US4287181A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Derivatives of 6β-hydroxyalkylpenicillanic acids as β-lactamase inhibitors
Assignee: Pfizer Inc
•
Filing: 1979-10-22
•
Granted: 1981-09-01
•
Expires: 1999-10-22
Abstract
Abstract 6 beta -Hydroxyalkylpenicillanic acids and derivatives thereof as useful enhancers of the effectiveness of several beta -lactam antibiotics against many beta -lactamase producing bacteria, and 6 beta -substituted penicillanic acid benzyl ester derivatives as useful intermediates leading to said agents which enhance the effectiveness of beta -lactam antibiotics.
Inventors
- 👤 Michael S. Kellogg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 12:30
CPC Classifications
C; C07; C07D; C07D499/00; A; A61; A61P; A61P31/00; A61P31/04; C07D499/04; C07D499/08; C07D499/21; C07D499/44; C07D499/74
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
140 words
A compound selected from the formulae ##STR21## or pharmaceutically acceptable base salt thereof, wherein R is 1-hydroxy-3-phenylpropyl; R 1 is selected from the group consisting of benzyl, hydrogen and ester-forming residues readily hydrolyzable in vivo; R 2 is ##STR22## wherein R 3 is selected from the group consisting of sulfo, hydrogen, alkoxycarbonyl having from two to four carbon atoms, alkanoyl having from two to eighteen carbon atoms, benzoyl, substituted benzoyl wherein said substituent is selected from the group consisting of amino, methyl, methoxy, fluoro, chloro, bromo and trifluoromethyl, alkylsulfonyl having from one to four carbon atoms, phenylsulfonyl and substituted phenylsulfonyl wherein said substituent is selected from the group consisting of methyl, methoxy, fluoro, chloro, bromo and trifluoromethyl; and R 4 is selected from the group consisting of hydrogen, alkyl having one to four carbon atoms, phenyl, pyridyl, benzyl and β-phenethyl.
Claim 2
Dependent Claim
140 words
A compound selected from the formulae ##STR21## or pharmaceutically acceptable base salt thereof, wherein R is 1-hydroxy-3-phenylpropyl; R 1 is selected from the group consisting of benzyl, hydrogen and ester-forming residues readily hydrolyzable in vivo; R 2 is ##STR22## wherein R 3 is selected from the group consisting of sulfo, hydrogen, alkoxycarbonyl having from two to four carbon atoms, alkanoyl having from two to eighteen carbon atoms, benzoyl, substituted benzoyl wherein said substituent is selected from the group consisting of amino, methyl, methoxy, fluoro, chloro, bromo and trifluoromethyl, alkylsulfonyl having from one to four carbon atoms, phenylsulfonyl and substituted phenylsulfonyl wherein said substituent is selected from the group consisting of methyl, methoxy, fluoro, chloro, bromo and trifluoromethyl; and R 4 is selected from the group consisting of hydrogen, alkyl having one to four carbon atoms, phenyl, pyridyl, benzyl and β-phenethyl.
Claim 3
Dependent Claim
12 words
A compound of claim 1, Formula II, wherein R 1 is hydrogen.
Claim 4
Dependent Claim
10 words
A compound of claim 2, wherein R 4 is hydrogen.
Claim 5
Dependent Claim
10 words
The compound of claim 3, wherein R 3 is hydrogen.
Claim 6
Dependent Claim
10 words
The compound of claim 3, wherein R 3 is acetyl.
Claim 7
Dependent Claim
10 words
The compound of claim 3, wherein R 3 is stearoyl.
Claim 8
Dependent Claim
10 words
The compound of claim 3, wherein R 3 is benzoyl.
Claim 9
Dependent Claim
22 words
A compound of claim 2, wherein R 3 is hydrogen and R 4 is alkyl having from one to four carbon atoms.
Claim 10
Dependent Claim
10 words
The compound of claim 8, wherein R 4 is methyl.
Claim 11
Dependent Claim
12 words
A compound of claim 1, Formula I, wherein R 1 is hydrogen.
Claim 12
Dependent Claim
9 words
The compound of claim 10, wherein R is 1-hydroxy-3-phenylpropyl.
Claim 13
Dependent Claim
199 words
A pharmaceutical composition useful for treating bacterial infections in mammals, which comprises a pharmaceutically acceptable carrier, a β-lactam antibiotic and a compound selected from the formulae ##STR23## or a pharmaceutically acceptable base salt thereof, wherein R is selected from the group consisting of alkylsulfonyloxymethyl having from one to four carbon atoms in the alkyl group, phenylsulfonyloxymethyl, substituted phenylsulfonyloxymethyl wherein said substituent is selected from the group consisting of methyl, methoxy, fluoro, chloro, bromo and trifluoromethyl and 1-hydroxy-3-phenylpropyl; R 2 is ##STR24## wherein R 3 is selected from the group consisting of sulfo, hydrogen, alkoxycarbonyl having from two to four carbon atoms, alkanoyl having from two to eighteen carbon atoms, benzoyl, substituted benzoyl wherein said substituent is selected from the group consisting of amino, methyl, methoxy, fluoro, chloro, bromo and trifluoromethyl, alkylsulfonyl having from one to four carbon atoms, phenylsulfonyl and substituted phenylsulfonyl wherein said substituent is selected from the group consisting of methyl, methoxy, fluoro, chloro, bromo and trifluoromethyl, and R 4 is selected from the group consisting of hydrogen, alkyl having one to four carbon atoms, phenyl, pyridyl, benzyl and β-phenethyl; R 5 is selected from the group consisting of hydrogen and ester-forming residues readily hydrolyzable in vivo.
Claim 14
Dependent Claim
199 words
A pharmaceutical composition useful for treating bacterial infections in mammals, which comprises a pharmaceutically acceptable carrier, a β-lactam antibiotic and a compound selected from the formulae ##STR23## or a pharmaceutically acceptable base salt thereof, wherein R is selected from the group consisting of alkylsulfonyloxymethyl having from one to four carbon atoms in the alkyl group, phenylsulfonyloxymethyl, substituted phenylsulfonyloxymethyl wherein said substituent is selected from the group consisting of methyl, methoxy, fluoro, chloro, bromo and trifluoromethyl and 1-hydroxy-3-phenylpropyl; R 2 is ##STR24## wherein R 3 is selected from the group consisting of sulfo, hydrogen, alkoxycarbonyl having from two to four carbon atoms, alkanoyl having from two to eighteen carbon atoms, benzoyl, substituted benzoyl wherein said substituent is selected from the group consisting of amino, methyl, methoxy, fluoro, chloro, bromo and trifluoromethyl, alkylsulfonyl having from one to four carbon atoms, phenylsulfonyl and substituted phenylsulfonyl wherein said substituent is selected from the group consisting of methyl, methoxy, fluoro, chloro, bromo and trifluoromethyl, and R 4 is selected from the group consisting of hydrogen, alkyl having one to four carbon atoms, phenyl, pyridyl, benzyl and β-phenethyl; R 5 is selected from the group consisting of hydrogen and ester-forming residues readily hydrolyzable in vivo.
Claim 15
Dependent Claim
82 words
A pharmaceutical composition of claim 12, wherein R 5 is selected from the group consisting of hydrogen and ester-forming residues readily hydrolyzable in vivo selected from the group consisting of alkanoyloxymethyl having from three to six carbon atoms, 1-(alkanoyloxy)ethyl having from four to seven carbon atoms, 1-methyl-1-(alkanoyloxy)ethyl having from five to eight carbon atoms, alkoxycarbonyloxymethyl having from three to six carbon atoms, 1-(alkoxycarbonyloxy)ethyl having from four to seven carbon atoms, 1-methyl-1-(alkoxycarbonyloxy)ethyl having from five to eight carbon atoms, 3-phthalidyl, 4-crotonolactonyl and γ-butyrolacton-4-yl.
Claim 16
Dependent Claim
124 words
A pharmaceutical composition of claim 13, wherein said β-lactam antibiotic is selected from the group consisting of: 6-(2-phenylacetamido)penicillanic acid, 6-(2-phenoxyacetamido)penicillanic acid, 6-(2-phenylpropionamido)penicillanic acid, 6-(D-2-amino-2-phenylacetamido)penicillanic acid, 6-(D-2-amino-2-[4-hydroxyphenyl]acetamido)penicillanic acid, 6-(D-2-amino-2-[1,4-cyclohexadienyl]acetamido)penicillanic acid, 6-(1-aminocyclohexanecarboxamido)penicillanic acid, 6-(2-carboxy-2-phenylacetamido)penicillanic acid, 6-(2-carboxy-2-[3-thienyl]acetamido)penicillanic acid, 6-(D-2-[4-ethylpiperazin-2,3-dione-1-carboxamido]-2-phenylacetamido)penicillanic acid, 6-(D-2-[4-hydroxy-1,5-naphthyridine-3-carboxamido]-2-phenylacetamido)-penicillanic acid, 6-(D-2-sulfo-2-phenylacetamido)penicillanic acid, 6-(D-2-sulfoamino-2-phenylacetamido)penicillanic acid, 6-(D-2-[imidazolidin-2-one-1-carboxamido]-2-phenylacetamido)penicillanic acid, 6-(D-2-[3-methylsulfonylimidazolidin-2-one-1-carboxamido]-2-phenylacetamido)penicillanic acid, 6-([hexahydro-1H-azepin-1-yl]methyleneamino)penicillanic acid, acetoxymethyl 6-(2-phenylacetamido)penicillanate, acetoxymethyl 6-(D-2-amino-2-phenylacetamido)penicillanate, acetoxymethyl 6-(D-2-amino-2-[4-hydroxyphenyl]acetamido)penicillanate, pivaloyloxymethyl 6-(2-phenylacetamido)penicillanate, pivaloyloxymethyl 6-(D-2-amino-2-phenylacetamido)penicillanate, pivaloyloxymethyl 6-(D-2-amino-2-[4-hydroxyphenyl]acetamido)penicillanate, 1-(ethoxycarbonyloxy)ethyl 6-(2-phenylacetamido)penicillanate, 1-(ethoxycarbonyloxy)ethyl 6-(D-2-amino-2-phenylacetamido)penicillanate, 1-(ethoxycarbonyloxy)ethyl 6-(D-2-amino-2-[4-hydroxyphenyl]acetamido)penicillanate, 3-phthalidyl 6-(2-phenylacetamido)penicillanate, 3-phthalidyl 6-(D-2-amino-2-phenylacetamido)penicillanate, 3-phthalidyl 6-(D-2-amino-2-[4-hydroxyphenyl]acetamido)penicillanate, 6-(2-phenoxycarbonyl-2-phenylacetamido)penicillanic acid, 6-(2-tolyloxycarbonyl-2-phenylacetamido)penicillanic acid, 6-(2-[5-indanyloxycarbonyl]-2-phenylacetamido)penicillanic acid, 6-(2-phenoxycarbonyl-2-[3-thienyl]acetamido)penicillanic acid, 6-(2-tolyloxycarbonyl-2-[3-thienyl]acetamido)penicillanic acid, 6-(2-[5-indanyloxycarbonyl]-2-[3-thienyl]acetamido)penicillanic acid, 6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)penicillanic acid, 7-(2-[2-thienyl]acetamido)cephalosporanic acid, 7-(2-[1-tetrazolyl]acetamido-3-(2-[5-methyl-1,3,4-thiadiazolyl]thiomethyl)-3-desacetoxymethylcephalosporanic acid, 7-(D-2-formyloxy-2-phenylacetamido)-3-(5-[1-methyltetrazolyl]thiomethyl)-3-desacetoxymethylcephalosporanic acid, 7-(D-2-amino-2-phenylacetamido)desacetoxycephalosporanic acid, 7-alpha-methoxy-7-(2-[2-thienyl]acetamido)-3-carbamoyloxymethyl-3-desacetoxymethylcephalosporanic acid, 7-(2-cyanoacetamido)cephalosporanic acid, 7-(D-2-hydroxy-2-phenylacetamido)-3-(5-[1-methyltetrazolyl]thiomethyl)-3-desacetoxymethylcephalosporanic acid, 7-(D-2-amino-2-p-hydroxyphenylacetamido)desacetoxycephalosporanic acid, 7-(2-[4-pyridylthio]acetamido)cephalosporanic acid, 7-(D-2-amino-2[1,4-cyclohexadienyl]acetamido)cephalosporanic acid, 7-(D-2-amino-2-phenylacetamido)cephalosporanic acid, 7-[D-(-)-alpha-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)alpha-(4-hydroxyphenyl)acetamido]-3-[(1-methyl-1,2-3,4-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid, 7-(D-2-amino-2-phenylacetamido)-3-chloro-3-cephem-4-carboxylic acid, 7-[2-(2-amino-4-thiazolyl)-2-(methoximino)acetamido]cephalosporanic acid, [6R,7R-3-carbamoyloxymethyl-7(2Z)-2-methoxyimino(fur-2-yl)acetamido-ceph-3-em-4-carboxylate] 7-[2-(2-aminothiazol-4-yl)acetamido]-3-[([1-2-dimethylaminoethyl)-1H-tetrazol-5-yl]thio)methyl]ceph-3-em-4-carboxylic acid, and a pharmaceutically acceptable salts thereof.
Claim 17
Dependent Claim
13 words
A pharmaceutical composition of claim 14, Formula IV, wherein R 5 is hydrogen.
Claim 18
Dependent Claim
15 words
A pharmaceutical composition of claim 15, wherein R 3 and R 4 are each hydrogen.
Claim 19
Dependent Claim
16 words
A pharmaceutical composition of claim 15, wherein R 3 is acetyl and R 4 is hydrogen.
Claim 20
Dependent Claim
16 words
A pharmaceutical composition of claim 15, wherein R 3 is stearoyl and R 4 is hydrogen.
Claim 21
Dependent Claim
16 words
A pharmaceutical composition of claim 15, wherein R 3 is benzoyl and R 4 is hydrogen.
Claim 22
Dependent Claim
16 words
A pharmaceutical composition of claim 15, wherein R 3 is hydrogen and R 4 is methyl.
Claim 23
Dependent Claim
13 words
A pharmaceutical composition of claim 14, Formula III, wherein R 5 is hydrogen.
Claim 24
Dependent Claim
10 words
A pharmaceutical composition of claim 21, wherein R is methylsulfonyloxymethyl.
Claim 25
Dependent Claim
10 words
A pharmaceutical composition of claim 21, wherein R is p-toluenesulfonyloxymethyl.
Claim 26
Dependent Claim
10 words
A pharmaceutical composition of claim 21, wherein R is 1-hydroxy-3-phenylpropyl.
Claim 27
Independent Claim
205 words
A method of increasing the effectiveness of a β-lactam antibiotic in a mammalian subject, which comprises co-administering to said subject a β-lactam antibiotic effectiveness increasing amount of a compound of the formulae ##STR25## or a pharmaceutically acceptable base salt thereof, wherein R is selected from the group consisting of alkylsulfonyloxymethyl having from one to four carbon atoms in the alkyl group, phenylsulfonyloxymethyl, substituted phenylsulfonyloxymethyl wherein said substituent is selected from the group consisting of methyl, methoxy, fluoro, chloro, bromo and trifluoromethyl and 1-hydroxy-3-phenylpropyl; R 2 is ##STR26## wherein R 3 is selected from the group consisting of sulfo, hydrogen, alkoxycarbonyl having from two to four carbon atoms, alkanoyl having from two to eighteen carbon atoms, benzoyl, substituted benzoyl wherein said substituent is selected from the group consisting of amino, methyl, methoxy, fluoro, chloro, bromo and trifluoromethyl, alkylsulfonyl having from one to four carbon atoms, phenylsulfonyl and substituted phenylsulfonyl wherein said substituent is selected from the group consisting of methyl, methoxy, fluoro, chloro, bromo and trifluoromethyl; and R 4 is selected from the group consisting of hydrogen, alkyl having one to four carbon atoms, phenyl, pyridyl, benzyl and β-phenethyl; R 5 is selected from the group consisting of hydrogen and ester-forming residues readily hydrolyzable in vivo.
Claim 28
Independent Claim
205 words
A method of increasing the effectiveness of a β-lactam antibiotic in a mammalian subject, which comprises co-administering to said subject a β-lactam antibiotic effectiveness increasing amount of a compound of the formulae ##STR25## or a pharmaceutically acceptable base salt thereof, wherein R is selected from the group consisting of alkylsulfonyloxymethyl having from one to four carbon atoms in the alkyl group, phenylsulfonyloxymethyl, substituted phenylsulfonyloxymethyl wherein said substituent is selected from the group consisting of methyl, methoxy, fluoro, chloro, bromo and trifluoromethyl and 1-hydroxy-3-phenylpropyl; R 2 is ##STR26## wherein R 3 is selected from the group consisting of sulfo, hydrogen, alkoxycarbonyl having from two to four carbon atoms, alkanoyl having from two to eighteen carbon atoms, benzoyl, substituted benzoyl wherein said substituent is selected from the group consisting of amino, methyl, methoxy, fluoro, chloro, bromo and trifluoromethyl, alkylsulfonyl having from one to four carbon atoms, phenylsulfonyl and substituted phenylsulfonyl wherein said substituent is selected from the group consisting of methyl, methoxy, fluoro, chloro, bromo and trifluoromethyl; and R 4 is selected from the group consisting of hydrogen, alkyl having one to four carbon atoms, phenyl, pyridyl, benzyl and β-phenethyl; R 5 is selected from the group consisting of hydrogen and ester-forming residues readily hydrolyzable in vivo.
Claim 29
Dependent Claim
81 words
The method of claim 25, wherein R 5 is selected from the group consisting of hydrogen and ester-forming residues readily hydrolyzable in vivo selected from the group consisting of alkanoyloxymethyl having from three to six carbon atoms, 1-(alkanoyloxy)ethyl having from four to seven carbon atoms, 1-methyl-1-(alkanoyloxy)ethyl having from five to eight carbon atoms, alkoxycarbonyloxymethyl having from three to six carbon atoms, 1-(alkoxycarbonyloxy)ethyl having from four to seven carbon atoms, 1-methyl-1-(alkoxycarbonyl)ethyl having from five to eight carbon atoms, 3-phthalidyl, 4-crotonolactonyl and γ-butyrolacton-4-yl.
Claim 30
Dependent Claim
123 words
The method of claim 26, wherein said β-lactam antibiotic is selected from the group consisting of: 6-(2-phenylacetamido)penicillanic acid, 6-(2-phenoxyacetamido)penicillanic acid, 6-(2-phenylpropionamido)penicillanic acid, 6-(D-2-amino-2-phenylacetamido)penicillanic acid, 6-(D-2-amino-2-[4-hydroxyphenyl]acetamido)penicillanic acid, 6-(D-2-amino-2-[1,4-cyclohexadienyl]acetamido)penicillanic acid, 6-(1-aminocyclohexanecarboxamido)penicillanic acid, 6-(2-carboxy-2-phenylacetamido)penicillanic acid, 6-(2-carboxy-2-[3-thienyl]acetamido)penicillanic acid, 6-(D-2-[4-ethylpiperazin-2,3-dione-1-carboxamido]-2-phenylacetamido)penicillanic acid, 6-(D-2-[4-hydroxy-1,5-naphthyridine-3-carboxamido]-2-phenylacetamido)-penicillanic acid, 6-(D-2-sulfo-2-phenylacetamido)penicillanic acid, 6-(D-2-sulfoamino-2-phenylacetamido)penicillanic acid, 6-(D-2-[imidazolidin-2-one-1-carboxamido]-2-phenylacetamido)penicillanic acid, 6-(D-2-[3-methylsulfonylimidazolidin-2-one-1-carboxamido]-2-phenylacetamido)penicillanic acid, 6-([hexahydro-1H-azepin-1-yl]methyleneamino)penicillanic acid, acetoxymethyl 6-(2-phenylacetamido)penicillanate, acetoxymethyl 6-(D-2-amino-2-phenylacetamido)penicillanate, acetoxymethyl 6-(D-2-amino-2-[4-hydroxyphenyl]acetamido)-penicillanate, pivaloyloxymethyl 6-(2-phenylacetamido)penicillanate, pivaloyloxymethyl 6-(D-2-amino-2-phenylacetamido)penicillanate, pivaloyloxymethyl 6-(D-2-amino-2-[4-hydroxyphenyl]acetamido)penicillanate, 1-(ethoxycarbonyloxy)ethyl 6-(2-phenylacetamido)penicillanate, 1-(ethoxycarbonyloxy)ethyl 6-(D-2-amino-2-phenylacetamido)penicillanate, 1-(ethoxycarbonyloxy)ethyl 6-(D-2-amino-2-[4-hydroxyphenyl]acetamido)penicillanate, 3-phthalidyl 6-(2-phenylacetamido)penicillanate, 3-phthalidyl 6-(D-2-amino-2-phenylacetamido)penicillanate, 3-phthalidyl 6-(D-2-amino-2-[4-hydroxyphenyl]acetamido)penicillanate, 6-(2-phenoxycarbonyl-2-phenylacetamido)penicillanic acid, 6-(2-tolyloxycarbonyl-2-phenylacetamido)penicillanic acid, 6-(2-[5-indanyloxycarbonyl]-2-phenylacetamido)penicillanic acid, 6-(2-phenoxycarbonyl-2-[3-thienyl]acetamido)penicillanic acid, 6-(2-tolyloxycarbonyl-2-[3-thienyl]acetamido)penicillanic acid, 6-(2-[5-indanyloxycarbonyl]-2-[3-thienyl]acetamido)penicillanic acid, 6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)penicillanic acid, 7-(2-[2-thienyl]acetamido)cephalosporanic acid, 7-(2-[1-tetrazolyl]acetamido-3-(2-[5-methyl-1,3,4-thiadiazolyl]thiomethyl)-3-desacetoxymethylcephalosporanic acid, 7-(D-2-formyloxy-2-phenylacetamido)-3-(5-[1-methyltetrazolyl]thiomethyl)-3-desacetoxymethylcephalosporanic acid, 7-(D-2-amino-2-phenylacetamido)desacetoxycephalosporanic acid, 7-alpha-methoxy-7-(2-[2-thienyl]acetamido)-3-carbamoyloxymethyl-3-desacetoxymethylcephalosporanic acid, 7-(2-cyanoacetamido)cephalosporanic acid, 7-(D-2-hydroxy-2-phenylacetamido)-3-(5-[1-methyltetrazolyl]thiomethyl)-3-desacetoxymethylcephalosporanic acid, 7-(D-2-amino-2-p-hydroxypehnylacetamido)desacetoxycephalosporanic acid, 7-(2-[4-pyridylthio]acetamido)cephalosporanic acid, 7-(D-2-amino-2[1,4-cyclohexadienyl]acetamido)cephalosporanic acid, 7-(D-2-amino-2-phenylacetamido)cephalosporanic acid, 7-[D-(-)-alpha-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)alpha-(4-hydroxyphenyl)acetamido]-3-[(1-methyl-1,2-3,4-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid, 7-(D-2-amino-2-phenylacetamido)-3-chloro-3-cephem-4-carboxylic acid, 7-[2-(2-amino-4-thiazolyl)-2-(methoximino)acetamido]cephalosporanic acid, [6R,7R-3-carbamoyloxymethyl-7(2Z)-2-methoxyimino(fur-2-yl)acetamido-ceph-3-em-4-carboxylate] 7-[2-(2-aminothiazol-4-yl)acetamido]-3-[([1-2-dimethylaminoethyl)-1H-tetrazol-5-yl]thio)methyl]ceph-3-em-4-carboxylic acid, and a pharmaceutically acceptable salts thereof.
Claim 31
Dependent Claim
12 words
The method of claim 27, Formula IV, wherein R 5 is hydrogen.
Claim 32
Dependent Claim
14 words
The method of claim 28, wherein R 3 and R 4 are each hydrogen.
Claim 33
Dependent Claim
15 words
The method of claim 28, wherein R 3 is acetyl and R 4 is hydrogen.
Claim 34
Dependent Claim
15 words
The method of claim 28, wherein R 3 is stearoyl and R 4 is hydrogen.
Claim 35
Dependent Claim
15 words
The method of claim 28, wherein R 3 is benzoyl and R 4 is hydrogen.
Claim 36
Dependent Claim
15 words
The method of claim 28, wherein R 3 is hydrogen and R 4 is methyl.
Claim 37
Dependent Claim
12 words
The method of claim 27, Formula III, wherein R 5 is hydrogen.
Claim 38
Dependent Claim
9 words
The method of claim 34, wherein R is methylsulfonyloxymethyl.
Claim 39
Dependent Claim
9 words
The method of claim 24, wherein R is p-toluenesulfonyloxymethyl.
Claim 40
Dependent Claim
9 words
The method of claim 34, wherein R is 1-hydroxy-3-phenylpropyl.
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) | 1984-08-31 | 1985-03-02 | 1985-09-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-31 | 1989-03-02 | 1989-09-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-31 | 1993-03-02 | 1993-09-01 | $7700.00 | Window Closed / Lapsed |