BRPI0616815A2 - compostos de pirimidina amida, composição farmacêutica que os compreende e uso dos mesmos - Google Patents

Info

Publication number

BRPI0616815A2

BRPI0616815A2 BRPI0616815-9A BRPI0616815A BRPI0616815A2 BR PI0616815 A2 BRPI0616815 A2 BR PI0616815A2 BR PI0616815 A BRPI0616815 A BR PI0616815A BR PI0616815 A2 BRPI0616815 A2 BR PI0616815A2

Authority

BR

Brazil

Prior art keywords

carboxylic acid

phenyl

pyrimidine

benzylamide

optionally substituted

Prior art date

2005-10-04

Links

• Espacenet
• Global Dossier
• Discuss

• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 16
• FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical class NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 114
• 208000006673 asthma Diseases 0.000 claims abstract description 10
• 208000010668 atopic eczema Diseases 0.000 claims abstract description 10
• 230000000172 allergic effect Effects 0.000 claims abstract description 9
• 206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 8
• 201000010105 allergic rhinitis Diseases 0.000 claims abstract description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 6
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 4
• -1 hydroxy, carboxy, amidino Chemical group 0.000 claims description 330
• 238000000034 method Methods 0.000 claims description 145
• 125000001072 heteroaryl group Chemical group 0.000 claims description 99
• 229910052757 nitrogen Inorganic materials 0.000 claims description 78
• 125000003545 alkoxy group Chemical group 0.000 claims description 77
• 229910052739 hydrogen Inorganic materials 0.000 claims description 75
• 150000003839 salts Chemical class 0.000 claims description 73
• 125000000217 alkyl group Chemical group 0.000 claims description 72
• 150000001204 N-oxides Chemical class 0.000 claims description 70
• 125000005843 halogen group Chemical group 0.000 claims description 69
• 125000003118 aryl group Chemical group 0.000 claims description 64
• 125000000623 heterocyclic group Chemical group 0.000 claims description 62
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 60
• 239000012453 solvate Substances 0.000 claims description 59
• DYPNEVXAPRDVCM-UHFFFAOYSA-N 2-(3-fluorophenyl)pyrimidine-5-carboxylic acid Chemical compound N1=CC(C(=O)O)=CN=C1C1=CC=CC(F)=C1 DYPNEVXAPRDVCM-UHFFFAOYSA-N 0.000 claims description 53
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
• BOAIYSRFGWBZCF-UHFFFAOYSA-N 2-phenylpyrimidine-5-carboxylic acid Chemical compound N1=CC(C(=O)O)=CN=C1C1=CC=CC=C1 BOAIYSRFGWBZCF-UHFFFAOYSA-N 0.000 claims description 43
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 43
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 36
• 239000002253 acid Substances 0.000 claims description 35
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 29
• 125000001188 haloalkyl group Chemical group 0.000 claims description 22
• 229910052760 oxygen Inorganic materials 0.000 claims description 22
• 239000001301 oxygen Substances 0.000 claims description 22
• 239000001257 hydrogen Substances 0.000 claims description 20
• 125000003282 alkyl amino group Chemical group 0.000 claims description 19
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 19
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 19
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 19
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 15
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 15
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 14
• 125000004414 alkyl thio group Chemical group 0.000 claims description 14
• 125000000304 alkynyl group Chemical group 0.000 claims description 14
• 238000002360 preparation method Methods 0.000 claims description 14
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• 125000002252 acyl group Chemical group 0.000 claims description 11
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
• 125000004104 aryloxy group Chemical group 0.000 claims description 10
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 10
• 125000002947 alkylene group Chemical group 0.000 claims description 9
• 125000003435 aroyl group Chemical group 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• AHVQYHFYQWKUKB-UHFFFAOYSA-N oxan-4-amine Chemical compound NC1CCOCC1 AHVQYHFYQWKUKB-UHFFFAOYSA-N 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 8
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
• 125000003386 piperidinyl group Chemical group 0.000 claims description 8
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 8
• FMVLDCBNRZZNPH-UHFFFAOYSA-N 3-(aminomethyl)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(CN)=C1 FMVLDCBNRZZNPH-UHFFFAOYSA-N 0.000 claims description 7
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 125000002883 imidazolyl group Chemical group 0.000 claims description 7
• 238000012360 testing method Methods 0.000 claims description 7
• 125000000335 thiazolyl group Chemical group 0.000 claims description 7
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 5
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 5
• FHOQDCKZUYVRRR-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[[3-(methylsulfamoyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound CNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=CC=2)=C1 FHOQDCKZUYVRRR-UHFFFAOYSA-N 0.000 claims description 5
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
• AFIQCJGNOINCFJ-UHFFFAOYSA-N 2-(2-fluorophenyl)-n-phenylpyrimidine-5-carboxamide Chemical compound FC1=CC=CC=C1C1=NC=C(C(=O)NC=2C=CC=CC=2)C=N1 AFIQCJGNOINCFJ-UHFFFAOYSA-N 0.000 claims description 4
• ORJYDEDAGKXIFL-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-phenylpyrimidine-5-carboxamide Chemical compound FC1=CC=CC(C=2N=CC(=CN=2)C(=O)NC=2C=CC=CC=2)=C1 ORJYDEDAGKXIFL-UHFFFAOYSA-N 0.000 claims description 4
• AWFZHOCQRKLVCJ-UHFFFAOYSA-N 2-(3-fluorophenyl)pyrimidine Chemical compound FC1=CC=CC(C=2N=CC=CN=2)=C1 AWFZHOCQRKLVCJ-UHFFFAOYSA-N 0.000 claims description 4
• KCGMHUJQPCHRQG-UHFFFAOYSA-N 2-cyclohexyl-n-phenylpyrimidine-5-carboxamide Chemical compound C=1N=C(C2CCCCC2)N=CC=1C(=O)NC1=CC=CC=C1 KCGMHUJQPCHRQG-UHFFFAOYSA-N 0.000 claims description 4
• JSFAAXVTHOLLEY-UHFFFAOYSA-N 2-phenyl-n-[(4-sulfamoylphenyl)methyl]pyrimidine-5-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1 JSFAAXVTHOLLEY-UHFFFAOYSA-N 0.000 claims description 4
• WXRJSXBKQORMJZ-UHFFFAOYSA-N 2-phenyl-n-pyrimidin-2-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)N=CC=1C(=O)NC1=NC=CC=N1 WXRJSXBKQORMJZ-UHFFFAOYSA-N 0.000 claims description 4
• OWPSRSOOIAIRMQ-UHFFFAOYSA-N 2-phenyl-n-pyrimidin-4-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)N=CC=1C(=O)NC1=CC=NC=N1 OWPSRSOOIAIRMQ-UHFFFAOYSA-N 0.000 claims description 4
• VSHUWCDFDWUCLV-UHFFFAOYSA-N 4-methyl-n-[[3-(methylsulfamoyl)phenyl]methyl]-2-pyridin-2-ylpyrimidine-5-carboxamide Chemical compound CNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C(=NC(=NC=2)C=2N=CC=CC=2)C)=C1 VSHUWCDFDWUCLV-UHFFFAOYSA-N 0.000 claims description 4
• 125000005872 benzooxazolyl group Chemical group 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• XNKJXBPHOHIUMR-UHFFFAOYSA-N n-(1-methylpiperidin-4-yl)-2-phenylpyrimidine-5-carboxamide Chemical compound C1CN(C)CCC1NC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1 XNKJXBPHOHIUMR-UHFFFAOYSA-N 0.000 claims description 4
• YLUBAEMLZQPIIN-UHFFFAOYSA-N n-(3-carbamoylphenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound NC(=O)C1=CC=CC(NC(=O)C=2C=NC(=NC=2)C=2C=CC=CC=2)=C1 YLUBAEMLZQPIIN-UHFFFAOYSA-N 0.000 claims description 4
• CLIURAAZONMVBJ-UHFFFAOYSA-N n-[[4-(methylsulfamoyl)phenyl]methyl]-2-phenylpyrimidine-5-carboxamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1CNC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1 CLIURAAZONMVBJ-UHFFFAOYSA-N 0.000 claims description 4
• BWLPNCHALCXPLE-UHFFFAOYSA-N n-[[6-(dimethylamino)pyridin-3-yl]methyl]-2-phenylpyrimidine-5-carboxamide Chemical compound C1=NC(N(C)C)=CC=C1CNC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1 BWLPNCHALCXPLE-UHFFFAOYSA-N 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 3
• NJPZIHDRWLSUDM-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-(2-pyrrolidin-1-ylsulfonylethyl)pyrimidine-5-carboxamide Chemical compound FC1=CC=CC(C=2N=CC(=CN=2)C(=O)NCCS(=O)(=O)N2CCCC2)=C1 NJPZIHDRWLSUDM-UHFFFAOYSA-N 0.000 claims description 3
• JLMZQOWMYYLDAN-UHFFFAOYSA-N 2-phenyl-n-(1,3-thiazol-2-yl)pyrimidine-5-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)N=CC=1C(=O)NC1=NC=CS1 JLMZQOWMYYLDAN-UHFFFAOYSA-N 0.000 claims description 3
• FEZLPKQNOIAVAR-UHFFFAOYSA-N 2-phenyl-n-(4-sulfamoylphenyl)pyrimidine-5-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1 FEZLPKQNOIAVAR-UHFFFAOYSA-N 0.000 claims description 3
• LNRLXJGRGPYMFQ-UHFFFAOYSA-N 2-phenyl-n-[1-(pyridin-3-ylmethyl)piperidin-4-yl]pyrimidine-5-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)N=CC=1C(=O)NC(CC1)CCN1CC1=CC=CN=C1 LNRLXJGRGPYMFQ-UHFFFAOYSA-N 0.000 claims description 3
• MJMYICPDERJUAB-UHFFFAOYSA-N 2-phenyl-n-[3-(2h-tetrazol-5-yl)phenyl]pyrimidine-5-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)N=CC=1C(=O)NC(C=1)=CC=CC=1C1=NN=NN1 MJMYICPDERJUAB-UHFFFAOYSA-N 0.000 claims description 3
• 150000001408 amides Chemical class 0.000 claims description 3
• JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 claims description 3
• DJSHBEVQUFMISX-UHFFFAOYSA-N ethyl 2-[(2-phenylpyrimidine-5-carbonyl)amino]-1,3-benzothiazole-5-carboxylate Chemical compound N=1C2=CC(C(=O)OCC)=CC=C2SC=1NC(=O)C(C=N1)=CN=C1C1=CC=CC=C1 DJSHBEVQUFMISX-UHFFFAOYSA-N 0.000 claims description 3
• 125000004494 ethyl ester group Chemical group 0.000 claims description 3
• 230000002757 inflammatory effect Effects 0.000 claims description 3
• BUPURDLTPRTENO-UHFFFAOYSA-N n-(oxan-4-ylmethyl)-2-phenylpyrimidine-5-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)N=CC=1C(=O)NCC1CCOCC1 BUPURDLTPRTENO-UHFFFAOYSA-N 0.000 claims description 3
• GJVUYZVCBGAFIX-UHFFFAOYSA-N n-[2-(dimethylsulfamoyl)ethyl]-2-phenylpyrimidine-5-carboxamide Chemical compound N1=CC(C(=O)NCCS(=O)(=O)N(C)C)=CN=C1C1=CC=CC=C1 GJVUYZVCBGAFIX-UHFFFAOYSA-N 0.000 claims description 3
• DTCSAYBEMASWLY-UHFFFAOYSA-N n-[3-(2-amino-1,3-thiazol-4-yl)phenyl]-2-phenylpyrimidine-5-carboxamide Chemical compound S1C(N)=NC(C=2C=C(NC(=O)C=3C=NC(=NC=3)C=3C=CC=CC=3)C=CC=2)=C1 DTCSAYBEMASWLY-UHFFFAOYSA-N 0.000 claims description 3
• RQUMHMIXKHWYLI-UHFFFAOYSA-N n-[[3-(2-hydroxyethylsulfamoyl)phenyl]methyl]-2-phenylpyrimidine-5-carboxamide Chemical compound OCCNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=CC=CC=2)=C1 RQUMHMIXKHWYLI-UHFFFAOYSA-N 0.000 claims description 3
• FMXRYQFMRGGKKX-UHFFFAOYSA-N n-[[4-(dimethylsulfamoyl)phenyl]methyl]-2-phenylpyrimidine-5-carboxamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1CNC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1 FMXRYQFMRGGKKX-UHFFFAOYSA-N 0.000 claims description 3
• FOQKZDWKUFDJRH-UHFFFAOYSA-N n-phenyl-2-pyridin-2-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(C=2N=CC=CC=2)N=CC=1C(=O)NC1=CC=CC=C1 FOQKZDWKUFDJRH-UHFFFAOYSA-N 0.000 claims description 3
• LZMNSJCIRQSESL-UHFFFAOYSA-N 2-(3-fluorophenyl)-4-methylpyrimidine-5-carboxylic acid Chemical compound C1=C(C(O)=O)C(C)=NC(C=2C=C(F)C=CC=2)=N1 LZMNSJCIRQSESL-UHFFFAOYSA-N 0.000 claims description 2
• MGLAZUFGVJVXGD-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[[3-[(2-hydroxy-2-methylpropyl)sulfamoyl]phenyl]methyl]pyrimidine-5-carboxamide Chemical compound CC(C)(O)CNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=CC=2)=C1 MGLAZUFGVJVXGD-UHFFFAOYSA-N 0.000 claims description 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
• XFOBBEWGMXKSFB-UHFFFAOYSA-N 2-phenyl-1H-pyrimidine-2-carboxylic acid Chemical compound C1(=CC=CC=C1)C1(NC=CC=N1)C(=O)O XFOBBEWGMXKSFB-UHFFFAOYSA-N 0.000 claims description 2
• FSBIAEYLUOBHLG-UHFFFAOYSA-N 2-phenylpyrimidine-5-carboxamide Chemical compound N1=CC(C(=O)N)=CN=C1C1=CC=CC=C1 FSBIAEYLUOBHLG-UHFFFAOYSA-N 0.000 claims description 2
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
• 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 2
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
• 150000002148 esters Chemical class 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• MFUGZXTWDXORQJ-GOSISDBHSA-N n-[4-[[(4r)-2-oxo-1,3-oxazolidin-4-yl]methyl]phenyl]-2-phenylpyrimidine-5-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)N=CC=1C(=O)NC(C=C1)=CC=C1C[C@@H]1COC(=O)N1 MFUGZXTWDXORQJ-GOSISDBHSA-N 0.000 claims description 2
• 125000001624 naphthyl group Chemical group 0.000 claims description 2
• 125000004043 oxo group Chemical group O=* 0.000 claims description 2
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 14
• VTEBEDCDQYZRBB-UHFFFAOYSA-N 3-(aminomethyl)-N-(2-hydroxypropyl)benzenesulfonamide Chemical compound CC(CNS(=O)(=O)C1=CC=CC(=C1)CN)O VTEBEDCDQYZRBB-UHFFFAOYSA-N 0.000 claims 2
• UHEWDCABYAJHHW-UHFFFAOYSA-N 1-[3-(aminomethyl)phenyl]-n-methylmethanesulfonamide Chemical compound CNS(=O)(=O)CC1=CC=CC(CN)=C1 UHEWDCABYAJHHW-UHFFFAOYSA-N 0.000 claims 1
• RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 claims 1
• NECCWLOCXNASTR-UHFFFAOYSA-N 2-(aminomethyl)-n-cyclohexylbenzenesulfonamide Chemical compound NCC1=CC=CC=C1S(=O)(=O)NC1CCCCC1 NECCWLOCXNASTR-UHFFFAOYSA-N 0.000 claims 1
• UWJZUXXHMQQJBO-UHFFFAOYSA-N 3-(aminomethyl)-n-(pyridin-2-ylmethyl)benzenesulfonamide Chemical compound NCC1=CC=CC(S(=O)(=O)NCC=2N=CC=CC=2)=C1 UWJZUXXHMQQJBO-UHFFFAOYSA-N 0.000 claims 1
• AMCVADKBFBXXFL-UHFFFAOYSA-N 3-(aminomethyl)-n-ethylbenzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC=CC(CN)=C1 AMCVADKBFBXXFL-UHFFFAOYSA-N 0.000 claims 1
• PCLAZAJARAIGGD-UHFFFAOYSA-N 5-methylsulfanyl-1,3,4-thiadiazol-2-amine Chemical compound CSC1=NN=C(N)S1 PCLAZAJARAIGGD-UHFFFAOYSA-N 0.000 claims 1
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
• 239000005711 Benzoic acid Substances 0.000 claims 1
• FYSLGKWJUYZREP-UHFFFAOYSA-N CON=C(C(=O)O)C=1N=C(SC1)NC(=O)C=1C=NC(=NC1)C1=CC=CC=C1 Chemical compound CON=C(C(=O)O)C=1N=C(SC1)NC(=O)C=1C=NC(=NC1)C1=CC=CC=C1 FYSLGKWJUYZREP-UHFFFAOYSA-N 0.000 claims 1
• WUKMCCYMNVEMLE-UHFFFAOYSA-N CS(NCC1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound CS(NCC1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O WUKMCCYMNVEMLE-UHFFFAOYSA-N 0.000 claims 1
• MHOUYCVPBXAVJD-UHFFFAOYSA-N N-benzyl-2-phenylpyrimidine-5-carboxamide N-phenyl-2-pyridin-4-ylpyrimidine-5-carboxamide Chemical group C1(=CC=CC=C1)NC(=O)C=1C=NC(=NC1)C1=CC=NC=C1.C(C1=CC=CC=C1)NC(=O)C=1C=NC(=NC1)C1=CC=CC=C1 MHOUYCVPBXAVJD-UHFFFAOYSA-N 0.000 claims 1
• JVWCPTYCAHLANG-UHFFFAOYSA-N N1N=CC2=CC(=CC=C12)C1=NC(=NC=C1C(=O)N)C1=CC=CC=C1 Chemical compound N1N=CC2=CC(=CC=C12)C1=NC(=NC=C1C(=O)N)C1=CC=CC=C1 JVWCPTYCAHLANG-UHFFFAOYSA-N 0.000 claims 1
• FRQWFQMOKWDJKD-UHFFFAOYSA-N NC1=CC(S(N)(=O)=O)=CC=C1.OC(C1=CN=C(C2=CC=CC=C2)N=C1)=O Chemical compound NC1=CC(S(N)(=O)=O)=CC=C1.OC(C1=CN=C(C2=CC=CC=C2)N=C1)=O FRQWFQMOKWDJKD-UHFFFAOYSA-N 0.000 claims 1
• HGKSBJKEDBNJJX-UHFFFAOYSA-N NCC1=CC(S(N2CCOCC2)(=O)=O)=CC=C1.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound NCC1=CC(S(N2CCOCC2)(=O)=O)=CC=C1.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O HGKSBJKEDBNJJX-UHFFFAOYSA-N 0.000 claims 1
• RLNPBDDJOSRYPT-UHFFFAOYSA-N NCC1=CC(S(NCC2OCCC2)(=O)=O)=CC=C1.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound NCC1=CC(S(NCC2OCCC2)(=O)=O)=CC=C1.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O RLNPBDDJOSRYPT-UHFFFAOYSA-N 0.000 claims 1
• VSNHKQSRGKRSFI-UHFFFAOYSA-N NCC1=CC(S(NCCCN2CCCC2)(=O)=O)=CC=C1.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound NCC1=CC(S(NCCCN2CCCC2)(=O)=O)=CC=C1.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O VSNHKQSRGKRSFI-UHFFFAOYSA-N 0.000 claims 1
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