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US4313889A Expired / Lapsed US ⏱️ 0.0 years remaining

Soft quaternary surface active agents

Assignee: Merck and Co Inc
•
Filing: 1980-06-10
•
Granted: 1982-02-02
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Expires: 2000-06-10
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Abstract

Abstract Soft quaternary surface active agents having the formula: <IMAGE> (I) <IMAGE> (II) wherein <IMAGE> represents a tertiary open chain or cyclic aliphatic amine; wherein <IMAGE> represents an unsaturated amine; wherein R represents a member selected from the group consisting of a hydrogen atom, a C1-C20 open chain or cyclo alkyl group, a C1-C20 alkoxyalkyl group, a C1-C20 acyloxyalkyl group, a C1-C20 haloalkyl group, a C1-C20 carboxyalkyl group, an aryl group, and a substituted aryl group, whose substituents are selected from the group consisting of a halogen atom, an O-C1-C4 alkyl group, an O-C1-C8 acyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R1 represents a C9-C22 straight or branched alkyl group, a -(CH2)n- <IMAGE> wherein R3, R4, R5 and R6 are each selected from the group consisting of a hydrogen atom, a methyl group or an ethyl group, a C0-C22 straight or branched alkyl <IMAGE> wherein n in each occurrence and m represent an integer of from 0 to 22, an <IMAGE> wherein A represents a C0-C22 straight or branched alkyl group as above or a -(CH2CH2O)p group, wherein the p represents an integer of from 0 to 22, and the residue of any naturally occurring bile acid or synthetic derivative thereof; and wherein X represents a halogen atom or any other organic or inorganic monovalent anion are disclosed. All compounds encompassed within the above-described generic formulae find use as "soft" antibacterial agents of extremely low toxicity.

Inventors

  • 👤 Nicolae S. Bodor

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 12:01
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/06; C07D213/16; C07D213/20; C07D213/60; C07D213/78; C07D213/81; C07D213/82; C07D487/00; C07D487/02; C07D487/08

Claims Analysis

Total Claims: 51
Claim 1
Independent Claim 219 words
A quaternary ammonium compound of the formula: ##STR199## wherein Am is a tertiary aliphatic amine; wherein R represents a member selected from the group consisting of hydrogen, C 1 -C 20 alkyl, cycloalkyl having up to 7 carbon atoms, alkoxyalkyl having up to 20 carbon atoms, C 1 -C 20 haloalkyl, carboxyalkyl having up to 20 carbon atoms, phenyl, naphthyl, substituted phenyl and substituted naphthyl whose substituents are selected from the group consisting of halogen, O--C 1 -C 4 alkyl, O--C 1 -C 8 acyl wherein said acyl group is derived from a carboxylic acid, nitro, carboxyl, and carboethoxy; wherein R 1 represents C 9 -C 22 straight or branched alkyl, ##STR200## wherein R 3 , R 4 , R 5 and R 6 are each selected from the group consisting of hydrogen, methyl, and ethyl, C 0 -C 22 straight or branched alkyl ##STR201## wherein n in each occurrence and m represents an integer of from 0 to 22, ##STR202## wherein A is selected from the group consisting of C 0 -C 22 straight or branched alkyl and --(CH 2 CH 2 O) p , wherein the p represents an integer of from 0 to 22, and the radical which results from decarboxylation of a naturally occurring bile acid; and wherein x is a nontoxic, pharmaceutically acceptable anion.
Claim 2
Dependent Claim 219 words
A quaternary ammonium compound of the formula: ##STR199## wherein Am is a tertiary aliphatic amine; wherein R represents a member selected from the group consisting of hydrogen, C 1 -C 20 alkyl, cycloalkyl having up to 7 carbon atoms, alkoxyalkyl having up to 20 carbon atoms, C 1 -C 20 haloalkyl, carboxyalkyl having up to 20 carbon atoms, phenyl, naphthyl, substituted phenyl and substituted naphthyl whose substituents are selected from the group consisting of halogen, O--C 1 -C 4 alkyl, O--C 1 -C 8 acyl wherein said acyl group is derived from a carboxylic acid, nitro, carboxyl, and carboethoxy; wherein R 1 represents C 9 -C 22 straight or branched alkyl, ##STR200## wherein R 3 , R 4 , R 5 and R 6 are each selected from the group consisting of hydrogen, methyl, and ethyl, C 0 -C 22 straight or branched alkyl ##STR201## wherein n in each occurrence and m represents an integer of from 0 to 22, ##STR202## wherein A is selected from the group consisting of C 0 -C 22 straight or branched alkyl and --(CH 2 CH 2 O) p , wherein the p represents an integer of from 0 to 22, and the radical which results from decarboxylation of a naturally occurring bile acid; and wherein x is a nontoxic, pharmaceutically acceptable anion.
Claim 3
Dependent Claim 10 words
The compound of claim 1 wherein Am is triloweralkyl amine.
Claim 4
Dependent Claim 11 words
The compound of claim 1 or 2 wherein R is hydrogen.
Claim 5
Dependent Claim 15 words
The compound of claim 1 or 2 wherein R is C 1 -C 20 alkyl.
Claim 6
Dependent Claim 19 words
The compound of claim 1 or 2 wherein R 1 is C 9 -C 22 straight or branched alkyl.
Claim 7
Dependent Claim 17 words
The compound of claim 1 or 2 wherein R is cycloalkyl having up to 7 carbon atoms.
Claim 8
Dependent Claim 17 words
The compound of claim 1 or 2 wherein R is alkoxyalkyl having up to 20 carbon atoms.
Claim 9
Dependent Claim 15 words
The compound of claim 1 or 2 wherein R is C 1 -C 20 haloalkyl.
Claim 10
Dependent Claim 17 words
The compound of claim 1 or 2 wherein R is carboxyalkyl having up to 20 carbon atoms.
Claim 11
Dependent Claim 11 words
The compound of claim 1 or 2 wherein R is phenyl.
Claim 12
Dependent Claim 11 words
The compound of claim 1 or 2 wherein R is naphthyl.
Claim 13
Dependent Claim 12 words
The compound of claim 1 or 2 wherein R is substituted phenyl.
Claim 14
Dependent Claim 12 words
The compound of claim 1 or 2 wherein R is substituted naphthyl.
Claim 15
Dependent Claim 12 words
The compound of claim 1 or 2 wherein R 1 is ##STR203##
Claim 16
Dependent Claim 20 words
The compound of claim 1 or 2 wherein R 1 is C 0 -C 22 straight or branched alkyl ##STR204##
Claim 17
Dependent Claim 18 words
The compound of claim 1 or 2 wherein R 1 is --(CH 2 CH 2 O) p .
Claim 18
Dependent Claim 21 words
The compound of claim 1 or 2 wherein X is selected from the group consisting of halide, methanesulfonate, fluorosulfonate and tosylate.
Claim 19
Dependent Claim 7 words
The compound of claim 1: n-Dodecanoyloxymethyltriethylammonium chloride.
Claim 20
Dependent Claim 7 words
The compound of claim 1: n-Octanoyloxymethyl-trimethylammonium chloride.
Claim 21
Dependent Claim 7 words
The compound of claim 1: n-Octanoyloxymethyl-trimethylammonium bromide.
Claim 22
Dependent Claim 7 words
The compound of claim 1: n-Octanoyloxymethyl-triethylammonium chloride.
Claim 23
Dependent Claim 7 words
The compound of claim 1: n-Octanoyloxymethyl-triethylammonium bromide.
Claim 24
Dependent Claim 7 words
The compound of claim 1: n-Decanoyloxymethyl-trimethylammonium chloride.
Claim 25
Dependent Claim 7 words
The compound of claim 1: n-Decanoyloxymethyl-trimethylammonium bromide.
Claim 26
Dependent Claim 7 words
The compound of claim 1: n-Decanoyloxymethyl-triethylammonium chloride.
Claim 27
Dependent Claim 7 words
The compound of claim 1: n-Decanoyloxymethyl-triethylammonium bromide.
Claim 28
Dependent Claim 7 words
The compound of claim 1: n-Dodecanoyloxymethyl-triethylammonium chloride.
Claim 29
Dependent Claim 7 words
The compound of claim 1: n-Dodecanoyloxymethyl-triethylammonium bromide.
Claim 30
Dependent Claim 7 words
The compound of claim 1: n-Tetradecanoyloxymethyl-trimethylammonium chloride.
Claim 31
Dependent Claim 7 words
The compound of claim 1: n-Tetradecanoyloxymethyl-trimethylammonium bromide.
Claim 32
Dependent Claim 7 words
The compound of claim 1: n-Tetradecanoyloxymethyl-triethylammonium chloride.
Claim 33
Dependent Claim 7 words
The compound of claim 1: Tetradecanoyloxymethyl-triethylammonium bromide.
Claim 34
Dependent Claim 7 words
The compound of claim 1: α-(n-Octanoyloxy)ethyl-trimethylammonium chloride.
Claim 35
Dependent Claim 7 words
The compound of claim 1: α-(n-Octanoyloxy)ethyl-trimethylammonium bromide.
Claim 36
Dependent Claim 7 words
The compound of claim 1: α-(n-Decanoyloxy)ethyl-trimethylammonium chloride.
Claim 37
Dependent Claim 7 words
The compound of claim 1: α-(n-Decanoyloxy)ethyl-trimethylammonium bromide.
Claim 38
Dependent Claim 7 words
The compound of claim 1: α-(n-Decanoyloxy)ethyl-triethylammonium chloride.
Claim 39
Dependent Claim 7 words
The compound of claim 1: α-(n-Decanoyloxy)ethyl-triethylammonium bromide.
Claim 40
Dependent Claim 7 words
The compound of claim 1: α-(n-Dodecanoyloxy)ethyl-trimethylammonium chloride.
Claim 41
Dependent Claim 7 words
The compound of claim 1: α-(n-Dodecanoyloxy)ethyl-trimethylammonium bromide.
Claim 42
Dependent Claim 7 words
The compound of claim 1: α-(n-Dodecanoyloxy)ethyl-triethylammonium chloride.
Claim 43
Dependent Claim 7 words
The compound of claim 1: α-(n-Dodecanoyloxy)ethyl-triethylammonium bromide.
Claim 44
Dependent Claim 7 words
The compound of claim 1: α-(n-Hexadecanoyloxy)ethyl-trimethylammonium chloride.
Claim 45
Dependent Claim 7 words
The compound of claim 1: α-(n-Hexadecanoyloxy)ethyl-trimethylammonium bromide.
Claim 46
Dependent Claim 7 words
The compound of claim 1: α-(n-Hexadecanoyloxy)ethyl-triethylammonium chloride.
Claim 47
Dependent Claim 7 words
The compound of claim 1: α-(n-Hexadecanoyloxy)ethyl-triethylammonium bromide.
Claim 48
Dependent Claim 7 words
The compound of claim 1: Oleyloxymethyl-trimethylammonium chloride.
Claim 49
Dependent Claim 7 words
The compound of claim 1: Oleyloxymethyl-trimethylammonium bromide.
Claim 50
Dependent Claim 7 words
The compound of claim 1: Oleyloxymethyl-triethylammonium chloride.
Claim 51
Dependent Claim 7 words
The compound of claim 1: Oleyloxymethyl-triethylammonium bromide.

References Cited (Backward Citations)

US2212654A Cited
US3873583A Cited
US3910971A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-02-01 1985-08-03 1986-02-02 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-02-01 1989-08-03 1990-02-02 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-02-01 1993-08-03 1994-02-02 $7700.00 Window Closed / Lapsed

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