US 2026/0092074 A1Published application

Annelated Pyridines as Steroidogenesis Inhibitors, Preparation Method and Use Thereof

AssigneeGuangzhou Vinnocent Pharmaceutical Limited

InventorsQingzhong Hu, Lina Yin, Haiyan Li

Life of this patent

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Abstract

Provided is a small-molecule steroid synthetase inhibitor. Further provided is use of the steroid synthetase inhibitors.

Claims27

Dependent claims

A compound of formula (I):

wherein:
n is 0, 1, or 2;
m is 0 or 1;
X is C, N, O, or S;
is a single bond or a double bond;
L1 is selected from the group consisting of hydrogen, —SO2—, —CO—, and —CH2—, when X is N, O, or S, and is a single bond or a double bond;
L1 is —CO—, when X is C, and is a single bond;
L1 is selected from the group consisting of —SO2—, and —CO—, when X is C, and is a double bond;
means that one or more carbon atoms are replaced by carbonyl groups or not;
R11 is selected from the group consisting of aryl, heteroaryl, spirocycloalkyl, azaspirocycloalkyl, oxaspirocycloalkyl, bicycloalkyl, azacycloalkyl, and azacyclic ketone;
said aryl, heteroaryl, spirocycloalkyl, bicycloalkyl, azacycloalkyl, and azacyclic ketone are optionally substituted with one or more substituents selected from halogen, cyano, acyl, nitro, alkoxy, alkoxycarbonyl, amino, sulfonyl, carboxy, sulfoximine, trifluoromethyl, hydroxyl, amide, urea, thioether, sulfuryl fluoride, boronate ester, cyclic ether, and alkyl optionally substituted with one to three halogens;
alternatively, R11 is of the following structure:
R12 is selected from the group consisting of hydrogen, alkyl, azacycloalkyl, bicyclic hydrocarbyl, spirocycloalkyl, azaspirocycloalkyl, oxaspirocycloalkyl, aryl, heteroaryl, and absent;
said alkyl, aryl, and heteroaryl are optionally substituted with one or more substituents selected from halogen, cyano, acyl, nitro, alkoxy, alkoxycarbonyl, amino, sulfonyl, carboxy, sulfoximine, trifluoromethyl, hydroxyl, amide, urea, thioether, sulfuryl fluoride, boronate ester, cyclic ether, and alkyl optionally substituted with one to three halogens;
said azacycloalkyl, bicyclic hydrocarbyl, and spirocycloalkyl are optionally substituted with cyano, fluorophenyl, fluorophenylalkyl, or fluorophenylamino;
alternatively, R12 is selected from the following structures:
wherein q1 and q2 are each independently selected from 1, 2, and 3;
R13 is selected from the group consisting of hydrogen, cyano, cyclic ether, and -L2-R14, where L2 is selected from —SO2—, —CO—, hydrocarbyl, or absent;
R14 is selected from aryl and heteroaryl, said aryl and heteroaryl are optionally substituted with one to three substituents selected from halogen, cyano, acyl, nitro, alkoxy, alkoxycarbonyl, amino, sulfonyl, carboxyl, sulfoximino, trifluoromethyl, hydroxyl, amido, ureido, thioether, sulfonyl fluoride, and boronate ester.

16 more elements

A compound selected from any of the following compounds:

4-(4-(phenylsulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O1);
4-(4-((4-fluorophenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O2);
4-(4-((3-fluorophenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O3);
4-(4-tosyl-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O4);
4-(4-(m-tolylsulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O5);
4-(4-((4-chlorophenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O6);
4-(4-((3-chlorophenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O7);
4-(4-((4-methoxyphenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O8);
4-(4-((4-nitrophenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O9);
4-(4-((3-nitrophenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O10);
4-(4-((4-(trifluoromethyl)phenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O11);
4-(4-((3-(trifluoromethyl)phenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O12);
4-(4-(pyridin-3-ylsulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O13);
4-(4-(methylsulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O14);
4-(4-(quinolin-8-ylsulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O15);
4-(4-(thiophen-2-ylsulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O16);
4-(4-(naphthalen-1-ylsulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O17);
4-(4-(naphthalen-2-ylsulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O18);
4-(4-(4-fluorobenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O19);
4-(4-(3-fluorobenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O20);
4-(4-(2-fluorobenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O21);
4-(4-(4-methoxybenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O22);
4-(4-(3-methoxybenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O23);
4-(4-(4-(trifluoromethyl)benzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O24);
4-(4-(3-(trifluoromethyl)benzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O25);
4-(4-(4-nitrobenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O26);
4-(4-(3-nitrobenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O27);
4-(4-(4-chlorobenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O28);
4-(4-(3-chlorobenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O29);
4-(4-nicotinoyl-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O30);
4-(4-(furan-2-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O31);
4-(4-(2-cyanoacetyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O32);
4-(4-(2-chloroacetyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O33);
4-(4-(2-bromoacetyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O34);
4-(4-(2,2,2-trifluoroacetyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O35);
4-(4-(2-(4-fluorophenyl)acetyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O36);
4-(4-(2-(3-fluorophenyl)acetyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O37);
4-(4-(2-(4-chlorophenyl)acetyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O38);
4-(4-(2-(3-chlorophenyl)acetyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O39);
4-(4-(2-(4-methoxyphenyl)acetyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O40);
4-(4-(2-(3-methoxyphenyl)acetyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O41);
4-(4-(2-(p-tolyl)acetyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O42);
4-(4-(2-(m-tolyl)acetyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O43);
4-(4-(2-(o-tolyl)acetyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O44);
4-(4-(2-(4-(trifluoromethyl)phenyl)acetyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O45);
4-(4-(2-(3-(trifluoromethyl)phenyl)acetyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O46);
4-(4-(3-(4-fluorophenyl)propanoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O47);
4-(4-(3-(3-fluorophenyl)propanoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O48);
4-(4-(3-(4-chlorophenyl)propanoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O49);
4-(4-(3-(3-chlorophenyl)propanoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O50);
4-(4-(3-(4-methoxyphenyl)propanoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O51);
4-(4-(3-(3-methoxyphenyl)propanoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O52);
4-(4-(3-(4-(trifluoromethyl)phenyl)propanoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O53);
4-(4-(3-(3-(trifluoromethyl)phenyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O54);
4-(4-(1-((3-fluorophenyl)sulfonyl)piperidine-4-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O55);
4-(4-(azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O56);
4-(4-(1-(4-fluorobenzoyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O57);
4-(4-(1-(3-fluorobenzoyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O58);
N-(2-(8-(4-cyanophenyl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]oxazin-4-yl)-2-oxoethyl)-4-fluorobenzamide (O59);
4-(4-(1-((4-fluorophenyl)sulfonyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O60);
4-(4-(1-((3-fluorophenyl)sulfonyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O61);
4-(4-(1-((4-nitrophenyl)sulfonyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O62);
4-(4-(1-((3-nitrophenyl)sulfonyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O63);
4-(4-(1-(thiophen-2-ylsulfonyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O64);
4-(4-(1-tosylazetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O65);
4-(4-(1-((3-methoxyphenyl)sulfonyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]-oxazin-8-yl)benzonitrile (O66);
4-(4-(1-((4-methoxyphenyl)sulfonyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]-oxazin-8-yl)benzonitrile (O67);
3-((3-(8-(4-cyanophenyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine-4-carbonyl)azetidin-1-yl)-sulfonyl)benzonitrile (O68);
4-((3-(8-(4-cyanophenyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine-4-carbonyl)azetidin-1-yl)-sulfonyl)benzonitrile (O69);
4-(4-(1-(m-tolylsulfonyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O70);
4-(4-(3-((3-fluorophenyl)amino)bicyclo[1.1.1]pentane-1-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O71);
4-(4-(5-(4-fluorophenoxy)thiophene-2-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O72);
4-(4-(6-(3-fluorobenzyl)-2,6-diazaspiro[3.3]heptane-2-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O73);
3-((3-(8-(4-cyanophenyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine-4-carbonyl)azetidin-1-yl)-sulfonyl)benzonitrile (O74);
4-((3-(8-(4-cyanophenyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine-4-carbonyl)azetidin-1-yl)-sulfonyl)benzonitrile (O75);
4-(4-(1-(3-methoxybenzoyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O76);
4-(4-(1-(4-methoxybenzoyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O77);
4-(4-(1-(3-fluorobenzyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O78);
4-(4-(1-(4-fluorobenzyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O79);
3-((3-(8-(4-cyanophenyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine-4-carbonyl)azetidin-1-yl)-methyl)benzonitrile (O80);
4-(4-(1-(4-cyanobenzyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O81);
4-(4-(1-(3-methoxybenzyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O82);
4-(4-(1-(4-methoxybenzyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O83);
4-(4-(1-(3-fluorophenyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O84);
4-(4-(1-(4-fluorophenyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O85);
3-(3-(8-(4-cyanophenyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine-4-carbonyl)azetidin-1-yl)-benzonitrile (O86);
4-(3-(8-(4-cyanophenyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine-4-carbonyl)azetidin-1-yl)-benzonitrile (O87);
(8-(benzo[d]thiazol-6-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]oxazin-4-yl)(1-(3-fluorobenzyl)-azetidin-3-yl)methanone (O88);
5-(4-(1-(3-fluorobenzyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-indolin-2-one (O89);
(1-(3-fluorobenzyl)azetidin-3-yl)(8-(imidazo[1,2-a]pyridin-6-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]oxazin-4-yl)methanone (O90);
(8-(6-chloro-1H-indol-2-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]oxazin-4-yl)(1-(3-fluorobenzyl)-azetidin-3-yl)methanone (O91);
2-(4-(1-(3-fluorobenzyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-1H-indole-6-carbonitrile (O92);
(8-(6-fluoro-1H-indol-2-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]oxazin-4-yl)(1-(3-fluorobenzyl)-azetidin-3-yl)methanone (O93);
2-(4-(1-(3-fluorobenzyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-1H-indole-5-carbonitrile (O94);
(8-(5-chlorobenzofuran-2-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]oxazin-4-yl)(1-(3-fluorobenzyl)-azetidin-3-yl)methanone (O95);
2-(4-(1-(3-fluorobenzyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzofuran-5-carbonitrile (O96);
4-(4-(1-(3-fluorobenzyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-3,6-dihydropyridine-1 (2H)-carbonitrile (O97);
4-(4-(1-(3-fluorobenzyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-piperazine-1-carbonitrile (O98);
4-(4-(1-(3-fluorobenzyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-3-oxopiperazine-1-carbonitrile (O99);
4-(4-((3-(3-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O100);
3-(5-((8-(4-cyanophenyl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]oxazin-4-yl)sulfonyl)-4,5-dihydro-isoxazol-3-yl)benzonitrile (O101);
4-(4-((3-phenyl-4,5-dihydroisoxazol-5-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O102);
4-(4-((3-benzyl-4,5-dihydroisoxazol-5-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O103);
(S)-4-(4-(1-(3-fluorobenzyl)pyrrolidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O104);
(R)-4-(4-(1-(3-fluorobenzyl)pyrrolidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O105);
2-(4-((S)-1-(3-fluorobenzyl)pyrrolidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-2,3-dihydrobenzofuran-5-carbonitrile (O106);
2-(4-((R)-1-(3-fluorobenzyl)pyrrolidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-2,3-dihydrobenzofuran-5-carbonitrile (O107);
8-(5-chlorobenzofuran-2-yl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (O108);
2-(3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzofuran-5-carbonitrile (O109);
4-(4-((1-(3-cyanobenzoyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (OI10);
4-(4-((1-(4-cyanobenzoyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (OI11);
4-(4-((1-(3-methoxybenzoyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O112);
4-(4-((1-(4-methoxybenzoyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzonitrile (O113);
4-((3-((8-(4-cyanophenyl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]oxazin-4-yl)sulfonyl)azetidin-1-yl)-sulfonyl)benzonitrile (O114);
3-((3-((8-(4-cyanophenyl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]oxazin-4-yl)sulfonyl)azetidin-1-yl)-sulfonyl)benzonitrile (O115);
4-(4-((1-((4-fluorophenyl)sulfonyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]-oxazin-8-yl)benzonitrile (O116);
4-(4-((1-((3-fluorophenyl)sulfonyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]-oxazin-8-yl)benzonitrile (O117);
4-(4-((1-((4-methoxyphenyl)sulfonyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]-oxazin-8-yl)benzonitrile (O118);
4-(4-((1-((3-methoxyphenyl)sulfonyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]-oxazin-8-yl)benzonitrile (O119);
3-((3-((8-(4-cyanophenyl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]oxazin-4-yl)sulfonyl)azetidin-1-yl)-methyl)benzonitrile (O120);
4-(4-((1-(4-cyanobenzyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O121);
4-(4-((1-(3-fluorobenzyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O122);
4-(4-((1-(4-fluorobenzyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O123);
4-(4-((1-(3-methoxybenzyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O124);
4-(4-((1-(4-methoxybenzyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O125);
4-(4-((1-(3-fluorophenyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O126);
4-(4-((1-(4-fluorophenyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O127);
4-((8-(5-chlorobenzofuran-2-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]oxazin-4-yl)sulfonyl)-benzonitrile (O128);
2-(4-((4-cyanophenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)benzofuran-5-carbonitril (O129);
4-((8-(4-cyanophenyl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]oxazin-4-yl)sulfonyl)benzonitrile (O130);
4-((8-(benzo[d]oxazol-6-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]oxazin-4-yl)sulfonyl)benzonitrile (O131);
4-((8-(2-oxoindolin-6-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]oxazin-4-yl)sulfonyl)benzonitrile (O132);
3-(4-(1-(3-Fluorobenzyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-bicyclo[1.1.1]pentane-1-carbonitrile (O133);
6-(4-(1-(3-Fluorobenzyl)azetidine-3-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-2,6-diazaspiro[3.3]heptane-2-carbonitrile (O134);
(8-(5,6-Dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7 (8H)-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]oxazin-4-yl)(1-(3-fluorobenzyl)azetidin-3-yl)methanone (O135);
4-(4-(3-(3-fluorobenzyl)azetidine-1-carbonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazin-8-yl)-benzonitrile (O136);
(8-(5,6-dihydroimidazo[1,2-a]pyrazin-7 (8H)-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]oxazin-4-yl)(1-(3-fluorobenzyl)azetidin-3-yl)methanone (O137);
4-(4-(3-fluorobenzyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S1);
4-(4-(4-fluorobenzyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S2);
4-(4-(3-nitrobenzyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S3);
4-(4-(3-fluorobenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S4);
4-(4-(4-fluorobenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S5);
4-(4-(4-methoxybenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S6);
4-(4-nicotinoyl-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S7);
4-(4-(phenylsulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S8);
4-(4-((3-fluorophenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S9);
4-(4-((4-fluorophenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S10);
4-(4-(m-tolylsulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S11);
4-(4-tosyl-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S12);
4-(4-((4-methoxyphenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S13);
4-(4-((3-chlorophenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S14);
4-(4-((4-chlorophenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S15);
4-(4-((3-(trifluoromethyl)phenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl) benzonitrile (S16);
4-(4-((4-(trifluoromethyl)phenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)-benzonitrile (S17);
4-(4-((3-nitrophenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S18);
4-(4-((4-nitrophenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S19);
3-((8-(4-cyanophenyl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)benzonitrile (S20);
4-((8-(4-cyanophenyl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)benzonitrile (S21);
4-(4-(naphthalen-1-ylsulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S22);
4-(4-(naphthalen-2-ylsulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S23);
4-(4-(thiophen-2-ylsulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S24);
4-(4-(pyridin-3-ylsulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S25);
4-(4-(quinolin-8-ylsulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S26);
3-(4-((4-methoxyphenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S27);
8-(4-chlorophenyl)-4-((4-methoxyphenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S28);
8-(3-chlorophenyl)-4-((4-methoxyphenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S29);
8-(4-fluorophenyl)-4-((4-methoxyphenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S30)
8-(3-fluorophenyl)-4-((4-methoxyphenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S31);
4-((4-methoxyphenyl) sulfonyl)-8-(4-(trifluoromethyl)phenyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S32);
8-(4-fluoro-3-methylphenyl)-4-((4-methoxyphenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]-thiazine (S33);
8-(3-chloro-4-fluorophenyl)-4-((4-methoxyphenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]-thiazine (S34);
2-fluoro-4-(4-((4-methoxyphenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)-benzonitrile (S35);
4-((4-methoxyphenyl) sulfonyl)-8-(thiophen-3-yl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S36);
4-((4-methoxyphenyl) sulfonyl)-8-(thiophen-2-yl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S37);
8-(furan-2-yl)-4-((4-methoxyphenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S38);
4-((4-methoxyphenyl)sulfonyl)-8-(1H-pyrazol-4-yl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S39);
4-((8-(benzofuran-2-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)benzonitrile (S40);
4-((8-(5-chlorobenzofuran-2-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)-benzonitrile (S41);
2-(4-((4-cyanophenyl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzofuran-5-carbonitrile (S42);
4-((8-(benzo[b]thiophen-2-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)benzonitrile (S43);
4-((8-(benzofuran-5-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)benzonitrile (S44);
4-((8-(1-methyl-1H-indazol-6-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)-benzonitrile (S45);
4-((8-(benzo[d]thiazol-6-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)benzonitrile (S46);
4-((8-(benzo[d]oxazol-6-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)benzonitrile (47);
4-((8-(1H-indazol-5-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)benzonitrile (S48);
4-((8-(1H-benzo[d]imidazol-6-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)-benzonitrile (S49);
4-((8-(imidazo[1,2-a]pyridin-7-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)-benzonitrile (S50);
4-((8-(2-oxoindolin-5-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)benzonitrile (S51);
4-((8-(8-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)benzonitrile (S52);
8-(5-Chlorobenzofuran-2-yl)-4-((6-methoxypyridin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S53);
5-((8-(5-chlorobenzofuran-2-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)pyridin-2-ol (S54);
8-(5-Chlorobenzofuran-2-yl)-4-((1-methyl-1H-pyrazol-4-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S55);
8-(5-chlorobenzofuran-2-yl)-4-((1-methyl-1H-pyrazol-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S56);
N-(5-((8-(5-Chlorobenzofuran-2-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)-4-methylthiazol-2-yl)acetamide (S57);
1-(5-((8-(5-Chlorobenzofuran-2-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)indolin-1-yl)ethan-1-one (S58);
6-((8-(5-Chlorobenzofuran-2-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)-2H-benzo[b][1,4]oxazin-3 (4H)-one (S59);
8-(5-Chlorobenzofuran-2-yl)-4-((5-chlorothiophen-2-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S60);
8-(5-Chlorobenzofuran-2-yl)-4-(piperidin-4-ylsulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S61);
4-(Azetidin-3-ylsulfonyl)-8-(5-chlorobenzofuran-2-yl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S62);
4-((8-(5-Chlorobenzofuran-2-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)piperidine-1-carbonitrile (S63);
3-((8-(5-Chlorobenzofuran-2-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)azetidine-1-carbonitrile (S64);
3-((8-(5-chlorobenzofuran-2-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)bicyclo[1.1.1]pentane-1-carbonitrile (S65);
4-((2-oxaspiro[3.3]heptan-6-yl)sulfonyl)-8-(5-chlorobenzofuran-2-yl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S66);
6-((8-(5-chlorobenzofuran-2-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)-2-azaspiro[3.3]heptane-2-carbonitrile (S67);
4-(4-((1-(4-fluorobenzoyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)-benzonitrile (S68);
4-(4-((1-(3-fluorobenzoyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)-benzonitrile (S69);
4-(4-((1-(4-cyanobenzoyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)-benzonitrile (S70);
3-(3-((8-(4-cyanophenyl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)azetidine-1-carbonyl)benzonitrile (S71);
4-(4-((1-(4-methoxybenzoyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S72);
4-(4-((1-(3-methoxybenzoyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S73);
4-(4-((1-((4-fluorophenyl)sulfonyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S74);
4-(4-((1-((3-fluorophenyl)sulfonyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S75);
4-((3-((8-(4-cyanophenyl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)azetidin-1-yl)-sulfonyl)benzonitrile (S76);
3-((3-((8-(4-cyanophenyl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)azetidin-1-yl)-sulfonyl)benzonitrile (S77);
4-(4-((1-((4-methoxyphenyl)sulfonyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]-thiazin-8-yl)benzonitrile (S78);
4-(4-((1-((3-methoxyphenyl)sulfonyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]-thiazin-8-yl)benzonitrile (S79);
4-(4-((1-(4-cyanobenzyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)-benzonitrile (S80);
3-((3-((8-(4-cyanophenyl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)azetidin-1-yl)-methyl)benzonitrile (S81);
4-(4-((1-(4-fluorobenzyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)-benzonitrile (S82);
4-(4-((1-(3-fluorobenzyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)-benzonitrile (S83);
4-(4-((1-(4-methoxybenzyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)-benzonitrile (S84);
4-(4-((1-(3-methoxybenzyl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)-benzonitrile (S85);
N-(2-(8-(4-cyanophenyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine-4-carbonyl)phenyl)acetamide (S86);
4-(4-(3-(trifluoromethyl)benzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S87);
4-(4-(4-(trifluoromethyl)benzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S88);
4-(4-(4-methylbenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S89);
4-(4-(2-methylbenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S90);
4-(4-(3-methylbenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S91);
4-(4-(4-chlorobenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S92);
4-(4-(3-chlorobenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S93);
4-(4-(4-cyanobenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S94);
3-(8-(4-cyanophenyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine-4-carbonyl)benzonitrile (S95);
4-(4-(3-methoxybenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S96);
4-(4-(4-methoxybenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S97);
2-(4-(4-methoxybenzoyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzofuran-5-carbonitrile (S98);
4-(3-oxo-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S99);
4-(4-(4-chlorobenzoyl)-3-oxo-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazin-8-yl)benzonitrile (S100);
1-((8-(5-Chlorobenzofuran-2-yl)-2,3-dihydro-4H-pyrido[4,3-b][1,4]thiazin-4-yl)sulfonyl)azetidine-3-carbonitrile (S101);
8-(5-Chlorobenzofuran-2-yl)-4-((5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7 (8H)-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S102);
8-(5-Chlorobenzofuran-2-yl)-4-((1-(oxetan-3-yl)azetidin-3-yl)sulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]thiazine (S103);
4-(1-tosyl-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C1);
4-(1-((4-nitrophenyl) sulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C2);
4-(1-((4-methoxyphenyl)sulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C3);
4-(1-((4-(trifluoromethyl)phenyl)sulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C4);
4-(1-((6-chloropyridin-3-yl)sulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C5);
4-(1-((3-fluorophenyl)sulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C6);
4-(1-((4-fluorophenyl)sulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C7);
4-(1-(m-tolylsulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C8);
4-(1-((3-nitrophenyl)sulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C9);
4-(1-(pyridin-3-ylsulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C10);
4-(1-(quinolin-8-ylsulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C11);
4-(1-(naphthalen-2-ylsulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C12);
4-(1-((4-chlorophenyl)sulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C13);
4-(1-((3-chlorophenyl)sulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C14);
4-((4-(4-cyanophenyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)sulfonyl)benzonitrile (C15);
3-((4-(4-cyanophenyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)sulfonyl)benzonitrile (C16);
4-(1-(thiophen-2-ylsulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C17);
4-(1-(naphthalen-1-ylsulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C18);
4-(1-((3-methoxyphenyl)sulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C19);
4-(1-((3-[trifluoromethyl]phenyl)sulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C20);
4-(1-(phenylsulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C21);
4-(1-(4-(trifluoromethyl)benzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C22);
4-(1-(3-(trifluoromethyl)benzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C23);
4-(1-(4-methoxybenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C24);
4-(1-(4-fluorobenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C25);
4-(1-(3-methoxybenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C26);
4-(1-(3-nitrobenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C27);
4-(1-(3-fluorobenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C28);
4-(1-nicotinoyl-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C29);
4-(1-(4-nitrobenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C30);
4-(1-(2-fluorobenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C31);
4-(1-(2-(trifluoromethyl)benzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C32);
4-(1-(4-methylbenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C33);
4-(1-(2-methoxybenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C34);
4-(1-(2-nitrobenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C35);
4-(1-(2-methylbenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C36);
3-(4-(4-cyanophenyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine-1-carbonyl)benzonitrile (C37);
4-(1-(4-chlorobenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C38);
4-(1-(3-chlorobenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C39);
4-(1-(3-methylbenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C40);
4-(1-benzoyl-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C41);
4-(1-pivaloyl-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C42);
4-(1-(2-chloroacetyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C43);
4-(1-(furan-2-carbonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C44);
4-(1-(3-methylthiophene-2-carbonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C45);
4-(1-(thiophene-2-carbonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C46);
Methyl 4-(4-(4-cyanophenyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine-1-carbonyl)benzoate (C47);
4-(1-(4-cyanobenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C48);
4-(1-(4-(bromomethyl)benzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C49);
(4-(1H-indazol-5-yl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)(2-fluorophenyl)methanone (C50);
(2-fluorophenyl)(4-(1-methyl-1H-indazol-5-yl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)-methanone (C51);
(2-fluorophenyl)(4-(3-fluorophenyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)methanone (C52);
(2-fluorophenyl)(4-(3-nitrophenyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)methanone (C53);
(4-(4-chlorophenyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)(2-fluorophenyl)methanone (C54);
3-(1-(2-fluorobenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C55);
(2-fluorophenyl)(4-(furan-3-yl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)methanone (C56);
(2-fluorophenyl)(4-(imidazo[1,2-a]pyridin-6-yl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)-methanone (C57);
(4-(benzo[d]thiazol-6-yl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)(2-fluorophenyl)methanone (C58);
(4-(1H-indol-2-yl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)(2-fluorophenyl)methanone (C59);
(4-(benzofuran-2-yl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)(2-fluorophenyl)methanone (C60);
(4-(benzo[b]thiophen-2-yl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)(2-fluorophenyl)methanone (C61);
(4-(1H-indol-5-yl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)(2-fluorophenyl)methanone (C62);
(4-(benzofuran-5-yl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)(2-fluorophenyl)methanone (C63);
4-(1-(2-(o-tolyl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C64);
4-(1-(2-(2-bromophenyl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C65);
4-(1-(2-(m-tolyl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C66);
4-(1-(2-(2-fluorophenyl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C67);
4-(1-(2-(3-methoxyphenyl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C68);
4-(1-(2-(4-fluorophenyl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C69);
4-(1-(2-(2-nitrophenyl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C70);
4-(1-(2-(3-chlorophenyl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C71);
4-(1-(2-(p-tolyl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C72);
4-(1-(2-(4-bromophenyl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C73);
4-(1-(2-(3-(trifluoromethyl)phenyl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C74);
4-(1-(2-(4-(trifluoromethyl)phenyl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C75);
4-(1-(2-(4-methoxyphenyl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C76);
4-(1-(2-(4-chlorophenyl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (C77);
4-((4-(5-chlorobenzofuran-2-yl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)sulfonyl)benzonitrile (C78);
2-(1-(4-methoxybenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzofuran-5-carbonitrile (C79);
(4-(5-chloro-1H-indol-2-yl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)(1-(3-fluorobenzyl)azetidin-3-yl)methanone (C80);
2-(1-(1-(3-fluorobenzyl)azetidine-3-carbonyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-1H-indole-5-carbonitrile (C81);
4-(1-(3-methoxybenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-3,6-dihydropyridine-1 (2H)-carbonitrile (C82);
4-(1-(3-methoxybenzoyl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)piperazine-1-carbonitrile (C83);
4-(1-((4-nitrophenyl)sulfonyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E1);
4-(1-tosyl-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E2);
4-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E3);
4-(1-(m-tolylsulfonyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E4);
4-(1-((3-(trifluoromethyl)phenyl)sulfonyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E5);
4-(1-((4-fluorophenyl)sulfonyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E6);
4-(1-((4-(trifluoromethyl)phenyl)sulfonyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E7);
4-(1-((4-chlorophenyl)sulfonyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E8);
4-(1-((4-methoxyphenyl)sulfonyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E9);
3-((4-(4-cyanophenyl)-1H-pyrrolo[2,3-c]pyridin-1-yl)sulfonyl)benzonitrile (E10);
4-(1-((3-chlorophenyl)sulfonyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E11);
4-(1-((3-fluorophenyl)sulfonyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E12);
4-(1-((3-nitrophenyl)sulfonyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E13);
4-((4-(4-cyanophenyl)-1H-pyrrolo[2,3-c]pyridin-1-yl)sulfonyl)benzonitrile (E14);
4-(1-(naphthalen-1-ylsulfonyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E15);
4-(1-(naphthalen-2-ylsulfonyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E16);
4-(1-(thiophen-2-ylsulfonyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E17);
4-(1-((6-chloropyridin-3-yl)sulfonyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E18);
4-(1-(perfluorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E19);
4-(1-(4-(trifluoromethyl)benzoyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E20);
4-(1-(2-iodobenzoyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E21);
4-(1-(3-nitrobenzoyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E22);
4-(1-(3-(trifluoromethyl)benzoyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E23);
4-(1-(3-methoxybenzoyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E24);
4-(1-(2-methoxybenzoyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E25);
4-(1-(2-(trifluoromethyl)benzoyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E26);
4-(1-(2-methylbenzoyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E27);
4-(1-(2-fluorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E28);
4-(1-(2-nitrobenzoyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E29);
4-(1-(4-fluorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile (E30);
(4-(benzo[b]thiophen-2-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)(4-fluorophenyl)methanone (E31);
(4-(benzofuran-2-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)(4-fluorophenyl)methanone (E32);
(4-(benzofuran-5-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)(4-fluorophenyl)methanone (E33);
(4-(1H-indol-2-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)(4-fluorophenyl)methanone (E34);
(4-fluorophenyl)(4-(1-methyl-1H-indazol-6-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)methanone (E35);
(4-(benzo[d]thiazol-6-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)(4-fluorophenyl)methanone (E36);
(4-fluorophenyl)(4-(imidazo[1,2-a]pyridin-6-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)methanone (E37);
(4-(benzo[d]oxazol-6-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)(4-fluorophenyl)methanone (E38);
(4-fluorophenyl)(4-(imidazo[1,2-a]pyridin-7-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)methanone (E39);
4-(1-Methyl-2,3-dioxo-1,2,3,4-tetrahydropyrido[3,4-b]pyrazin-8-yl)benzonitrile (N1);
8-(4-Fluorophenyl)-1-methyl-1,4-dihydropyrido[3,4-b]pyrazine-2,3-dione (N2);
4-(1-Methyl-1,2,3,4-tetrahydropyrido[3,4-b]pyrazin-8-yl)benzonitrile (N3);
4-((8-(4-Cyanophenyl)-1-methyl-2,3-dihydropyrido[3,4-b]pyrazin-4 (1H)-yl)sulfonyl)benzonitrile (N4);
4-(4-(4-Fluorobenzoyl)-1-methyl-1,2,3,4-tetrahydropyrido[3,4-b]pyrazin-8-yl)benzonitrile (N5);
4-(1-Methyl-1H-imidazo[4,5-c]pyridin-7-yl)benzonitrile (N6);
4-(1-Cyclopropyl-1H-imidazo[4,5-c]pyridin-7-yl)benzonitrile (N7).

366 more elements

Dependencies are inferred from the claim text.

Facts

Application: 19/113,669Filed 25 Sep 2023
Priority: CN 202211162092.423 Sep 2022
Published: 2 Apr 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification15 codes

A61P 9/00
Drugs for disorders of the cardiovascular system
C07D 519/00
Heterocyclic compounds containing more than one system of two or more relevant
A61K 31/437
Ortho- or peri-condensed with heterocyclic ring systems: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring…
A61K 31/444
Containing further heterocyclic ring systems: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone

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A compound of formula (I):

wherein:
n is 0, 1, or 2;
m is 0 or 1;
X is C, N, O, or S;
is a single bond or a double bond;
L1 is selected from the group consisting of hydrogen, —SO2—, —CO—, and —CH2—, when X is N, O, or S, and is a single bond or a double bond;
L1 is —CO—, when X is C, and is a single bond;
L1 is selected from the group consisting of —SO2—, and —CO—, when X is C, and is a double bond;
means that one or more carbon atoms are replaced by carbonyl groups or not;
R11 is selected from the group consisting of aryl, heteroaryl, spirocycloalkyl, azaspirocycloalkyl, oxaspirocycloalkyl, bicycloalkyl, azacycloalkyl, and azacyclic ketone;
said aryl, heteroaryl, spirocycloalkyl, bicycloalkyl, azacycloalkyl, and azacyclic ketone are optionally substituted with one or more substituents selected from halogen, cyano, acyl, nitro, alkoxy, alkoxycarbonyl, amino, sulfonyl, carboxy, sulfoximine, trifluoromethyl, hydroxyl, amide, urea, thioether, sulfuryl fluoride, boronate ester, cyclic ether, and alkyl optionally substituted with one to three halogens;
alternatively, R11 is of the following structure:
R12 is selected from the group consisting of hydrogen, alkyl, azacycloalkyl, bicyclic hydrocarbyl, spirocycloalkyl, azaspirocycloalkyl, oxaspirocycloalkyl, aryl, heteroaryl, and absent;
said alkyl, aryl, and heteroaryl are optionally substituted with one or more substituents selected from halogen, cyano, acyl, nitro, alkoxy, alkoxycarbonyl, amino, sulfonyl, carboxy, sulfoximine, trifluoromethyl, hydroxyl, amide, urea, thioether, sulfuryl fluoride, boronate ester, cyclic ether, and alkyl optionally substituted with one to three halogens;
said azacycloalkyl, bicyclic hydrocarbyl, and spirocycloalkyl are optionally substituted with cyano, fluorophenyl, fluorophenylalkyl, or fluorophenylamino;
alternatively, R12 is selected from the following structures:
wherein q1 and q2 are each independently selected from 1, 2, and 3;
R13 is selected from the group consisting of hydrogen, cyano, cyclic ether, and -L2-R14, where L2 is selected from —SO2—, —CO—, hydrocarbyl, or absent;
R14 is selected from aryl and heteroaryl, said aryl and heteroaryl are optionally substituted with one to three substituents selected from halogen, cyano, acyl, nitro, alkoxy, alkoxycarbonyl, amino, sulfonyl, carboxyl, sulfoximino, trifluoromethyl, hydroxyl, amido, ureido, thioether, sulfonyl fluoride, and boronate ester.

16 more elements

Facts

Application

19/113,669Filed 25 Sep 2023

Priority

CN 202211162092.423 Sep 2022

Published

2 Apr 2026

Term ends

Not estimatedThe source records don’t support an estimate.

Classification15 codes

A61P 9/00
Drugs for disorders of the cardiovascular system
C07D 519/00
Heterocyclic compounds containing more than one system of two or more relevant
A61K 31/437
Ortho- or peri-condensed with heterocyclic ring systems: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring…
A61K 31/444
Containing further heterocyclic ring systems: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone