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US 6,635,653 B2Granted
Spiropyrazole compounds
AssigneeEuro-Celtique S.A.
InventorsR. Richard Goehring, Gary Lee, Parviz Gharagozloo, Sam Victory, Donald Kyle
Life of this patent
Estimating the term…
Abstract
A compound of the formula (I): wherein Z, W, A, B, C, R1, R2, Q and n are as disclosed herein.
Claims19
A compound of formula (I):
- wherein W is hydrogen, C1-10 alkyl, C3-12 cycloalkyl, C3-12 cycloalkylC1-4alkyl-, C1-10 alkoxy, C3-12 cycloalkoxy, C1-10 alkyl substituted with 1-3 halogen, C3-12 cycloalkyl substituted with 1-3 halogen, C3-12 cycloalkylC1-4alkyl-substituted with 1-3 halogen, C1-10 alkoxy substituted with 1-3 halogen, C3-12 cycloalkoxy-substituted with 1-3 halogen, —COOV1, —C1-4COOV1, —CH2OH, —SO2N(V1)2, hydroxyC1-10alkyl-, hydroxyC3-10cycloalkyl-, cyanoC1-10alkyl-, cyanoC3-10cycloalkyl-, —CON(V1)2, NH2SO2C1-4alkyl-, NH2SOC1-4alkyl-, sulfonylaminoC1-10alkyl-, diaminoalkyl-, -sulfonylC1-4alkyl, a 6-membered aromatic ring, a 6-membered aromaticC1-4 alkyl-, —C1-5(═O)W1, —C1-5(═NH)W1, —C1-5NHC(═O)W1, —C1-5NHS(═O)2, W1, —C1-5NHS(═O)W1, wherein W1 is hydrogen, C1-10 alkyl C3-12 cycloalkyl, C1-10 alkoxy, C3-12 cycloalkoxy, —CH2OH, amino, C1-4alkylamino-, or diC1-4alkylamino-;
- wherein each V1 is independently selected from H, C1-6 alkyl, C3-6 cycloalkyl, benzyl or phenyl, provided that V1 is a C3-6 cycloalkyl, benzyl or phenyl whjen a substituent of R1;
- Q is a 6 membered aromatic group;
- n is an integer from 0 to 3;
- A, B and C are hydrogen;
- Z is selected from the group consisting of a bond, methyl or ethyl;
- R1 is selected from the group consisting of C3-12 cycloalkyl, C3-12cycloalkylamino-, —COOV1, —C1-4COOV1, cyanoC3-10cycloalkyl-, benzyl, C3-12 cycloalkenyl-, a monocyclic, bicyclic or tricyclic aryl, and a spiro ring system of the formula (II):
- wherein X1 and X2 are CH2;
- and wherein said cycloalkyl, C3-12cycloalkylamino-, or benzyl of R1 is optionally substituted with 1-3 substituents selected from the group consisting of halogen, hydroxy, C1-10 alkyl, C1-10 alkoxy, nitro, trifluoromethyl-, cyano, —COOV1, —C1-4COOV1, cyanoC1-10alkyl-, —C1-5═OW1, —C1-5NHS(═O)2W1, —C1-5NHS(═O)W1, phenyl, benzyl, benzyloxy, said phenyl, benzyl, and benzyloxy optionally being substituted with 1-3 substituents selected from the group consisting of halogen, C1-10 alkyl-, C1-10 alkoxy-, and cyano;
- and wherein said C3-12 cycloalkyl, C3-12 cycloalkenyl, monocyclic, bicyclic or tricyclic aryl, or spiro ring system of the formula (II) is optionally substituted with 1-3 substituents selected from the group consisting of halogen, C1-10 alkyl, C1-10 alkoxy, nitro, trifluoromethyl-, phenyl, benzyl, phenyloxy and benzyloxy, wherein said phenyl, benzyl, phenyloxy or benzyloxy is optionaly substituted with 1-3 substituents selected from the group consisting of halogen, C1-10 alkyl, C1-10 alkoxy, and cyano;
- R2 is selected from the group consisting of hydrogen, C1-10 alkyl, C3-12 cycloalkyl and halogen, said alkyl or cycloalkyl optionally substituted with an oxo, amino, alkylamino or dialkylamino group;
- or a pharmaceutically acceptable salt thereof or solvate thereof.
9 more elements
A compound of formula (IA):
- wherein
- n is an integer from 0 to 3;
- Z is selected from the group consisting of a bond, —CH2—, and —CH2CH2—;
- R1 is selected from the group consisting of C3-12cycloalkyl, C3-12cycloalkylamino, benzyl, C3-12 cycloalkenyl, a monocyclic, bicyclic or tricyclic aryl, and a spiro ring system, and a spiro ring system of the formula (II):
- wherein X1 and X2 are CH2;
- wherein said cycloalkyl, C3-12cycloalkylamino, or benzyl is optionally substituted with 1-3 substituents selected from the group consisting of halogen, C1-10 alkyl, C1-10 alkoxy, nitro, trifluoromethyl, cyano, phenyl, benzyl, benzyloxy, said phenyl, benzyl, and benzyloxy optionally being substituted with 1-3 substituents selected from the group consisting of halogen, C1-10 alkyl, C1-10 alkoxy, and cyano;
- wherein said C3-12 cycloalkyl, C3-12 cycloalkenyl, monocyclic, bicyclic or tricyclic aryl, and spiro ring system of the formula (II) are optionally substituted with 1-3 substituents selected from the group consisting of halogen, C1-10 alkyl, C1-10 alkoxy, nitro, trifluoromethyl, phenyl, benzyl, phenyloxy and benzyloxy, wherein said phenyl, benzyl, phenyloxy and benzyloxy are optionally substituted with 1-3 substituents selected from the group consisting of halogen, C1-10 alkyl, C1-10 alkoxy, and cyano;
- R2 is selected from the group consisting of hydrogen, C1-10 alkyl, C3-12 cycloalkyl and halogen, said alkyl optionally substituted with an oxo group;
- or a pharmaceutically acceptable salt thereof.
6 more elements
A compound of formula (IA):
- wherein
- R2 is selected from the group consisting of hydrogen, C1-10 alkyl, C3-12 cycloalkyl and halogen, said alkyl optionally substituted with an oxo group;
- n is an integer from 0 to 3;
- and ZR1 is
- wherein
- Y1 is R3—(C1-C12)alkyl, R4-aryl, R6—(C3-C12)cyclo-alkyl, —CO2(C1-C6)alkyl, CN or —C(O)NR8R9;
- Y2 is hydrogen or Y1;
- Y3, together with the carbon to which they are attached, form one of the following structures:
- wherein r is 0 to 3;
- w and u are each 0-3, provided that the sum of w and u is 1-3;
- c and d are independently 1 or 2;
- s is 1 to 5;
- and ring E is a fused R4-phenyl ring;
- R10 is 1 to 3 substituents independently selected from the group consisting of H, (C1-C6)alkyl, —OR8, —(C1-C6)alkyl-OR8, —NR8R9 and —(C1-C6)alkyl-NR8R9;
- R11 is 1 to 3 substituents independently selected from the group consisting of R10, —CF3, —OCF3, NO2 and halo;
- R8 and R9 are independently selected from the group consisting of hydrogen, (C1-C6)alkyl, (C3-C12)cycloalkyl, aryl and aryl(C1-C6)alkyl;
- R3 is 1 to 3 substituents independently selected from the group consisting of H, R4-aryl, R6—(C3-C12)cycloalkyl, —NR8R9, —OR12 and —S(O)0-2R12;
- R6 is 1 to 3 substituents independently selected from the group consisting of H, (C1-C6)alkyl, R4-aryl, —NR8R9, —OR12 and —SR12;
- R4 is 1 to 3 substituents independently selected from the group consisting of hydrogen, halo, (C1-C6)alkyl, R13-aryl, (C3-C12)cycloalkyl, —CN, —CF3, —OR8, —(C1-C6)alkyl-OR8, —OCF3, —NR8R9, —(C1-C6)alkyl —NR8R9, —NHSO2R8, —SO2N(R14)2, —SO2R8, —SOR8, —SR8, —NO2, —CONR8R9, —NR9COR8, —COR8, —COCF3, —OCOR8, —OCO2R8, —COOR8, —(C1-C6)alkyl-NHCOOC(CH3)3, —C1-C6)alkyl-NHCOCF3, —(C1-C6)alkyl-NHSO2—(C1-C6)alkyl, and —(C1-C6alkyl-NHCONH—(C1-C6)-alkyl;
- R5 is 1 to 3 substituents independently selected from the group consisting of hydrogen, halo, (C1-C6)alkyl, R13-aryl, (C3-C12)cycloalkyl, —CN, —CF3, —OR8, —(C1-C6)alkyl-OR8, —OCF3, —NR8R9, —(C1-C6)alkyl-NR8R9, —NHSO2R8, —SO2N(R14)2, —NO2, —CONR8R9, —NR9COR8, —COR8, —OCOR8, —OCO2R8 and —COOR8;
- R7 is H, (C1-C6)alkyl, —OR8, —(C1-C6)alkyl-OR8, —NR8R9 or —(C1-C6)alkyl-NR8R9;
- R12 is H, (C1-C6)alkyl, R4-aryl, —(C1-C6)alkyl-OR8, —(C1-C6)alkyl-NR8R9, —(C1-C6)alkyl-SR8, or aryl (C1-C6)alkyl;
- R13 is 1-3 substituents independently selected from the group consisting of H, (C1-C6)alkyl, (C1-C6)alkoxy and halo;
- R14 is independently selected from the group consisting of H, (C1-C6)alkyl and R13—C6H4—CH2—;
- or a pharmaceutically acceptable salt thereof.
22 more elements
Dependencies are inferred from the claim text.