Patent US5256604A successfully refreshed from Google Patents.
Patent US4180571A successfully refreshed from Google Patents.
US4180571A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Arylmalonamido-1-oxadethiacephalosporins
Assignee: Shionogi and Co Ltd
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Filing: 1978-11-13
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Granted: 1979-12-25
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Expires: 1998-11-13
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 , 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.
Inventors
- 👤 Masayuki Narisada
- 👤 Wataru Nagata
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 13:40
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/535; C; C07; C07D; C07D205/00; C07D265/00; C07D498/00; C07D498/02; C07D498/04; C07D505/00
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
123 words
A compound selected from the group consisting of (a) a compound of the formula ##STR27## wherein Ar is ##STR28## COB 1 and COB 2 each is carboxy, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, 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, tetrahydropyranyloxycarbonyl, 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, phenoxycarbony, naphthyloxycarbonyl, tolyloxycarbonyl, dimethylphenoxycarbonyl, nitrophenoxycarbonyl, methoxyphenoxycarbonyl, methanesulfonylphenoxycarbonyl, chlorophenoxycarbonyl, pentachlorophenoxycarbonyl, indanyloxycarbonyl, pyridyloxycarbonyl, sodiooxycarbonyl, potassiooxycarbonyl, magnesiooxycarbonyl, calciooxycarbonyl, or a sat of carboxy group with procain, xylocain, triethylamine, or dicyclohexylamine; and (b) when at least one of COB 1 and COB 2 is carboxy, a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
123 words
A compound selected from the group consisting of (a) a compound of the formula ##STR27## wherein Ar is ##STR28## COB 1 and COB 2 each is carboxy, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, 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, tetrahydropyranyloxycarbonyl, 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, phenoxycarbony, naphthyloxycarbonyl, tolyloxycarbonyl, dimethylphenoxycarbonyl, nitrophenoxycarbonyl, methoxyphenoxycarbonyl, methanesulfonylphenoxycarbonyl, chlorophenoxycarbonyl, pentachlorophenoxycarbonyl, indanyloxycarbonyl, pyridyloxycarbonyl, sodiooxycarbonyl, potassiooxycarbonyl, magnesiooxycarbonyl, calciooxycarbonyl, or a sat of carboxy group with procain, xylocain, triethylamine, or dicyclohexylamine; and (b) when at least one of COB 1 and COB 2 is carboxy, a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
10 words
A compound according to claim 1 wherein Ar is 3-thienyl.
Claim 4
Dependent Claim
57 words
A compound selected from the group consisting of (a) a compound according to claim 1, wherein each of COB 1 and COB 2 is carboxy, phthalidyloxycarbonyl, acetoxymethoxycarbonyl, pivaloyloxymethoxycarbonyl, acetoxyethoxycarbonyl, propionyloxyethoxycarbonyl, indanyloxycarbonyl, phenoxycarbonyl, tolyloxycarbonyl, dimethylphenoxycarbonyl, methoxyphenoxycarbonyl, methoxycarbonyloxyethoxycarbonyl, ethoxycarbonyloxymethoxycarbonyl, or phenacyloxycarbonyl, and (b) when at least one COB 1 or COB 2 is carboxy, a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
12 words
A compound according to claim 1, said compound being 7β-[α -(3-thienyl)-α-carboxyacetamido]-7α-methoxy-3-(1-methyltetrazol-5-yl)-thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 6
Dependent Claim
14 words
A compound according to claim 1, said compound being sodium salt of 7β-[α-(3-thienyl)-α-carboxyacetamido]-7α-methoxy-3-(1methyltetrazol-5yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 7
Dependent Claim
15 words
A compound according to claim 1, said compound being potassium salt of 7β-[α-(3-thienyl)-60 -carboxyacetamido]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 8
Dependent Claim
11 words
A compound according to claim 1, said compound being 7β-[α-3-thienyl)-α-(5-indanyloxy)carbonylacetamido]-7.beta.-methoxy-3-(1methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 9
Dependent Claim
14 words
A compound according to claim 1 said compound being sodium salt of 7β-[α-(3-thienyl)-α-(5indanyloxy)carbonylacetamido]-7.alpha.-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3cephem-4-carboxylic acid.
Claim 10
Dependent Claim
11 words
A compound according to claim 1, said compound being 7β-[α-(3-thienyl)-α-phenoxycarbonylacetamido]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 11
Dependent Claim
15 words
A compound according to claim 1, said compound being sodium salt of 7β-[α-(3-thienyl)-α-phenoxycarbonylacetamido]-7α-methoxy-3-(1methyltetrazol-5-yl) -yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 12
Dependent Claim
12 words
A compound according to claim 1, said compound being 7β-[α-(3-thienyl)-α-(3,4-dimethylphenoxycarbonyl)acetamido]-7α-methoxy-3-(1-methyltetrazol-5-yl) thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 13
Dependent Claim
14 words
A compound according to claim 1, said compound being sodium salt of 7β-[α-(3thienyl)-α-(3,4-dimethylphenoxycarbonyl)acetamido]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 14
Dependent Claim
8 words
7β-[.alpha.-(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 15
Dependent Claim
8 words
7β-[.alpha.-(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
47 words
A compound selected from the group consisting of (a) a compound according to claim 1 wherein COB 1 is carboxy, acetoxymethoxycarbonyl, pivaloyloxymethoxycarbonyl, acetoxyethoxycarbonyl, propionyloxyethoxycarbonyl, indanyloxycarbonyl, phenoxycarbonyl, tolyloxycarbonyl, dimethylphenoxycarbonyl, methoxyphenoxycarbonyl, methoxycaronyloxyethoxycarbonyl, ethoxycarbonyloxymethoxycarbonyl or phenacyloxycarbonyl, and (b) when COB 1 is carboxy, a pharmaceutically acceptable salt of the compound.
Claim 17
Dependent Claim
27 words
A compound selected from the group consisting of (a) a compound according to claim 14 wherein COB 2 is carboxy and (b) a pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim
19 words
A bactericidal composition comprising a bactericidally effective amount of a compound according to claim 1 and a pharmaceutical carrier.
Claim 19
Dependent Claim
17 words
A composition according to claim 16 containing 0.01% to 99% of a compound according to claim 1.
Claim 20
Dependent Claim
10 words
A composition according to claim 17 in dosage unit form.
Claim 21
Dependent Claim
9 words
A composition according to claim 18 suitable for injection.
Claim 22
Dependent Claim
17 words
A composition according to claim 19 in a form suitable for injection in an ampule or vial.
Claim 23
Dependent Claim
18 words
A composition according to claim 19 in the form of powder, crystals, microcrystals or lypholizate in a vial.
Claim 24
Dependent Claim
28 words
A composition according to claim 19 wherein Ar is 3-thienyl and COB 1 and COB 2 each is carboxy in the form of the sodium or potassium salt.
Claim 25
Dependent Claim
18 words
A composition according to claim 16 wherein the compound is sodium or potassium salt of 7β-[α-(3-thienyl)-α -carboxyacetamido]-7α-methoxy-3-(1-methyltetrazol-5-yl)-thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 26
Dependent Claim
10 words
A pharmaceutical composition according to claim 16 for enteral administration.
Claim 27
Dependent Claim
16 words
A pharmaceutical composition according to claim 24 in a form of capsule, tablet or dry syrup.
Claim 28
Dependent Claim
27 words
A method for treating human or veterinary bacterial infection comprising the administration to a host of a bactericidally effective amount of a compound according to claim 1.
Claim 29
Dependent Claim
59 words
A method according to claim 26 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.
Claim 30
Dependent Claim
31 words
A method according to claim 26 wherein the compound is administered at a daily dose of 0.05 to 50 mg per kilogram body weight when the compound is given by injection.
Claim 31
Dependent Claim
31 words
A method according to claim 26 wherein the compound is administered at a daily dose of 0.05 to 200 mg per kilogram of body weight when the compound is administered orally.
Claim 32
Dependent Claim
27 words
A method according to claim 26 wherein the compound is administered at a daily dose of 1 μg to 1 mg when the compound is given topically.
Claim 33
Dependent Claim
32 words
A method according to claim 26 wherein in the compound Ar is 3-thienyl and COB 1 and COB 2 each are carboxy in the form of free acid or pharmaceutically acceptable salt.
Claim 34
Dependent Claim
18 words
A method according to claim 26 wherein the compound is sodium or potassium salt of 7β-[α-(3-thienyl)-α -carboxyacetamido]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid.
Claim 35
Dependent Claim
36 words
A method according to claim 26 wherein the compound is that having Ar 3-thienyl, COB 1 is phenoxycarbonyl, dimethylphenoxycarbonyl, or indanyloxycarbonyl and COB 2 is carboxy in the form of free acid or pharmaceutically acceptable salt.
Claim 36
Dependent Claim
16 words
A method according to claim 32 wherein the compound is 7β-[α-(3-thienyl)-α-(5-indanyloxy)carbonylacetamido]-7.alpha.-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1-oxadethia-3-cephem-4-carboxylic acid and its sodium salt.
Claim 37
Dependent Claim
17 words
A method according to claim 32, wherein the compound is 7β-[α-(3-thienyl)-α -phenoxycarbonylacetamido]-7α-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-1oxadethia-3-cephem-4-carboxylic acid or its sodium salt.
Claim 38
Dependent Claim
16 words
A method according to claim 32, wherein the compound is 7β-[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.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-12-24 | 1983-06-25 | 1983-12-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-12-24 | 1987-06-25 | 1987-12-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-12-24 | 1991-06-25 | 1991-12-25 | $7700.00 | Window Closed / Lapsed |