US 11,746,112 B2
Pharmaceutically effective compounds inhibiting selectively the myosin 2 isoforms
András Málnási-Csizmadia, Budapest (HU); Maté Gyimesi, Budapest (HU); András Szabó, Budapest (HU); Péter Hári, Veresegyház (HU); Suthar Sharad Kumar, Budapest (HU); Mihály Kovács, Kecskemét (HU); Ádám István Horváth, Balatonfüred (HU); Máté Pénzes, Budapest (HU); István Lörincz, Budapest (HU); László Végner, Budapest (HU); Zoltán Simon, Oroszlány (HU); Sándor Bátori, Budapest (HU); Zoltán Szönyegi, Budapest (HU); Vajk Horváth, Budapest (HU); and József Répási, Érd (HU)
Assigned to EÖTVÖS LORÁND TUDOMÁNYEGYETEM, Budapest (HU); and PRINTNET KERESKEDELMI ÉS SZOLGÁLTATÓ KFT., Veresegyház (HU)
Appl. No. 17/48,206
Filed by PRINTNET KERESKEDELMI ÉS SZOLGÁLTATÓ KFT., Veresegyház (HU); and EÖTVÖS LORÁND TUDOMÁNYEGYETEM, Budapest (HU)
PCT Filed Apr. 18, 2019, PCT No. PCT/HU2019/050017
§ 371(c)(1), (2) Date Oct. 16, 2020,
PCT Pub. No. WO2019/202346, PCT Pub. Date Oct. 24, 2019.
Claims priority of application No. P1800129 (HU), filed on Apr. 18, 2018.
Prior Publication US 2021/0087201 A1, Mar. 25, 2021
Int. Cl. C07D 487/14 (2006.01)
CPC C07D 487/14 (2013.01) 23 Claims
 
1. A compound of formula (I) or (II), or a pharmaceutically acceptable salt, tautomer, or stereoisomer thereof:

OG Complex Work Unit Chemistry
wherein:
Q1, Q2, Q3 and Q4 are each independently selected from the group consisting of N and CH, wherein at least one of Q1, Q2, Q3 and Q4 is N;
Q5, Q6, and Q7 are each independently selected from the group consisting of S, O, N, NR20, and CR20, provided that the aromatic nature of the ring is retained and wherein at least one of Q5, Q6 and Q7 is S, O, N, or NR20,
R20 is H, C1-C6 alkyl, or haloalkyl;
R2, R3, R4, and R5 are individually selected from the group consisting of H, halogen, and C1-C6 alkyl;
R1 is H or a 5-, 6-, or 7-membered, saturated, partially saturated, unsaturated, or aromatic heterocyclic group containing one or more N, O, S atoms, and which may be substituted by one or more groups selected from:
C1-C12 straight chain alkyl;
C3-C12 branched chain alkyl;
C3-C12 cycloalkyl;
C2-12 straight chain alkenyl;
C3-C12 branched chain alkenyl;
C2-C12 straight chain alkynyl;
C3-C12 branched chain alkynyl;
—OH;
C1-C12 hydroxyalkyl;
C3-C12 hydroxycycloalkyl;
NH2;
C1-C12 alkylamino, C3-C12 cycloalkylamino, C1-C12 dialkylamino, wherein the amino group may be acylated with a C1-C6 straight chain carboxylic acid, a cyclic carboxylic acid, or an aromatic carboxylic acid, or sulfonylated with C1-C6 straight chain sulfonic acid, a cyclic sulfonic acid, or an aromatic sulfonic acid;
—NO2;
—CN;
C1-C12 alkylcyano;
C3-C12 cycloalkylcyano;
C1-C12 saturated carboxylic acid;
C1-C12 unsaturated carboxylic acid;
aromatic carboxylic acid;
C1-12 carboxylic acid amide formed with a saturated amine, unsaturated amine, or arylamine, wherein the carboxylic acid amide is a group according to formula —C(O)NH2, —C(O)NHR11 or —C(O)NR11R12;
C1-C12 alkoxy, C2-C12 alkenyloxy, C3-C12 alkynyloxy or C1-C12 alkoxyalkyl, wherein the alkyl, alkenyl, alkynyl, and alkoxy groups may be substituted by one or more halogen atoms;
F, Cl, Br, or I;
C1-C12 carboxylic acid ester formed with a saturated alcohol, unsaturated alcohol, or aryl alcohol;
C1-C12 alkylthio, C3-C12 cycloalkylthio, C2-C12 alkenylthio, C2-C12 alkynylthio or alkylthioalkyl, wherein the alkyl, cycloalkyl, alkenyl and alkynyl groups may be substituted with one or more halogen;
methanesulfonylaminomethyl;
trifluoromethanesulfonylamino;
N,N-dimethylaminocarbonylmethyl[CH2—CO—N(CH3)2];
acetyl; and
methanesulfonylamino;
R11 and R12 are each independently C1-C6 straight chain alkyl, C1-C6 branched chain alkyl, C3-C12 cycloalkyl, C2-C6 alkenyl, or C6-C12 aryl,
or R1 is:

OG Complex Work Unit Chemistry
R6 and R10 are H:
R7, R8, and R9 are each independently:
H;
a 5-, 6-, or 7-membered, saturated, partially saturated, unsaturated or aromatic heterocyclic group containing one or more N, O, S atoms, and which may be substituted by one or more groups selected from the group consisting of:
C1-C12 straight chain alkyl;
C3-C12 branched chain alkyl;
C3-C12 cycloalkyl;
C2-12 straight chain alkenyl;
C3-C12 branched chain alkenyl;
C2-C12 straight chain alkynyl;
C3-C12 branched chain alkynyl;
—OH;
C1-C12 hydroxyalkyl;
C3-C12 hydroxycycloalkyl;
NH2;
C1-C12 alkylamino, C3-C12 cycloalkylamino or C1-C12 dialkylamino, wherein the amino group may be acylated with a C1-C6 straight chain carboxylic acid, a cyclic carboxylic acid, or an aromatic carboxylic acid, or sulfonylated with C1-C6 straight chain sulfonic acid, a cyclic sulfonic acid, or an aromatic sulfonic acid;
—NO2;
—CN;
C1-C12 alkylcyano;
C3-C12 cycloalkylcyano;
C1-C12 saturated carboxylic acid;
C1-C12 unsaturated carboxylic acid;
aromatic carboxylic acid;
C1-12 carboxylic acid amide formed with a saturated amine, unsaturated amine, or arylamine, wherein the carboxylic acid amide is a group according to formula —C(O)NH2, —C(O)NHR11, or —C(O)NR11R12;
C1-C12 alkoxy, C2-C12 alkenyloxy, C3-C12 alkynyloxy or C1-C12 alkoxyalkyl, wherein the alkyl, alkenyl, alkynyl, and alkoxy groups may be substituted by one or more halogen atoms;
F, Cl, Br, or I;
C1-C12 carboxylic acid ester formed with a saturated alcohol, unsaturated alcohol, or aryl alcohol;
C1-C12 alkylthio, C3-C12 cycloalkylthio, C2-C12 alkenylthio, C2-C12 alkynylthio or alkylthioalkyl, wherein the alkyl, cycloalkyl, alkenyl and alkynyl groups may be substituted with one or more halogen;
methanesulfonylaminomethyl;
trifluoromethanesulfonylamino;
N,N-dimethylaminocarbonylmethyl [CH2—CO—N(CH3)2];
acetyl; and
methanesulfonylamino; or
any group selected from the group consisting of:
C1-C12 straight chain alkyl;
C3-C12 branched chain alkyl;
C3-C12 cycloalkyl;
C2-12 straight chain alkenyl;
C3-C12 branched chain alkenyl;
C2-C12 straight chain alkynyl;
C3-C12 branched chain alkynyl;
C1-C12 hydroxyalkyl;
C3-C12 hydroxycycloalkyl;
C3-C12 cycloalkylamino or C1-C12 dialkylamino;
—NO2;
—CN;
C1-C12 alkylcyano;
C3-C12 cycloalkylcyano;
aromatic carboxylic acid;
C1-12 carboxylic acid amide formed with a saturated amine, unsaturated amine, or arylamine, wherein the carboxylic acid amide is a group according to formula —C(O)NH2, —C(O)NHR11, or —C(O)NR11R12;
C1-C12 alkoxy, C2-C12 alkenyloxy, C3-C12 alkynyloxy or C1-C12 alkoxyalkyl, wherein the alkyl, alkenyl, alkynyl, and alkoxy groups may be substituted by one or more halogen atoms;
F, Cl, Br, or I;
C1-C12 carboxylic acid ester formed with a saturated alcohol, unsaturated alcohol, or aryl alcohol;
C1-C12 alkylthio, C3-C12 cycloalkylthio, C2-C12 alkenylthio, C2-C12 alkynylthio or alkylthioalkyl, wherein the alkyl, cycloalkyl, alkenyl and alkynyl groups may be substituted with one or more halogen;
methanesulfonylaminomethyl;
trifluoromethanesulfonylamino;
N,N-dimethylaminocarbonylmethyl [CH2—CO—N(CH3)2];
acetyl; and
methanesulfonylamino.