NO20110871A1 - Triazolopyridiner som fosfodiesteraseinhibitorer for behandling av hudsykdommer - Google Patents

Info

Publication number

NO20110871A1

NO20110871A1 NO20110871A NO20110871A NO20110871A1 NO 20110871 A1 NO20110871 A1 NO 20110871A1 NO 20110871 A NO20110871 A NO 20110871A NO 20110871 A NO20110871 A NO 20110871A NO 20110871 A1 NO20110871 A1 NO 20110871A1

Authority

NO

Norway

Prior art keywords

methoxy

triazolo

pyridin

cyclopropyl

phenyl

Prior art date

2008-12-19

Links

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• 238000011282 treatment Methods 0.000 title claims abstract description 21
• 208000017520 skin disease Diseases 0.000 title claims description 7
• 239000002571 phosphodiesterase inhibitor Substances 0.000 title description 2
• 150000008523 triazolopyridines Chemical class 0.000 title description 2
• 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 324
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
• 201000010099 disease Diseases 0.000 claims abstract description 19
• 230000002500 effect on skin Effects 0.000 claims abstract description 15
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 9
• 230000002062 proliferating effect Effects 0.000 claims abstract description 7
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 155
• 125000000217 alkyl group Chemical group 0.000 claims description 113
• 238000000034 method Methods 0.000 claims description 63
• -1 -S(0)2alkyl Chemical group 0.000 claims description 57
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 48
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 48
• 229910052736 halogen Inorganic materials 0.000 claims description 39
• 150000002367 halogens Chemical class 0.000 claims description 39
• XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 claims description 39
• 125000003118 aryl group Chemical group 0.000 claims description 37
• 125000001072 heteroaryl group Chemical group 0.000 claims description 36
• 239000001257 hydrogen Substances 0.000 claims description 36
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 125000001424 substituent group Chemical group 0.000 claims description 32
• SDNXQWUJWNTDCC-UHFFFAOYSA-N 2-methylsulfonylethanamine Chemical compound CS(=O)(=O)CCN SDNXQWUJWNTDCC-UHFFFAOYSA-N 0.000 claims description 31
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
• 125000003545 alkoxy group Chemical group 0.000 claims description 26
• 125000003342 alkenyl group Chemical group 0.000 claims description 24
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
• JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 claims description 20
• RTVWJWNJHGNHTD-UHFFFAOYSA-N 2-amino-n,n-dimethylethanesulfonamide Chemical compound CN(C)S(=O)(=O)CCN RTVWJWNJHGNHTD-UHFFFAOYSA-N 0.000 claims description 18
• AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 claims description 18
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• 125000004043 oxo group Chemical group O=* 0.000 claims description 18
• 150000001408 amides Chemical class 0.000 claims description 16
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• 238000004519 manufacturing process Methods 0.000 claims description 15
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 13
• 150000003839 salts Chemical class 0.000 claims description 13
• 201000004624 Dermatitis Diseases 0.000 claims description 12
• 206010040799 Skin atrophy Diseases 0.000 claims description 12
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 12
• WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 12
• NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims description 12
• 125000004414 alkyl thio group Chemical group 0.000 claims description 11
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 11
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 10
• 201000008937 atopic dermatitis Diseases 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 claims description 10
• 206010052428 Wound Diseases 0.000 claims description 9
• 208000027418 Wounds and injury Diseases 0.000 claims description 9
• 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 230000001154 acute effect Effects 0.000 claims description 8
• CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 8
• 125000005015 aryl alkynyl group Chemical group 0.000 claims description 8
• 230000001684 chronic effect Effects 0.000 claims description 8
• 208000035475 disorder Diseases 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 8
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 8
• 230000009759 skin aging Effects 0.000 claims description 8
• 239000012453 solvate Substances 0.000 claims description 8
• KNTZCGBYFGEMFR-UHFFFAOYSA-N (propan-2-ylazaniumyl)formate Chemical compound CC(C)NC(O)=O KNTZCGBYFGEMFR-UHFFFAOYSA-N 0.000 claims description 7
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 7
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 7
• OQQXGCLLMDQESN-UHFFFAOYSA-N cyclohexylcarbamic acid Chemical compound OC(=O)NC1CCCCC1 OQQXGCLLMDQESN-UHFFFAOYSA-N 0.000 claims description 7
• KBJXDTIYSSQJAI-UHFFFAOYSA-N propylcarbamic acid Chemical compound CCCNC(O)=O KBJXDTIYSSQJAI-UHFFFAOYSA-N 0.000 claims description 7
• MVQXBXLDXSQURK-UHFFFAOYSA-N 2-aminoethanesulfonamide Chemical compound NCCS(N)(=O)=O MVQXBXLDXSQURK-UHFFFAOYSA-N 0.000 claims description 6
• 208000002874 Acne Vulgaris Diseases 0.000 claims description 6
• 201000004384 Alopecia Diseases 0.000 claims description 6
• 206010012442 Dermatitis contact Diseases 0.000 claims description 6
• APRJFNLVTJWEPP-UHFFFAOYSA-N Diethylcarbamic acid Chemical compound CCN(CC)C(O)=O APRJFNLVTJWEPP-UHFFFAOYSA-N 0.000 claims description 6
• 206010061218 Inflammation Diseases 0.000 claims description 6
• 150000001204 N-oxides Chemical class 0.000 claims description 6
• 208000003251 Pruritus Diseases 0.000 claims description 6
• 201000004681 Psoriasis Diseases 0.000 claims description 6
• 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims description 6
• 208000024780 Urticaria Diseases 0.000 claims description 6
• 206010000496 acne Diseases 0.000 claims description 6
• 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims description 6
• 231100000360 alopecia Toxicity 0.000 claims description 6
• 208000010668 atopic eczema Diseases 0.000 claims description 6
• 208000010247 contact dermatitis Diseases 0.000 claims description 6
• 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 6
• 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 6
• 125000005366 cycloalkylthio group Chemical group 0.000 claims description 6
• DWLVWMUCHSLGSU-UHFFFAOYSA-N dimethylcarbamic acid Chemical compound CN(C)C(O)=O DWLVWMUCHSLGSU-UHFFFAOYSA-N 0.000 claims description 6
• 150000004677 hydrates Chemical class 0.000 claims description 6
• 230000004054 inflammatory process Effects 0.000 claims description 6
• GCDZDXVTDCMNMN-UHFFFAOYSA-N n-(2-aminoethyl)methanesulfonamide Chemical compound CS(=O)(=O)NCCN GCDZDXVTDCMNMN-UHFFFAOYSA-N 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 208000008742 seborrheic dermatitis Diseases 0.000 claims description 6
• 150000003431 steroids Chemical class 0.000 claims description 6
• 206010028980 Neoplasm Diseases 0.000 claims description 5
• 201000011510 cancer Diseases 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 238000002560 therapeutic procedure Methods 0.000 claims description 5
• ISQATORZDJOLJP-UHFFFAOYSA-N 3-[2-[1-(hydroxymethyl)cyclopropyl]-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound N12N=C(C3(CO)CC3)N=C2C(OC)=CC=C1C1=CC=CC(C#N)=C1 ISQATORZDJOLJP-UHFFFAOYSA-N 0.000 claims description 4
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• XHZATVSDPWJIKI-UHFFFAOYSA-N n-(2-aminoethyl)-n-methylmethanesulfonamide Chemical compound CS(=O)(=O)N(C)CCN XHZATVSDPWJIKI-UHFFFAOYSA-N 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 4
• 125000004953 trihalomethyl group Chemical group 0.000 claims description 4
• JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 3
• 206010051246 Photodermatosis Diseases 0.000 claims description 3
• 125000003282 alkyl amino group Chemical group 0.000 claims description 3
• DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 claims description 3
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
• 230000008845 photoaging Effects 0.000 claims description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
• LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 claims description 3
• 239000003981 vehicle Substances 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• RKXZIARGENBWKB-UHFFFAOYSA-N 1-[3-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl]ethanone Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=CC(C(C)=O)=C1 RKXZIARGENBWKB-UHFFFAOYSA-N 0.000 claims description 2
• JBPJCYUXAZIWTQ-UHFFFAOYSA-N 1-[4-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl]ethanone Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=C(C(C)=O)C=C1 JBPJCYUXAZIWTQ-UHFFFAOYSA-N 0.000 claims description 2
• IGXNNQSDJNCUQF-UHFFFAOYSA-N 1-[5-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)thiophen-2-yl]ethanone Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=C(C(C)=O)S1 IGXNNQSDJNCUQF-UHFFFAOYSA-N 0.000 claims description 2
• LJBAMFOTWQIJIK-UHFFFAOYSA-N 1-[5-(3-cyanophenyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-n-(2-hydroxyethyl)cyclopropane-1-carboxamide Chemical compound N12N=C(C3(CC3)C(=O)NCCO)N=C2C(OC)=CC=C1C1=CC=CC(C#N)=C1 LJBAMFOTWQIJIK-UHFFFAOYSA-N 0.000 claims description 2
• XOBBHHBWSLLWKU-UHFFFAOYSA-N 1-[5-(4-cyanophenyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-n-methylcyclopropane-1-carboxamide Chemical compound N1=C2C(OC)=CC=C(C=3C=CC(=CC=3)C#N)N2N=C1C1(C(=O)NC)CC1 XOBBHHBWSLLWKU-UHFFFAOYSA-N 0.000 claims description 2
• XZSPPXRCZWHLLA-UHFFFAOYSA-N 2-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)pyridine-4-carbonitrile Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC(C#N)=CC=N1 XZSPPXRCZWHLLA-UHFFFAOYSA-N 0.000 claims description 2
• IUVCOQHNFNOBJU-UHFFFAOYSA-N 2-cyclopropyl-5-(2,4-dichlorophenyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=C(Cl)C=C1Cl IUVCOQHNFNOBJU-UHFFFAOYSA-N 0.000 claims description 2
• IBHNSTIMPCUQIL-UHFFFAOYSA-N 2-cyclopropyl-5-(2-fluorophenyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=CC=C1F IBHNSTIMPCUQIL-UHFFFAOYSA-N 0.000 claims description 2
• YJEBJDJEBSSDKR-UHFFFAOYSA-N 2-cyclopropyl-5-(3,4-dimethoxyphenyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(OC)C2=NC(C3CC3)=NN12 YJEBJDJEBSSDKR-UHFFFAOYSA-N 0.000 claims description 2
• XLMHJAJAYFZTNI-UHFFFAOYSA-N 2-cyclopropyl-5-(3-fluorophenyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=CC(F)=C1 XLMHJAJAYFZTNI-UHFFFAOYSA-N 0.000 claims description 2
• JVDTVXNBLAEQLV-UHFFFAOYSA-N 2-cyclopropyl-5-(4-fluorophenyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=C(F)C=C1 JVDTVXNBLAEQLV-UHFFFAOYSA-N 0.000 claims description 2
• XZNGCIZJWFHYLC-UHFFFAOYSA-N 2-cyclopropyl-8-methoxy-5-(3-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound COC1=CC=CC(C=2N3N=C(N=C3C(OC)=CC=2)C2CC2)=C1 XZNGCIZJWFHYLC-UHFFFAOYSA-N 0.000 claims description 2
• IOXBHRQKYAUURF-UHFFFAOYSA-N 2-cyclopropyl-8-methoxy-5-(3-methylsulfonylphenyl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 IOXBHRQKYAUURF-UHFFFAOYSA-N 0.000 claims description 2
• ZPKIHGNRMWQFHW-UHFFFAOYSA-N 2-cyclopropyl-8-methoxy-5-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CC(OC)=CC=C1C1=CC=C(OC)C2=NC(C3CC3)=NN12 ZPKIHGNRMWQFHW-UHFFFAOYSA-N 0.000 claims description 2
• PYKGFUCOSJIFKD-UHFFFAOYSA-N 2-cyclopropyl-8-methoxy-5-(4-methylsulfonylphenyl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=C(S(C)(=O)=O)C=C1 PYKGFUCOSJIFKD-UHFFFAOYSA-N 0.000 claims description 2
• QWLHQAVVYHNNTD-UHFFFAOYSA-N 2-cyclopropyl-8-methoxy-5-[3-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=CC(OC(F)(F)F)=C1 QWLHQAVVYHNNTD-UHFFFAOYSA-N 0.000 claims description 2
• DZROUGGSZWKVSW-UHFFFAOYSA-N 2-cyclopropyl-8-methoxy-5-[4-(2-methoxyethoxy)phenyl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CC(OCCOC)=CC=C1C1=CC=C(OC)C2=NC(C3CC3)=NN12 DZROUGGSZWKVSW-UHFFFAOYSA-N 0.000 claims description 2
• VSLJGBNXJXSHFG-UHFFFAOYSA-N 2-cyclopropyl-8-methoxy-5-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=C(C(F)(F)F)C=C1 VSLJGBNXJXSHFG-UHFFFAOYSA-N 0.000 claims description 2
• WKTXWSHVPSGHJA-UHFFFAOYSA-N 2-cyclopropyl-8-methoxy-5-phenyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=CC=C1 WKTXWSHVPSGHJA-UHFFFAOYSA-N 0.000 claims description 2
• CCKRYMYNWHKDMJ-UHFFFAOYSA-N 2-cyclopropyl-8-methoxy-5-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=CN=C1 CCKRYMYNWHKDMJ-UHFFFAOYSA-N 0.000 claims description 2
• YLJVADJRFUXYHP-UHFFFAOYSA-N 2-cyclopropyl-8-methoxy-5-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=NC=C1 YLJVADJRFUXYHP-UHFFFAOYSA-N 0.000 claims description 2
• JFURWSPZGSCRIJ-UHFFFAOYSA-N 2-cyclopropyl-8-methoxy-5-pyrimidin-5-yl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CN=CN=C1 JFURWSPZGSCRIJ-UHFFFAOYSA-N 0.000 claims description 2
• LDNYVJRZICBRKQ-UHFFFAOYSA-N 2-cyclopropyl-8-methoxy-5-thiophen-2-yl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=CS1 LDNYVJRZICBRKQ-UHFFFAOYSA-N 0.000 claims description 2
• XDWNQWZZTFZSHZ-UHFFFAOYSA-N 2-methoxy-4-[8-methoxy-2-[1-(2-methylpropoxymethyl)cyclopropyl]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound C1=C(C#N)C(OC)=CC(C=2N3N=C(N=C3C(OC)=CC=2)C2(COCC(C)C)CC2)=C1 XDWNQWZZTFZSHZ-UHFFFAOYSA-N 0.000 claims description 2
• DMSPIJAYBKABJZ-UHFFFAOYSA-N 3-(2-cyclopropyl-5-methoxy-[1,2,4]triazolo[1,5-a]pyridin-8-yl)benzonitrile Chemical compound C12=NC(C3CC3)=NN2C(OC)=CC=C1C1=CC=CC(C#N)=C1 DMSPIJAYBKABJZ-UHFFFAOYSA-N 0.000 claims description 2
• LOPASKZJXIGCNI-UHFFFAOYSA-N 3-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-5-(hydroxymethyl)benzonitrile Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC(CO)=CC(C#N)=C1 LOPASKZJXIGCNI-UHFFFAOYSA-N 0.000 claims description 2
• LCWJEWBSWFOTJE-UHFFFAOYSA-N 3-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-5-fluorobenzonitrile Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC(F)=CC(C#N)=C1 LCWJEWBSWFOTJE-UHFFFAOYSA-N 0.000 claims description 2
• CBQSDJCQRSMTLX-UHFFFAOYSA-N 3-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-5-methoxybenzonitrile Chemical compound COC1=CC(C#N)=CC(C=2N3N=C(N=C3C(OC)=CC=2)C2CC2)=C1 CBQSDJCQRSMTLX-UHFFFAOYSA-N 0.000 claims description 2
• QKNNSFJRLSJBDE-UHFFFAOYSA-N 3-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-n,n-dimethylbenzamide Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=CC(C(=O)N(C)C)=C1 QKNNSFJRLSJBDE-UHFFFAOYSA-N 0.000 claims description 2
• CKLBBEHUOAUPEE-UHFFFAOYSA-N 3-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(C=2N3N=C(N=C3C(OC)=CC=2)C2CC2)=C1 CKLBBEHUOAUPEE-UHFFFAOYSA-N 0.000 claims description 2
• QGXLBOYQKWLJOQ-UHFFFAOYSA-N 3-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzamide Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=CC(C(N)=O)=C1 QGXLBOYQKWLJOQ-UHFFFAOYSA-N 0.000 claims description 2
• TYSOYNIBRDCGSX-UHFFFAOYSA-N 3-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzoic acid Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=CC(C(O)=O)=C1 TYSOYNIBRDCGSX-UHFFFAOYSA-N 0.000 claims description 2
• NGEYFNPXMVFDKR-UHFFFAOYSA-N 3-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=CC(C#N)=C1 NGEYFNPXMVFDKR-UHFFFAOYSA-N 0.000 claims description 2
• VTWYBQZXWIXYQY-UHFFFAOYSA-N 3-[8-methoxy-2-[1-(morpholine-4-carbonyl)cyclopropyl]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound N12N=C(C3(CC3)C(=O)N3CCOCC3)N=C2C(OC)=CC=C1C1=CC=CC(C#N)=C1 VTWYBQZXWIXYQY-UHFFFAOYSA-N 0.000 claims description 2
• RVFBRGMOXPSVKQ-UHFFFAOYSA-N 3-[8-methoxy-2-[1-(phenylmethoxymethyl)cyclopropyl]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound N12N=C(C3(COCC=4C=CC=CC=4)CC3)N=C2C(OC)=CC=C1C1=CC=CC(C#N)=C1 RVFBRGMOXPSVKQ-UHFFFAOYSA-N 0.000 claims description 2
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