US 12,747,240 B2Granted

Substituted [1,2,4]triazolo[4,3-a]quinoxalines, dosage forms containing them, and methods of using them to treat or prevent pain and/or inflammation

AssigneeGruenenthal GmbH

InventorsJo Alen, Florian Jakob, Sebastian Krueger, Daniela Friebe, Stephanie Hennen

Life of this patent

Estimating the term…

Abstract

The present invention relates to compounds according to general formula (I) which act as modulators of the glucocorticoid receptor and can be used in the treatment and/or prophylaxis of disorders which are at least partially mediated by the glucocorticoid receptor.

Claims20

Dependent claims

A compound according to the following formula:

or a physiologically acceptable salt or stereoisomer thereof,
wherein:
R1 is C(O)NH—C1-6 alkylene-aryl, C3-10 cycloalkyl, 3- to 7-membered heterocycloalkyl, aryl, or 5- to 10-membered heteroaryl, wherein the C1-6 alkylene is linear or branched and is saturated or unsaturated;
R3 is H or C1-10 alkyl, wherein the C1-10 alkyl is linear or branched and is saturated or unsaturated;
R4 is H or C1-10 alkyl, wherein the C1-10 alkyl is linear or branched and is saturated or unsaturated;
R5 is F, Cl, Br, I, C1-10 alkyl, OC1-10 alkyl, or C3-10 cycloalkyl, wherein each C1-10 alkyl is independently linear or branched and is independently saturated or unsaturated;
R6 is H, F, Cl, Br, I, C1-10 alkyl, OC1-10 alkyl, or C3-10 cycloalkyl, wherein each C1-10 alkyl is independently linear or branched and is independently saturated or unsaturated;
R7 is H, F, Cl, Br, I, OH, C1-10 alkyl, SC1-10 alkyl, or C3-10 cycloalkyl, wherein each C1-10 alkyl is independently linear or branched and is independently saturated or unsaturated;
or R6 and R7, taken together with the carbon atoms to which they are attached, form a C3-10 cycloalkyl or 3- to 7-membered heterocycloalkyl;
and
R10 is C1-10 alkyl or C3-10 cycloalkyl, wherein the C1-10 alkyl is linear or branched and is saturated or unsaturated;
wherein each C1-10 alkyl, C1-6 alkylene, C3-10 cycloalkyl, and 3- to 7-membered heterocycloalkyl is optionally and independently substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, CN, C1-6 alkyl, CF3, CF2H, CFH2, CF2Cl, CFCl2, C(O)C1-6 alkyl, C(O)OH, C(O)OC1-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, OH, ═O, OCF3, OCF2H, OCFH2, OCF2Cl, OCFCl2, OC1-6 alkyl, OC(O)C1-6 alkyl, OC(O)OC1-6 alkyl, OC(O)NHC1-6 alkyl, OC(O)N(C1-6 alkyl)2, OS(O)2NH2, OS(O)2NHC1-6 alkyl, OS(O)2N(C1-6 alkyl)2, NH2, NHC1-6 alkyl, N(C1-6 alkyl)2, NHC(O)C1-6 alkyl, NHC(O)OC1-6 alkyl, NHC(O)NH2, NHC(O)NHC1-6 alkyl, NHC(O)N(C1-6 alkyl)2, N(C1-6 alkyl)-C(O)C1-6 alkyl, N(C1-6 alkyl)-C(O)OC1-6 alkyl, N(C1-6 alkyl)-C(O)NH2, N(C1-6 alkyl)-C(O)NHC1-6 alkyl, N(C1-6 alkyl)-C(O)N(C1-6 alkyl)2, NHS(O)2OH, NHS(O)2C1-6 alkyl, NHS(O)2OC1-6 alkyl, NHS(O)2NH2, NHS(O)2NHC1-6 alkyl, NHS(O)2N(C1-6 alkyl)2, N(C1-6 alkyl)-S(O)2OH, N(C1-6 alkyl)-S(O)2C1-6 alkyl, N(C1-6 alkyl)-S(O)2OC1-6 alkyl, N(C1-6 alkyl)-S(O)2NH2, N(C1-6 alkyl)-S(O)2NHC1-6 alkyl, N(C1-6 alkyl)-S(O)2N(C1-6 alkyl)2, SCF3, SCF2H, SCFH2, SC1-6 alkyl, S(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2OH, S(O)2OC1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, S(O)2N(C1-6 alkyl)2, C3-6 cycloalkyl, 3- to 7-membered heterocycloalkyl, phenyl, 5- or 6-membered heteroaryl, OC3-6 cycloalkyl, O(3- to 7-membered heterocycloalkyl), Ophenyl, O(5- or 6-membered heteroaryl), C(O)C3-6 cycloalkyl, C(O)(3- to 7-membered heterocycloalkyl), C(O)phenyl, C(O)(5- or 6-membered heteroaryl), S(O)2C3-6 cycloalkyl, S(O)2(3- to 7-membered heterocycloalkyl), S(O)2phenyl, and S(O)2(5- or 6-membered heteroaryl), wherein each C1-6 alkyl is independently linear or branched and is independently saturated or unsaturated;
wherein each aryl and 5- to 10-membered heteroaryl is optionally and independently substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, CN, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C2-6 alkynylene-CH(OH)CH3, C2-6 alkynylene-C(CH3)2OH, CF3, CF2H, CFH2, CF2C1, CFCl2, C1-6 alkylene-CF3, C1-6 alkylene-CF2H, C1-6 alkylene-CFH2, C1-6 alkylene-OH, C1-6 alkylene-OC1-6 alkyl, C(O)C1-6 alkyl, C(O)OH, C(O)OC1-6 alkyl, C(O)NHOH, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, OH, ═O, OCF3, OCF2H, OCFH2, OCF2Cl, OCFCl2, OC1-6 alkyl, OC3-6 cycloalkyl, O(3- to 7-membered heterocycloalkyl), NH2, NHC1-6 alkyl, N(C1-6 alkyl)2, NHC(O)C1-6 alkyl, N(C1-6 alkyl)-C(O)C1-6 alkyl, NHC(O)NH2, NHC(O)NHC1-6 alkyl, NHC(O)N(C1-6 alkyl)2, N(C1-6 alkyl)-C(O)NHC1-6 alkyl, N(C1-6 alkyl)-C(O)N(C1-6 alkyl)2, NHS(O)2C1-6 alkyl, SCF3, SC1-6 alkyl, S(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2C3-6 cycloalkyl, S(O)2—C1-6 alkylene-C3-6 cycloalkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, S(O)2N(C1-6 alkyl)2, C3-6 cycloalkyl, C1-6 alkylene-C3-6 cycloalkyl, 3- to 7-membered heterocycloalkyl;
C1-6 alkylene-(3- to 7-membered heterocycloalkyl), phenyl;
and 5- or 6-membered heteroaryl, wherein each C1-6 alkylene and C1-6 alkyl is independently linear or branched and is independently saturated or unsaturated;
with the proviso that if R1 is indolyl or indazolyl and R7 is H, F or Cl, then the indolyl or indazolyl of R1 is bound via its 5-membered ring to the remainder of the compound.

13 more elements

A compound according to the following formula:

or a physiologically acceptable salt or stereoisomer thereof,
wherein:
R1 is:
(i) imidazopyridinyl, pyrrolopyridinyl, pyrazolopyridinyl, dihydropyrrolopyrazolyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, CH2-pyrrolidinyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, furanyl, thienyl, triazolyl, thiadiazolyl, 4,5,6,7-tetrahydro-2H-indazolyl, 2,4,5,6-tetrahydrocyclopenta[c]pyrazolyl, benzofuranyl, benzoimidazolyl, benzothienyl, dihydrobenzodioxinyl, benzothiadiazolyl, benzothiazolyl, benzotriazolyl, benzooxazolyl, benzooxadiazolyl, quinazolinyl, quinoxalinyl, carbazolyl, quinolinyl, dihydroquinolinonyl, dibenzofuranyl, dibenzothienyl, imidazothiazolyl, indazolyl, indolizinyl, indolyl, indolinyl, isoquinolinyl, naphthyridinyl, oxazolyl, oxadiazolyl, phenazinyl, phenothiazinyl, phthalazinyl, purinyl, phenazinyl, tetrazolyl, triazinyl, or C(O)NHCH2-phenyl;
or
(ii) phenyl or naphthalenyl, wherein the phenyl or naphthalenyl is optionally substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, CH3, CH2CH3, OCH3, CF3, C3-10 cycloalkyl, CH2C3-10 cycloalkyl, S(O)2C3-10 cycloalkyl, S(O)2CH2C3-10 cycloalkyl, S(O)2CH3, S(O)2CH2CH3, CH2CH2OCH3, OCH3, C≡CCH3, CH2CH2C(O)NH2, CH2CH2C(O)N(CH3)2, C(O)CH3, CH═CH2, NH2, and CH2CH2O;
or
(iii) pyridinyl, wherein the pyridinyl is optionally substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, CH3, CH2CH3, OCH3, CF3, C3-10 cycloalkyl, CH2C3-10 cycloalkyl, S(O)2C3-10 cycloalkyl, S(O)2CH2C3-10 cycloalkyl, S(O)2CH3, S(O)2CH2CH3, CH2CH2OCH3, OCH2CH2OH, C≡CCH3, CH2CH2C(O)NH2, C(O)CH3, CH═CH2, NH2, and CH2CH2OH;
or
(iv) any of the following structures (II), (III), (IV), (V) or (VI):
wherein
X is S, O, N, NR13, or CR13;
Z is S, O, N, NR13, or CR13;
each R11, R12 and R13 is independently H, F, Cl, Br, I, CN, CF3, CH2CHF2, C1-10 alkyl, C3-10 cycloalkyl, CH2C3-10 cycloalkyl, 3- to 7-membered heterocycloalkyl, S(O)C1-10 alkyl, S(O)C3-10 cycloalkyl, S(O)(3- to 7-membered heterocycloalkyl), S(O)2C1-10 alkyl, S(O)2C3-10 cycloalkyl, S(O)2CH2C3-10 cycloalkyl, S(O)2(3- to 7-membered heterocycloalkyl), P(O)(C1-10 alkyl)2, P(O)(C1-10 alkyl)(C3-10 cycloalkyl), P(O)(C1-10 alkyl)(3- to 7-membered heterocycloalkyl), P(O)(OC1-10 alkyl)2, P(O)(OC1-10 alkyl)(OC3-10 cycloalkyl), P(O)(OC1-10 alkyl)(O(3- to 7-membered heterocycloalkyl)), OC1-10 alkyl, SC1-10 alkyl, NHC1-10 alkyl, N(C1-10 alkyl)2, C(O)C1-10 alkyl, C(O)OC1-10 alkyl, C(O)NH2, C(O)NHC1-10 alkyl, C(O)N(C1-10 alkyl)2, OC3-10 cycloalkyl, NHC3-10 cycloalkyl, N(C1-10 alkyl)(C3-10 cycloalkyl), C(O)C3-10 cycloalkyl, C(O)OC3-10 cycloalkyl, C(O)NHC3-10 cycloalkyl;
C(O)N(C1-10 alkyl)(C3-10 cycloalkyl), O(3- to 7-membered heterocycloalkyl), NH(3- to 7-membered heterocycloalkyl), N(C1-10 alkyl)(3- to 7-membered heterocycloalkyl), C(O)(3- to 7-membered heterocycloalkyl), C(O)O(3- to 7-membered heterocycloalkyl), C(O)N(H)(3- to 7-membered heterocycloalkyl), C(O)N(C1-10 alkyl)(3- to 7-membered heterocycloalkyl), —CH2CH2OCH2—, CH2CH2OCH3, C≡CCH(OH)CH3, C≡CC(OH)(CH3)2, or CH2CH2OH, wherein each C1-10 alkyl is independently linear or branched and is independently saturated or unsaturated;
and
n is 0, 1, 2 or 3;
or
(v) any of the following structures (1), (2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13), (14), (15), (16), or (17):
wherein each of (6), (7), (8), or (16) is optionally substituted with one substituent selected from the group consisting of F and CH3;
R3 is H or C1-10 alkyl, wherein the C1-10 alkyl is linear or branched and is saturated or unsaturated;
R4 is H or C1-10 alkyl, wherein the C1-10 alkyl is linear or branched and is saturated or unsaturated;
R5 is F, Cl, Br, I, C1-10 alkyl, OC1-10 alkyl, or C3-10 cycloalkyl, wherein each C1-10 alkyl is independently linear or branched and is independently saturated or unsaturated;
R6 is H, F, Cl, Br, I, C1-10 alkyl, OC1-10 alkyl, or C3-10 cycloalkyl, wherein each C1-10 alkyl is independently linear or branched and is independently saturated or unsaturated;
R7 is H, F, Cl, Br, I, OH, C1-10 alkyl, SC1-10-alkyl, or C3-10 cycloalkyl, wherein each C1-10 alkyl is independently linear or branched and is independently saturated or unsaturated;
or R6 and R7, taken together with the carbon atoms to which they are attached, form a C3-10 cycloalkyl or 3- to 7-membered heterocycloalkyl;
and
R10 is C1-10 alkyl or C3-10 cycloalkyl, wherein the C1-10 alkyl is linear or branched and is saturated or unsaturated;
wherein each C1-10 alkyl, C1-6 alkylene, C3-10 cycloalkyl and 3- to 7-membered heterocycloalkyl is optionally and independently substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, CN, C1-6 alkyl, CF3, CF2H, CFH2, CF2Cl, CFCl2, C(O)C1-6 alkyl, C(O)OH, C(O)OC1-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, CON(C1-6 alkyl)2, OH, ═O, OCF3, OCF2H, OCFH2, OCF2Cl, OCFCl2, O—C1-6 alkyl, OC(O)C1-6 alkyl, OC(O)OC1-6 alkyl, OC(O)NHC1-6-alkyl, OC(O)N(C1-6 alkyl)2;
OS(O)2NH2, OS(O)2NHC1-6 alkyl, OS(O)2N(C1-6 alkyl)2, NH2, NHC1-6 alkyl, N(C1-6 alkyl)2, NHC(O)C1-6 alkyl, NHC(O)OC1-6 alkyl, NHC(O)NH2, NHC(O)NHC1-6 alkyl, NHC(O)N(C1-6 alkyl)2, N(C1-6 alkyl)-C(O)C1-6 alkyl, N(C1-6 alkyl)-C(O)OC1-6 alkyl, N(C1-6 alkyl)-C(O)NH2, N(C1-6 alkyl)-C(O)NHC1-6 alkyl, N(C1-6 alkyl)-C(O)N(C1-6 alkyl)2, NHS(O)2OH, NHS(O)2C1-6 alkyl, NHS(O)2OC1-6 alkyl, NHS(O)2NH2, NHS(O)2NHC1-6 alkyl, NHS(O)2N(C1-6 alkyl)2, N(C1-6 alkyl)-S(O)2OH, N(C1-6 alkyl)-S(O)2C1-6 alkyl, N(C1-6 alkyl)-S(O)2OC1-6 alkyl, N(C1-6 alkyl)-S(O)2NH2, N(C1-6 alkyl)-S(O)2NHC1-6 alkyl, N(C1-6 alkyl)-S(O)2N(C1-6 alkyl)2, SCF3, SCF2H, SCFH2, SC1-6 alkyl, S(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2OH, S(O)2OC1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, S(O)2N(C1-6 alkyl)2, C3-6 cycloalkyl, 3- to 7-membered heterocycloalkyl, phenyl, 5- or 6-membered heteroaryl, OC3-6 cycloalkyl, O(3- to 7-membered heterocycloalkyl), Ophenyl;
O(5- or 6-membered heteroaryl), C(O)C3-6 cycloalkyl, C(O)(3- to 7-membered heterocycloalkyl), C(O)phenyl, C(O)(5- or 6-membered heteroaryl), S(O)2C3-6 cycloalkyl, S(O)2(3- to 7-membered heterocycloalkyl, S(O)2phenyl, and S(O)2(5- or 6-membered heteroaryl), wherein each C1-6 alkyl is independently linear or branched and is independently saturated or unsaturated;
and
with the proviso that if R1 is indolyl or indazolyl and R7 is H, F or Cl, then the indolyl or indazolyl of R1 is bound via its 5-membered ring to the remainder of the compound.

30 more elements

A compound selected from the group consisting of:

1 3,5,11,11-tetramethyl-6-(1-(methylsulfonyl)-1H-indol-4-yl)-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
2 6-(1-(ethylsulfonyl)-1H-indol-4-yl)-3,5,11,11-tetramethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
3 6-(5-chloro-2-methoxypyridin-3-yl)-3,5,11,11-tetramethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
4 2-(6-fluoro-4-(3,5,11,11-tetramethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxalin-6-yl)-1H-indol-1-yl) ethan-1-ol;
5 6-(1-(cyclopropylsulfonyl)-1H-indol-4-yl)-3,5,11,11-tetramethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
6 6-(1-(2,2-difluoroethyl)-1H-indol-4-yl)-3,5,11,11-tetramethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
7 6-(1-(isopropylsulfonyl)-1H-indol-4-yl)-3,5,11,11-tetramethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
8 3,5,11,11-tetramethyl-6-(3-methyl-1H-indol-7-yl)-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
9 6-(6-fluoro-1-(methylsulfonyl)-1H-indol-4-yl)-3,5,11,11-tetramethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
10 6-(1-(2,2-difluoroethyl)-1H-indol-4-yl)-3,11,11-trimethyl-5-(trifluoromethyl)-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
11 6-(1-(2,2-difluoroethyl)-6-fluoro-1H-indazol-4-yl)-3,11,11-trimethyl-5-(trifluoromethyl)-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
12 6-(6-fluoro-1-(methylsulfonyl)-1H-indol-4-yl)-3,11,11-trimethyl-5-(trifluoromethyl)-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
13 6-(3-cyclopropyl-5-fluoro-1H-indol-7-yl)-5-fluoro-3,11,11-trimethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
14 5-fluoro-6-(5-fluoro-3-methyl-1H-indol-7-yl)-3,11,11-trimethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
15 5-fluoro-3,11,11-trimethyl-6-(3-methyl-1H-indol-7-yl)-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
16 5-fluoro-6-(1H-indol-4-yl)-3,11,11-trimethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
17 5-fluoro-6-(6-fluoro-1-(methylsulfonyl)-1H-indol-4-yl)-3,11,11-trimethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
18 5-fluoro-6-(6-fluoro-1-methyl-1H-indol-4-yl)-3,11,11-trimethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
19 5-chloro-6-(1-(ethylsulfonyl)-1H-indol-4-yl)-3,11,11-trimethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
20 5-chloro-6-(1-(cyclopropylsulfonyl)-1H-indol-4-yl)-3,11,11-trimethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
21 5-chloro-6-(1-(2,2-difluoroethyl)-6-fluoro-1H-indazol-4-yl)-3,11,11-trimethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
22 5-chloro-6-(5-chloro-2-methoxypyridin-3-yl)-3,11,11-trimethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
23 5-chloro-6-(1-(2,2-difluoroethyl)-1H-indol-4-yl)-3,11,11-trimethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
24 5-chloro-6-(1-(isopropylsulfonyl)-1H-indol-4-yl)-3,11,11-trimethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
25 5-chloro-6-(4-fluoro-1H-indazol-6-yl)-3,11,11-trimethyl-8,9,10,11-tetrahydrofuro[3,2-f][1,2,4]triazolo[4,3-a]quinoxaline;
26 6-Ethyl-9-fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
27 8-(1-Cyclopropyl-6-fluoro-1H-indol-4-yl)-6-ethyl-9-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
28 6-Ethyl-9-fluoro-8-(1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
29 6-Ethyl-9-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
30 6-Ethyl-9-fluoro-8-(5-fluoro-3-tetrahydro-furan-3-yl-1H-indol-7-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
31 2-[7-(6-Ethyl-9-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-5-fluoro-1H-indol-3-yl]-ethanol;
32 6-Ethyl-9-fluoro-8-[2-methoxy-5-(trifluoromethyl)-pyridin-3-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
33 8-(6-Fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4,6-tetramethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
34 8-(5-Fluoro-3-prop-1-ynyl-1H-indol-7-yl)-1,4,4,6-tetramethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
35 2-[6-Fluoro-4-[1,4,4,6-tetramethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]-1H-indol-1-yl]-ethanol;
36 8-(1-Cyclopropyl-6-fluoro-1H-indol-4-yl)-9-fluoro-1,4,4,6-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
37 9-Fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4,6-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
38 9-Fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4,6-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
39 9-Fluoro-8-(1H-indol-4-yl)-1,4,4,6-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
40 4-[5-Fluoro-7-(9-fluoro-1,4,4,6-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-3-yl]-but-3-yn-2-ol;
41 9-Fluoro-1,4,4,6-tetramethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
42 9-Fluoro-8-(5-fluoro-3-prop-1-ynyl-1H-indol-7-yl)-1,4,4,6-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
43 4-[5-Fluoro-7-(9-fluoro-1,4,4,6-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-3-yl]-2-methyl-but-3-yn-2-ol;
44 8-(3-Cyclopropyl-5-fluoro-1H-indol-7-yl)-9-fluoro-1,4,4,6-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
45 9-Fluoro-1,4,4,6-tetramethyl-8-pyrazolo[1,5-a]pyridin-4-yl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
46 2-[5-Fluoro-7-(9-fluoro-1,4,4,6-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-3-yl]-ethanol;
47 2-[5-Fluoro-4-(9-fluoro-1,4,4,6-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-1-yl]-ethanol;
48 9-Fluoro-8-imidazo[1,2-a]pyridin-5-yl-1,4,4,6-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
49 5-fluoro-6-(5-fluoro-3-methyl-1H-indol-7-yl)-3,11,11-trimethyl-8,9,10,11-tetrahydro-7H-cyclopenta[f][1,2,4]triazolo[4,3-a]quinoxaline;
50 6-(1-cyclopropyl-6-fluoro-1H-indol-4-yl)-5-fluoro-3,11,11-trimethyl-8,9,10,11-tetrahydro-7H-cyclopenta[f][1,2,4]triazolo[4,3-a]quinoxaline;
51 5-fluoro-6-(6-fluoro-1-(methylsulfonyl)-1H-indol-4-yl)-3,11,11-trimethyl-8,9,10,11-tetrahydro-7H-cyclopenta[f][1,2,4]triazolo[4,3-a]quinoxaline;
52 5-fluoro-6-(5-fluoro-3-(tetrahydrofuran-3-yl)-1H-indol-7-yl)-3,11,11-trimethyl-8,9,10,11-tetrahydro-7H-cyclopenta[f][1,2,4]triazolo[4,3-a]quinoxaline;
53 9-Fluoro-8-(6-fluoro-1H-indol-4-yl)-1,4,4-trimethyl-6-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
54 9-Fluoro-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-6-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
55 9-Fluoro-8-[6-fluoro-1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4-trimethyl-6-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
56 9-Fluoro-1,4,4-trimethyl-8-(1H-pyrrolo[2,3-b]pyridin-4-yl)-6-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
57 8-[1-(2,2-Difluoro-ethyl)-6-fluoro-1H-indazol-4-yl]-9-fluoro-1,4,4-trimethyl-6-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
58 9-Fluoro-8-[6-fluoro-1-(2-methoxy-ethyl)-1H-indazol-4-yl]-1,4,4-trimethyl-6-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
59 8-(5-Fluoro-3-methyl-1H-indol-7-yl)-1,4,4,9-tetramethyl-6-methylsulfanyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
60 1,4,4,9-Tetramethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxalin-6-ol;
61 2-[9-Fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-6-yl]-propan-2-ol;
62 6-Fluoro-8-(6-fluoro-pyrazolo[1,5-a]pyridin-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
63 8-(5-Chloro-2-methoxy-pyridin-3-yl)-9-(difluoro-methyl)-7-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
64 7-Fluoro-1,4,4-trimethyl-8-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
65 8-(5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
66 8-(5-Chloro-2-methoxy-pyridin-3-yl)-9-cyclopropyl-7-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
67 7,9-Difluoro-1,4,4-trimethyl-8-naphthalen-1-yl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
68 8-(Benzofuran-4-yl)-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
69 7,9-Difluoro-8-(3-fluoro-5-vinyl-phenyl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
70 7,9-Difluoro-8-(3-fluoro-5-methyl-phenyl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
71 8-(5-Chloro-2-methoxy-pyridin-3-yl)-7-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
72 6-Fluoro-8-(6-fluoro-pyrazolo[1,5-a]pyridin-4-yl)-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
73 8-(5-Fluoro-1H-indol-1-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
74 8-(3-Ethyl-5-fluoro-phenyl)-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
75 8-(5-Chloro-2-methoxy-pyridin-3-yl)-9-(difluoro-methyl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
76 7-Chloro-8-(5-chloro-2-methoxy-pyridin-3-yl)-6-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
77 8-(1-Cyclopropyl-1H-indol-3-yl)-6-fluoro-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
78 7,9-Difluoro-8-(3-fluoro-5-methoxy-phenyl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
79 8-(5-Chloro-2-methoxy-pyridin-3-yl)-6,7-difluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
80 7-Fluoro-8-(5-fluoro-2-methoxy-pyridin-3-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
81 9-(Difluoro-methyl)-6-fluoro-1,4,4-trimethyl-8-pyrazolo[1,5-a]pyridin-4-yl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
82 6-Chloro-8-(5-chloro-2-methoxy-pyridin-3-yl)-7-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
83 8-(5-Chloro-2-methoxy-pyridin-3-yl)-1,4,4,9-tetramethyl-7-(trifluoromethyloxy)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
84 [3-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-5-fluoro-phenyl]-amine;
85 9-(Difluoro-methyl)-7-fluoro-1,4,4-trimethyl-8-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
86 7-Fluoro-8-(2-methoxy-5-methyl-pyridin-3-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
87 1-Ethyl-7,9-difluoro-4,4-dimethyl-8-[(3-pyridin-3-yl-pyrrolidin-1-yl)-methyl]-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
88 7,9-Difluoro-1,4,4-trimethyl-8-quinolin-5-yl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
89 8-(4-Fluoro-1H-indol-1-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
90 7,9-Difluoro-8-[2-methoxy-5-(trifluoromethyl)-pyridin-3-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
91 9-Ethyl-6-fluoro-1,4,4-trimethyl-8-pyrazolo[1,5-a]pyridin-4-yl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
92 7,9-Difluoro-1,4,4-trimethyl-8-pyrazolo[1,5-a]pyridin-3-yl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
93 1,4,4,9-Tetramethyl-8-(5-methyl-1H-indol-1-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
94 7-Fluoro-9-methoxy-1,4,4-trimethyl-8-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
95 8-(1H-Indol-1-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
96 7,9-Difluoro-8-(1H-indol-3-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
97 9-(Difluoro-methyl)-7-fluoro-8-(7-fluoro-1H-indol-3-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
98 5-(7-Fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1-methyl-3,4-dihydro-1H-quinolin-2-one;
99 7,9-Difluoro-1,4,4-trimethyl-8-(1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
100 7,9-Difluoro-8-(5-fluoro-spiro[1,2-dihydro-indole-3,1′-cyclopropane]-7-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
101 8-(5-Chloro-2-methoxy-pyridin-3-yl)-9-cyclopropyl-6-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
102 3-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-5-fluoro-phenol;
103 8-(5-Ethyl-2-methoxy-pyridin-3-yl)-7-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
104 8-(5-Cyclopropyl-2-methoxy-pyridin-3-yl)-7-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
105 7,9-Difluoro-1,4,4-trimethyl-8-(1H-pyrrolo[2,3-b]pyridin-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
106 8-(2,3-Dihydro-[1,4] benzodioxin-5-yl)-7-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
107 6-Fluoro-9-methoxy-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-3-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
108 1-[2-[4-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-pyrazol-1-yl]-ethyl]-pyrrolidin-2-one;
109 7,9-Difluoro-1,4,4-trimethyl-8-spiro[1,2-dihydro-indole-3,1′-cyclopropane]-7-yl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
110 4-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-6-fluoro-benzothiazole;
111 8-(1H-Benzotriazol-4-yl)-6-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
112 8-(1-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-fluoro-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
113 8-(3-Chloro-2-methoxy-phenyl)-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
114 4-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-2-fluoro-phenol;
115 5-(7-Fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-3,4-dihydro-1H-quinolin-2-one;
116 1-Cyclopropyl-6-fluoro-8-(6-fluoro-pyrazolo[1,5-a]pyridin-4-yl)-4,4,9-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
117 8-(5-Chloro-2-methoxy-pyridin-3-yl)-7-(difluoro-methyl)-9-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
118 8-(5-Chloro-2-methoxy-pyridin-3-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
119 7,9-Difluoro-1,4,4-trimethyl-8-(1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
120 1,4,4,9-Tetramethyl-8-(4-methyl-1H-indol-1-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
121 7,9-Difluoro-8-(2-fluoro-3-methoxy-phenyl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
and
122 7,9-Difluoro-N-[(3-methoxyphenyl)-methyl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxylic acid amide;
or a physiologically acceptable salt or stereoisomer thereof.

121 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/866,670Filed 18 Jul 2022 · continuation
Priority: EP 2015246517 Jan 2020
Published: US 2022/0396578 A115 Dec 2022
Granted: 29 Sep 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification4 codes

C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07D 491/147
Ortho-condensed systems: the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
C07D 519/00
Heterocyclic compounds containing more than one system of two or more relevant
C07D
Heterocyclic compounds

Family

PCT/EP2021/050840Parent of this continuation · filed 15 Jan 2021
US 2022/0396578 A1Pre-grant publication · published 15 Dec 2022
US 12,747,240 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound according to the following formula:

or a physiologically acceptable salt or stereoisomer thereof,
wherein:
R1 is C(O)NH—C1-6 alkylene-aryl, C3-10 cycloalkyl, 3- to 7-membered heterocycloalkyl, aryl, or 5- to 10-membered heteroaryl, wherein the C1-6 alkylene is linear or branched and is saturated or unsaturated;
R3 is H or C1-10 alkyl, wherein the C1-10 alkyl is linear or branched and is saturated or unsaturated;
R4 is H or C1-10 alkyl, wherein the C1-10 alkyl is linear or branched and is saturated or unsaturated;
R5 is F, Cl, Br, I, C1-10 alkyl, OC1-10 alkyl, or C3-10 cycloalkyl, wherein each C1-10 alkyl is independently linear or branched and is independently saturated or unsaturated;
R6 is H, F, Cl, Br, I, C1-10 alkyl, OC1-10 alkyl, or C3-10 cycloalkyl, wherein each C1-10 alkyl is independently linear or branched and is independently saturated or unsaturated;
R7 is H, F, Cl, Br, I, OH, C1-10 alkyl, SC1-10 alkyl, or C3-10 cycloalkyl, wherein each C1-10 alkyl is independently linear or branched and is independently saturated or unsaturated;
or R6 and R7, taken together with the carbon atoms to which they are attached, form a C3-10 cycloalkyl or 3- to 7-membered heterocycloalkyl;
and
R10 is C1-10 alkyl or C3-10 cycloalkyl, wherein the C1-10 alkyl is linear or branched and is saturated or unsaturated;
wherein each C1-10 alkyl, C1-6 alkylene, C3-10 cycloalkyl, and 3- to 7-membered heterocycloalkyl is optionally and independently substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, CN, C1-6 alkyl, CF3, CF2H, CFH2, CF2Cl, CFCl2, C(O)C1-6 alkyl, C(O)OH, C(O)OC1-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, OH, ═O, OCF3, OCF2H, OCFH2, OCF2Cl, OCFCl2, OC1-6 alkyl, OC(O)C1-6 alkyl, OC(O)OC1-6 alkyl, OC(O)NHC1-6 alkyl, OC(O)N(C1-6 alkyl)2, OS(O)2NH2, OS(O)2NHC1-6 alkyl, OS(O)2N(C1-6 alkyl)2, NH2, NHC1-6 alkyl, N(C1-6 alkyl)2, NHC(O)C1-6 alkyl, NHC(O)OC1-6 alkyl, NHC(O)NH2, NHC(O)NHC1-6 alkyl, NHC(O)N(C1-6 alkyl)2, N(C1-6 alkyl)-C(O)C1-6 alkyl, N(C1-6 alkyl)-C(O)OC1-6 alkyl, N(C1-6 alkyl)-C(O)NH2, N(C1-6 alkyl)-C(O)NHC1-6 alkyl, N(C1-6 alkyl)-C(O)N(C1-6 alkyl)2, NHS(O)2OH, NHS(O)2C1-6 alkyl, NHS(O)2OC1-6 alkyl, NHS(O)2NH2, NHS(O)2NHC1-6 alkyl, NHS(O)2N(C1-6 alkyl)2, N(C1-6 alkyl)-S(O)2OH, N(C1-6 alkyl)-S(O)2C1-6 alkyl, N(C1-6 alkyl)-S(O)2OC1-6 alkyl, N(C1-6 alkyl)-S(O)2NH2, N(C1-6 alkyl)-S(O)2NHC1-6 alkyl, N(C1-6 alkyl)-S(O)2N(C1-6 alkyl)2, SCF3, SCF2H, SCFH2, SC1-6 alkyl, S(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2OH, S(O)2OC1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, S(O)2N(C1-6 alkyl)2, C3-6 cycloalkyl, 3- to 7-membered heterocycloalkyl, phenyl, 5- or 6-membered heteroaryl, OC3-6 cycloalkyl, O(3- to 7-membered heterocycloalkyl), Ophenyl, O(5- or 6-membered heteroaryl), C(O)C3-6 cycloalkyl, C(O)(3- to 7-membered heterocycloalkyl), C(O)phenyl, C(O)(5- or 6-membered heteroaryl), S(O)2C3-6 cycloalkyl, S(O)2(3- to 7-membered heterocycloalkyl), S(O)2phenyl, and S(O)2(5- or 6-membered heteroaryl), wherein each C1-6 alkyl is independently linear or branched and is independently saturated or unsaturated;
wherein each aryl and 5- to 10-membered heteroaryl is optionally and independently substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, CN, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C2-6 alkynylene-CH(OH)CH3, C2-6 alkynylene-C(CH3)2OH, CF3, CF2H, CFH2, CF2C1, CFCl2, C1-6 alkylene-CF3, C1-6 alkylene-CF2H, C1-6 alkylene-CFH2, C1-6 alkylene-OH, C1-6 alkylene-OC1-6 alkyl, C(O)C1-6 alkyl, C(O)OH, C(O)OC1-6 alkyl, C(O)NHOH, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, OH, ═O, OCF3, OCF2H, OCFH2, OCF2Cl, OCFCl2, OC1-6 alkyl, OC3-6 cycloalkyl, O(3- to 7-membered heterocycloalkyl), NH2, NHC1-6 alkyl, N(C1-6 alkyl)2, NHC(O)C1-6 alkyl, N(C1-6 alkyl)-C(O)C1-6 alkyl, NHC(O)NH2, NHC(O)NHC1-6 alkyl, NHC(O)N(C1-6 alkyl)2, N(C1-6 alkyl)-C(O)NHC1-6 alkyl, N(C1-6 alkyl)-C(O)N(C1-6 alkyl)2, NHS(O)2C1-6 alkyl, SCF3, SC1-6 alkyl, S(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2C3-6 cycloalkyl, S(O)2—C1-6 alkylene-C3-6 cycloalkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, S(O)2N(C1-6 alkyl)2, C3-6 cycloalkyl, C1-6 alkylene-C3-6 cycloalkyl, 3- to 7-membered heterocycloalkyl;
C1-6 alkylene-(3- to 7-membered heterocycloalkyl), phenyl;
and 5- or 6-membered heteroaryl, wherein each C1-6 alkylene and C1-6 alkyl is independently linear or branched and is independently saturated or unsaturated;
with the proviso that if R1 is indolyl or indazolyl and R7 is H, F or Cl, then the indolyl or indazolyl of R1 is bound via its 5-membered ring to the remainder of the compound.

13 more elements

Facts

Application

17/866,670Filed 18 Jul 2022 · continuation

Priority

EP 2015246517 Jan 2020

Published

US 2022/0396578 A115 Dec 2022

Granted

29 Sep 2026

Term ends

Not estimatedThe source records don’t support an estimate.

Classification4 codes

C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07D 491/147
Ortho-condensed systems: the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
C07D 519/00
Heterocyclic compounds containing more than one system of two or more relevant
C07D
Heterocyclic compounds