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EP0282127A2
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Beta-aminoethyl-substituted phenyl compounds, and anti-inflammatory or analgesic compositions containing them
Assignee: Procter and Gamble Co
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Filing: 1988-03-01
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Granted: —
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Expires: 2008-03-01
Abstract
Abstract The present invention relates to beta-aminoethyl-substituted phenyl compounds, especially beta-aminoethoxy-substituted phenyl compounds, having the general structure: wherein: the W-X moiety is selected from -C(O)NH-, -C(S)NH-, -S(O)₂NH-, -NHC(O)O-, -NHC(S)O-, -NHC(O)NH-, and -NHC(S)NH- wherein either available bond of the W-X moiety is bonded to the R moiety and the remaining bond is attached to the benzyl carbon atom; Z is selected from hydrogen, hydroxy, and methoxy; R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from about 1 to about 5 carbon atoms, alkyl having from about 1 to about 5 carbon atoms, and alkoxy having from about 1 to about 5 carbon atoms; each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from about 1 to about 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from about 3 to about 7 carbon atoms in the ring; R is a C₆-C₂₄ alkyl moiety; and Y is selected from -O-, -S- and -NH-. The present invention also relates to pharmaceutical compositions comprising a safe and effective amount of a compound of the present invention and a pharmaceutically-acceptable carrier. The present invention further relates to methods for producing analgesia and reducing inflammation, in humans and lower animals, by administering the compounds or compositions of the present invention. In addition, the present invention relates to methods for making compounds of the present invention and intermediates useful in these synthesis methods.
Inventors
- 👤 Joseph H. Garnder
- 👤 Gerald B. Kasting
- 👤 Thomas L. Cupps
- 👤 Richard S. Echler
- 👤 Thomas W. Gibson
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 19:26
CPC Classifications
C; C07; C07C; C07C233/00; C07C335/00; C07C335/04; C07C335/06; C07C335/10; C07C335/12; A; A61; A61P; A61P25/00; A61P25/04; A61P29/00
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
207 words
Beta-aminoethyl-substituted phenyl compounds which are effective as anti-inflammatory or analgesic agents, and the pharmaceutically-acceptable salts and amides thereof, characterized in that they have the general structure: wherein: (a) the W-X moiety is selected from -C(O)NH-, -C(S)NH-, -S(O)₂NH-, -NHC(O)O-, -NHC(S)O-, -NHC(O)NH- and -NHC(S)NH- wherein either available bond of the W-X moiety is bonded to the R moiety and the remaining bond is attached to the benzyl carbon atom; (b) Y is a moiety selected from -O-, -S- and -NH-, and is preferably -O-; (c) Z is selected from hydrogen, hydroxy, and methoxy, and is preferably methoxy; (d) R is an alkyl group having from 6 to 24 carbon atoms; (e) R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from 1 to 5 carbon atoms, alkyl having from 1 to 5 carbon atoms, and alkoxy having from 1 to 5 carbon atoms, and is preferably hydrogen, hydroxy or methyl; and (f) each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from 1 to 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from 3 to 7 carbon atoms in the ring; and R² is preferably hydrogen.
Claim 2
Dependent Claim
207 words
Beta-aminoethyl-substituted phenyl compounds which are effective as anti-inflammatory or analgesic agents, and the pharmaceutically-acceptable salts and amides thereof, characterized in that they have the general structure: wherein: (a) the W-X moiety is selected from -C(O)NH-, -C(S)NH-, -S(O)₂NH-, -NHC(O)O-, -NHC(S)O-, -NHC(O)NH- and -NHC(S)NH- wherein either available bond of the W-X moiety is bonded to the R moiety and the remaining bond is attached to the benzyl carbon atom; (b) Y is a moiety selected from -O-, -S- and -NH-, and is preferably -O-; (c) Z is selected from hydrogen, hydroxy, and methoxy, and is preferably methoxy; (d) R is an alkyl group having from 6 to 24 carbon atoms; (e) R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from 1 to 5 carbon atoms, alkyl having from 1 to 5 carbon atoms, and alkoxy having from 1 to 5 carbon atoms, and is preferably hydrogen, hydroxy or methyl; and (f) each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from 1 to 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from 3 to 7 carbon atoms in the ring; and R² is preferably hydrogen.
Claim 3
Dependent Claim
237 words
Beta-aminoethyl-substituted phenyl compounds which are effective as anti-inflammatory or analgesic agents, and the pharmaceutically-acceptable salts and amides thereof, characterized in that they have the general structure: wherein: (a) Q is selected from oxygen or sulfur, and is preferably oxygen; (b) Y is a moiety selected from -O-, -S- and -NH-, and is preferably -O-; (c) Z is selected from hydrogen, hydroxy, and methoxy, and is preferably methoxy; (d) R is an alkyl group having from 6 to 24 carbon atoms, and is preferably selected from n-octanyl; n-nonanyl; n-decanyl; 9E- or 9Z- tetradecenyl; 9E- or 9Z-hexadecenyl; 9E- or 9Z-octadecenyl; 6E- or 6Z-octadecenyl; 11E or 11Z-octadecenyl; 10E- or 10Z-nonadecenyl; 13E- or 13Z- docosenyl; 9-methylene-1-octadecanyl; 9Z,12Z-octadecadienyl; 9E, 12E-octadecadienyl; 9Z, 12E-octadecadienyl; 9Z, 11E-octadecadienyl; 10E, 13E-nonadecadienyl; 11E,14E-eicosadienyl; 9Z, 12Z, 15Z-octadecatrienyl; 6Z, 9Z, 12Z-octadecatrienyl; 11Z, 14Z, 17Z-eicosatrienyl; 5Z, 8Z, 11Z, 14Z-eicosatetraenyl; and 9-octadecynyl; (e) R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from 1 to 5 carbon atoms, alkyl having from 1 to 5 carbon atoms, and alkoxy having from 1 to 5 carbon atoms, and is preferably hydrogen, hydroxy or methyl; and (f) each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from 1 to 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from 3 to 7 carbon atoms in the ring; and all R² are preferably hydrogen.
Claim 4
Dependent Claim
237 words
Beta-aminoethyl-substituted phenyl compounds which are effective as anti-inflammatory or analgesic agents, and the pharmaceutically-acceptable salts and amides thereof, characterized in that they have the general structure: wherein: (a) Q is selected from oxygen or sulfur, and is preferably oxygen; (b) Y is a moiety selected from -O-, -S- and -NH-, and is preferably -O-; (c) Z is selected from hydrogen, hydroxy, and methoxy, and is preferably methoxy; (d) R is an alkyl group having from 6 to 24 carbon atoms, and is preferably selected from n-octanyl; n-nonanyl; n-decanyl; 9E- or 9Z- tetradecenyl; 9E- or 9Z-hexadecenyl; 9E- or 9Z-octadecenyl; 6E- or 6Z-octadecenyl; 11E or 11Z-octadecenyl; 10E- or 10Z-nonadecenyl; 13E- or 13Z- docosenyl; 9-methylene-1-octadecanyl; 9Z,12Z-octadecadienyl; 9E, 12E-octadecadienyl; 9Z, 12E-octadecadienyl; 9Z, 11E-octadecadienyl; 10E, 13E-nonadecadienyl; 11E,14E-eicosadienyl; 9Z, 12Z, 15Z-octadecatrienyl; 6Z, 9Z, 12Z-octadecatrienyl; 11Z, 14Z, 17Z-eicosatrienyl; 5Z, 8Z, 11Z, 14Z-eicosatetraenyl; and 9-octadecynyl; (e) R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from 1 to 5 carbon atoms, alkyl having from 1 to 5 carbon atoms, and alkoxy having from 1 to 5 carbon atoms, and is preferably hydrogen, hydroxy or methyl; and (f) each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from 1 to 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from 3 to 7 carbon atoms in the ring; and all R² are preferably hydrogen.
Claim 5
Dependent Claim
19 words
Beta-aminoethyl-substituted phenyl compounds, and the pharmaceutically-acceptable salts and amides thereof, according to Claim 2, selected from N-(9Z-octadecenyl)-4-(2-aminoethoxy)-3-methoxyphenylacetamide; and N-octanyl-4-(2-aminoethoxy)-3-methoxyphenylacetamide.
Claim 6
Dependent Claim
235 words
Beta-aminoethyl-substituted phenyl compounds which are effective as anti-inflammatory or analgesic agents, and the pharmaceutically-acceptable salts and amides thereof, characterized in that they have the general structure: wherein: (a) Q is selected from oxygen or sulfur, and is preferably oxygen; (b) Y is a moiety selected from -O-, -S- and -NH-, and is preferably -O-; (c) Z is selected from hydrogen, hydroxy, and methoxy, and is preferably methoxy; (d) R is an alkyl group having from 6 to 24 carbon atoms, and is preferably selected from n-heptanyl; n-octanyl; n-nonanyl; 8E- or 8Z-tridecenyl; 8E- or 8Z-pentadecenyl; 8E- or 8Z-heptadecenyl; 5E- or 5Z-heptadecenyl; 10E- or 10Z-heptadecenyl; 9E- or 9Z-octadecenyl; 12E-or 12Z-nonadecenyl; 8-methylene-1-heptadecanyl; 8Z, 11Z-heptadecadienyl; 8E, 11E-heptadecadienyl; 8Z, 11E- heptadecadienyl, 8Z, 10E-heptadecadienyl; 9E, 12E-octadecadienyl; 10E,13E-nonadecadienyl; 8Z, 11Z, 14Z-heptadecatrienyl; 5Z, 8Z, 11Z-heptadecatrienyl; 10Z, 13Z, 16Z-nonadecatrienyl; 4Z, 7Z, 10Z, 13Z-nonadecatetraenyl; and 8-heptadecynyl; (e) R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from 1 to 5 carbon atoms, alkyl having from 1 to 5 carbon atoms, and alkoxy having from 1 to 5 carbon atoms, and is preferably hydrogen, hydroxy or methyl; and (f) each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from 1 to 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from 3 to 7 carbon atoms in the ring; and R² is preferably hydrogen.
Claim 7
Dependent Claim
235 words
Beta-aminoethyl-substituted phenyl compounds which are effective as anti-inflammatory or analgesic agents, and the pharmaceutically-acceptable salts and amides thereof, characterized in that they have the general structure: wherein: (a) Q is selected from oxygen or sulfur, and is preferably oxygen; (b) Y is a moiety selected from -O-, -S- and -NH-, and is preferably -O-; (c) Z is selected from hydrogen, hydroxy, and methoxy, and is preferably methoxy; (d) R is an alkyl group having from 6 to 24 carbon atoms, and is preferably selected from n-heptanyl; n-octanyl; n-nonanyl; 8E- or 8Z-tridecenyl; 8E- or 8Z-pentadecenyl; 8E- or 8Z-heptadecenyl; 5E- or 5Z-heptadecenyl; 10E- or 10Z-heptadecenyl; 9E- or 9Z-octadecenyl; 12E-or 12Z-nonadecenyl; 8-methylene-1-heptadecanyl; 8Z, 11Z-heptadecadienyl; 8E, 11E-heptadecadienyl; 8Z, 11E- heptadecadienyl, 8Z, 10E-heptadecadienyl; 9E, 12E-octadecadienyl; 10E,13E-nonadecadienyl; 8Z, 11Z, 14Z-heptadecatrienyl; 5Z, 8Z, 11Z-heptadecatrienyl; 10Z, 13Z, 16Z-nonadecatrienyl; 4Z, 7Z, 10Z, 13Z-nonadecatetraenyl; and 8-heptadecynyl; (e) R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from 1 to 5 carbon atoms, alkyl having from 1 to 5 carbon atoms, and alkoxy having from 1 to 5 carbon atoms, and is preferably hydrogen, hydroxy or methyl; and (f) each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from 1 to 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from 3 to 7 carbon atoms in the ring; and R² is preferably hydrogen.
Claim 8
Dependent Claim
19 words
Beta-aminoethyl-substituted phenyl compounds, and the pharmaceutically-acceptable salts and amides thereof, according to Claim 4, selected from N-((4-(2-aminoethoxy)-3-methoxyphenyl)-methyl)-9Z-octadecenamide; and N-((4-(2-aminoethoxy)-3-methoxyphenyl)-methyl)-nonanamide.
Claim 9
Dependent Claim
193 words
Substituted phenyl compounds characterized in that they have the structure: wherein: (a) the W-X moiety is selected from -C(O)NH-, -C(S)NH-, -S(O)₂NH-, -NHC(O)O-, -NHC(S)O-, -NHC(O)NH- and -NHC(S)NH- wherein either available bond of the W-X moiety is bonded to the R moiety and the remaining bond is attached to the benzyl carbon atom; and W-X is preferably -C(O)NH-; (b) A is selected from halogen and -N₃, and is preferably bromide or -N₃; (c) Z is selected from hydrogen, hydroxy, and methoxy, and is preferably methoxy; (d) R is an alkyl group having from 6 to 24 carbon atoms; (e) R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from 1 to 5 carbon atoms, alkyl having from 1 to 5 carbon atoms, and alkoxy having from 1 to 5 carbon atoms, and is preferably hydrogen; and (f) each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from 1 to 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from 3 to 7 carbon atoms in the ring; and all R² are preferably hydrogen.
Claim 10
Dependent Claim
193 words
Substituted phenyl compounds characterized in that they have the structure: wherein: (a) the W-X moiety is selected from -C(O)NH-, -C(S)NH-, -S(O)₂NH-, -NHC(O)O-, -NHC(S)O-, -NHC(O)NH- and -NHC(S)NH- wherein either available bond of the W-X moiety is bonded to the R moiety and the remaining bond is attached to the benzyl carbon atom; and W-X is preferably -C(O)NH-; (b) A is selected from halogen and -N₃, and is preferably bromide or -N₃; (c) Z is selected from hydrogen, hydroxy, and methoxy, and is preferably methoxy; (d) R is an alkyl group having from 6 to 24 carbon atoms; (e) R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from 1 to 5 carbon atoms, alkyl having from 1 to 5 carbon atoms, and alkoxy having from 1 to 5 carbon atoms, and is preferably hydrogen; and (f) each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from 1 to 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from 3 to 7 carbon atoms in the ring; and all R² are preferably hydrogen.
Claim 11
Dependent Claim
193 words
Substituted phenyl compounds characterized in that they have the structure: wherein: (a) the W-X moiety is selected from -C(O)NH-, -C(S)NH-, -S(O)₂NH-, -NHC(O)O-, -NHC(S)O-, -NHC(O)NH- and -NHC(S)NH- wherein either available bond of the W-X moiety is bonded to the R moiety and the remaining bond is attached to the benzyl carbon atom; and W-X is preferably -C(O)NH-; (b) A is selected from halogen and phthalimide, and is preferably bromide or phthalimide; (c) Z is selected from hydrogen, hydroxy, and methoxy, and is preferably methoxy; (d) R is an alkyl group having from 6 to 24 carbon atoms; (e) R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from 1 to 5 carbon atoms, alkyl having from 1 to 5 carbon atoms, and alkoxy having from 1 to 5 carbon atoms, and is preferably hydrogen; and (f) each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from 1 to 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from 3 to 7 carbon atoms in the ring; and all R² are preferably hydrogen.
Claim 12
Dependent Claim
193 words
Substituted phenyl compounds characterized in that they have the structure: wherein: (a) the W-X moiety is selected from -C(O)NH-, -C(S)NH-, -S(O)₂NH-, -NHC(O)O-, -NHC(S)O-, -NHC(O)NH- and -NHC(S)NH- wherein either available bond of the W-X moiety is bonded to the R moiety and the remaining bond is attached to the benzyl carbon atom; and W-X is preferably -C(O)NH-; (b) A is selected from halogen and phthalimide, and is preferably bromide or phthalimide; (c) Z is selected from hydrogen, hydroxy, and methoxy, and is preferably methoxy; (d) R is an alkyl group having from 6 to 24 carbon atoms; (e) R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from 1 to 5 carbon atoms, alkyl having from 1 to 5 carbon atoms, and alkoxy having from 1 to 5 carbon atoms, and is preferably hydrogen; and (f) each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from 1 to 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from 3 to 7 carbon atoms in the ring; and all R² are preferably hydrogen.
Claim 13
Dependent Claim
27 words
Pharmaceutical compositions characterized in that they comprise: (a) a safe and effective amount of a compound according to any of Claims 1-5; and (b) a pharmaceutically-acceptable carrier.
Claim 14
Dependent Claim
27 words
The use of a compound according to any of Claims 1-5 for manufacture of a medicament for producing analgesia and reducing inflammation in humans or lower animals.
Claim 15
Dependent Claim
231 words
Methods for synthesizing beta-aminoethoxy phenyl compounds, said methods characterized in that they comprise the steps of: (a) reacting, to form a beta-haloethoxy phenyl compound: (i) a phenol compound having the structure: wherein: the W-X moiety is selected from -C(O)NH-, -C(S)NH-, -S(O)₂NH-, -NHC(O)O-, -NHC(S)O-, -NHC(O)NH- and -NHC(S)NH- wherein either available bond of the W-X moiety is bonded to the R moiety and the remaining bond is attached to the benzyl carbon atom; Z is selected from hydrogen, hydroxy, and methoxy; R is an alkyl group having from 6 to 24 carbon atoms; R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from 1 to 5 carbon atoms, alkyl having from 1 to 5 carbon atoms, and alkoxy having from 1 to 5 carbon atoms; and (ii) a vicinal dihalide having the structure: X-CR²₂-CR²₂-X wherein: X is halogen, and is preferably bromide; and each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from 1 to 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from 3 to 7 carbon atoms in the ring; followed by (b) reacting the beta-haloethoxy phenyl compound with an azide salt to form a beta-azidoethoxy phenyl compound; followed by (c) reducing the azido moiety, preferably with SnCl₂, to an amino moiety to form the beta-aminoethoxy phenyl compound.
Claim 16
Dependent Claim
231 words
Methods for synthesizing beta-aminoethoxy phenyl compounds, said methods characterized in that they comprise the steps of: (a) reacting, to form a beta-haloethoxy phenyl compound: (i) a phenol compound having the structure: wherein: the W-X moiety is selected from -C(O)NH-, -C(S)NH-, -S(O)₂NH-, -NHC(O)O-, -NHC(S)O-, -NHC(O)NH- and -NHC(S)NH- wherein either available bond of the W-X moiety is bonded to the R moiety and the remaining bond is attached to the benzyl carbon atom; Z is selected from hydrogen, hydroxy, and methoxy; R is an alkyl group having from 6 to 24 carbon atoms; R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from 1 to 5 carbon atoms, alkyl having from 1 to 5 carbon atoms, and alkoxy having from 1 to 5 carbon atoms; and (ii) a vicinal dihalide having the structure: X-CR²₂-CR²₂-X wherein: X is halogen, and is preferably bromide; and each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from 1 to 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from 3 to 7 carbon atoms in the ring; followed by (b) reacting the beta-haloethoxy phenyl compound with an azide salt to form a beta-azidoethoxy phenyl compound; followed by (c) reducing the azido moiety, preferably with SnCl₂, to an amino moiety to form the beta-aminoethoxy phenyl compound.
Claim 17
Dependent Claim
232 words
Methods for synthesizing beta-aminoethoxy phenyl compounds, said methods characterized in that they comprise the steps of: (a) reacting, to form a beta-haloethoxy phenyl compound: (i) a phenol compound having the structure: wherein: the W-X moiety is selected from -C(O)NH-, -C(S)NH-, -S(O)₂NH-, -NHC(O)O- -NHC(S)O-, -NHC(O)NH- and -NHC(S)NH- wherein either available bond of the W-X moiety is bonded to the R moiety and the remaining bond is attached to the benzyl carbon atom; Z is selected from hydrogen, hydroxy, and methoxy; R is an alkyl group having from 6 to 24 carbon atoms; R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from 1 to 5 carbon atoms, alkyl having from 1 to 5 carbon atoms, and alkoxy having from 1 to 5 carbon atoms; and (ii) a vicinal dihalide having the structure: X-CR²₂-CR²₂-X wherein: X is halogen, and is preferably bromide; and each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from 1 to 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from 3 to 7 carbon atoms in the ring; followed by (b) reacting the beta-haloethoxy phenyl compound with a phthalimide salt to form a beta-phthalimidoethoxy phenyl compound; followed by (c) reacting the beta-phthalimidoethoxy phenyl compound with hydrazine to remove the phthalimido group and form the beta-aminoethoxy phenyl compound.
Claim 18
Dependent Claim
232 words
Methods for synthesizing beta-aminoethoxy phenyl compounds, said methods characterized in that they comprise the steps of: (a) reacting, to form a beta-haloethoxy phenyl compound: (i) a phenol compound having the structure: wherein: the W-X moiety is selected from -C(O)NH-, -C(S)NH-, -S(O)₂NH-, -NHC(O)O- -NHC(S)O-, -NHC(O)NH- and -NHC(S)NH- wherein either available bond of the W-X moiety is bonded to the R moiety and the remaining bond is attached to the benzyl carbon atom; Z is selected from hydrogen, hydroxy, and methoxy; R is an alkyl group having from 6 to 24 carbon atoms; R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from 1 to 5 carbon atoms, alkyl having from 1 to 5 carbon atoms, and alkoxy having from 1 to 5 carbon atoms; and (ii) a vicinal dihalide having the structure: X-CR²₂-CR²₂-X wherein: X is halogen, and is preferably bromide; and each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from 1 to 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from 3 to 7 carbon atoms in the ring; followed by (b) reacting the beta-haloethoxy phenyl compound with a phthalimide salt to form a beta-phthalimidoethoxy phenyl compound; followed by (c) reacting the beta-phthalimidoethoxy phenyl compound with hydrazine to remove the phthalimido group and form the beta-aminoethoxy phenyl compound.
Claim 19
Dependent Claim
213 words
Methods for synthesizing beta-aminoethoxy phenyl compounds, said methods characterized in that they comprise the steps of: (a) reacting, to form a nitrogen-substituted beta-aminoethoxy phenyl compound: (i) a phenol compound having the structure: wherein: the W-X moiety is selected from -C(O)NH-, -C(S)NH-, -S(O)₂NH-, -NHC(O)O-, -NHC(S)O-, -NHC(O)NH- and -NHC(S)NH- wherein either available bond of the W-X moiety is bonded to the R moiety and the remaining bond is attached to the benzyl carbon atom; Z is selected from hydrogen, hydroxy, and methoxy; R is an alkyl group having from 6 to 24 carbon atoms; and R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from 1 to 5 carbon atoms, alkyl having from 1 to 5 carbon atoms, and alkoxy having from 1 to 5 carbon atoms; and (ii) an aziridine compound having the structure: wherein each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from 1 to 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from 3 to 7 carbon atoms in the ring; followed by (b) reducing the nitrogen substituent off of the nitrogen-substituted beta-aminoethoxy phenyl compound, preferably with sodium metal in liquid ammonia, to form the beta-aminoethoxy phenyl compound.
Claim 20
Dependent Claim
213 words
Methods for synthesizing beta-aminoethoxy phenyl compounds, said methods characterized in that they comprise the steps of: (a) reacting, to form a nitrogen-substituted beta-aminoethoxy phenyl compound: (i) a phenol compound having the structure: wherein: the W-X moiety is selected from -C(O)NH-, -C(S)NH-, -S(O)₂NH-, -NHC(O)O-, -NHC(S)O-, -NHC(O)NH- and -NHC(S)NH- wherein either available bond of the W-X moiety is bonded to the R moiety and the remaining bond is attached to the benzyl carbon atom; Z is selected from hydrogen, hydroxy, and methoxy; R is an alkyl group having from 6 to 24 carbon atoms; and R¹ is selected from hydrogen, hydroxy, alkyl esters of hydroxy having from 1 to 5 carbon atoms, alkyl having from 1 to 5 carbon atoms, and alkoxy having from 1 to 5 carbon atoms; and (ii) an aziridine compound having the structure: wherein each R² is independently selected from hydrogen, halogen, unsubstituted or substituted alkyl having from 1 to 5 carbon atoms, substituted or unsubstituted aryl, and carboxylate, or two R² moieties are covalently bonded to form a substituted or unsubstituted alkyl ring having from 3 to 7 carbon atoms in the ring; followed by (b) reducing the nitrogen substituent off of the nitrogen-substituted beta-aminoethoxy phenyl compound, preferably with sodium metal in liquid ammonia, to form the beta-aminoethoxy phenyl compound.
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