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US 2002/0173632 A1Published application
Synthesis of furanose and aminofuranose compounds
AssigneeWarner-Lambert Company
InventorsArmen M. Boldi, Elaine B. Krueger, Michael A. Walters, Thutam P. Hopkins, Meghan T. Keaney
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Abstract
The present invention provides compounds and methods of synthesizing furanose and aminofuranose compounds of Formula I 1 which are useful fro treating rheumatoid arthritis, immunomodulatory diseases and disorders, inflammation, and diseases and disorders characterized by exhibiting tissue proliferation.
Claims50
A method for the synthesis of a compound of Formula Ia:
- 116
- wherein:
- R1 is selected from the group consisting of —C1-14alkyl and —(CH2)0-4-aryl;
- R2 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl;
- R3 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl;
- or R2 and R3 can be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl;
- and
- R4 is selected from the group consisting of H, —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —C2-8alkynyl and —(CH2)1-2-heterocycloalkyl;
- which comprises the steps of:
- (a) reacting a compound of Formula 1:
- 117
- with an alkylating agent of Formula (2):
- R1—X (2)
- in the presence of a deprotonation agent in a suitable solvent;
- where X is iodo or bromo and R1 is as defined above, to yield an ether compound of Formula (3):
- 118
- (b) reacting a compound of Formula (3) with a hydrolysing agent to form a diol compound of Formula (4):
- 119
- (c) reacting a compound of Formula (4) with a cleaving agent in a suitable solvent to form an aldehyde compound of Formula (5):
- 120
- (d) reacting a compound of Formula (5) with a secondary amine compound of Formula (6):
- R2R3NH (6)
- where R2 and R3 are as defined above, and a reducing agent in a suitable solvent followed by treatment with a reducing agent scavenger resin in a suitable solvent and an amine scavenger resin in a suitable solvent to form a tertiary amine compound of Formula (7):
- 121
- (e) reacting a compound of Formula (7) with a compound of Formula (8):
- R4OH (8)
- where R4 is selected from the group consisting of H, —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —C2-8alkynyl and —(CH2)1-2-heterocycloalkyl, and an acid in a suitable solvent followed by treatment with an acid scavenger resin in a suitable solvent to form a compound of Formula Ia.
24 more elements
A method for the synthesis of a compound of Formula Ib:
- 122
- wherein:
- R1 is selected from the group consisting of —C1-14alkyl and —(CH2)0-4-aryl;
- R3 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl;
- or R6 and R3 can be taken together with the carbon and nitrogen atoms, respectively, to which they are attached to form a heterocycloalkyl containing an oxo (═O) substitution at the carbon atom;
- and
- R6 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2—O-aryl, —C2-6alkenyl, —(CH2)0-2-cycloalkyl and —(CH2)1-4-aryl;
- which comprises the steps of:
- (a) reacting a compound of Formula (1):
- 123
- with an alkylating agent of Formula (2):
- R1—X (2)
- in the presence of a deprotonation agent in a suitable solvent;
- where X is iodo or bromo and R1 is as defined above, to yield an ether compound of Formula (3):
- 124
- (b) reacting a compound of Formula (3) with a hydrolysing agent, to form a diol compound of Formula (4):
- 125
- (c) reacting a compound of Formula (4) with a cleaving agent in a suitable solvent to form an aldehyde compound of Formula (5):
- 126
- (d′) reacting a compound of Formula (5) with a primary amine compound of Formula (6′):
- R3NH2 (6′)
- where R3 is as defined above, and a reducing agent in a suitable solvent followed by treatment with a reducing agent scavenger resin in a suitable solvent and an amine scavenger resin in a suitable solvent to form a secondary amine compound of Formula (7′):
- 127
- (e′) reacting a compound of Formula (7′) with an acid chloride compound of Formula (9):
- R6COCl (9)
- where R6 is as defined above, and a suitable base in a suitable solvent followed by treatment with an acid chloride scavenger resin in a suitable solvent to form a compound of Formula Ib.
23 more elements
A method for the synthesis of a compound of Formula Ic:
- 128
- wherein:
- R1 is selected from the group consisting of —C1-14alkyl and —(CH2)0-4-aryl;
- R3 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl;
- or R6 and R3 can be taken together with the carbon and nitrogen atoms, respectively, to which they are attached to form a heterocycloalkyl containing an oxo (═O) substitution at the carbon atom;
- and
- R6 is selected from the group consisting of —C1-4alkyl, —(CH2)0-2—O-aryl, —C2-6alkenyl, —(CH2)0-2-cycloalkyl and —(CH2)1-4-aryl;
- which comprises the steps of:
- (a) reacting a compound of Formula 1:
- 129
- with an alkylating agent of Formula (2):
- R1—X (2)
- in the presence of a deprotonation agent in a suitable solvent;
- where X is iodo or bromo and R1 is as defined above, to yield an ether compound of Formula (3):
- 130
- (b) reacting a compound of Formula (3) with a hydrolysing agent, to form a diol compound of Formula (4):
- 131
- (c) reacting a compound of Formula (4) with a cleaving agent in a suitable solvent to form an aldehyde compound of Formula (5):
- 132
- (d′) reacting a compound of Formula (5) with a primary amine compound of Formula (6′):
- R3NH2 (6′)
- where R3 is as defined above, and a reducing agent in a suitable solvent followed by treatment with a reducing agent scavenger resin in a suitable solvent and an amine scavenger resin in a suitable solvent to form a secondary amine compound of Formula (7′):
- 133
- (e″) reacting a compound of Formula (7′) with an isocyanate compound of Formula (10):
- R6NCO (10)
- where R6 is as defined above, in a suitable solvent followed by treatment with an isocyanate scavenger resin in a suitable solvent to form a compound of Formula Ic.
23 more elements
A method for the synthesis of a compound of Formula (7):
- 134
- wherein:
- R1 is selected from the group consisting of —C1-14alkyl and —(CH2)0-4-aryl;
- R2 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl, —(CH2)0-2—O-aryl, —C(O)—R6 and —C(O)—NHR6, where R6 is selected from the group consisting of —C1-4alkyl, —(CH2)0-2—O-aryl, —C2-6alkenyl, —(CH2)0-2-cycloalkyl and —(CH2)1-4-aryl;
- and
- R3 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl;
- or R2 and R3 can be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl;
- which comprises the steps of:
- (a) reacting a compound of Formula 1:
- 135
- with an alkylating agent of Formula (2):
- R1—X (2)
- in the presence of a deprotonation agent in a suitable solvent;
- where X is iodo or bromo and R1 is as defined above, to yield an ether compound of Formula (3):
- 136
- (b) reacting a compound of Formula (3) with a hydrolysing agent, to form a diol compound of Formula (4):
- 137
- (c) reacting a compound of Formula (4) with a cleaving agent in a suitable solvent to form an aldehyde compound of Formula (5):
- 138
- (d) reacting a compound of Formula (5) with a secondary amine compound of Formula (6):
- R2R3NH (6)
- where R2 and R3 are as defined above, and a reducing agent in a suitable solvent followed by treatment with a reducing agent scavenger resin in a suitable solvent and an amine scavenger resin in a suitable solvent to form a tertiary amine compound of Formula (7).
19 more elements
A method for the synthesis of a compound of Formula (7′):
- 139
- wherein:
- R1 is selected from the group consisting of —C1-14alkyl and —(CH2)0-4-aryl;
- and
- R3 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl;
- which comprises the steps of:
- (a) reacting a compound of Formula 1:
- 140
- with an alkylating agent of Formula (2):
- R1—X (2)
- in the presence of a deprotonation agent in a suitable solvent;
- where X is iodo or bromo and R1 is as defined above, to yield an ether compound of Formula (3):
- 141
- (b) reacting a compound of Formula (3) with a hydrolysing agent, to form a diol compound of Formula (4):
- 142
- (c) reacting a compound of Formula (4) with a cleaving agent in a suitable solvent to form an aldehyde compound of Formula (5):
- 143
- (d′) reacting a compound of Formula (5) with a primary amine compound of Formula (6′):
- R3NH2 (6′)
- where R3 is as defined above, and a reducing agent in a suitable solvent followed by treatment with a reducing agent scavenger resin in a suitable solvent and an amine scavenger resin in a suitable solvent to form a secondary amine compound of Formula (7′).
17 more elements
A method for the synthesis of a compound of Formula Ia:
- 144
- wherein:
- R1 is selected from the group consisting of —C1-14alkyl and —(CH2)0-4-aryl;
- R2 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl;
- R3 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl;
- or R2 and R3 can be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl;
- and
- R4 is selected from the group consisting of H, —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —C2-8alkynyl and —(CH2)1-2-heterocycloalkyl;
- which comprises the step of:
- (a) reacting a compound of Formula (7)
- 145
- where R1, R2, and R3 are as defined above, with a compound of Formula (8):
- R4OH (8)
- where R4 is selected from the group consisting of H, —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —C2-8alkynyl and —(CH2)1-2-heterocycloalkyl, and an acid in a suitable solvent followed by treatment with an acid scavenger resin in a suitable solvent to form a compound of Formula Ia.
11 more elements
A method for the synthesis of a compound of Formula Ib:
- 146
- wherein:
- R1 is selected from the group consisting of —C1-14alkyl and —(CH2)0-4-aryl;
- R3 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl;
- or R6 and R3 can be taken together with the carbon and nitrogen atoms, respectively, to which they are attached to form a heterocycloalkyl containing an oxo (═O) substitution at the carbon atom;
- and
- R6 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2—O-aryl, —C2-6alkenyl, —(CH2)0-2-cycloalkyl and —(CH2)1-4-aryl;
- which comprises the step of:
- (a) reacting a compound of Formula (7′)
- 147
- with an acid chloride compound of Formula (9):
- R6COCl (9)
- where R6 is as defined above, and a suitable base in a suitable solvent followed by treatment with an acid chloride scavenger resin in a suitable solvent to form a compound of Formula Ib.
10 more elements
A method for the synthesis of a compound of Formula Ic:
- 148
- wherein:
- R1 is selected from the group consisting of —C1-14alkyl and —(CH2)0-4-aryl;
- R3 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl;
- or R6 and R3 can be taken together with the carbon and nitrogen atoms respectively, to which they are attached to form a heterocycloalkyl containing an oxo (═O) substitution at the carbon atom;
- and
- R6 is selected from the group consisting of —C1-4alkyl, —(CH2)0-2—O-aryl, —C2-6alkenyl, —(CH2)0-2-cycloalkyl and —(CH2)1-4-aryl;
- which comprises the steps of:
- (a) reacting a compound of Formula (7′)
- 149
- with an isocyanate compound of Formula (10):
- R6NCO (10)
- where R6 is as defined above, in a suitable solvent followed by treatment with an isocyanate scavenger resin in a suitable solvent to form a compound of Formula Ic.
10 more elements
A method for the synthesis of an array compounds of Formula Ia:
- 150
- wherein:
- R1 is selected from the group consisting of —C1-14alkyl and —(CH2)0-4-aryl;
- R2 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl;
- R3 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl;
- or R2 and R3 can be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl;
- and
- R4 is selected from the group consisting of H, —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —C2-8alkynyl and —(CH2)1-2-heterocycloalkyl;
- which comprises the step of:
- (a) reacting an array of compounds of Formula (7)
- 151
- where R1, R2, and R3 are as defined above, with an array of compounds of Formula (8):
- R4OH (8)
- where R4 is selected from the group consisting of H, —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —C2-8alkynyl and —(CH2)1-2-heterocycloalkyl, and an acid in a suitable solvent followed by treatment with an acid scavenger resin in a suitable solvent to form an array of compounds of Formula Ia.
11 more elements
A method for the synthesis of an array of compounds of Formula Ib:
- 152
- wherein:
- R1 is selected from the group consisting of —C1-14alkyl and —(CH2)0-4-aryl;
- R3 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl;
- or R6 and R3 can be taken together with the carbon and nitrogen atoms, respectively, to which they are attached to form a heterocycloalkyl containing an oxo (═O) substitution at the carbon atom;
- and
- R6 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2—O-aryl, —C2-6alkenyl, —(CH2)0-2-cycloalkyl and —(CH2)1-4-aryl;
- which comprises the step of:
- (a) reacting an array of compounds of Formula (7′)
- 153
- with an array of acid chloride compounds of Formula (9):
- R6COCl (9)
- where R6 is as defined above, and a suitable base in a suitable solvent followed by treatment with an acid chloride scavenger resin in a suitable solvent to form an array of compounds of Formula Ib.
10 more elements
A method for the synthesis of an array of compounds of Formula Ic:
- 154
- wherein:
- R1 is selected from the group consisting of —C1-14alkyl and —(CH2)0-4-aryl;
- R3 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl;
- or R6 and R3 can be taken together with the carbon and nitrogen atoms, respectively, to which they are attached to form a heterocycloalkyl containing an oxo (═O) substitution at the carbon atom;
- and
- R6 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2—O-aryl, —C2-6alkenyl, —(CH2)0-2-cycloalkyl and —(CH2)1-4-aryl;
- which comprises the steps of:
- (a) reacting an array of compounds of Formula (7′)
- 155
- with an array of isocyanate compounds of Formula (10):
- R6NCO (10)
- where R6 is as defined above, in a suitable solvent followed by treatment with an isocyanate scavenger resin in a suitable solvent to form an array compounds of Formula Ic.
10 more elements
A method for the solid phase synthesis of a compound of Formula IIIa
- 156
- wherein:
- R1 is selected from the group consisting of —C1-14alkyl and —(CH2)0-4-aryl;
- R6 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2—O-aryl, —C2-6alkenyl, —(CH2)0-2cycloalkyl and —(CH2)1-4-aryl;
- R7 is an amino acid side chain;
- and
- n is an integer from 1-14;
- which comprises the step of:
- (a) reacting a compound of Formula (23)
- 157
- where SS is a solid support, and R1, R6, R7, and n are as defined above, with an acid in a suitable solvent to form a compound of Formula IIIa.
8 more elements
A method for the solid phase synthesis of a compound of Formula IIIb
- 158
- wherein:
- R1 is selected from the group consisting of —C1-14alkyl and —(CH2)0-4-aryl;
- R6 is selected from the group consisting of —C1-4alkyl, —(CH2)0-2—O-aryl, —C2-6alkenyl, —(CH2)0-2-cycloalkyl and —(CH2)1-4-aryl;
- R7 is an amino acid side chain;
- and
- n is an integer from 1-14;
- which comprises the step of:
- (a) reacting a compound of Formula (23)
- 159
- where SS is a solid support, and R1, R6, R7, and n are as defined above, with an acid in an aqueous solvent to form a compound of Formula IIIb.
8 more elements
A compound of Formula (7)
- 160
- where
- R1 is selected from the group consisting of —C1-14alkyl and —(CH2)0-4-aryl;
- R2 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl;
- and
- R3 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl;
- or R2 and R3 can be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl.
4 more elements
A compound of Formula (7′)
- 161
- where
- R1 is selected from the group consisting of —C1-14alkyl and —(CH2)0-4-aryl;
- and
- R3 is selected from the group consisting of —C1-14alkyl, —(CH2)0-2-cycloalkyl, —C2-6alkenyl, —(CH2)1-4-aryl, —(CH2)0-4-heterocycloalkyl, —(CH2)1-4-heteroaryl and —(CH2)0-2—O-aryl.
2 more elements
A compound selected from:
- 4-Ethoxy-2-isopropoxy-5(4-phenyl-piperzin-1-ylmethyl)-tetrahydro-furan-3-ol;
- 5-[(Benzyl-phenethyl-amino)-methyl]-4-ethoxy-2-(2-methoxy-ethoxy)-tetrahydro-furan-3-ol;
- 4-Ethoxy-2-methoxy-5-(1,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-ylmethyl)-tetrahydro-3-ol;
- 5-[4-(3-Chloro-phenyl)-piperazin-1-ylmethyl]-2-cyclopropylmethoxy-4-ethoxy-tetrahydro-furan-3-ol;
- 5-Dialkylaminomethyl-2-isobutoxy-4-(naphthalen-2-ylmethoxy)tetrahydro-furan-3-ol;
- 2-(3-Methoxy-3-methyl-butoxy)-5-morpholin-4-ylmethyl-4-(naphthalen-2-yl methoxy)-tetrahydro-3-furan-3-ol;
- 5-[(Benzyl-methyl-amino)-methyl]-4-(naphthalen-2-yl methoxy)-2-pent-2-ynyloxy-tetrahydro-furan-3-ol;
- 4-Methoxy-5-(4-phenyl-piperazin-1-ylmethyl)-2-propoxy-tetrahydro-furan-3-ol;
- 2-Cyclopropylmethoxy-5-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)-4-methoxy-tetrahydro-furan-3-ol;
- 5-[(Benzyl-methyl-amino)-methyl]-4-methoxy-2-pent-2-ynyloxy-tetrahydro-furan-3-ol;
- 4-Butoxy-2-(2-methoxy-ethoxy)-5-[(methyl-phenethyl-amino)-methyl]-tetrahydro-furan-3-ol;
- 4-Butoxy-2-methoxy-5-(1,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-ylmethyl)-tetrahydro-furan-3-ol;
- 4-(3-Methoxy-benzyloxy)-2-(3-methoxy-3-methyl-butoxy)-5-morpholin-4-ylmethyl-tetrahydro-furan-3-ol;
- 5-Dialkylaminomethyl-2-isobutoxy-4-(3-methoxy-benzyloxy)-tetrahydro-furan-3-ol;
- and
- 5-[(Dibenzylamino)-methyl]-2-ethoxy-4-(3-methoxy-benzyioxy)-tetrahydro-furan-3-ol.
13 more elements
A compound selected from:
- Cyclohexanecarboxylic acid (6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-(2-diethylamino-ethyl)-amide;
- N-(6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-N-(2-methoxy-benzyl)-2,2-diphenyl-acetamide;
- N-Butyl-N-[6-(3-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl]-benzamide;
- N-(2,4-Dimethoxy-benzyl)-N-(6-methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol -5-ylmethyl)-2,2-diphenyl-acetamide;
- Cyclohexanecarboxylic acid (6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-(3-methoxy-propyl)-amide;
- and
- N-(1-Benzyl-pyrrolidin-3-yl)-N-[6-(3-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl]-benzamide.
4 more elements
A compound selected from:
- 1-Benzyl-3-ethyl-1-(6-methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-urea;
- 1-(6-Methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-3-phenyl-1(4-trifluoromethoxy-benzyl)-urea;
- 1-Cyclopropylmethyl-3-isopropyl-1-[6-(3-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl]-urea;
- 3-Ethyl-1-(6-methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-1-phenethyl-urea;
- 1-(6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-3-ethyl-1-[2-(1H-indol-2-yl)-ethyl]-urea;
- and
- 1-Allyl-1-[6-(3-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl]-3-phenyl-urea.
4 more elements
A compound selected from:
- N-(4,5-Dihydroxy-3-methoxy-tetrahydro-furan-2-ylmethyl)-N-(2-methoxy-benzyl)-2,2-diphenyl-acetamide;
- and
- N-Butyl-N-[4,5-dihydroxy-3-(3-methoxy-benzyloxy)-tetrahydro-furan-2-ylmethyl]-benzamide.
A compound named 1-(3-benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-ylmethyl)-3-phenyl-1-(4-trifluoromethoxy-benzyl)-urea.
Dependencies are inferred from the claim text.