US4053609A
Expired / Lapsed
US
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Penicillins and processes for preparing the same
Assignee: Tanabe Pharma Corp
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Filing: 1976-08-05
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Granted: 1977-10-11
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Expires: 1996-08-05
Abstract
Abstract A compound of the formula: ##STR1## wherein R 1 is hydrogen or hydroxy, R 2 is a group of the formula: --CO-CH(NH 2 )-CH 2 COR 3 or --COCH 2 -CH(NH 2 )-COR 3 , and R 3 is selected from the group consisting of hydroxy, lower alkylamino, di-lower alkylamino, lower alkoxy and hydroxy-lower alkylamino, or R 3 is amino when R 2 is hydroxy. Several methods of preparing the compound [I] are also disclosed. The compound [I] and a pharmaceutically acceptable salt thereof are useful as antimicrobial agents.
Inventors
- 👤 Mitsutaka Kawazu
- 👤 Mitsuyoshi Wagatsuma
- 👤 Masahiko Seto
- 👤 Toshikazu Miyagishima
- 👤 Totaro Yamaguchi
- 👤 Satoshi Ohshima
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 15:53
CPC Classifications
C; C07; C07C; C07C271/00; C07C271/06; C07C271/08; C07C271/10; C07C271/22; C07D; C07D207/00; C07D207/46; C07D499/00
Claims Analysis
Total Claims: 51
Claim 1
Independent Claim
71 words
A compound of the formula: ##STR13## wherein R 1 is hydrogen or hydroxy, R 2 is a group of the formula: --CO-CH(NH 2 )--CH 2 COR 3 or --COCH 2 -CH(NH 2 )-COR 3 , and R 3 is selected from the group consisting of hydroxy, lower alkylamino, di-lower alkylamino, lower alkoxy and hydroxy-lower alkylamino, or R 3 is amino when R 1 is hydroxy, or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
71 words
A compound of the formula: ##STR13## wherein R 1 is hydrogen or hydroxy, R 2 is a group of the formula: --CO-CH(NH 2 )--CH 2 COR 3 or --COCH 2 -CH(NH 2 )-COR 3 , and R 3 is selected from the group consisting of hydroxy, lower alkylamino, di-lower alkylamino, lower alkoxy and hydroxy-lower alkylamino, or R 3 is amino when R 1 is hydroxy, or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
56 words
The compound claimed in claim 1, in which R 1 is hydrogen or hydroxy, R 2 is a group of the formula: --CO-CH(NH 2 )--CH 2 COR 3 or --COCH 2 --CH(NH 2 )-COR 3 , and R 3 is selected from the group consisting of hydroxy, lower alkylamino, di-lower alkylamino, lower alkoxy and hydroxy-lower alkylamino.
Claim 4
Dependent Claim
42 words
The compound claimed in claim 1, in which R 1 is hydrogen or hydroxy, R 2 is a group of the formula: --CO-CH(NH 2 )--CH 2 COR 3 , and R 3 is lower alkylamino, di-lower alkylamino, lower alkoxy or hydroxy-lower alkylamino.
Claim 5
Dependent Claim
36 words
The compound claimed in claim 1, in which R 1 is hydroxy, R 2 is a group of the formula: --CO-CH(NH 2 )-CH 2 COR 3 , and R 3 is lower alkylamino or lower alkoxy.
Claim 6
Dependent Claim
39 words
The compound claimed in claim 1, in which R 1 is hydrogen, R 2 is a group of the formula:--CO-CH(NH 2 )-CH 2 COR 3 , and R 3 is lower alkylamino, di-lower alkylamino, lower alkoxy or hydroxy-lower alkylamino.
Claim 7
Dependent Claim
37 words
The compound claimed in claim 1, in which R 1 is hydrogen, R 2 is a group of the formula: --COCH 2 -CH(NH 2 )-COR 3 , and R 3 is hydroxy, lower alkylamino or di-lower alkylamino.
Claim 8
Dependent Claim
35 words
The compound claimed in claim 1, in which R 1 is hydrogen or hydroxy, R 2 is a group of the formula: --CO-CH(NH 2 )-CH 2 COR 3 , and R 3 is lower alkylamino.
Claim 9
Dependent Claim
33 words
The compound claimed in claim 1, in which R 1 is hydroxy, R 2 is a group of the formula: --CO-CH(NH 2 )-CH 2 COR 3 , and R 3 is lower alkylamino.
Claim 10
Dependent Claim
12 words
The compound claimed in claim 4, in which R 3 is methylamino.
Claim 11
Dependent Claim
12 words
The compound claimed in claim 4, in which R 3 is isopropylamino.
Claim 12
Dependent Claim
12 words
The compound claimed in claim 4, in which R 3 is butylamino.
Claim 13
Dependent Claim
12 words
The compound claimed in claim 4, in which R 3 is n-hexylamino.
Claim 14
Dependent Claim
11 words
The compound in claim 4, in which R 3 is methoxy.
Claim 15
Dependent Claim
12 words
The compound claimed in claim 5, in which R 3 is methylamino.
Claim 16
Dependent Claim
12 words
The compound claimed in claim 5, in which R 3 is ethylamino.
Claim 17
Dependent Claim
11 words
The compound claimed in claim 5, in which R 3 dimethylamino.
Claim 18
Dependent Claim
12 words
The compound claimed in claim 5, in which R 3 is methoxy.
Claim 19
Dependent Claim
12 words
The compound claimed in claim 5, in which R 3 is β-hydroxymethylamino.
Claim 20
Dependent Claim
12 words
The compound claimed in claim 5, in which R 3 is n-butylamino.
Claim 21
Dependent Claim
12 words
The compound claimed in claim 6, in which R 3 is hydroxy.
Claim 22
Dependent Claim
12 words
The compound claimed in claim 6, in which R 3 is ethylamino.
Claim 23
Dependent Claim
12 words
The compound claimed in claim 6, in which R 3 is n-propylamino.
Claim 24
Dependent Claim
12 words
The compound claimed in claim 6, in which R 3 is dimethylamino.
Claim 25
Dependent Claim
8 words
6[-D-2-(D-2-amino-3-N-methylcarbamoyl-propionamido)-2-p-hydroxyphenylacetamido]penicillanic acid or a pharmaceutically acceptable salt thereof.
Claim 26
Dependent Claim
8 words
6[-D-2-(D-2-amino-3-N-methylcarbamoyl-propionamido)-2-p-hydroxyphenylacetamido]penicillanic acid or a pharmaceutically acceptable salt thereof.
Claim 27
Dependent Claim
8 words
6-[D-2-(D-2-amino-3-N-isopropylcarbamoyl-propionamido)-2-p-hydroxyphenylacetamido]penicillanic acid or a pharmaceutically acceptable salt thereof.
Claim 28
Dependent Claim
8 words
6-[D-2-(D-2-amino-3-N-isopropylcarbamoyl-propionamido)-2-p-hydroxyphenylacetamido]penicillanic acid or a pharmaceutically acceptable salt thereof.
Claim 29
Dependent Claim
8 words
6-[D-2-(D-2-amino-3-N-n-butylcarbamoyl-propionamido)-2-p-hydroxyphenylacetamido]penicillanic acid or a pharmaceutically acceptable salt thereof.
Claim 30
Dependent Claim
8 words
6-[D-2-(D-2-amino-3-N-n-butylcarbamoyl-propionamido)-2-p-hydroxyphenylacetamido]penicillanic acid or a pharmaceutically acceptable salt thereof.
Claim 31
Dependent Claim
8 words
6-[D-2-(D-2-amino-3-N-n-hexylcarbamoyl-propionamido)-2-p-hydroxyphenylacetamido]penicillanic acid or a pharmaceutically acceptable salt thereof.
Claim 32
Dependent Claim
8 words
6-[D-2-(D-2-amino-3-N-n-hexylcarbamoyl-propionamido)-2-p-hydroxyphenylacetamido]penicillanic acid or a pharmaceutically acceptable salt thereof.
Claim 33
Dependent Claim
8 words
6-[D-2-(DL-2-amino-3-N-methylcarbamoyl-propionamido)-2-phenylacetamido]penicillanic acid or a pharmaceutically acceptable salt thereof.
Claim 34
Dependent Claim
8 words
6-[D-2-(DL-2-amino-3-N-methylcarbamoyl-propionamido)-2-phenylacetamido]penicillanic acid or a pharmaceutically acceptable salt thereof.
Claim 35
Dependent Claim
8 words
6-[D-2-(DL-2-amino-3-N-n-butylcarbamoyl-propionamido)-2-phenylacetamido]penicillanic acid or a pharmaceutically acceptable salt thereof.
Claim 36
Dependent Claim
8 words
6-[D-2-(DL-2-amino-3-N-n-butylcarbamoyl-propionamido)-2-phenylacetamido]penicillanic acid or a pharmaceutically acceptable salt thereof.
Claim 37
Dependent Claim
8 words
6-[D-2-(DL-3-amino-3-hydroxycarbonyl-propionamido)-2-phenylacetamido]penicillanic acid or a pharmaceutically acceptable salt thereof.
Claim 38
Dependent Claim
8 words
6-[D-2-(DL-3-amino-3-hydroxycarbonyl-propionamido)-2-phenylacetamido]penicillanic acid or a pharmaceutically acceptable salt thereof.
Claim 39
Dependent Claim
23 words
A pharmaceutical composition which is essentially consisting of an antimicrobially effective amount of the compound of claim 1 and a pharmaceutically acceptable carrier.
Claim 40
Dependent Claim
23 words
A pharmaceutical composition which is essentially consisting of an antimicrobially effective amount of the compound of claim 3 and a pharmaceutically acceptable carrier.
Claim 41
Dependent Claim
23 words
A pharmaceutical composition which is essentially consisting of an antimicrobially effective amount of the compound of claim 4 and a pharmaceutically acceptable carrier.
Claim 42
Dependent Claim
23 words
A pharmaceutical composition which is essentially consisting of an antimicrobially effective amount of the compound of claim 5 and a pharmaceutically acceptable carrier.
Claim 43
Dependent Claim
23 words
A pharmaceutical composition which is essentially consisting of an antimicrobially effective amount of the compound of claim 6 and a pharmaceutically acceptable carrier.
Claim 44
Dependent Claim
23 words
A pharmaceutical composition which is essentially consisting of an antimicrobially effective amount of the compound of claim 7 and a pharmaceutically acceptable carrier.
Claim 45
Dependent Claim
23 words
A pharmaceutical composition which is essentially consisting of an antimicrobially effective amount of the compound of claim 8 and a pharmaceutically acceptable carrier.
Claim 46
Dependent Claim
25 words
The composition of claim 31 wherein said effective amount is that which is necessary to produce an antimicrobial effect by administration to a warm-blooded animal.
Claim 47
Dependent Claim
25 words
The composition of claim 36 wherein said effective amount is that which is necessary to produce an antimicrobial effect by administration to a warm-blooded animal.
Claim 48
Dependent Claim
25 words
The composition of claim 37 wherein said effective amount is that which is necessary to produce an antimicrobial effect by administration to a warm-blooded animal.
Claim 49
Dependent Claim
16 words
The composition of claim 31 wherein said effective amount is 0.25 to 20 grams/adult human body/day.
Claim 50
Dependent Claim
16 words
The composition of claim 36 wherein said effective amount is 0.25 to 20 grams/adult human body/day.
Claim 51
Dependent Claim
16 words
The composition of claim 37 wherein said effective amount is 0.25 to 20 grams/adult human body/day.
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) | 1980-10-10 | 1981-04-11 | 1981-10-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-10-10 | 1985-04-11 | 1985-10-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-10-10 | 1989-04-11 | 1989-10-11 | $7700.00 | Window Closed / Lapsed |