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US 2004/0110745 A1Published application
Therapeutic chroman compounds
OwnerMarc Chapdelaine, Timothy Davenport +5inventors
InventorsMarc Chapdelaine, Timothy Davenport, Markus Haeberlein, Carey Horchler, John McCauley, Edward Pierson, Daniel Sohn
Life of this patent
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Abstract
Provided herein is a compound represented by the Formula (I) wherein said compounds are useful for the treatment of migraine. Also provided are processes for the preparation of compounds of Formula (I) and intermediates.
Claims15
A compound represented by the formula (I):
- 258
- wherein
- R1 is, at each position, independently represented by hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, thiomethoxy, —NHA, —NA2, —NHC(═O)A, aminocarbonyl, —C(═O)NHA, —C(═O)NA2, halogen, hydroxy, —OA, cyano or aryl;
- A is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl or optionally substituted alkynyl;
- R2 is represented by (i), (ii), (iii), or (iv) below:
- 259
- R3 is independently at each position represented by —H, optionally substituted C1-6alkyl, optionally substituted C2-6alkenyl, optionally substituted C2-6alkynyl, optionally substituted C3-6cycloalkyl or AOH;
- n is 2, 3 or 4;
- P is a heterocyclic ring;
- R6 is —H or methyl;
- Y is —C(═O)NH—, —C(═O)NA—, —C(═O)N(A)—, —NHC(═O)—, —C(═S)NH—, —CH2NH—, —C(═O)— —C(═O)CH2—, —CH2C(═O)—, —C(═O)-piperazine-, —NAC(═O)—, —C(═S)N(A)—, CH2NA, NACH2 or a 5-membered heterocyclic.
- R7 is a monocyclic or bicyclic aromatic ring or a heterocycle optionally substituted by one or more substituents selected from R8-R9 and R10;
- wherein R7 is connected to Y either by a single bond or by a ring fusion;
- R8 is —CH2—, —C(═O)—, —SO2—, —SO2NH—, —C(═O)NH—, —O—, —S—, —S(═O)—, a single bond as tether from R7 to R9, 5-membered heterocycle connected to R7 by a ring fusion or a single bond as tether;
- R9 optionally substituted heterocycle, optionally substituted aryl, optionally substituted piperazinyl-R11, optionally substituted morpholinyl-R11, optionally substituted thiomorpholinyl , or —C(═O)A;
- R10 is optionally substituted alkyl, optionally substituted cycloalkyl, hydroxy, aryl, cyano, halogen, —C(═O)NH2—, methylthio, —NHA, —NA2, —NHC(═O)A, C(═O)NHA, C(═O)NA2, or OA;
- R11 is —H, alkyl, AOH, —SO2A, —SO2NH2, —SO2NHA, —SO2NA2, —SO2NHAR9, —C(═O)R9, -alkylR9, C(═O)A, C(═O)NH2, C(═O)NHA, C(═O)NA2 or —C(═O)OA;
- or a pharmaceutically acceptable salt of said compound.
15 more elements
A method of treatment of a human or animal suffering from migraine by administering to such animal an effective amount of a compound of Formula I or a pharmaceutically acceptable salt of said compound.
A compound of the Formula (VIe):
- 260
- wherein R1 is, at each position, independently represented by hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, methoxy, thiomethoxy, —NHA, —NA2, —NHC(═O)A, aminocarbonyl, —C(═O)NHA, —C(═O)NA2, halogen, hydroxy, —OA, cyano or aryl;
- A is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl or optionally substituted alkynyl;
- R2 is represented by (i), (ii), (iii), or (iv) below:
- 261
- and X is represented by O;
- or a pharmaceutically acceptable salt of said compound.
4 more elements
The compound of Formula (VIf1):
- 262
- wherein R1 is, at each position, independently represented by hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, methoxy, thiomethoxy, —NHA, —NA2, —NHC(═O)A, aminocarbonyl, —C(═O)NHA, —C(═O)NA2, halogen, hydroxy, —OA, cyano or aryl;
- A is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl or optionally substituted alkynyl;
- R2 is represented by (i), (ii), (iii), or (iv) below:
- 263
- and X is represented by O, S, or N, or a pharmaceutically acceptable salt thereof.
3 more elements
A compound of Formula (VIg1)
- 264
- wherein R1 is, at each position, independently represented by hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, methoxy, thiomethoxy, —NHA, —NA2, —NHC(═O)A, aminocarbonyl, —C(═O)NHA, —C(═O)NA2, halogen, hydroxy, —OA, cyano or aryl;
- A is optionally substituted alkyd optionally substituted cycloalkyl, optionally substituted alkenyl or optionally substituted alkynyl;
- L represents a leaving group.
- R2 is represented by (i), (ii), (iii), or (iv) below:
- 265
- and X is represented by O;
- or a pharmaceutically acceptable salt of said compound.
5 more elements
A compound of Formula (VIh)
- 266
- wherein R1 is, at each position, independently represented by hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, methoxy, thiomethoxy, —NHA, —NA2, —NHC(═O)A, aminocarbonyl, —C(═O)NHA, —C(═O)NA2, halogen, hydroxy, —OA, cyano or aryl;
- A is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl or optionally substituted alkynyl;
- R2 is represented by (i), (ii), (iii), or (iv) below:
- 267
- and X is represented by O;
- or a pharmaceutically acceptable salt of said compound.
4 more elements
Dependencies are inferred from the claim text.