G. Daus Assistant Examiner-Anne Marie T. Tighe Attorney, Agent, or Firm-Richard K. Jackson; Vito Victor Bellino 5 7 ABSTRACT 3 Claims, No Drawings 7-(2-[1-(PHENYLSULFONYL)-2- in which YRR LID R is a member selected from the group consisting of PORANIC ACIDS -H, alkyl of l to 3 carbon atoms, halo, nitro, al- 5 kanoylamido of 2 to 6 carbon atoms and trifluorometh l.
DESCRIPTION OF THE lNVhNTlON The inl ermediate carboxylic acids are prepared by In accordance with this invention there is provided a reacting a thioglycolic acid with an appropriately subgroup of 7-(2-[ l-(phenyland substituted phenylsulfostituted N-(4,4-diethoxybutyl)benzene sulfonamide in nyl)-2-pyrrolidinylthiolacetamido)cephalosporanic the presence of a catalytic amount of a mineral acid,
acids and salts of the formula 10 thusly 0C .,ll R
R so,
sem'oui L, :r\ .I :1 v a "J T g l v f\.
. r -scHc0 ch 5: l (l N H l CO H in which The intermediate carboxylic acid is coupled with the R is a member selected from the group consisting of 7-amino cephalosporanic acid derivative by either the alkyl 0f 1 t0 3 Carbon atoms, halo, Him), dehydrative coupling or mixed anhydride technique kanoylamido of 2 to 6 carbon atoms, and trifluorocommonly employed in the production of amide linkmethyl; ages as in the field of polypeptide production. The free R is a member selected from the group consisting of carboxyl group of the 7-amino cephalosporanic acid H and alkyl of l to 3 carbon atoms; derivative may be converted to a salt (e.g. alkali metal, is 11 member Selected mm the group ccmsisting of ammonium or trialkylamine) before or after the coulk n yl xy 0f 2 t0 6 carbon atOmS, pling reaction by techniques well known in the art.
x,\ l i t l t h'- CH f'h or when I v taken M1 th the q-wm'bom group.
M is a member selected from the group consisting of The preferred anti-bacterial agents of this invention an alk "16ml 11nd from the standpoint of production economies are those In addition, this invention provides intermediate of the formula: compounds for the production of the cephalosporin derivatives described in the foregoing paragraph. The intermediate [l-(ph'enyl and substituted phenyl- R 2 sulfonyl)Lpyrrolidinylthiolacctic acids present the structural formula scacdiiii 8 t l r R (C 2 s l I y I 002'."
in wh ch R is a member selected from the group consisting of Cl, Br and NO- R is a member selected from the group consisting of -H and acetoxy; and M is a member selected from the group consisting of H, sodium and potassium.
The cephalosporin derivatives of this invention have been found to be active anti-bacterial agents effective against gram-positive and gram-negative test organisms as well as penicillin resistant staphlococcus, in the well known and scientifically accepted agar serial dilution testing procedure. Thus. the cephalosporin derivatives of this invention are useful in the fields of comparative pharmacology and in microbiology and for the treatment of bacterial infections amenable to treatment with penicillin and cephalosporin derivatives. The intermediate carboxylic acids of this invention are useful for the preparation of the disclosed anti-bacterial ceph- 2O alosporin derivatives.
The following examples illustrate the preparation of representative intermediate carboxylic acids and representative cephalosporanic acid derivatives of those carboxylie acid reactants. The cephalosporanic acid alkali metal salts were recovered in each instance, the free carboxylic acids being readily produced by known methods. The small amount of residual solvent present in some of the products exemplified is readily removed, if desired by vacuum stripping. The activity of each of the cephalosporin derivatives is provided for the specific bacterial strains against which the compound exemplified was active at or below 250 micrograms per milliliter. The representative nature of the bacterial strains employed to demonstrate anti-bacterial activity are indicative of the broader applicability of the compounds of this invention in the control of bacterial infestations other than those specifically referred to in each of the following examples:
NE CA Nt'isxcria calurrlialix BA SU Bacillus .rubtilis BO BR Bordelellu bmm'hisuplicu ES C O Escherichia 0011' SA PA Salmonella paralyplii KL PN Klelzriella pneunmniae ST AU Sluphyloc'm'cux aureus EXAMPLE l l-( p-Bromophenylsulfonyl)-2-pyrrolidinylthio]acetic Acid p-Bromo-N-(4,4-diethoxybutyl)benzene sulfonamide (3.8 grams, 0.01 milliliter) and thioglycolic acid (1.0 gram) were dissolved in dimethoxyethane and the solution was heated on a steam bath, in the presence of a few drops of 6N HCl solution for 3 hours. After removal of the solvent, the residue was dissolved in henzene. The benzene solution was extracted with a dilute NaHCO- solution and extracted several times with benzene. The benzene extracts were dried over anhydrous MgSO After the benzene was removed, the residue was recrystallized from a mixture of diethyl ether and pentane to afford the title compound, m.p. 8689C.
Elemental Analysis for H,,BrNo.s.
Calc'd: C. 37.89; H, 3.7]; N, 3118. Found: C, 38.05; H. 3. 2; N. 3.74.
EXAMPLE ll l-(p-Acetamidophenylsulfonyl)-2-pyrrolidinylthio]acetic Acid.
5 The title compound (m.p. l47l49C. from CH CN) was prepared by a similar procedure to that described in Example I except that p-acetamido-N- (4,4-diethoxybutyl)benzene sulfonamide was utilized at room temperature.
Elemental Analysis for C H,,.N ();,S
(alcdz C, 46.9]; H. 5.061N. 7.8 Found: C, 46.94; H. 5.09; 8 3
EXAMPLE 1]] l-(p-Nitrophenylsulfonyl)2-pyrrolidinylthio]acetic Acid.
The title compound (m.p. l-l38C. from benzene) was prepared by a similar procedure to that described in Example I except that p-nitro-N-(4,4-die thoxybutyl)benzenc sulfonamide was utilized at room temperature.
Elemental Analysis for C H N O S lIIZC H Calcd: C. 42.54: H. 3.l4: N, 7.94.
30 Found: C. 42.94; H, 4.26; N, 8.05.
EXAMPLE lV 7-(2-[1-(p-Bromophenylsulfonyl)-2- pyrroidinylthio]acetamido)cephalosporanic Acid.
To l-(p-bromophenylsulfonyl )-2-pyrrolidinylthio]acetic acid (0.76 gram, 2 millimole) in 4 milliliter dimethylformamide was added carbonyl diimidazole (0.32 gram, 2 millimole) in one portion. The mixture was stirred under nitrogen atmosphere for /2 hour and under vacuum for /2 hour. To the above solution in an ice bath was added a cold solution of 7-aminocephalos- 5 poranic acid (0.56 gram, 2 millimole) and triethylamine (020 gram) in methlene chloride. The solution was stirred in an ice bath for 1 hour and at room temperature for l hour. Some insoluble material was filtered off. The filtrate was evaporated under reduced pressure at approximately 30C. To the residue dissolved in methylene chloride was added one milliliter of a 2M potassium Z-ethyl hexanoate. Addition of anhydrous diethyl ether caused precipitation of a salt, which was collected, washed with diethyl ether and dried.
Elemental Analysis for C H .BrN .,o.s ,K:
7-(2-l l-(p-Nitrophenylsulfonyl )-2- pyrrolidinylthiolacetamido)cephalosporanic Acid.
The title compound was prepared by a procedure in which similar to that described in Example IV except that [1- I (p-nitrophenylsulfonyl)-2-pyrrolidinylthio]acetic acid R 15 a member Elected from the group conslstlng of was utilized. H, Cl, Br and NO 5 R is a member selected from the group consisting of l-l and acetoxy; and
El tlAl"fCHNOK.
men a 82 5 2 Z% r 5& '3??? M 15 a member selected from the group consisting of Found: c, 40.12; H. 3,67; N, 8.25 H, sodium and potassium. BA SU 6633 .244 B0 BR 4617 250 is (2 1?I 138;? 2235 2. The compound of claim 1 which is 7-(2-[1-(p- SA PA 1 1737 bromophenylsulfonyD-Z sT AU 6538p 244 pyrrolldmylthio]acetamido)cephalosporamc acid. ST AU SMITH .244 ST AU CHP .976 ST AU 53480 3. The compound of claim 1 which is 7-(2-[l-(p- I nitrophenylsulfonyl)-2- what clalmed pyrrolidinylthio]acetamido)cephalosporanic acid.
1. A compound of the formula:
Claims (3)
1. A COMPOUND OF THE FORMULA
2. The compound of claim 1 which is 7-(2-(1-(p-bromophenylsulfonyl)-2-pyrrolidinylthio)acetamido)cephalosporanic acid.
3. The compound of claim 1 which is 7-(2-(1-(p-nitrophenylsulfonyl)-2-pyrrolidinylthio)acetamido)cephalosporanic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US452011A US3890311A (en) | 1974-03-18 | 1974-03-18 | 7-(2-(1-(phenylsulfonyl)-2-pyrrolidinylthio)acetamino)cephalosporanic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US452011A US3890311A (en) | 1974-03-18 | 1974-03-18 | 7-(2-(1-(phenylsulfonyl)-2-pyrrolidinylthio)acetamino)cephalosporanic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3890311A true US3890311A (en) | 1975-06-17 |
Family
ID=23794644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US452011A Expired - Lifetime US3890311A (en) | 1974-03-18 | 1974-03-18 | 7-(2-(1-(phenylsulfonyl)-2-pyrrolidinylthio)acetamino)cephalosporanic acids |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3890311A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7078424B2 (en) | 1998-06-03 | 2006-07-18 | Gpi Nil Holdings, Inc. | N-linked sulfonamides of N-heterocyclic carboxylic acids or carboxylic acid isosteres |
| US20110200695A1 (en) * | 1999-06-11 | 2011-08-18 | Annette Bianchi | Gel composition for filling a breast milk duct prior to surgical excision of the duct or other breast tissue |
| US8182842B1 (en) | 2010-11-10 | 2012-05-22 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Physico-chemical-managed killing of penicillin-resistant static and growing gram-positive and gram-negative vegetative bacteria |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3658799A (en) * | 1967-08-21 | 1972-04-25 | Glaxo Lab Ltd | Cephalosporin compounds |
-
1974
- 1974-03-18 US US452011A patent/US3890311A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3658799A (en) * | 1967-08-21 | 1972-04-25 | Glaxo Lab Ltd | Cephalosporin compounds |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7078424B2 (en) | 1998-06-03 | 2006-07-18 | Gpi Nil Holdings, Inc. | N-linked sulfonamides of N-heterocyclic carboxylic acids or carboxylic acid isosteres |
| US7459473B2 (en) | 1998-06-03 | 2008-12-02 | Glia Med, Inc. | N-linked sulfonamides of N-heterocyclic carboxylic acids or carboxylic acid isosteres |
| US20110200695A1 (en) * | 1999-06-11 | 2011-08-18 | Annette Bianchi | Gel composition for filling a breast milk duct prior to surgical excision of the duct or other breast tissue |
| US8182842B1 (en) | 2010-11-10 | 2012-05-22 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Physico-chemical-managed killing of penicillin-resistant static and growing gram-positive and gram-negative vegetative bacteria |
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