Patent FR1180461A successfully refreshed from Google Patents.
Patent US4323567A successfully refreshed from Google Patents.
US4323567A
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Arylmalonamido-1-oxadethiacephalosporins
Assignee: Individual
•
Filing: 1980-06-05
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Granted: 1982-04-06
•
Expires: 2000-06-05
Abstract
Abstract Antibacterial 1-oxadethiacephalosporins of the formula: ##STR1## wherein Ar is ##STR2## (in which Acyl is organic or inorganic acyl); COB 1 and COB 2 each is carboxy or protected carboxy; Het is ##STR3## (in which COB 3 is carboxy or protected carboxy); and Y is hydrogen or methoxy; and when COB 1 and COB 2 , and/or COB 3 is carboxy, pharmaceutically acceptable salts thereof are included, but with a proviso that when Y is methoxy, Het is ##STR4## a pharmaceutical or veterinary composition comprising the said 1-oxadethiacephalosporins and pharmaceutical carrier, and a method for treating or preventing human or veterinary infectious diseases comprising administering the said 1-oxadethiacephalosporin. Also disclosed are epimers of the compounds of formula (I) wherein the asymmetric carbon of the malonic methine is in the D(R)- or L(S)- configuration. The individual epimers are separable by column chromatography and/or crystallization. The bactericidal activity of the D-epimers is greater than that of the L-epimers or the mixtures of the epimers.
Inventors
- 👤 Masayuki Narisada
- 👤 Wataru Nagata
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 22:03
CPC Classifications
C; C07; C07D; C07D498/00; C07D498/02; C07D498/04; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/535; A61P; A61P31/00; A61P31/04; C07D205/00; C07D265/00; C07D505/00
Claims Analysis
Total Claims: 65
Claim 1
Independent Claim
121 words
A substantially pure compound of the following formula: ##STR39## wherein Ar is ##STR40## in which Acyl is alkanoyl containing 1 to 5 carbon atoms, carbamoyl, N-alkylcarbamoyl containing 2 to 6 carbon atoms, or ureidocarbonyl, and COB 1 and COB 2 each independently represent carboxy, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, n-butoxycarbony, t-butoxycarbonyl, pentyloxycarbonyl, cyclopropylmethoxycarbonyl, monohydroxy-t-butoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, chloromethoxycarbonyl, cyanomethoxycarbonyl, methanesulfonylethoxycarbonyl, acetylmethoxycarbonyl, acetoxymethoxycarbonyl, acetoxyethoxycarbonyl, propionyloxymethoxycarbonyl, propionyloxyethoxycarbonyl, pivaloyloxymethoxycarbonyl, benzoyloxymethoxycarbonyl, methoxymethoxycarbonyl, phenoxymethoxycarbonyl, methylthiomethoxycarbonyl, phenylthiomethoxycarbonyl, tetrahydropyranyloxy carbonyl, phthaliminomethoxycarbonyl, α,α-dimethylpropargyloxycarbonyl, methoxycarbonyloxyethoxycarbonyl, ethoxycarbonylethoxycarbonyl, methoxycarbonyloxypropoxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl, phenethyloxycarbonyl, tolylmethoxycarbonyl, dimethylbenzyloxycarbonyl, nitrobenzyloxycarbonyl, halobenzyloxycarbonyl, methoxybenzyloxycarbonyl, phthalidyloxycarbonyl, p-hydroxy-di-t-butylbenzyloxycarbonyl, diphenylmethoxycarbonyl, trityloxycarbonyl, phenacyloxycarbonyl, chlorophenacyloxycarbonyl, bromophenacyloxycarbonyl, nitrophenacyloxycarbonyl, methylphenacyloxycarbonyl, trimethylsilyloxycarbonyl, dimethylmethoxysilyloxycarbonyl, trimethylstannyloxycarbonyl, phenoxycarbonyl, naphthyloxycarbonyl, tolyloxycarbonyl, dimethylphenoxycarbonyl, nitrophenoxycarbonyl, methoxyphenoxycarbonyl, methanesulfonylphenoxycarbonyl, chlorophenoxycarbonyl, pentachlorophenoxycarbonyl, indanyloxycarbonyl, pyridyloxycarbonyl, sodiooxycarbonyl, potassiooxycarbonyl, magnesiooxycarbonyl, calciooxycarbonyl, or a salt of carboxy group with procain, xylocain, triethylamine, or dicyclohexylamine.
Claim 2
Dependent Claim
121 words
A substantially pure compound of the following formula: ##STR39## wherein Ar is ##STR40## in which Acyl is alkanoyl containing 1 to 5 carbon atoms, carbamoyl, N-alkylcarbamoyl containing 2 to 6 carbon atoms, or ureidocarbonyl, and COB 1 and COB 2 each independently represent carboxy, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, n-butoxycarbony, t-butoxycarbonyl, pentyloxycarbonyl, cyclopropylmethoxycarbonyl, monohydroxy-t-butoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, chloromethoxycarbonyl, cyanomethoxycarbonyl, methanesulfonylethoxycarbonyl, acetylmethoxycarbonyl, acetoxymethoxycarbonyl, acetoxyethoxycarbonyl, propionyloxymethoxycarbonyl, propionyloxyethoxycarbonyl, pivaloyloxymethoxycarbonyl, benzoyloxymethoxycarbonyl, methoxymethoxycarbonyl, phenoxymethoxycarbonyl, methylthiomethoxycarbonyl, phenylthiomethoxycarbonyl, tetrahydropyranyloxy carbonyl, phthaliminomethoxycarbonyl, α,α-dimethylpropargyloxycarbonyl, methoxycarbonyloxyethoxycarbonyl, ethoxycarbonylethoxycarbonyl, methoxycarbonyloxypropoxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl, phenethyloxycarbonyl, tolylmethoxycarbonyl, dimethylbenzyloxycarbonyl, nitrobenzyloxycarbonyl, halobenzyloxycarbonyl, methoxybenzyloxycarbonyl, phthalidyloxycarbonyl, p-hydroxy-di-t-butylbenzyloxycarbonyl, diphenylmethoxycarbonyl, trityloxycarbonyl, phenacyloxycarbonyl, chlorophenacyloxycarbonyl, bromophenacyloxycarbonyl, nitrophenacyloxycarbonyl, methylphenacyloxycarbonyl, trimethylsilyloxycarbonyl, dimethylmethoxysilyloxycarbonyl, trimethylstannyloxycarbonyl, phenoxycarbonyl, naphthyloxycarbonyl, tolyloxycarbonyl, dimethylphenoxycarbonyl, nitrophenoxycarbonyl, methoxyphenoxycarbonyl, methanesulfonylphenoxycarbonyl, chlorophenoxycarbonyl, pentachlorophenoxycarbonyl, indanyloxycarbonyl, pyridyloxycarbonyl, sodiooxycarbonyl, potassiooxycarbonyl, magnesiooxycarbonyl, calciooxycarbonyl, or a salt of carboxy group with procain, xylocain, triethylamine, or dicyclohexylamine.
Claim 3
Dependent Claim
10 words
A compound according to claim 1, wherein Ar is thienyl.
Claim 4
Dependent Claim
10 words
A compound according to claim 2, wherein Ar is 3-thienyl.
Claim 5
Dependent Claim
45 words
A compound according to claim 1, wherein COB 1 and COB 2 are independently carboxy, phthalidyloxycarbonyl, acetoxymethoxycarbonyl, pivaloyloxymethoxycarbonyl, acetoxyethoxycarbonyl, propionyloxyethoxycarbonyl, indanyloxycarbonyl, phenoxycarbonyl, tolyloxycarbonyl, dimethylphenoxycarbonyl, methoxyphenoxycarbonyl, methoxycarbonyloxyethoxycarbonyl, ethoxycarbonyloxymethoxycarbonyl, or phenacyloxycarbonyl, or when COB 1 or COB 2 is carboxy, a pharmaceutically acceptable salt of the compound.
Claim 6
Dependent Claim
10 words
A compound according to claim 1, that is 7β-[D-[α-(3-thienyl)-α-carboxyacetamido]]-7α-methoxy-3-(1-methyltetrazol-5-yl)-thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 7
Dependent Claim
13 words
A compound according to claim 1, that is sodium salt of 7β-[D-[α-(3-thienyl)-α-carboxyacetamido]]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 8
Dependent Claim
13 words
A compound according to claim 1, that is potassium salt of 7β-[D-[α-(3-thienyl)-α-carboxyacetamido]]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 9
Dependent Claim
10 words
A compound according to claim 1, that is 7β-[D-[α-(3-thienyl)-α-(5-indanyloxy)carbonylacetamido]]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 10
Dependent Claim
13 words
A compound according to claim 1, that is sodium salt of 7β-[D-[α-(3-thienyl)-α-(5-indanyloxy)carbonylacetamido]]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 11
Dependent Claim
10 words
A compound according to claim 1, that is 7β-[D-[α-(3-thienyl)-α-phenoxycarbonylacetamido]]-7.alpha.-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 12
Dependent Claim
13 words
A compound according to claim 1, that is sodium salt of 7β-[D-[α-(3-thienyl)-α-phenoxycarbonylacetamido]]-7.alpha.-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 13
Dependent Claim
10 words
A compound according to claim 1, that is 7β-[D-[α-(3-thienyl)-α-(3,4-dimethylphenoxycarbonyl)acetamido]]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 14
Dependent Claim
13 words
A compound according to claim 1, that is sodium salt of 7β-[D-[α-(3-thienyl)-α-(3,4-dimethylphenoxycarbonyl)-acetamido]]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 15
Dependent Claim
10 words
Substantially pure 7β-[D-[α-(2-thienyl)-α-carboxyacetamido]]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid and its sodium or potassium salt.
Claim 16
Dependent Claim
10 words
Substantially pure 7β-[D-[α-(2-thienyl)-α-carboxyacetamido]]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid and its sodium or potassium salt.
Claim 17
Dependent Claim
10 words
Substantially pure 7β-[D-(α-phenyl-α-carboxy-α-acetamido)]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid and its sodium or potassium salt.
Claim 18
Dependent Claim
10 words
Substantially pure 7β-[D-(α-phenyl-α-carboxy-α-acetamido)]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid and its sodium or potassium salt.
Claim 19
Dependent Claim
10 words
A compound according to claim 1, wherein Ar is p-hydroxyphenyl.
Claim 20
Dependent Claim
38 words
A compound according to claim 16, wherein COB 1 is carboxy, phthalidyloxycarbonyl, acetoxymethoxycarbonyl, pivaloyloxymethoxycarbonyl, acetoxyethoxycarbonyl, propionyloxyethoxycarbonyl, indanyloxycarbonyl, phenoxycarbonyl, tolyloxycarbonyl, dimethylphenoxycarbonyl, methoxyphenoxycarbonyl, methoxycarbonyloxyethoxycarbonyl, ethoxycarbonyloxymethoxycarbonyl, or phenacyloxycarbonyl, or when COB 1 is carboxy, a pharmaceutically acceptable salt of the compound.
Claim 21
Dependent Claim
17 words
A compound according to claim 17, wherein COB 2 is carboxy, or a pharmaceutically acceptable salt thereof.
Claim 22
Dependent Claim
10 words
A compound according to claim 1, that is 7β-[D-[α-p-hydroxyphenyl-α-carboxyacetamido]]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 23
Dependent Claim
13 words
A compound according to claim 1, that is sodium salt of 7β-[D-(α-p-hydroxyphenyl-α-carboxyacetamido)]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 24
Dependent Claim
13 words
A compound according to claim 1, that is potassium salt of 7β-[D-(α-p-hydroxyphenyl-α-carboxyacetamido)]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 25
Dependent Claim
10 words
A compound according to claim 1, that is 7β-[D-[α-p-hydroxyphenyl-α-(5-indanyloxy)carbonylacetamido]]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 26
Dependent Claim
13 words
A compound according to claim 1, that is sodium salt of 7β-[D-[α-p-hydroxyphenyl-α-(5-indanyloxy)carbonylacetamido]]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 27
Dependent Claim
15 words
A compound according to claim 1, wherein Ar is p-acyloxyphenyl as defined in claim 1.
Claim 28
Dependent Claim
10 words
A compound according to claim 24, wherein Ar is carbamoyloxyphenyl.
Claim 29
Dependent Claim
38 words
A compound according to claim 25, wherein COB 1 is carboxy, phthalidyloxycarbonyl, acetoxymethoxycarbonyl, pivaloyloxymethoxycarbonyl, acetoxyethoxycarbonyl, propionyloxyethoxycarbonyl, indanyloxycarbonyl, phenoxycarbonyl, tolyloxycarbonyl, dimethylphenoxycarbonyl, methoxyphenoxycarbonyl, methoxycarbonyloxyethoxycarbonyl, ethoxycarbonyloxymethoxycarbonyl, or phenacyloxycarbonyl, or when COB 1 is carboxy, a pharmaceutically acceptable salt of the compound.
Claim 30
Dependent Claim
10 words
A compound according to claim 26, that is 7β-[D-(α-p-carbamoyloxyphenyl-α-carboxyacetamido)]-7.alpha.-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 31
Dependent Claim
13 words
A compound according to claim 26, that is sodium salt of 7β-[D-(α-p-carbamoyloxyphenyl-α-carboxyacetamido)]-7.alpha.-methoxy-3-(1-methyl-tetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 32
Dependent Claim
13 words
A compound according to claim 26, that is potassium salt of 7β-[D-(α-p-carbamoyloxyphenyl-α-carboxyacetamido)]-7.alpha.-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 33
Dependent Claim
8 words
7β-[D-(α-p-acetoxyphenyl-α-carboxyacetamido)]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid or its sodium or potassium salt.
Claim 34
Dependent Claim
8 words
7β-[D-(α-p-acetoxyphenyl-α-carboxyacetamido)]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid or its sodium or potassium salt.
Claim 35
Dependent Claim
10 words
Substantially pure 7β-[D-(α-p-N-methylcarbamoyloxyphenyl-α-carboxyacetamido)]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid or its sodium or potassium salt.
Claim 36
Dependent Claim
10 words
Substantially pure 7β-[D-(α-p-N-methylcarbamoyloxyphenyl-α-carboxyacetamido)]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid or its sodium or potassium salt.
Claim 37
Dependent Claim
10 words
Substantially pure 7β-[D-(α-p-ureidocarbonyloxyphenyl-α-carboxyacetamido)]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid or its sodium or potassium salt.
Claim 38
Dependent Claim
10 words
Substantially pure 7β-[D-(α-p-ureidocarbonyloxyphenyl-α-carboxyacetamido)]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid or its sodium or potassium salt.
Claim 39
Dependent Claim
21 words
A pharmaceutical composition which comprises a bactericidally effective amount of a compound according to claim 1 and a pharmaceutical carrier therefor.
Claim 40
Dependent Claim
18 words
A pharmaceutical composition according to claim 33 containing 0.01% to 99% of a compound according to claim 1.
Claim 41
Dependent Claim
12 words
A pharmaceutical composition according to claim 34 in a unit dosage form.
Claim 42
Dependent Claim
9 words
A pharmaceutical composition according to claim 35 for injection.
Claim 43
Dependent Claim
17 words
A pharmaceutial composition according to claim 36 in a form of injection in an ampoule or vial.
Claim 44
Dependent Claim
19 words
A pharmaceutical composition according to claim 36 in a form of powder, crystals, microcrystals, or lyophilizate in a vial.
Claim 45
Dependent Claim
39 words
A pharmaceutical composition according to claim 36 wherein the compound is one in which Ar is 2-thienyl, 3-thienyl, p-hydroxyphenyl, or p-carbamoyloxyphenyl and COB 1 and COB 2 each are carboxy in the form of its sodium or potassium salt.
Claim 46
Dependent Claim
18 words
A pharmaceutical composition according to claim 36 wherein the compound is sodium or potassium salt of 7β-[D-[α-(3-thienyl)-α-carboxyacetamido]]-7α-methoxy-3-(1-methyltetrazol-5-yl)-thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 47
Dependent Claim
18 words
A pharmaceutical composition according to claim 36 wherein the compound is sodium or potassium salt of 7β-[D-(α-p-hydroxyphenyl-α-carboxyacetamido)]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 48
Dependent Claim
18 words
A pharmaceutical composition according to claim 36 wherein the compound is sodium or potassium salt of 7β-[D-(α-p-carbamoyloxyphenyl-α-carboxyacetamido)]-7.alpha.-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 49
Dependent Claim
10 words
A pharmaceutical composition according to claim 35 for enteral administration.
Claim 50
Dependent Claim
16 words
A pharmaceutical composition according to claim 43 in a form of capsule, tablet or dry syrup.
Claim 51
Dependent Claim
39 words
A pharmaceutical composition according to claim 43, wherein the compound is one in which Ar is 2-thienyl, 3-thienyl, p-hydroxyphenyl, or carbamoyloxyphenyl; COB 1 is indanyl, phenyl, or dimethylphenyl; COB 2 is carboxy or a sodium or potassium salt thereof.
Claim 52
Dependent Claim
33 words
A method for treating human or veterinary bacterial infection which comprises administering to a human or veterinary subject suffering from such infection an antibacterially effective amount of a compound according to claim 1.
Claim 53
Dependent Claim
60 words
A method according to claim 46 for treating human or veterinary diseases selected from pneumonia, bronchitis, pneumonitis, empyema, nasopharyngitis, tonsillitis, rhinitis, dermatitis, pustulosis, ulceration, absess, wound and soft tissue infection, ear infections, osteomyelitis, septicemia, gastroenteritis, enteritis, urinary tract infections, and pyelonephritis, when caused by bacteria sensitive to a compound according to claim 1, or for preventing post operative infection therefrom.
Claim 54
Dependent Claim
26 words
A method according to claim 46 at a daily dose of 0.05 to 50 mg per kilogram body weight when the compound is given by injection.
Claim 55
Dependent Claim
26 words
A method according to claim 46 at a daily dose of 0.5 to 200 mg per kilogram of body weight when the compound is administered orally.
Claim 56
Dependent Claim
22 words
A method according to claim 46 at a daily dose of 1 μg to 1 mg when the compound is given topically.
Claim 57
Dependent Claim
40 words
A method according to claim 46, wherein the compound is one in which Ar is 3-thienyl, p-hydroxyphenyl, or p-carbamoyloxyphenyl and COB 1 and COB 2 each are carboxy in the form of the free acid or a pharmaceutically acceptable salt.
Claim 58
Dependent Claim
17 words
A method according to claim 46, wherein the compound is sodium or potassium salt of 7β-[D-[α-(3-thienyl)-α-carboxyacetamido]]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 59
Dependent Claim
18 words
A method according to claim 46, wherein the compound is sodium or potassium salt of 7β-[D-(α-p-hydroxyphenyl -α-carboxyacetamido)]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 60
Dependent Claim
17 words
A method according to claim 46, wherein the compound is sodium or potassium salt of 7β-[D-(α-p-carbamoyloxyphenyl-α-carboxyacetamido)]-7.alpha.-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 61
Dependent Claim
42 words
A method according to claim 46, wherein the compound is one in which Ar is 3-thienyl, p-hydroxyphenyl, or p-carbamoyloxyphenyl; COB 1 is phenoxycarbonyl, dimethylphenoxycarbonyl, or indanyloxycarbonyl and COB 2 is carboxy in the form of free acid or a pharmaceutically acceptable salt.
Claim 62
Dependent Claim
17 words
A method according to claim 55, wherein the compound is 7β-[D-[α-(3-thienyl)-α-(5-indanyloxy)carbonylacetamido]]-7α- methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid or its sodium salt.
Claim 63
Dependent Claim
16 words
A method according to claim 55, wherein the compound is 7β-[D-[α-(3-thienyl)-α-phenoxycarbonylacetamido]]-7.alpha.-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid or its sodium salt.
Claim 64
Dependent Claim
16 words
A method according to claim 55, wherein the compound is 7β-[D-[α-(3-thienyl)-α-(3,4-dimethylphenoxy)carbonylacetamido]]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid or its sodium salt.
Claim 65
Dependent Claim
16 words
A method according to claim 55, wherein the compound is 7β-[D-[α-p-hydroxyphenyl-α-(5-indanyloxy)carbonylacetamido]]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid or its sodium salt.
References Cited (Backward Citations)
US4138486A
Cited
US4180571A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-04-05 | 1985-10-05 | 1986-04-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-04-05 | 1989-10-05 | 1990-04-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-04-05 | 1993-10-05 | 1994-04-06 | $7700.00 | Window Closed / Lapsed |