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US 12,527,760 B2Granted
Synthesis of pro-resolving analogs and compositions therefor
AssigneeNocendra Inc.
InventorsThomas E. Van Dyke, Charles N. Serhan
Life of this patent
Estimating the term…
Abstract
This disclosure relates to methods of synthesizing certain lipoxin analogs (e.g., lipoxin mimetics, etc.) and pharmaceutical compositions comprising these pro-resolving compounds. Methods of administering the lipoxin mimetics (e.g., lipoxin A4 mimetics, lipoxin B4 mimetics, etc.) to patients in need thereof are also provided.
Claims10
A method comprising:
- a) contacting a compound having the structure of Formula (I):
- with a compound having the structure of Formula (II):
- in a reaction environment having a pH greater than 7;
- to form a compound having the structure of Formula (III):
- b) deprotecting said compound of Formula (III) to produce a compound having the structure of Formula (IV):
- c) reacting said compound having the structure of Formula (IV) with an alkylating agent to form a compound having the structure of Formula (V):
- wherein p is an integer from 0-4;
- R1 is selected from hydrogen, saturated or unsaturated C1-C7 alkyl optionally substituted one or more times, and C1-C7 heteroalkyl optionally substituted one or more times;
- R2 is selected from hydrogen, halogen, hydroxy, cyano, nitro, saturated or unsaturated C1-C7 alkyl optionally substituted one or more times, and C1-C7 heteroalkyl optionally substituted one or more times;
- R3 is independently selected at each occurrence from hydrogen, hydroxy, halogen, cyano, nitro, saturated or unsaturated C1-C7 alkyl optionally substituted one or more times, saturated or unsaturated C1-C7 alkoxy optionally substituted one or more times, and C1-C7 heteroalkyl optionally substituted one or more times;
- R4 is selected from saturated or unsaturated C1-C7 alkyl optionally substituted one or more times, and C1-C7 heteroalkyl optionally substituted one or more times;
- RL is absent or a divalent C1-C7 hydrocarbon optionally substituted one or more times;
- P1-P3 are each independently an oxygen protecting group;
- and
- X is a halogen.
12 more elements
A method comprising:
- a) deprotecting a compound of Formula (III):
- to produce a compound having the structure of Formula (IV):
- b) contacting said compound having the structure of Formula (IV) with an alkylating agent to form a compound having the structure of Formula (V):
- wherein p is an integer from 0-4;
- R1 is selected from hydrogen, saturated or unsaturated C1-C7 alkyl optionally substituted one or more times, and C1-C7 heteroalkyl optionally substituted one or more times;
- R2 is selected from hydrogen, halogen, hydroxy, cyano, nitro, saturated or unsaturated C1-C7 alkyl optionally substituted one or more times, and C1-C7 heteroalkyl optionally substituted one or more times;
- R3 is independently selected at each occurrence from hydrogen, hydroxy, halogen, cyano, nitro, saturated or unsaturated C1-C7 alkyl optionally substituted one or more times, saturated or unsaturated C1-C7 alkoxy optionally substituted one or more times, and C1-C7 heteroalkyl optionally substituted one or more times;
- wherein R4 is selected from saturated or unsaturated C1-C7 alkyl optionally substituted one or more times, and C1-C7 heteroalkyl optionally substituted one or more times;
- RL is absent or a divalent C1-C7 hydrocarbon optionally substituted one or more times;
- P1-P3 are each independently a protecting group;
- and
- said deprotecting step occurs in a reaction environment with a pH greater than 7.
9 more elements
A method comprising:
- contacting a compound having the structure of Formula (VI):
- with a compound having the structure of Formula (VII):
- under in an environment suitable with a pH greater than 7 to form a compound having the structure of Formula (VIII):
- wherein p is an integer from 0-4;
- R1 is selected from hydrogen, saturated or unsaturated C1-C7 alkyl optionally substituted one or more times, and C1-C7 heteroalkyl optionally substituted one or more times;
- R2 is selected from hydrogen, halogen, hydroxy, cyano, nitro, saturated or unsaturated C1-C7 alkyl optionally substituted one or more times, and C1-C7 heteroalkyl optionally substituted one or more times;
- R3 is independently selected at each occurrence from hydrogen, hydroxy, halogen, cyano, nitro, saturated or unsaturated C1-C7 alkyl optionally substituted one or more times, saturated or unsaturated C1-C7 alkoxy optionally substituted one or more times, and C1-C7 heteroalkyl optionally substituted one or more times;
- RL is absent or a divalent C1-C7 hydrocarbon optionally substituted one or more times;
- P1-P3 are each independently an oxygen protecting group;
- and
- X is a halogen.
8 more elements
Dependencies are inferred from the claim text.