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US 2004/0110839 A1Published application
Compounds and compositions for delivering active agents
AssigneeEmisphere Technologies, Inc.
InventorsAndrea Leone-Bay, Koc-Kan Ho, Donald J. Sarubbi, Sam J. Milstein
Life of this patent
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Abstract
Modified, amino acid compounds useful in the delivery of active agents are provided. The active agents can be peptides, such as rhGH. Methods of administration, such as oral, subcutaneous, sublingual, and intranasal administration, are provided, and methods of preparation of the modified amino acid compound are provided.
Claims29
A compound selected from the group consisting of
- 67 68 69
- or salts thereof.
A compound selected from the group consisting of
- 9 70 A Compound n m X XXXVII 0 0 4-Cl XXXVIII 3 0 H XXXIX 3 1 4-CH3 XL 3 1 2-F XLI 3 1 2-CH3 XLII 3 0 3-CF3 XLIII 3 4 H XLIV 3 0 3-Cl XLV 3 0 3-F XLVI 3 0 3-CH3 XLVII 0 0 2-CF3 XLVIII 1 2 H XLIX 3 2 2-F L 3 0 3,4-OCH2O— LI 3 0 2-COOH LII 1 0 2-OH LIII 3 0 2,6-dihydroxy LIV 2 0 2-OH LV 0 0 2,4-difluoro LVI 2 0 2,6-dihydroxy LVII 0 0 4-CF3 LVIIl 3 0 3-NMe2 LIX 2 0 3-NMe2 LX 3 0 2,6-dimethyl LXI 3 .0 2-NO2 LXII 3 0 2-CF3 LXIII 3 0 4-n-Pr LXIV 3 0 2-NH2 LXV 3 0 2-OCH3 LXVI 3 0 3-NO2 LXVII 3 0 3-NH2 LXVIII 2 0 2-NO2 LXIX 2 0 2-NH2 LXX 3 0 2-OCF3 LXXI 2 0 2-OCH3 LXXII 2 0 2-OCF3
- or salts thereof.
A compound selected from the group consisting of
- 10 71 B Compound n X LXXIII 3 4-CF3 LXXIV 1 2-F LXXV 1 4-CF3 LXXVI 3 3,4-dimethoxy LXXVII 0 3-OCH3 LXXVIII 3 3-OCH3 LXXIX 3 2,6-difluoro LXXX 3 4-CH3 LXXXI 1 4-OCH3 LXXXII 2 2-F LXXXIII 0 2-F LXXXIV 2 4-OGH3 LXXXV 0 2-OCH3 LXXXVI 2 2-OCH3 LXXXVII 0 4-CF3 LXXXVIII 3 3-F LXXXIX 3 2-OCH3
- or salts thereof.
A compound selected from the group consisting of
- 11 72 C Compound n m X XC 3 0 2-carboxycyclohexyl XCI 3 3 cyclohexyl XCII 3 0 2-adamantyl XCIII 3 0 1-morpholino
- or salts thereof.
A compound selected from the group consisting of
- 12 73 D Compound m XCIV 0 XCV 3
- or salts thereof.
A compound selected from the group consisting of
- 13 E 74 Compound X XCVI OH XCVII ═O
- or salts thereof.
A compound selected from the group consisting of
- 14 75 F Compound n XCVIII 0 XCIX 2
- or salts thereof.
A compound selected from the group consisting of
- 15 76 G Compound n m X CXI 6 0 2-OH CXII 7 3 H CXIII 7 0 2-I CXIV 7 0 2-Br CXV 7 0 3-NO2 CXVI 7 0 3-N(CH3)2 CXVII 7 0 2-NO2 CXVIII 7 0 4-NO2 CXIX 9 0 2-OH
- or salts thereof.
A compound, selected from the group consisting of
- 16 77 H Compound X CXX 1-morphohno CXXI O-t-Butyl CXXII CH(CH2Ph)NC(O)O-t-Bu CXXIII 2-hydroxyphenyl
- or salts thereof.
A composition comprising
- (a) an active agent;
- and
- (b) a compound selected from the group consisting of
- 17 78 I 79 II 80 III 81 IV 82 V 83 VI 84 VII 85 VIII 86 IX 87 X 88 XI 89 XII 90 XIII 91 XIV 92 XV 93 XVI 94 XVII 95 XVIII 96 XIX 97 XX 98 XXI 99 XXII 100 XXIII 101 XXIV 102 XXV 103 XXVI 104 XXVII 105 XXVIII 106 XXIX 107 XXX 108 XXXI 109 XXXII 110 XXXIII 111 XXXIV 112 XXXV 113 XXXVI 114 CI 115 CII 116 CIII 117 CIV 118 CV 119 CVI 120 CVII 121 CVIII 122 CIX 123 CX 124 CXI
- or salts thereof.
2 more elements
A composition comprising
- (a) an active agent;
- and
- (b) a compound selected from the group consisting of
- 18 A 125 Compound n m X XXXVII 0 0 4-Cl XXXVIII 3 0 H XXXIX 3 1 4-CH3 XL 3 1 2-F XLI 3 1 2-CH3 XLII 3 0 3-CF3 XLIII 3 4 H XLIV 3 0 3-Cl XLV 3 0 3-F XLVI 3 0 3-CH3 XLVII 0 0 2-CF3 XLVIII 1 2 H XLIX 3 2 2-F L 3 0 3,4-OCH2O— LI 3 0 2-COOH LII 1 0 2-OH LIII 3 0 2,6-dihydroxy LIV 2 0 2-OH LV 0 0 2,4-difluoro LVI 2 0 2,6-dihydroxy LVII 0 0 4-CF3 LVIII 3 0 3-NMe2 LIX 2 0 3-NMe2 LX 3 0 2,6-dimethyl LXI 3 0 2-NO2 LXII 3 0 2-CF3 LXIII 3 0 4-n-Pr LXIV 3 0 2-NH2 LXV 3 0 2-OCH3 LXVI 3 0 3-NO2 LXVII 3 0 3-NH2 LXVIII 2 0 2-NO2 LXIX 2 0 2-NH2 LXX 3 0 2-OCF3 LXXI 2 0 2-OCH3 LXXII 2 0 2-OCF3
- or salts thereof.
2 more elements
A composition comprising
- (a) an active agent;
- and
- (b) a compound selected from the group consisting of
- 19 B 126 Compound n X LXXIII 3 4-CF3 LXXIV 1 2-F LXXV 1 4-CF3 LXXVI 3 3,4-dimethoxy LXXVII 0 3-OCH3 LXXVIII 3 3-OCH3 LXXIX 3 2,6-difluoro LXXX 3 4-CH3 LXXXI 1 4-OCH3 LXXXII 2 2-F LXXXIII 0 2-F LXXXIV 2 4-OCH3 LXXXV 0 2-OCH3 LXXXVI 2 2-OCH3 LXXXVII 0 4-CF3 LXXXVIII 3 3-F LXXXIX 3 2-OCH3
- or salts thereof.
2 more elements
A composition comprising
- (a) an active agent;
- and
- (b) a compound selected from the group consisting of
- 20 C 127 Compound n m X XC 3 0 2-carboxycyclohexyl XCI 3 3 cyclohexyl XCII 3 0 2-adamantyl XCIII 3 0 1-morpholino
- or salts thereof.
2 more elements
A composition comprising
- (a) an active agent;
- and
- (b) a compound selected from the group consisting of
- 21 D 128 Compound n XCIV 0 XCV 3
- or salts thereof.
2 more elements
A composition comprising
- (a) an active agent;
- and
- (b) a compound selected from the group consisting of
- 22 E 129 Compound X XCVI OH XCVII ═O
- or salts thereof.
2 more elements
A composition comprising
- (a) an active agent;
- and
- (b) a compound selected from the group consisting of
- 23 F 130 Compound n XCVIII 0 XCIX 2
- or salts thereof.
2 more elements
A composition comprising
- (a) an active agent;
- and
- (b) a compound selected from the group consisting of
- 24 G 131 Compound n m X CXI 6 0 2-OH CXII 7 3 H CXIII 7 0 2-I CXIV 7 0 2-Br CXV 7 0 3-NO2 CXVI 7 0 3-N(CH3)2 CXVII 7 0 2-NO2 CXVIII 7 0 4-NO2 CXIX 9 0 2-OH
- or salts thereof.
2 more elements
A composition comprising
- (a) an active agent;
- and
- (b) a compound selected from the group consisting of
- 25 H 132 Compound X CXX 1-morpholino CXXI O-t-Butyl CXXII CH(CH2Ph)NC(O)O-t-Bu CXXIII 2-hydroxyphenyl
- or salts thereof.
2 more elements
26 A method for preparing a composition, said method comprising mixing:
- (A) at least one biologically-active agent;
- (B) at least one compound as defined in claim 1;
- and
- (C) optionally a dosing vehicle
1 more element
A method for preparing a compound having the formula
- 133
- wherein Y is
- 134
- or SO2;
- R1 is C3-C24 alkyl, C2-C20 alkenyl, C2-C20 alkyne, cycloalkyl, or aromatic;
- R2 is hydrogen, C1-C4 alkyl or C2-C4 alkenyl;
- and
- R3 is C3-C10 alkyl, C3-C10 cycloalkyl, aryl, thienyl, pyrrolo, or pyridyl, where R3 is optionally substituted by one or more C1-C5 alkyl group, C2-C4 alkenyl group, F, Cl, OH, SO2, COOH or, SO3H;
- said method comprising
- (a) reacting in water and the presence of a base, a compound having the formula
- 135
- with a compound having the formula
- R3—Y—X, wherein
- Y. R1, R2, and R3 are as above and X is a leaving group.
11 more elements
A pharmacological composition comprising:
- (A) at least one biologically-active agent;
- and
- (B) at least one carrier compound having the formula
- 2-HO—Ar—CONR8—R7—COOH
- wherein Ar is a substituted or unsubstituted phenyl or naphthyl;
- R7 is selected from the group consisting of C4 to C20 alkyl, C4 to C20 alkenyl, phenyl, naphthyl, (C1 to C10 alkyl) phenyl, (C1 to C10 alkenyl) phenyl, (C1 to C10 alkyl) naphthyl, (C1 to C10 alkenyl) naphthyl, phenyl (C1 to C10 alkyl), phenyl (C1 to C10 alkenyl), naphthyl (C1 to C10 alkyl), and naphthyl (C1 to C10 alkenyl);
- R8 is selected from the group consisting of hydrogen, C1 to C4 alkyl, C1 to C4 alkenyl, C1 to C4 alkenyl, hydroxy, and C1 to C4 alkoxy;
- R8 is optionally substituted with C1 to C4 alkyl, C1 to C4 alkenyl, C1 to C4 alkoxy, —OH, —SH and —CO2R9 or any combination thereof;
- R9 is hydrogen, C1 to C4 alkyl or C1 to C4 alkenyl;
- R7 is optionally interrupted by oxygen, nitrogen, sulfur or any combination thereof;
- with the proviso that the compounds are not substituted with an amino group in the position alpha to the acid group;
- or salts thereof.
9 more elements
Dependencies are inferred from the claim text.