US4244965A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Azetidinoyl ethers
Assignee: Beecham Group PLC
•
Filing: 1978-09-14
•
Granted: 1981-01-13
•
Expires: 1998-09-14
Abstract
Abstract Compounds of the formula (I): ##STR1## and salts and esters thereof, wherein R 1 is a hydrogen atom or a lower alkyl, aryl or aralkyl group, R 2 and R 3 are independently hydrogen, aryl, aralkyl, lower alkyl or substituted lower alkyl, or R 3 is joined to R 1 to form a 4-, 5-, or 6- membered ring or is joined to R 2 to form a 5- or 6- membered ring with the proviso that when R 2 is hydrogen, R 1 is not hydrogen and R 1 and R 3 are not joined to form a group of the sub-formula (a) ##STR2## wherein R 4 is a hydrogen atom or a NH.CO.R 5 group wherein R 5 is a lower alkyl, lower alkoxy lower alkyl, aryl, aralkyl, aryloxyalkyl, lower alkoxy or aryloxy group have β-lactamase inhibitory and anti-bacterial properties.
Inventors
- 👤 Thomas T. Howarth
- 👤 Eric Hunt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 17:49
CPC Classifications
C; C07; C07C; C07C271/00; C07C271/06; C07C271/08; C07C271/10; C07C271/22; C07D; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D205/085; C07D503/00
Claims Analysis
Total Claims: 110
Claim 1
Independent Claim
149 words
A compound of the formula (I) ##STR59## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 3 is joined to R 1 to form a 4-, 5- or 6-membered ring or is joined to R 2 to form a 5- or 6-membered ring wherein R 1 is hydrogen or lower alkyl and R 2 and R 3 are hydrogen, lower alkyl or lower alkyl substituted by lower alkoxy, aryloxy, carboxylic acid or a pharmaceutically acceptable salt or lower alkyl or aralkyl ester thereof, or by amino or aryl, with the proviso that when R 2 is hydrogen, R 1 is not hydrogen and R 1 and R 3 are not joined to form a group of the sub-formula (a): ##STR60## wherein R 4 is hydrogen or NH.CO.R 5 , wherein R 5 is lower alkyl, lower alkoxy lower alkyl, aryl, aralkyl, aryloxyalkyl, lower alkoxy or aryloxy.
Claim 2
Dependent Claim
149 words
A compound of the formula (I) ##STR59## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 3 is joined to R 1 to form a 4-, 5- or 6-membered ring or is joined to R 2 to form a 5- or 6-membered ring wherein R 1 is hydrogen or lower alkyl and R 2 and R 3 are hydrogen, lower alkyl or lower alkyl substituted by lower alkoxy, aryloxy, carboxylic acid or a pharmaceutically acceptable salt or lower alkyl or aralkyl ester thereof, or by amino or aryl, with the proviso that when R 2 is hydrogen, R 1 is not hydrogen and R 1 and R 3 are not joined to form a group of the sub-formula (a): ##STR60## wherein R 4 is hydrogen or NH.CO.R 5 , wherein R 5 is lower alkyl, lower alkoxy lower alkyl, aryl, aralkyl, aryloxyalkyl, lower alkoxy or aryloxy.
Claim 3
Dependent Claim
41 words
A compound of the formula (VI): ##STR61## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 10 and R 11 are joined so that the CHR 10 --NH--COR 11 moiety forms a group of the sub-formula (b): ##STR62##
Claim 4
Dependent Claim
41 words
A compound of the formula (VI): ##STR61## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 10 and R 11 are joined so that the CHR 10 --NH--COR 11 moiety forms a group of the sub-formula (b): ##STR62##
Claim 5
Dependent Claim
95 words
A compound according to claim 1 of the formula (IX): ##STR63## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 14 is joined to R 12 to from a 4-, 5- or 6-membered ring or is joined to R 13 to from a 5-or 6-membered ring wherein R 12 is hydrogen or lower alkyl, R 13 is lower alkyl or lower alkyl substituted by lower alkoxy, aryloxy, carboxylic acid or a pharmaceutically acceptable salt or lower alkyl or aralkyl ester thereof, or by amino or aryl and R 14 is lower alkyl.
Claim 6
Dependent Claim
17 words
The compound of the formula (XII): ##STR64## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof.
Claim 7
Dependent Claim
17 words
The compound of the formula (XII): ##STR64## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof.
Claim 8
Dependent Claim
26 words
A compound of the formula (XIII): ##STR65## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 16 is H or CO 2 H.
Claim 9
Dependent Claim
26 words
A compound of the formula (XIII): ##STR65## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 16 is H or CO 2 H.
Claim 10
Dependent Claim
16 words
A compound according claim 1 in the form of its sodium, potassium, magnesium or t-butylamine salt.
Claim 11
Dependent Claim
14 words
A compound according to claim 1 in the form of a pharmaceutically acceptable salt.
Claim 12
Dependent Claim
107 words
A compound according to claim 1 in the form of an ester wherein the ester moiety has the sub-formula (e) or (f): ##STR66## wherein A 1 is alkyl of 1-6 carbon atoms unsubstituted or substituted by alkoxyl or acyloxyl of 1-7 carbon atoms; A 2 is alkenyl of up to 5 carbon atoms or is phenyl unsubstituted or substituted by fluorine, chlorine, bromine, nitro or alkyl or alkoxyl of up to 4 carbon atoms; and A 3 is hydrogen atom, alkyl of up to 4 carbon atoms or phenyl unsubstituted or substituted by fluorine, chlorine, bromine, nitro or alkyl or alkoxyl of up to 4 carbon atoms.
Claim 13
Dependent Claim
28 words
A compound according to claim 1 in the form of its ester wherein said ester is the methyl, ethyl, methoxymethyl, acetoxymethyl, acetoxyethyl, phthalidyl, ethoxycarbonyloxymethyl, α-ethoxycarbonyloxyethyl or pivaloyloxymethyl esters.
Claim 14
Dependent Claim
13 words
A compound according to claim 1 in the form of the sodium salt.
Claim 15
Dependent Claim
13 words
A compound according to claim 1 in the form of the potassium salt.
Claim 16
Dependent Claim
13 words
A compound according to claim 1 in the form of the calcium salt.
Claim 17
Dependent Claim
13 words
A compound according to claim 1 in the form of the magnesium salt.
Claim 18
Dependent Claim
152 words
The lithium salt of a compound of the formula (I): ##STR67## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 3 is joined to R 1 to form a 4-, 5-, or 6-membered ring of is joined to R 2 to form a 5- or 6-membered ring wherein R 1 is hydrogen or lower alkyl and R 2 and R 3 are hydrogen, lower alkyl or lower alkyl substituted by lower alkoxy, aryloxy, carboxylic acid or a pharmaceutically acceptable salt or lower alkyl or aralkyl thereof, or by amino or aryl, with the proviso that when R 2 is hydrogen, R 1 is not hydrogen and R 1 and R 3 are not joined to form a group of the sub-formula (a): ##STR68## wherein R 4 is hydrogen or NH.CO.R 5 , wherein R 5 is lower alkyl, lower alkoxy lower alkyl, aryl, aralkyl, aryloxyalkyl, lower alkoxy or aryloxy.
Claim 19
Dependent Claim
152 words
The lithium salt of a compound of the formula (I): ##STR67## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 3 is joined to R 1 to form a 4-, 5-, or 6-membered ring of is joined to R 2 to form a 5- or 6-membered ring wherein R 1 is hydrogen or lower alkyl and R 2 and R 3 are hydrogen, lower alkyl or lower alkyl substituted by lower alkoxy, aryloxy, carboxylic acid or a pharmaceutically acceptable salt or lower alkyl or aralkyl thereof, or by amino or aryl, with the proviso that when R 2 is hydrogen, R 1 is not hydrogen and R 1 and R 3 are not joined to form a group of the sub-formula (a): ##STR68## wherein R 4 is hydrogen or NH.CO.R 5 , wherein R 5 is lower alkyl, lower alkoxy lower alkyl, aryl, aralkyl, aryloxyalkyl, lower alkoxy or aryloxy.
Claim 20
Dependent Claim
11 words
The lithium salt according to claim 14 of the formula ##STR69##
Claim 21
Dependent Claim
11 words
The lithium salt according to claim 14 of the formula: ##STR70##
Claim 22
Dependent Claim
11 words
The lithium salt according to claim 14 of the formula: ##STR71##
Claim 23
Dependent Claim
11 words
The lithium salt according to claim 14 of the formula: ##STR72##
Claim 24
Dependent Claim
11 words
The lithium salt according to claim 14 of the formula: ##STR73##
Claim 25
Dependent Claim
9 words
The compound according to claim 1 which is ##STR74##
Claim 26
Dependent Claim
9 words
The compound according to claim 1 which is ##STR75##
Claim 27
Dependent Claim
9 words
The compound according to claim 1 which is ##STR76##
Claim 28
Dependent Claim
9 words
The compound according to claim 1 which is ##STR77##
Claim 29
Dependent Claim
9 words
The compound according to claim 1 which is ##STR78##
Claim 30
Dependent Claim
9 words
The compound according to claim 1 which is ##STR79##
Claim 31
Dependent Claim
9 words
The compound according to claim 1 which is ##STR80##
Claim 32
Dependent Claim
9 words
The compound according to claim 1 which is ##STR81##
Claim 33
Dependent Claim
9 words
The compound according to claim 1 which is ##STR82##
Claim 34
Dependent Claim
9 words
The compound according to claim 1 which is ##STR83##
Claim 35
Dependent Claim
9 words
The compound according to claim 1 which is ##STR84##
Claim 36
Dependent Claim
9 words
The compound according to claim 1 which is ##STR85##
Claim 37
Dependent Claim
9 words
The compound according to claim 1 which is ##STR86##
Claim 38
Dependent Claim
9 words
The compound according to claim 1 which is ##STR87##
Claim 39
Dependent Claim
9 words
The compound according to claim 1 which is ##STR88##
Claim 40
Dependent Claim
9 words
The compound according to claim 1 which is ##STR89##
Claim 41
Dependent Claim
9 words
The compound according to claim 1 which is ##STR90##
Claim 42
Dependent Claim
9 words
The compound according to claim 1 which is ##STR91##
Claim 43
Dependent Claim
9 words
The compound according to claim 1 which is ##STR92##
Claim 44
Dependent Claim
196 words
A pharmaceutical composition useful for treating bacterial infections in humans and animals and for effecting β-lactamase inhibition in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount of a β-lactamase inhibitory amount of a compound of the formula (I): ##STR93## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 3 is joined to R 1 to form a 4-,5- or 6-membered ring or is joined to R 2 to form a 5- or 6-membered ring wherein R 1 is hydrogen or lower alkyl and R 2 and R 3 are hydrogen, lower alkyl or lower alkyl substituted by lower alkoxy, aryloxy, carboxylic acid or a pharmaceutically acceptable salt or lower alkyl or aralkyl ester thereof, or by amino or aryl with the proviso that when R 2 is hydrogen, R 1 is not hydrogen and R 1 abd R 3 are not joined to form a group of the subformula (a): ##STR94## wherein R 4 is hydrogen or NH.CO.R 5 wherein R 5 is lower alkyl, lower alkoxy, lower alkyl, aryl, aralkyl, aryloxyalkyl, lower alkoxy or aryloxy, in combination with a pharmaceutically acceptable carrier.
Claim 45
Dependent Claim
196 words
A pharmaceutical composition useful for treating bacterial infections in humans and animals and for effecting β-lactamase inhibition in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount of a β-lactamase inhibitory amount of a compound of the formula (I): ##STR93## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 3 is joined to R 1 to form a 4-,5- or 6-membered ring or is joined to R 2 to form a 5- or 6-membered ring wherein R 1 is hydrogen or lower alkyl and R 2 and R 3 are hydrogen, lower alkyl or lower alkyl substituted by lower alkoxy, aryloxy, carboxylic acid or a pharmaceutically acceptable salt or lower alkyl or aralkyl ester thereof, or by amino or aryl with the proviso that when R 2 is hydrogen, R 1 is not hydrogen and R 1 abd R 3 are not joined to form a group of the subformula (a): ##STR94## wherein R 4 is hydrogen or NH.CO.R 5 wherein R 5 is lower alkyl, lower alkoxy, lower alkyl, aryl, aralkyl, aryloxyalkyl, lower alkoxy or aryloxy, in combination with a pharmaceutically acceptable carrier.
Claim 46
Dependent Claim
90 words
A pharmaceutical composition useful for treating bacterial infections in humans and animals and for affecting β-lactamase inhibition in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount or a β-lactamase inhibitory amount of a compound of the formula (VI): ##STR95## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 10 and R 11 are joined so that the CHR 10 -NH-COR 11 moiety forms a group of the sub-formula (b): ##STR96## in combination with a pharmaceutically acceptable carrier.
Claim 47
Dependent Claim
90 words
A pharmaceutical composition useful for treating bacterial infections in humans and animals and for affecting β-lactamase inhibition in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount or a β-lactamase inhibitory amount of a compound of the formula (VI): ##STR95## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 10 and R 11 are joined so that the CHR 10 -NH-COR 11 moiety forms a group of the sub-formula (b): ##STR96## in combination with a pharmaceutically acceptable carrier.
Claim 48
Dependent Claim
99 words
A composition according to claim 39 wherein the compound is of the formula (IX): ##STR97## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 14 is joined to R 12 to from a 4-,5- or 6-membered ring or is joined to R 13 to from a 5- or 6-membered ring wherein R 12 is hydrogen or lower alkyl, R 13 is lower alkyl or lower alkyl substituted by lower alkoxy, aryloxy, carboxylic acid or a pharmaceutically acceptable salt or lower alkyl or aralkyl ester thereof, or by amino or aryl and R 14 is lower alkyl.
Claim 49
Dependent Claim
66 words
A pharmaceutical composition useful for treating bacterial infections in humans and animals and for effecting β-lactamase inhibition in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount or a β-lactamase inhibitory amount of a compound of the formula (XII): ##STR98## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof, in combination with a pharmaceutically acceptable carrier.
Claim 50
Dependent Claim
66 words
A pharmaceutical composition useful for treating bacterial infections in humans and animals and for effecting β-lactamase inhibition in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount or a β-lactamase inhibitory amount of a compound of the formula (XII): ##STR98## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof, in combination with a pharmaceutically acceptable carrier.
Claim 51
Dependent Claim
49 words
A pharmaceutical composition useful for treating bacterial infections in humans and animals and for effecting β-lactamase inhibition in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount or a β-lactamase inhibitory amount of a compound of the formula (XIII): ##STR99##
Claim 52
Dependent Claim
49 words
A pharmaceutical composition useful for treating bacterial infections in humans and animals and for effecting β-lactamase inhibition in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount or a β-lactamase inhibitory amount of a compound of the formula (XIII): ##STR99##
Claim 53
Dependent Claim
22 words
A composition according to claim 39 wherein the compound is in the form of its sodium, potassium magnesium or t-butyl amine salt.
Claim 54
Dependent Claim
18 words
A composition according to claim 39 wherein the compound is in the form of a pharmaceutically acceptable salt.
Claim 55
Dependent Claim
110 words
A composition according to claim 39 wherein the compound is in the form of an ester wherein the ester moiety has the sub-formula (e) or (f) ##STR100## wherein A 1 is alkyl or 1-6 carbon atoms unsubstituted or substituted by alkoxyl or acyloxyl of 1-7 carbon atoms; A 2 is alkenyl of up to 5 carbon atoms or is phenyl unsubstituted or substituted by fluorine, chlorine, bromine, nitro or alkyl or alkoxyl of up to 4 carbon atoms; and A 3 is hydrogen atom of up to 4 carbon atoms or phenyl unsubstituted or substituted by fluorine, chlorine, bromine, nitro or alkyl or alkoxyl of up to 4 carbon atoms.
Claim 56
Dependent Claim
34 words
A composition according to claim 39 wherein the compound is in the form of an ester selected from the group consisting of the methyl, ethyl, methoxymethyl, acetoxymethyl, acetoxyethyl, phthalidyl, ethoxycarbonyloxymethyl, α-ethoxycarbonyloxyethyl or pivaloyloxymethyl esters.
Claim 57
Dependent Claim
10 words
A composition according to claim 39 in oral administration form.
Claim 58
Dependent Claim
10 words
A composition according to claim 39 in parenteral administration form.
Claim 59
Dependent Claim
10 words
A composition according to claim 39 in topical application form.
Claim 60
Dependent Claim
11 words
A composition according to claim 39 wherein the compound is ##STR101##
Claim 61
Dependent Claim
11 words
A composition according to claim 39 wherein the compound is ##STR102##
Claim 62
Dependent Claim
11 words
A composition according to claim 39 wherein the compound is ##STR103##
Claim 63
Dependent Claim
11 words
A composition according to claim 39 wherein the compound is ##STR104##
Claim 64
Dependent Claim
11 words
A composition according to claim 39 wherein the compound is ##STR105##
Claim 65
Dependent Claim
11 words
A composition according to claim 39 wherein the compound is ##STR106##
Claim 66
Dependent Claim
11 words
A composition according to claim 39 wherein the compound is ##STR107##
Claim 67
Dependent Claim
11 words
A composition according to claim 39 wherein the compound is ##STR108##
Claim 68
Dependent Claim
11 words
A composition according to claim 35 wherein the compound is ##STR109##
Claim 69
Dependent Claim
11 words
A composition according to claim 35 wherein the compound is ##STR110##
Claim 70
Dependent Claim
11 words
A composition according to claim 35 wherein the compound is ##STR111##
Claim 71
Dependent Claim
11 words
A composition according to claim 39 wherein the compound is ##STR112##
Claim 72
Dependent Claim
11 words
A composition according to claim 39 wherein the compound is ##STR113##
Claim 73
Dependent Claim
11 words
A composition according to claim 39 wherein the compound is ##STR114##
Claim 74
Dependent Claim
11 words
A composition according to claim 39 wherein the compound is ##STR115##
Claim 75
Dependent Claim
11 words
A composition according to claim 39 wherein the compound is ##STR116##
Claim 76
Dependent Claim
11 words
A composition according to claim 39 wherein the compound is ##STR117##
Claim 77
Dependent Claim
11 words
A composition according to claim 39 wherein the compound is ##STR118##
Claim 78
Dependent Claim
11 words
A composition according to claim 39 wherein the compound is ##STR119##
Claim 79
Independent Claim
174 words
A method for treating bacterial infections in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount of a compound of the formula (I): ##STR120## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 3 is joined to R 1 to form a 4-,5- or 6-membered ring or is joined to R 2 to form a 5- or 6-membered ring wherein R 1 is hydrogen or lower alkyl and R 2 and R 3 are hydrogen, lower alkyl or lower alkyl substituted by lower alkoxy, aryloxy, carboxylic acid or a pharmaceutically acceptable salt or lower alkyl or aralkyl ester thereof, or by amino or aryl, with the proviso that when R 2 is hydrogen, R 1 is not hydrogen and R 1 and R 3 are not joined to form a group of the sub-formula (a): ##STR121## wherein R 4 is hydrogen or NH.CO.R 5 , wherein R 5 is lower alkyl, lower alkoxy lower alkyl, aryl, aralkyl, aryloxyalkyl, lower alkoxy or aryloxy.
Claim 80
Independent Claim
174 words
A method for treating bacterial infections in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount of a compound of the formula (I): ##STR120## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 3 is joined to R 1 to form a 4-,5- or 6-membered ring or is joined to R 2 to form a 5- or 6-membered ring wherein R 1 is hydrogen or lower alkyl and R 2 and R 3 are hydrogen, lower alkyl or lower alkyl substituted by lower alkoxy, aryloxy, carboxylic acid or a pharmaceutically acceptable salt or lower alkyl or aralkyl ester thereof, or by amino or aryl, with the proviso that when R 2 is hydrogen, R 1 is not hydrogen and R 1 and R 3 are not joined to form a group of the sub-formula (a): ##STR121## wherein R 4 is hydrogen or NH.CO.R 5 , wherein R 5 is lower alkyl, lower alkoxy lower alkyl, aryl, aralkyl, aryloxyalkyl, lower alkoxy or aryloxy.
Claim 81
Dependent Claim
56 words
A method according to claim 70 wherein the compound is of the formula (VI): ##STR122## or a pharmaceutically acceptable salt of pharmaceutically acceptable ester thereof wherein R 10 and R 11 are joined so that the CHR 10 --NH--COR 11 moiety forms a group of the sub-formula (b): ##STR123## in combination with a pharmaceutically acceptable carrier.
Claim 82
Dependent Claim
100 words
A method according to claim 70 wherein the compound is of the formula (IX): ##STR124## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 14 is joined to R 12 to form a 4-, 5- or 6-membered ring or is joined to R 13 to from a 5- or 6-membered ring wherein R 12 is hydrogen or lower alkyl, R 13 is lower alkyl or lower alkyl substituted by lower alkoxy, aryloxy, carboxylic acid or a pharmaceutically acceptable salt or lower alkyl or aralkyl ester thereof, or by amino or aryl and R 14 is lower alkyl.
Claim 83
Dependent Claim
32 words
A method according to claim 70 wherein the compound if of the formula (XII): ##STR125## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof, in combination with a pharmaceutically acceptable carrier.
Claim 84
Dependent Claim
41 words
A method according to claim 70 wherein the compound is of the formula (XIII): ##STR126## or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof wherein R 16 is H or CO 2 H, in combination with a pharmaceutically acceptable carrier.
Claim 85
Dependent Claim
22 words
A method according to claim 70 wherein the compound is in the form of its sodium, potassium, magnesium or t-butyl amine salt.
Claim 86
Dependent Claim
18 words
A method according to claim 70 wherein the compound is in the form of a pharmaceutically acceptable salt.
Claim 87
Dependent Claim
110 words
A method according to claim 70 wherein the compound is in the form of an ester wherein the ester moiety has the sub-formula (e) or (f): ##STR127## wherein A 1 is alkyl or 1-6 carbon atoms unsubstituted or substituted by alkoxy or acyloxy of 1-7 carbon atoms; A 2 is alkenyl of up to 5 carbon atoms or is phenyl unsubstituted or substituted by fluorine, chlorine, bromine, nitro or alkyl or alkoxyl of up to 4 carbon atoms; and A 3 is hydrogen atom of up to 4 carbon atoms or phenyl unsubstituted or substituted by fluorine, chlorine, bromine, nitro or alkyl or alkoxyl of up to 4 carbon atoms.
Claim 88
Dependent Claim
34 words
A method according to claim 70 wherein the compound is in the form of an ester selected from the group consisting of the methyl, ethyl, methoxymethyl, acetoxymethyl, acetoxyethyl, phthalidyl, ethoxycarbonyloxymethyl, α-ethoxycarbonyloxyethyl or pivaloxyloxymethyl esters.
Claim 89
Dependent Claim
11 words
A method according to claim 70 wherein the administration is oral.
Claim 90
Dependent Claim
11 words
A method according to claim 70 wherein the administration is parenteral.
Claim 91
Dependent Claim
13 words
A method according to claim 70 wherein the administration is by topical application.
Claim 92
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR128##
Claim 93
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR129##
Claim 94
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR130##
Claim 95
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR131##
Claim 96
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR132##
Claim 97
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR133##
Claim 98
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR134##
Claim 99
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR135##
Claim 100
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR136##
Claim 101
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR137##
Claim 102
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR138##
Claim 103
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR139##
Claim 104
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR140##
Claim 105
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR141##
Claim 106
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR142##
Claim 107
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR143##
Claim 108
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR144##
Claim 109
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR145##
Claim 110
Dependent Claim
11 words
A method according to claim 70 wherein the compound is ##STR146##
References Cited (Backward Citations)
DE2646000A1
Cited
DE2646004A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-01-13 | 1984-07-14 | 1985-01-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-01-13 | 1988-07-14 | 1989-01-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-01-13 | 1992-07-14 | 1993-01-13 | $7700.00 | Window Closed / Lapsed |