HRP20160488T1 - Triazolopiridini kao inhibitori fosfodiesteraze za liječenje kožnih bolesti - Google Patents
Triazolopiridini kao inhibitori fosfodiesteraze za liječenje kožnih bolesti Download PDFInfo
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- HRP20160488T1 HRP20160488T1 HRP20160488TT HRP20160488T HRP20160488T1 HR P20160488 T1 HRP20160488 T1 HR P20160488T1 HR P20160488T T HRP20160488T T HR P20160488TT HR P20160488 T HRP20160488 T HR P20160488T HR P20160488 T1 HRP20160488 T1 HR P20160488T1
- Authority
- HR
- Croatia
- Prior art keywords
- methoxy
- triazolo
- pyridin
- phenyl
- cyano
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims 5
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 title 1
- 201000010099 disease Diseases 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title 1
- 230000002500 effect on skin Effects 0.000 title 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 title 1
- 150000008523 triazolopyridines Chemical class 0.000 title 1
- -1 cyano, amino Chemical group 0.000 claims 98
- 125000000217 alkyl group Chemical group 0.000 claims 32
- 150000001875 compounds Chemical class 0.000 claims 29
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000004043 oxo group Chemical group O=* 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 201000004624 Dermatitis Diseases 0.000 claims 5
- APRJFNLVTJWEPP-UHFFFAOYSA-N Diethylcarbamic acid Chemical compound CCN(CC)C(O)=O APRJFNLVTJWEPP-UHFFFAOYSA-N 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 5
- 208000017520 skin disease Diseases 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 4
- 206010040799 Skin atrophy Diseases 0.000 claims 4
- OQQXGCLLMDQESN-UHFFFAOYSA-N cyclohexylcarbamic acid Chemical compound OC(=O)NC1CCCCC1 OQQXGCLLMDQESN-UHFFFAOYSA-N 0.000 claims 4
- KBJXDTIYSSQJAI-UHFFFAOYSA-N propylcarbamic acid Chemical compound CCCNC(O)=O KBJXDTIYSSQJAI-UHFFFAOYSA-N 0.000 claims 4
- 230000009759 skin aging Effects 0.000 claims 4
- KNTZCGBYFGEMFR-UHFFFAOYSA-N (propan-2-ylazaniumyl)formate Chemical compound CC(C)NC(O)=O KNTZCGBYFGEMFR-UHFFFAOYSA-N 0.000 claims 3
- AHPZFZNYDYJLIG-UHFFFAOYSA-N 1-[5-(4-cyanophenyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropane-1-carboxylic acid Chemical compound N12N=C(C3(CC3)C(O)=O)N=C2C(OC)=CC=C1C1=CC=C(C#N)C=C1 AHPZFZNYDYJLIG-UHFFFAOYSA-N 0.000 claims 3
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 3
- DWLVWMUCHSLGSU-UHFFFAOYSA-N dimethylcarbamic acid Chemical compound CN(C)C(O)=O DWLVWMUCHSLGSU-UHFFFAOYSA-N 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 3
- OIRGDOJEJXFGIB-UHFFFAOYSA-N 1-[5-(3-acetylphenyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropane-1-carboxylic acid Chemical class N12N=C(C3(CC3)C(O)=O)N=C2C(OC)=CC=C1C1=CC=CC(C(C)=O)=C1 OIRGDOJEJXFGIB-UHFFFAOYSA-N 0.000 claims 2
- WUDHKQUCZMKQJW-UHFFFAOYSA-N 1-[5-(3-cyanophenyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropane-1-carboxylic acid Chemical compound N12N=C(C3(CC3)C(O)=O)N=C2C(OC)=CC=C1C1=CC=CC(C#N)=C1 WUDHKQUCZMKQJW-UHFFFAOYSA-N 0.000 claims 2
- ZEVNFRHGVNFOKO-UHFFFAOYSA-N 4-(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=C(C(O)=O)C=C1 ZEVNFRHGVNFOKO-UHFFFAOYSA-N 0.000 claims 2
- 208000002874 Acne Vulgaris Diseases 0.000 claims 2
- 201000004384 Alopecia Diseases 0.000 claims 2
- 208000017667 Chronic Disease Diseases 0.000 claims 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims 2
- 206010012442 Dermatitis contact Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- 208000003251 Pruritus Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims 2
- 206010072170 Skin wound Diseases 0.000 claims 2
- 208000024780 Urticaria Diseases 0.000 claims 2
- 206010000496 acne Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 231100000360 alopecia Toxicity 0.000 claims 2
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 2
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 2
- 201000008937 atopic dermatitis Diseases 0.000 claims 2
- 208000010668 atopic eczema Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 2
- 208000010247 contact dermatitis Diseases 0.000 claims 2
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims 2
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims 2
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims 2
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 230000007803 itching Effects 0.000 claims 2
- 150000004702 methyl esters Chemical class 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 208000008742 seborrheic dermatitis Diseases 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 150000003431 steroids Chemical class 0.000 claims 2
- 230000036561 sun exposure Effects 0.000 claims 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- YXHNLIGBYIURGE-UHFFFAOYSA-N 1-[3-(2-cyclopropyl-8-hydroxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C=2N3N=C(N=C3C(O)=CC=2)C2CC2)=C1 YXHNLIGBYIURGE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- SOTIMVAXWBNKDD-UHFFFAOYSA-N 1-[3-[8-methoxy-2-[1-(4-methylpiperazine-1-carbonyl)cyclopropyl]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]phenyl]ethanone Chemical compound N12N=C(C3(CC3)C(=O)N3CCN(C)CC3)N=C2C(OC)=CC=C1C1=CC=CC(C(C)=O)=C1 SOTIMVAXWBNKDD-UHFFFAOYSA-N 0.000 claims 1
- RQPNVCFLTNVYHA-UHFFFAOYSA-N 1-[3-[8-methoxy-2-[1-(morpholine-4-carbonyl)cyclopropyl]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]phenyl]ethanone Chemical compound N12N=C(C3(CC3)C(=O)N3CCOCC3)N=C2C(OC)=CC=C1C1=CC=CC(C(C)=O)=C1 RQPNVCFLTNVYHA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- AILMQPVWNWLQEO-UHFFFAOYSA-N 1-[5-(3-acetylphenyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-n-benzylcyclopropane-1-carboxamide Chemical compound N12N=C(C3(CC3)C(=O)NCC=3C=CC=CC=3)N=C2C(OC)=CC=C1C1=CC=CC(C(C)=O)=C1 AILMQPVWNWLQEO-UHFFFAOYSA-N 0.000 claims 1
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- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- WOVYDEFYASRZAO-UHFFFAOYSA-N 2-cyclopropyl-8-methoxy-5-piperidin-1-yl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1N1CCCCC1 WOVYDEFYASRZAO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- UGUXKJUAMDVORH-UHFFFAOYSA-N 3-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-4-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=NNC(=O)CC1C UGUXKJUAMDVORH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
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- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- BZUZTKDIPCRTOC-UHFFFAOYSA-N 3-[8-methoxy-2-[1-(pyrrolidine-1-carbonyl)cyclopropyl]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound N12N=C(C3(CC3)C(=O)N3CCCC3)N=C2C(OC)=CC=C1C1=CC=CC(C#N)=C1 BZUZTKDIPCRTOC-UHFFFAOYSA-N 0.000 claims 1
- FYRFCTUZXSLXDN-UHFFFAOYSA-N 4-(2-cyclopropyl-5-methoxy-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-2,3-dihydroinden-1-one Chemical compound N=1N2C(OC)=CC=C(C=3C=4CCC(=O)C=4C=CC=3)C2=NC=1C1CC1 FYRFCTUZXSLXDN-UHFFFAOYSA-N 0.000 claims 1
- KPAMKQUDHBZXEQ-UHFFFAOYSA-N 4-(2-cyclopropyl-5-methoxy-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-2-methoxybenzonitrile Chemical compound C1=C(C#N)C(OC)=CC(C=2C3=NC(=NN3C(OC)=CC=2)C2CC2)=C1 KPAMKQUDHBZXEQ-UHFFFAOYSA-N 0.000 claims 1
- BPWWNFLQMWSBKS-UHFFFAOYSA-N 4-(2-cyclopropyl-5-methoxy-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-2-methylbenzonitrile Chemical compound C12=NC(C3CC3)=NN2C(OC)=CC=C1C1=CC=C(C#N)C(C)=C1 BPWWNFLQMWSBKS-UHFFFAOYSA-N 0.000 claims 1
- FPGDJOTYUNWKJK-UHFFFAOYSA-N 4-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-2,3-dihydroinden-1-one Chemical compound N1=C2C(OC)=CC=C(C=3C=4CCC(=O)C=4C=CC=3)N2N=C1C1CC1 FPGDJOTYUNWKJK-UHFFFAOYSA-N 0.000 claims 1
- POUYJHJUQUWTNI-UHFFFAOYSA-N 4-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-2-fluorobenzonitrile Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=C(C#N)C(F)=C1 POUYJHJUQUWTNI-UHFFFAOYSA-N 0.000 claims 1
- MYRFKQBUZXJYIF-UHFFFAOYSA-N 4-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-2-methoxybenzonitrile Chemical compound C1=C(C#N)C(OC)=CC(C=2N3N=C(N=C3C(OC)=CC=2)C2CC2)=C1 MYRFKQBUZXJYIF-UHFFFAOYSA-N 0.000 claims 1
- CISZNYOPTOHAGO-UHFFFAOYSA-N 4-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-2-methylbenzonitrile Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=C(C#N)C(C)=C1 CISZNYOPTOHAGO-UHFFFAOYSA-N 0.000 claims 1
- BGBJZTHWGMYMOZ-UHFFFAOYSA-N 4-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-3h-2-benzofuran-1-one Chemical compound N1=C2C(OC)=CC=C(C=3C=4COC(=O)C=4C=CC=3)N2N=C1C1CC1 BGBJZTHWGMYMOZ-UHFFFAOYSA-N 0.000 claims 1
- FGQWVUZGUCQTLP-UHFFFAOYSA-N 4-(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=C(C(=O)N(C)C)C=C1 FGQWVUZGUCQTLP-UHFFFAOYSA-N 0.000 claims 1
- ULZFAVXBEUPDRN-UHFFFAOYSA-N 4-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-n-(2-hydroxyethyl)benzenesulfonamide Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=C(S(=O)(=O)NCCO)C=C1 ULZFAVXBEUPDRN-UHFFFAOYSA-N 0.000 claims 1
- QNOFDVREHPSCPM-UHFFFAOYSA-N 4-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CC=C(OC)C2=NC(C3CC3)=NN12 QNOFDVREHPSCPM-UHFFFAOYSA-N 0.000 claims 1
- FTPMFTNHEFYHHZ-UHFFFAOYSA-N 4-(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=C(C(N)=O)C=C1 FTPMFTNHEFYHHZ-UHFFFAOYSA-N 0.000 claims 1
- OMBYRPQDGVBGLR-UHFFFAOYSA-N 4-(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=C(C#N)C=C1 OMBYRPQDGVBGLR-UHFFFAOYSA-N 0.000 claims 1
- AXUIKLMXSIKQRM-UHFFFAOYSA-N 4-[2-[1-(hydroxymethyl)cyclopropyl]-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-2-methoxybenzonitrile Chemical compound C1=C(C#N)C(OC)=CC(C=2N3N=C(N=C3C(OC)=CC=2)C2(CO)CC2)=C1 AXUIKLMXSIKQRM-UHFFFAOYSA-N 0.000 claims 1
- ISLGJXYLNUQJCX-UHFFFAOYSA-N 4-[4-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl]sulfonylmorpholine Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C(C=C1)=CC=C1S(=O)(=O)N1CCOCC1 ISLGJXYLNUQJCX-UHFFFAOYSA-N 0.000 claims 1
- KHLADQHEPNUKHU-UHFFFAOYSA-N 4-[8-methoxy-2-[1-(4-methylpiperazine-1-carbonyl)cyclopropyl]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound N12N=C(C3(CC3)C(=O)N3CCN(C)CC3)N=C2C(OC)=CC=C1C1=CC=C(C#N)C=C1 KHLADQHEPNUKHU-UHFFFAOYSA-N 0.000 claims 1
- CFARNRWDENQAOI-UHFFFAOYSA-N 4-[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=C(C#N)C=C1 CFARNRWDENQAOI-UHFFFAOYSA-N 0.000 claims 1
- ZUQIQHQMVOSJDF-UHFFFAOYSA-N 5-(2-cyclopropyl-5-methoxy-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-2,3-dihydroinden-1-one Chemical compound N=1N2C(OC)=CC=C(C=3C=C4CCC(=O)C4=CC=3)C2=NC=1C1CC1 ZUQIQHQMVOSJDF-UHFFFAOYSA-N 0.000 claims 1
- UNUDTVYQYQTLAS-UHFFFAOYSA-N 5-(2-cyclopropyl-5-methoxy-[1,2,4]triazolo[1,5-a]pyridin-8-yl)pyridine-3-carbonitrile Chemical compound C12=NC(C3CC3)=NN2C(OC)=CC=C1C1=CN=CC(C#N)=C1 UNUDTVYQYQTLAS-UHFFFAOYSA-N 0.000 claims 1
- BBWOFZWEQZLMPY-UHFFFAOYSA-N 5-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-2,3-dihydroinden-1-one Chemical compound N1=C2C(OC)=CC=C(C=3C=C4CCC(=O)C4=CC=3)N2N=C1C1CC1 BBWOFZWEQZLMPY-UHFFFAOYSA-N 0.000 claims 1
- MJDVQWJNMVVIPW-UHFFFAOYSA-N 5-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-2,3-dihydroisoindol-1-one Chemical compound N1=C2C(OC)=CC=C(C=3C=C4CNC(=O)C4=CC=3)N2N=C1C1CC1 MJDVQWJNMVVIPW-UHFFFAOYSA-N 0.000 claims 1
- WVPXHNNEZBHHFC-UHFFFAOYSA-N 5-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-3h-2-benzofuran-1-one Chemical compound N1=C2C(OC)=CC=C(C=3C=C4COC(=O)C4=CC=3)N2N=C1C1CC1 WVPXHNNEZBHHFC-UHFFFAOYSA-N 0.000 claims 1
- CBAPXNGRVIZOEE-UHFFFAOYSA-N 5-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)pyridine-3-carbonitrile Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CN=CC(C#N)=C1 CBAPXNGRVIZOEE-UHFFFAOYSA-N 0.000 claims 1
- NNJSAOLGXHVBQX-UHFFFAOYSA-N 5-(3-butoxyphenyl)-2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CCCCOC1=CC=CC(C=2N3N=C(N=C3C(OC)=CC=2)C2CC2)=C1 NNJSAOLGXHVBQX-UHFFFAOYSA-N 0.000 claims 1
- JNGVEAVFCQJJOP-UHFFFAOYSA-N 5-[2-[1-(hydroxymethyl)cyclopropyl]-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl]pyridine-3-carbonitrile Chemical compound N12N=C(C3(CO)CC3)N=C2C(OC)=CC=C1C1=CN=CC(C#N)=C1 JNGVEAVFCQJJOP-UHFFFAOYSA-N 0.000 claims 1
- HFWWMTUHICRJAK-UHFFFAOYSA-N 5-[8-methoxy-2-[1-(2-methylpropoxymethyl)cyclopropyl]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]pyridine-3-carbonitrile Chemical compound N12N=C(C3(COCC(C)C)CC3)N=C2C(OC)=CC=C1C1=CN=CC(C#N)=C1 HFWWMTUHICRJAK-UHFFFAOYSA-N 0.000 claims 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
- PTOXHZSBUZCZLS-UHFFFAOYSA-N COc1ccc(-c2cccc(c2)C#N)n2nc(nc12)C1(CNC(O)=O)CC1 Chemical compound COc1ccc(-c2cccc(c2)C#N)n2nc(nc12)C1(CNC(O)=O)CC1 PTOXHZSBUZCZLS-UHFFFAOYSA-N 0.000 claims 1
- AETQJVGOJBVECK-UHFFFAOYSA-N N1=C2C(C=3C=4CCC(=O)C=4C=CC=3)=CC=C(O)N2N=C1C1(C(=O)NC(C)C)CC1 Chemical compound N1=C2C(C=3C=4CCC(=O)C=4C=CC=3)=CC=C(O)N2N=C1C1(C(=O)NC(C)C)CC1 AETQJVGOJBVECK-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- WLPPWTRPCMMKCE-UHFFFAOYSA-N methyl 3-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N3N=C(N=C3C(OC)=CC=2)C2CC2)=C1 WLPPWTRPCMMKCE-UHFFFAOYSA-N 0.000 claims 1
- DAKZISABEDGGSV-UHFFFAOYSA-N n-(2-aminoethyl)acetamide Chemical compound CC(=O)NCCN DAKZISABEDGGSV-UHFFFAOYSA-N 0.000 claims 1
- GOOJLJGAEWUHMJ-UHFFFAOYSA-N n-[3-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl]acetamide Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=CC(NC(C)=O)=C1 GOOJLJGAEWUHMJ-UHFFFAOYSA-N 0.000 claims 1
- PLXYKKIUWCCECW-UHFFFAOYSA-N n-[3-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl]methanesulfonamide Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=CC(NS(C)(=O)=O)=C1 PLXYKKIUWCCECW-UHFFFAOYSA-N 0.000 claims 1
- VWOCMHDYPHHHNJ-UHFFFAOYSA-N n-[4-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl]acetamide Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=C(NC(C)=O)C=C1 VWOCMHDYPHHHNJ-UHFFFAOYSA-N 0.000 claims 1
- VKDIAPPKLGGJDC-UHFFFAOYSA-N n-[[1-[5-(3-cyanophenyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropyl]methyl]-2-methylpropanamide Chemical compound N12N=C(C3(CNC(=O)C(C)C)CC3)N=C2C(OC)=CC=C1C1=CC=CC(C#N)=C1 VKDIAPPKLGGJDC-UHFFFAOYSA-N 0.000 claims 1
- XBMLZAWOHDMMPU-UHFFFAOYSA-N n-[[4-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl]methyl]acetamide Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=C(CNC(C)=O)C=C1 XBMLZAWOHDMMPU-UHFFFAOYSA-N 0.000 claims 1
- QKBIFPIIWFCJOB-UHFFFAOYSA-N n-[[4-(2-cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)phenyl]methyl]methanesulfonamide Chemical compound N12N=C(C3CC3)N=C2C(OC)=CC=C1C1=CC=C(CNS(C)(=O)=O)C=C1 QKBIFPIIWFCJOB-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Epidemiology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Toxicology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (30)
1. Spoj opće formule I,
[image]
naznačen time da R1 je C1-6 alkoksi, kao što su metoksi, mono-, di- ili trifluormetoksi, halogen, ili hidroksi;
R2 je alkil, cikloalkil, alkilcikloalkil, ili cikloalkil(C(O)NR7R8), od kojih je svaki po izboru supstituiran s jednim ili više supstituenata izabranih između R4;
R3 je vodik, halogen, aril, heteroaril, hidroksi, alkil, cikloalkil, heterocikloalkil, alkoksi, okso, cijano, amino, aminoalkil, alkilamino ili dialkilamino;
R4 je vodik, halogen, hidroksi, okso, cijano, karboksi, ili trihalometil, ili R4 je NR5R6, -C(O)NR7R8, -C(O)R7, -COOR7, -NR5C(O)NR7R8, -OC(O)NR7R8, -OC(O)R3, NC(O)R7, -OR7, -NC(O)OR3, -NSO2R7, -SO2NR7R8, ili -SO2R7R8, alkil, cikloalkil, alkenil, alkinil, aril, heteroaril, cikloalkilalkil, cikloalkilalkenil, cikloalkilalkinil, cikloalkenilalkil, cikloalkenilalkenil, cikloalkenilalkinil, heterocikloalkil, heterocikloalkilalkil, heterocikloalkenil, heterocikloalkenilalkil, heterocikloalkenilalkenil, heterocikloalkenilalkinil, arilalkil, arilalkenil, arilalkinil, heteroarilalkil, heteroarilalkenil, heteroarilalkinil, alkoksi, cikloalkiloksi, alkiltio, cikloalkiltio, sulfamoil, sulfinamoil, alkilamino ili cikloalkilamino, od kojih je svaki po izboru supstituiran s jednim ili više supstituenata izabranih između R9;
svaki R5 i R6 nezavisno predstavlja vodik, alkil, alkenil, cikloalkil, heterocikloalkil, -C(O)alkil, -C(O)Oalkil, -C(O)cikloalkil, -C(O)N-alkil, karboksialkil, -C(O)alkil-C(O)OH, -C(O)alkil-C(O)N-alkil, -C(O)N-aril, -S(O)2alkil, -S(O)alkil, -S(O)2aril, -S(O)2N-alkil, -S(O)aril, aril, heteroaril alkilaril ili alkilheteroaril, od kojih je svaki po izboru supstituiran s hidroksi ili jednim ili više halogena, ili R5 i R6 zajedno s atomom dušika za koji su vezani formiraju heterocikloalkil prsten, pri čemu je spomenuti prsten po izboru supstituiran s jednom ili više alkil grupa;
svaki R7 i R8 nezavisno predstavlja vodik, alkil, cikloalkil, alkenil, heteroaril, heterocikloalkil, karboksialkil, karbamoilalkil, alkiloksialkil, alkeniloksialkil, aril, arilalkil, alkilaril, heteroaril, heteroarilalkil, ili alkilheteroaril, od kojih je svaki po izboru supstituiran s jednim ili više supstituenata izabranih iz grupe koju čine hidroksi, halogen, okso, cijano, alkil, cikloalkil, alkenil, alkoksi, aril, heteroaril, heterocikloalkil, -S(O)2-alkil, -S(O)2-NR11R12, -NC(O)-alkil, -C(O)N-alkil, -NC(O)O-alkil, -OC(O)N-alkil, -NC(O)NR11R12, -NR11SO2-alkil, -S(O)-alkil, ili R7 i R8 zajedno s atomom dušika za koji su vezani formiraju heterocikloalkil prsten, pri čemu je spomenuti prsten po izboru supstituiran s jednom ili više alkil grupa;
R9 je vodik, halogen, hidroksi, alkoksi, karboksi ili trihalometil;
X i Y su ili C i N ili N i C, respektivno;
A je aril, cikloalkil, cikloalkenil, heteroaril, heterocikloalkil ili heterocikloalkenil, od kojih je svaki po izboru supstituiran s jednim ili više supstituenata izabranih iz grupe koja se sastoji od R10;
R10 je vodik, cijano, halogen, hidroksi, ili okso, ili je R10 alkil, cikloalkil, alkenil, alkinil, aril, heteroaril, cikloalkilalkil, cikloalkilalkenil, cikloalkilalkinil, cikloalkenilalkil, cikloalkenilalkenil, cikloalkenilalkinil, heterocikloalkil, heterocikloalkenil, heterocikloalkenilalkil, heterocikloalkenilalkenil, heterocikloalkenilalkinil, arilalkil, arilalkenil, arilalkinil, heteroarilalkil, heteroarilalkenil, heteroarilalkinil, alkoksi, cikloalkiloksi, alkiltio, cikloalkiltio, -S(O)alkil, -S(O)2-alkil, sulfamoil, sulfinamoil, -C(O)OR3, -C(O)R3, -NR5R6, -alkil(NR5R6), -cikloalkil(NR5R6), -cikloalkilalkil(NR5R6), -alkilcikloalkil(NR5R6), -C(O)NR7R8, -alkil(C(O)NR7R8), -cikloalkil(C(O)NR7R8), -cikloalkilalkil(C(O)NR7R8) ili -alkilcikloalkil(C(O)NR7R8), od kojih je svaki po izboru supstituiran s jednim ili više supstituenata izabranih između R4;
R11 i R12 svaki nezavisno predstavlja vodik ili alkil;
i njegove farmaceutski prihvatljive soli, hidrati, N-oksidi ili solvati.
2. Spoj prema zahtjevu 1, naznačen time da je A po izboru supstituiran s R10, pri čemu je R10 različit od vodika.
3. Spoj prema zahtjevu 1, naznačen time da je A po izboru supstituirani aril.
4. Spoj prema zahtjevu 1, naznačen time da je A po izboru supstituirani fenil ili po izboru supstituirani indanil.
5. Spoj prema zahtjevu 4, naznačen time da R10 je cijano, halogen, alkil, aril, heteroaril, sulfamoil, -C(O)R3, -C(O)OR3, -NR5R6, pri čemu su R3, R5 i R6 onakvi kao što je naznačeno u zahtjevu 1.
6. Spoj prema zahtjevu 1, naznačen time da je A po izboru supstituirani heteroaril.
7. Spoj prema zahtjevu 6, naznačen time da je A po izboru supstituirani piridil, po izboru supstituirani benzofuranil, po izboru supstituirani 3H-izobenzofuran-1-on-il ili po izboru supstituirani 2,3-dihidro-izoindol-1-on-il.
8. Spoj prema zahtjevu 1, naznačen time da je A po izboru supstituirani heterocikloalkil ili po izboru supstituirani heterocikloalkenil.
9. Spoj prema zahtjevu 8, naznačen time da je A po izboru supstituirani piperidinil ili po izboru supstituirani piridazinil.
10. Spoj prema bilo kom od zahtjeva 3, 4, 6, 7, 8, ili 9, naznačen time da je R10 vodik, cijano, halogen, okso, alkil, alkoksi, cikloalkiloksi, -S(O)alkil, -S(O)2-alkil, -C(O)R3, -C(O)OR3, -C(O)NR7R8, pri čemu su R3, R7 i R8 onakvi kao što je naznačeno u zahtjevu 1.
11. Spoj prema zahtjevu 10, naznačen time da je R10 cijano, halogen, okso, alkil, alkoksi, ili -C(O)R3, pri čemu je R3 onakav kao što je naznačeno u zahtjevu 1.
12. Spoj prema bilo kojem od prethodnih zahtjeva, opće formule Ia
[image]
naznačen time da su R1, R2 i A onakvi kao što je definirano u zahtjevu 1.
13. Spoj prema bilo kojem od zahtjeva 1-11, opće formule Ib
[image]
naznačen time da su R1, R2 i A onakvi kao što je definirano u zahtjevu 1.
14. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da R2 je po izboru supstituirani C1-6alkil ili po izboru supstituirani C3-6cikloalkil.
15. Spoj prema zahtjevu 14, naznačen time da R2 je po izboru supstituiran ciklopropil.
16. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da R3 je halogen, alkil, cikloalkil, heterocikloalkil, ili okso.
17. Spoj prema zahtjevu 16, naznačen time da R3 je alkil ili heterocikloalkil
18. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da je R4 halogen, hidroksi, ili cijano, ili R4 je NR5R6, -C(O)NR7R8, -COOR7, -NR5C(O)NR7R8, -OC(O)NR7R8, -OC(O)R3, -NC(O)R7, -OR7, -NC(O)OR3, -NSO2R7, -SO2NR7R8, -SO2R7R8, alkil, cikloalkil, cikloalkilalkil, heterocikloalkil, ili heterocikloalkilalkil, od kojih je svaki po izboru supstituiran s jednim ili više supstituenata izabranih između R9;
pri čemu su R3, R5, R6, R7, R8, i R9 onakvi kao što je definirano u bilo kojem od prethodnih zahtjeva.
19. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da je R4 hidroksi ili cijano,
ili je R4 -C(O)NR7R8, -COOR7, -NR5C(O)NR7R8, -OC(O)NR7R8, -NC(O)R7, -OR7, -NC(O)OR3, alkil, koji je po izboru supstituiran s jednim ili više supstituenata izabranih između R9; pri čemu je R9 vodik, halogen, ili hidroksil, i pri čemu su R3, R7 i R8 kao što je definirano u bilo kojem od prethodnih zahtjeva.
20. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da svaki R5 i R6 nezavisno predstavlja vodik, alkil, alkenil, cikloalkil, ili heterocikloalkil, ili R5 i R6 zajedno s atomom dušika za koji su vezani formiraju heterocikloalkil prsten, pri čemu je spomenuti prsten po izboru supstituiran s jednom ili više alkil grupa.
21. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da svaki R7 i R8 nezavisno predstavlja vodik, alkil, cikloalkil, heterocikloalkil, ili alkeniloksialkil, od kojih je svaki po izboru supstituiran s jednim ili više supstituenata izabranih iz grupe koja se sastoji od slijedećih: hidroksi, halogen, okso, cijano, alkil, cikloalkil, alkoksi, aril, heteroaril, heterocikloalkil, -S(O)2-alkil, -S(O)2-NR11R12, -NC(O)-alkil, -C(O)N-alkil, -NC(O)O-alkil, -OC(O)N-alkil, -NR11SO2-alkil, -S(O)-alkil, ili R7 i R8 zajedno s atomom dušika za koji su vezani formiraju heterocikloalkil prsten, pri čemu je spomenuti prsten po izboru supstituiran s jednom ili više alkil grupa; pri čemu R11 i R12 su vodik ili C1-4alkil.
22. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da svaki R7 i R8 nezavisno predstavlja vodik, alkil, cikloalkil, alkeniloksialkil, od kojih je svaki po izboru supstituiran s jednim ili više supstituenata izabranih iz grupe koja se sastoji od slijedećih: hidroksi, okso, cijano, alkil, cikloalkil, alkoksi, aril, heteroaril, -S(O)2-alkil, -S(O)2-NR11R12, -NC(O)-alkil, -NR11SO2-alkil, ili R7 i R8 zajedno s atomom dušika za koji su vezani formiraju heterocikloalkil prsten, pri čemu je spomenuti prsten po izboru supstituiran s jednom ili više alkil grupa; pri čemu su R11 i R12 vodik ili C1-4alkil.
23. Spoj prema bilo kojem od zahtjeva 1-22 izabran iz grupe koja se sastoji od:
2-ciklopropil-8-metoksi-5-(3-acetil-fenil)-[1,2,4]triazolo[1,5-a]piridin,
2-ciklopropil-8-metoksi-5-fenil-[1,2,4]triazolo[1,5-a]piridin,
2-ciklopropil-8-metoksi-5-(4-metoksi-fenil)-[1,2,4]triazolo[1,5-a]piridin,
2-ciklopropil-8-metoksi-5-(4-trifluorometil-fenil)-[1,2,4]triazolo[1,5-a]piridin,
2-ciklopropil-5-(3,4-dimetoksi-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin,
2-ciklopropil-8-metoksi-5-tiofen-2-il-[1,2,4]triazolo[1,5-a]piridin,
N-[3-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-fenil]-acetamid,
2-ciklopropil-8-metoksi-5-(3-trifluorometoksi-fenil)-[1,2,4]triazolo[1,5-a]piridin,
2-ciklopropil-8-metoksi-5-(3-metoksi-fenil)-[1,2,4]triazolo[1,5-a]piridin,
1-[5-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-tiofen-2-il]-etanon,
2-ciklopropil-8-metoksi-5-pirimidin-5-il-[1,2,4]triazolo[1,5-a]piridin,
2-ciklopropil-5-(3-metansulfonil-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin,
N-[3-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-fenil]-metansulfonamid,
3-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-N-metil-benzamid,
2-ciklopropil-8-metoksi-5-(4-acetil-fenil)-[1,2,4]triazolo[1,5-a]piridin,
N-[4-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-fenil]-acetamid,
metil ester 3-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-benzojeve kiseline,
2-ciklopropil-8-metoksi-5-piridin-3-il-[1,2,4]triazolo[1,5-a]piridin,
metil ester 4-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-benzojeve kiseline,
2-ciklopropil-5-(4-metansulfonil-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin,
2-ciklopropil-5-(2-fluoro-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin,
2-ciklopropil-8-metoksi-5-[4-(2-metoksi-etoksi)-fenil]-[1,2,4]triazolo[1,5-a]piridin,
4-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-benzamid,
5-(3-butoksi-fenil)-2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin,
2-ciklopropil-5-(3-fluoro-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin,
2-ciklopropil-8-metoksi-5-piridin-4-il-[1,2,4]triazolo[1,5-a]piridin,
2-ciklopropil-5-(2,4-dihloro-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin,
2-ciklopropil-8-metoksi-5-[4-(morfolin-4-sulfonil)-fenil]-[1,2,4]triazolo[1,5-a]piridin,
N-[4-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-benzil]-acetamid,
N-[4-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-benzil]-metansulfonamid,
2-ciklopropil-5-(4-fluoro-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin,
4-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-benzonitril,
metil ester 3-[4-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-fenil]-propionska kiselina,
4-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-N-(2-hidroksi-etil)-benzolsulfonamid,
3-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-benzonitril,
3-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-benzojeva kiselina,
[3-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-fenil]-metanol,
3-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-N,N-dimetil-benzamid,
3-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-benzamid,
4-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-benzojeva kiselina,
4-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-N,N-dimetil-benzamid,
4-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-N-metil-benzamid,
2-ciklopropil-8-metoksi-5-piperidin-1-il-[1,2,4]triazolo[1,5-a]piridin,
1-[3-(2-ciklopropil-8-hidroksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-fenil]-etanon,
2-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-izonikotinonitril,
etil ester 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilna kiselina,
amid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
izopropilamid 1-[5-(5-cijano-piridin-3-il)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
3-[2-(1-hidroksimetil-ciklopropil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il]-benzonitril,
1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester pirolidin-1-karboksilne kiseline,
1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester izopropil-karbaminske kiseline,
3-[2-(1-benziloksimetil-ciklopropil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il]-benzonitril,
N-{1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil}-izobutiramid,
ciklopentil ester {1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil}-karbaminske kiseline,
{1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4] triazolo[1,5-a]piridin-2-il]-ciklopropilmetil}-amid pirolidin-1-karboksilne kiseline,
6-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-5-metil-4,5-dihidro-2H-piridazin-3-on,
5-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-nikotinonitril,
5-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-indan-1-on,
4-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-2-metil-benzonitril,
4-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-indan-1-on,
3-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-5-fluoro-benzonitril,
4-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-2-fluoro-benzonitril,
4-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-2-metoksi-benzonitril,
5-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-3H-izobenzofuran-1-on,
3-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-5-hidroksimetil-benzonitril,
3-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-5-metoksi-benzonitril,
4-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-3H-izobenzofuran-1-on,
5-(2-ciklopropil-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il)-2,3-dihidro-izoindol-1-on,
benzilamid 1-[8-metoksi-5-(1-okso-indan-4-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
benzilamid 1-[5-(5-cijano-piridin-3-il)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
cikloheksilmetil-amid 1-[5-(4-cijano-3-metoksi-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropan karboksilne kiseline,
izopropilamid 1-[5-(4-cijano-3-metoksi-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropan karboksilne kiseline,
cikloheksilmetil-amid 1-[8-metoksi-5-(1-okso-indan-4-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-metansulfonil-etil)-amid 1-[5-(4-cijano-3-metoksi-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
benzilamid 1-[5-(4-cijano-3-metoksi-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropan karboksilne kiseline,
benzilamid 1-[8-metoksi-5-(1-okso-1,3-dihidro-izobenzofuran-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
izopropilamid 1-[8-metoksi-5-(1-okso-indan-4-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
izopropilamid 1-[8-metoksi-5-(1-okso-indan-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
benzilamid 1-[8-metoksi-5-(1-okso-indan-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-metansulfonil-etil)-amid 1-[8-metoksi-5-(1-okso-indan-4-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilna kiselina,
(2-metansulfonil-etil)-amid 1-[8-metoksi-5-(1-okso-indan-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilna kiselina,
cikloheksilmetil-amid 1-[5-(5-cijano-piridin-3-il)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilna kiselina,
(2-metansulfonil-etil)-amid 1-[5-(5-cijano-piridin-3-il)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilna kiselina,
(2-dimetilsulfamoil-etil)-amid 1-[8-metoksi-5-(1-okso-1,3-dihidro-izobenzofuran-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilna kiselina,
etil ester 1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
etil ester 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
etil ester 1-[5-(3-acetil-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilna kiselina,
1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilna kiselina,
1-[5-(3-acetil-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilna kiselina,
izopropilamid 1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(piridin-3-ilmetil)-amid 1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
3-{8-metoksi-2-[1-(morfolin-4-karbonil)-ciklopropil]-[1,2,4]triazolo-[1,5-a]piridin-5-il}-benzonitril,
benzilamid 1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-sulfamoiletil)-amid 1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-metansulfonil-etil)-amid 1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
3-{8-metoksi-2-[1-(pirolidin-1-karbonil)-ciklopropil]-[1,2,4]triazolo[1,5-a]piridin-5-il}-benzonitril,
2-({1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarbonil}-amino)-etil ester 2-metil-akrilne kiseline,
(2-metoksietil)-amid 1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(piridin-3-ilmetil)-amid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
4-{8-metoksi-2-[1-(4-metil-piperazin-1-karbonil)-ciklopropil]-[1,2,4]triazolo[1,5-a]piridin-5-il}-benzonitril,
4-{8-metoksi-2-[1-(morfolin-4-karbonil)-ciklopropil]-[1,2,4]triazolo[1,5-a]piridin-5-il}-benzonitril,
benzilamid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-sulfamoiletil)-amid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-metansulfonil-etil)-amid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
izopropilamid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
metilamid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
etilamid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
propilamid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
ciklopropilamid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
1 izobutilamid -[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
cijanometilamid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-acetilamino-etil)-amid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
1(2-metansulfonilamino-etil)-amid -[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(3-morfolin-4-il-3-okso-propil)-amid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-dimetilsulfamoil-etil)-amid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
[2-(metansulfonil-metil-amino)-etil]-amid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(piridin-3-ilmetil)-amid 1-[5-(3-acetil-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
1-(3-{8-metoksi-2-[1-(4-metil-piperazin-1-karbonil)-ciklopropil]-[1,2,4]triazolo[1,5-a]piridin-5-il}-fenil)-etanon,
1-(3-{8-metoksi-2-[1-(morfolin-4-karbonil)-ciklopropil]-[1,2,4]triazolo[1,5-a]piridin-5-il}-fenil)-etanon,
benzilamid 1-[5-(3-acetil-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-sulfamoiletil)-amid 1-[5-(3-acetil-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-metansulfonil-etil)-amid 1-[5-(3-acetil-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
2-({1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a] piridin-2-il]-ciklopropankarbonil}-amino)-etil ester 2-metil-akrilne kiseline,
(2-hidroksietil)-amid 1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
1-[5-(5-cijano-piridin-3-il)-8-metoksi-[1,2,4] triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester cikloheksil-karbaminske kiseline,
1-[8-metoksi-5-(1-okso-indan-5-il)-[1,2,4]triazolo [1,5-a]piridin-2-il]-ciklopropilmetil ester propil-karbaminske kiseline,
1-[5-(4-cijano-3-metoksi-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester dimetil-karbaminske kiseline,
1-[5-(5-cijano-piridin-3-il)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester izopropil-karbaminske kiseline,
1-[8-metoksi-5-(1-okso-indan-4-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester propil-karbaminske kiseline,
1-[5-(4-cijano-3-metoksi-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester pirolidin-1-karboksilne kiseline,
1-[5-(4-cijano-3-metoksi-fenil)-8-metoksi-1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester izopropil-karbaninske kiseline,
1-[5-(5-cijano-piridin-3-il)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil estar propil-karbaminske kiseline,
1-[5-(4-cijano-3-metoksi-fenil)-8-metoksi-[1,2,4] triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester propil-karbaminske kiseline,
1-[8-metoksi-5-(1-okso-indan-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester pirolidin-1-karboksilne kiseline,
1-[8-metoksi-5-(1-okso-indan-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester izopropil-karbaminske kiseline,
1-[8-metoksi-5-(1-okso-indan-4-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester cikloheksil-karbaminske kiseline,
1-[5-(4-cijano-3-metoksi-fenil)-8-metoksi-1, 2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester cikloheksil-karbaminske kiseline,
1-[5-(5-cijano-piridin-3-il)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester pirolidin-1-karboksilne kiseline,
1-[8-metoksi-5-(1-okso-indan-5-il)-[1,2,4]triazo lo[1,5-a]piridin-2-il]-ciklopropilmetil ester dimetil-karbaminske kiseline,
1-[5-(5-cijano-piridin-3-il)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester dimetil-karbaminske kiseline,
1-[5-(4-cijano-3-metoksi-fenil)-8-metoksi-1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester dietil-karbaminske kiseline,
1-[8-metoksi-5-(1-okso-indan-4-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester dietil-karbaminske kiseline,
1-[5-(5-cijano-piridin-3-il)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester dietil-karbaminske kiseline,
5-[2-(1-hidroksimetil-ciklopropil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il]-nikotinonitril,
4-(2-ciklopropil-5-metoksi-[1,2,4]triazolo[1,5-a]piridin-8-il)-2-metoksi-benzonitril,
4-(2-ciklopropil-5-metoksi-[1,2,4]triazolo[1,5-a]piridin-8-il)-2-metil-benzonitril,
3-(2-ciklopropil-5-metoksi-[1,2,4]triazolo[1,5-a]piridin-8-il)-benzonitril,
5-(2-ciklopropil-5-metoksi-[1,2,4]triazolo[1,5-a]piridin-8-il)-indan-1-on,
4-(2-ciklopropil-5-metoksi-[1,2,4]triazolo[1,5-a]piridin-8-il)-indan-1-on,
izopropilamid 1-[8-(4-cijano-3-metoksi-fenil)-5-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropan karboksilne kiseline,
izopropilamid 1-[5-metoksi-8-(1-okso-1,3-dihidro-izobenzofuran-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
izopropilamid 1-[5-metoksi-8-(1-okso-indan-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
izopropilamid 1-[5-hidroksi-8-(1-okso-indan-4-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-metansulfonil-etil)-amid 1-[5-metoksi-8-(1-okso-indan-4-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-metansulfonil-etil)-amid 1-[8-(5-cijano-piridin-3-il)-5-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
izopropilamid 1-[5-metoksi-8-(1-okso-indan-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
izobutilamid 1-[5-metoksi-8-(1-okso-indan-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
izopropilamid 1-[5-metoksi-8-(1-okso-1,3-dihidro-izobenzofuran-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
izopropilamid 1-[8-(4-cijano-3-metoksi-fenil)-5-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropan karboksilne kiseline,
(2-metansulfonil-etil)-amid 1-[8-(4-cijano-3-metoksi-fenil)-5-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-metansulfonil-etil)-amid 1-[5-metoksi-8-(1-okso-indan-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-metansulfonil-etil)-amid 1-[5-metoksi-8-(1-okso-1,3-dihidro-izobenzofuran-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
izobutil-amid 1-[8-(4-cijano-3-metoksi-fenil)-5-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropan karboksilne kiseline,
izopropilamid 1-[5-hidroksi-8-(1-okso-indan-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-metansulfonil-etil)-amid 1-[8-metoksi-5-(1-okso-1,3-dihidro-izobenzofuran-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
cikloheksilmetil-amid 1-[8-metoksi-5-(1-okso-1,3-dihidro-izobenzofuran-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-dimetilsulfamoil-etil)-amid 1-[8-metoksi-5-(1-okso-1,3-dihidro-izobenzofuran-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
1-[8-metoksi-5-(1-okso-indan-4-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester dietil-karbaminske kiseline,
1-[8-metoksi-5-(1-okso-1,3-dihidro-izobenzofuran -5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester dimetil-karbaminske kiseline,
1-[5-(5-cijano-piridin-3-il)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester dietil-karbaminske kiseline,
1-[5-(4-cijano-3-metoksi-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester dietil-karbaminske kiseline,
1-[8-metoksi-5-(1-okso-1,3-dihidro-izobenzofuran-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropilmetil ester cikloheksil-karbaminske kiseline,
4-[2-(1-hidroksimetil-ciklopropil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il]-2-metoksi-benzonitril,
4-[2-(1-izobutoksimetil-ciklopropil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il]-2-metoksi-benzonitril,
izobutilamid 1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-metansulfonilamino-etil)-amid 1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
ciklopropilamid 1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
cikloheksilmetil-amid 1-[5-(3-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
5-[2-(1-izobutoksimetil-ciklopropil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-5-il]-nikotinonitril,
5-(2-ciklopropil-5-metoksi-[1,2,4]triazolo[1,5-a]piridin-8-il)-nikotinonitril,
(2-dimetilsulfamoil-etil)-amid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
[2-(metansulfonil-metil-amino)-etil]-amid 1-[5-(4-cijano-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-dimetilsulfamoil-etil)-amid 1-[5-(4-cijano-3-metoksi-fenil)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-dimetilsulfamoil-etil)-amid 1-[5-(5-cijano-piridin-3-il)-8-metoksi-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
(2-dimetilsulfamoil-etil)-amid 1-[8-metoksi-5-(1-okso-indan-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-il]-ciklopropankarboksilne kiseline,
i njegove farmaceutski prihvatljive soli, hidrati, N-oksidi ili solvati.
24. Spoj prema bilo kojem od zahtjeva 1-23 za primjenu u liječenju.
25. Spoj prema bilo kojem od zahtjeva 1-23 za primjenu u liječenju kožnih bolesti ili stanja ili akutnih ili kroničnih poremećaja rana kože.
26. Spoj prema zahtjevu 25 za primjenu u liječenju proliferativnih i upalnih kožnih poremećaja, psorijaze, raka, epidermalnih upala, alopecije, atrofije kože, atrofije kože izazvane steroidima, starenja kože, starenja kože uslijed izlaganja suncu, akni, dermatitisa, atopičkog dermatitisa, seboreičnog dermatitisa, kontaktnog dermatitisa, urtikarije, svraba, i ekcema.
27. Farmaceutske kompozicije koji sadrže spoj prema bilo kojem od zahtjeva 1-23 zajedno s farmaceutski prihvatljivim pomoćnim sredstvom ili ekscipijensom ili farmaceutski prihvatljivim nosačem, odnosno nosačima.
28. Farmaceutske kompozicije prema zahtjevu 27 koje dalje sadrže jedan ili više drugih terapeutski aktivnih spojeva.
29. Primjena spoja prema bilo kojem od zahtjeva 1-23 u proizvodnji lijekova za profilaksu, liječenje ili poboljšanje kožnih bolesti ili stanja, ili akutnih ili kroničnih poremećaja kožnih rana.
30. Primjena prema zahtjevu 29, naznačena time da je kožna bolest ili stanje izabrano iz grupe koja se sastoji od: proliferativni i upalni kožni poremećaji, psorijaza, epidermalna upala, alopecija, atrofija kože, atrofija kože izazvana steroidima, starenje kože, starenje kože uslijed izlaganja suncu, akne, dermatitis, atopički dermatitis, seboreični dermatitis, kontaktni dermatitis, urtikarija, svrab, i ekcem.
Applications Claiming Priority (3)
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US13944508P | 2008-12-19 | 2008-12-19 | |
PCT/DK2009/000262 WO2010069322A1 (en) | 2008-12-19 | 2009-12-18 | Triazolopyridines as phosphodiesterase inhibitors for treatment of dermal diseases |
EP09795687.4A EP2379548B1 (en) | 2008-12-19 | 2009-12-18 | Triazolopyridines as phosphodiesterase inhibitors for treatment of dermal diseases |
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HRP20160488T1 true HRP20160488T1 (hr) | 2016-06-17 |
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HRP20160488TT HRP20160488T1 (hr) | 2008-12-19 | 2016-05-09 | Triazolopiridini kao inhibitori fosfodiesteraze za liječenje kožnih bolesti |
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US (1) | US8952162B2 (hr) |
EP (1) | EP2379548B1 (hr) |
JP (2) | JP5743901B2 (hr) |
KR (1) | KR20110094355A (hr) |
CN (1) | CN102317287B (hr) |
AU (1) | AU2009328752B2 (hr) |
BR (1) | BRPI0922452A2 (hr) |
CA (1) | CA2747022A1 (hr) |
CY (1) | CY1117562T1 (hr) |
DK (1) | DK2379548T3 (hr) |
ES (1) | ES2570769T3 (hr) |
HK (1) | HK1165791A1 (hr) |
HR (1) | HRP20160488T1 (hr) |
HU (1) | HUE027770T2 (hr) |
IL (1) | IL213570A (hr) |
MX (1) | MX2011006428A (hr) |
NO (1) | NO20110871A1 (hr) |
NZ (1) | NZ593595A (hr) |
PL (1) | PL2379548T3 (hr) |
RS (1) | RS54752B1 (hr) |
RU (1) | RU2544011C2 (hr) |
SG (1) | SG172206A1 (hr) |
SI (1) | SI2379548T1 (hr) |
WO (1) | WO2010069322A1 (hr) |
ZA (1) | ZA201104422B (hr) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
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AU2010254806C1 (en) | 2009-06-05 | 2016-07-07 | Cephalon, Inc. | Preparation and uses of 1,2,4-triazolo [1,5a] pyridine derivatives |
PT2455381E (pt) | 2009-07-17 | 2014-06-24 | Japan Tobacco Inc | Composto de triazolopiridina e sua acção como inibidor da prolil-hidroxilase e indutor da produção de eritropoietina |
EP2343294A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Substituted triazolopyridines |
CN102770125B (zh) | 2009-12-22 | 2015-02-11 | 利奥制药有限公司 | 钙泊三醇一水化合物纳米晶体 |
JP5873439B2 (ja) | 2009-12-22 | 2016-03-01 | レオ ファーマ アクティーゼルスカブ | ビタミンd類似体および溶媒と界面活性剤の混合物を含む皮膚組成物 |
NZ601001A (en) | 2009-12-22 | 2014-07-25 | Leo Pharma As | Pharmaceutical composition comprising solvent mixture and a vitamin d derivative or analogue |
JP2014511393A (ja) * | 2011-03-07 | 2014-05-15 | セルジーン コーポレイション | イソインドリン化合物を用いた疾患の治療方法 |
BR112014014802A2 (pt) | 2011-12-21 | 2017-06-13 | Leo Pharma As | composto, composição farmacêutica, uso de um composto, métodos para tratamento ou para alívio de uma doença ou de um distúrbio ou de uma condição, e para tratamento ou melhora de doenças ou de condições |
CN104822392B (zh) * | 2012-11-30 | 2017-09-08 | 利奥制药有限公司 | 抑制活化的t‑细胞中il‑22表达的方法 |
WO2014206903A1 (en) | 2013-06-25 | 2014-12-31 | Leo Pharma A/S | METHODS FOR THE PREPARATION OF SUBSTITUTED [1,2,4]TRIAZOLO[1,5-a]PYRIDINES |
WO2017089347A1 (en) | 2015-11-25 | 2017-06-01 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods and pharmaceutical compositions for the treatment of braf inhibitor resistant melanomas |
JP7203846B2 (ja) | 2017-12-15 | 2023-01-13 | ユニオン・セラピューティクス・アクティエセルスカブ | 置換アゼチジンジヒドロチエノピリジンおよびホスホジエステラーゼ阻害剤としてのそれらの使用 |
JP2021155336A (ja) * | 2018-06-27 | 2021-10-07 | Meiji Seikaファルマ株式会社 | 新規pde4阻害剤 |
AR114977A1 (es) * | 2018-06-27 | 2020-11-11 | Meiji Seika Pharma Co Ltd | Cristales de derivado de benzoxazol |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
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CN1163493C (zh) | 1995-05-19 | 2004-08-25 | 协和发酵工业株式会社 | 含氧杂环化合物 |
EP0943613A4 (en) | 1996-11-19 | 2002-07-10 | Kyowa Hakko Kogyo Kk | HETEROCYCLIC COMPOUNDS CONTAINING OXYGEN |
US6514989B1 (en) * | 2001-07-20 | 2003-02-04 | Hoffmann-La Roche Inc. | Aromatic and heteroaromatic substituted 1,2,4-triazolo pyridine derivatives |
US6693116B2 (en) * | 2001-10-08 | 2004-02-17 | Hoffmann-La Roche Inc. | Adenosine receptor ligands |
WO2006095666A1 (ja) * | 2005-03-07 | 2006-09-14 | Kyorin Pharmaceutical Co., Ltd. | ピラゾロピリジン-4-イルピリダジノン誘導体とその付加塩及びそれらを有効成分とするpde阻害剤 |
JP2007091597A (ja) * | 2005-09-27 | 2007-04-12 | Kyorin Pharmaceut Co Ltd | ピラゾロピリジン−4−イルピラゾロン誘導体とその付加塩及びそれを有効成分とするホスホジエステラーゼ阻害剤 |
US20090196284A1 (en) * | 2006-06-28 | 2009-08-06 | Nokia Siemens Networks Gmbh & Co.Kg | Method for Providing an Emergency Call Service for VoIP Subscribers |
WO2008006540A1 (en) | 2006-07-12 | 2008-01-17 | Syngenta Participations Ag | Triazolopyridine derivatives as herbicides |
JP2008024599A (ja) * | 2006-07-18 | 2008-02-07 | Kyorin Pharmaceut Co Ltd | ピリダジノン誘導体、それらを有効成分とするpde阻害剤及び医薬 |
JP2008069144A (ja) * | 2006-08-17 | 2008-03-27 | Kyorin Pharmaceut Co Ltd | ピラゾロン誘導体及びそれらを有効成分とするpde阻害剤 |
EP2146989B1 (en) | 2007-04-16 | 2012-01-04 | Leo Pharma A/S | Triazolopyridines as phosphodiesterase inhibitors for treatment of dermal diseases |
EP2168960A1 (en) * | 2007-06-19 | 2010-03-31 | Kyorin Pharmaceutical Co., Ltd. | Pyrazolone derivative and pde inhibitor containing the same as active ingredient |
CA2692248A1 (en) * | 2007-06-19 | 2008-12-24 | Kyorin Pharmaceutical Co., Ltd. | Pyridazinone derivative and pde inhibitor containing the same as active ingredient |
JP2009040711A (ja) | 2007-08-08 | 2009-02-26 | Kyorin Pharmaceut Co Ltd | カルボスティリル誘導体及びそれらを有効成分とするpde阻害剤 |
WO2010035745A1 (ja) | 2008-09-25 | 2010-04-01 | 杏林製薬株式会社 | ヘテロ環ビアリール誘導体及びそれらを有効成分とするpde阻害剤 |
TW201020233A (en) | 2008-10-09 | 2010-06-01 | Kyorin Seiyaku Kk | Isoquinoline derivative, and pde inhibitor comprising same as active ingredient |
-
2009
- 2009-12-18 AU AU2009328752A patent/AU2009328752B2/en not_active Ceased
- 2009-12-18 PL PL09795687T patent/PL2379548T3/pl unknown
- 2009-12-18 CA CA2747022A patent/CA2747022A1/en not_active Abandoned
- 2009-12-18 NZ NZ593595A patent/NZ593595A/xx not_active IP Right Cessation
- 2009-12-18 SG SG2011044203A patent/SG172206A1/en unknown
- 2009-12-18 EP EP09795687.4A patent/EP2379548B1/en active Active
- 2009-12-18 ES ES09795687T patent/ES2570769T3/es active Active
- 2009-12-18 MX MX2011006428A patent/MX2011006428A/es active IP Right Grant
- 2009-12-18 KR KR1020117016745A patent/KR20110094355A/ko not_active Application Discontinuation
- 2009-12-18 JP JP2011541089A patent/JP5743901B2/ja not_active Expired - Fee Related
- 2009-12-18 RU RU2011129786/04A patent/RU2544011C2/ru active
- 2009-12-18 BR BRPI0922452A patent/BRPI0922452A2/pt active Search and Examination
- 2009-12-18 WO PCT/DK2009/000262 patent/WO2010069322A1/en active Application Filing
- 2009-12-18 DK DK09795687.4T patent/DK2379548T3/en active
- 2009-12-18 US US13/140,505 patent/US8952162B2/en not_active Expired - Fee Related
- 2009-12-18 CN CN200980156864.XA patent/CN102317287B/zh not_active Expired - Fee Related
- 2009-12-18 RS RS20160308A patent/RS54752B1/sr unknown
- 2009-12-18 HU HUE09795687A patent/HUE027770T2/en unknown
- 2009-12-18 SI SI200931410A patent/SI2379548T1/sl unknown
-
2011
- 2011-06-14 ZA ZA2011/04422A patent/ZA201104422B/en unknown
- 2011-06-15 IL IL213570A patent/IL213570A/en not_active IP Right Cessation
- 2011-06-17 NO NO20110871A patent/NO20110871A1/no not_active Application Discontinuation
-
2012
- 2012-06-25 HK HK12106184.9A patent/HK1165791A1/xx not_active IP Right Cessation
-
2014
- 2014-12-18 JP JP2014256695A patent/JP2015096535A/ja not_active Withdrawn
-
2016
- 2016-05-06 CY CY20161100373T patent/CY1117562T1/el unknown
- 2016-05-09 HR HRP20160488TT patent/HRP20160488T1/hr unknown
Also Published As
Publication number | Publication date |
---|---|
SI2379548T1 (sl) | 2016-06-30 |
AU2009328752A1 (en) | 2011-07-07 |
RS54752B1 (sr) | 2016-10-31 |
DK2379548T3 (en) | 2016-05-17 |
HUE027770T2 (en) | 2016-11-28 |
WO2010069322A1 (en) | 2010-06-24 |
ES2570769T3 (es) | 2016-05-20 |
IL213570A (en) | 2015-10-29 |
PL2379548T3 (pl) | 2016-08-31 |
KR20110094355A (ko) | 2011-08-23 |
CN102317287B (zh) | 2014-10-08 |
RU2544011C2 (ru) | 2015-03-10 |
MX2011006428A (es) | 2011-07-28 |
CA2747022A1 (en) | 2010-06-24 |
NZ593595A (en) | 2013-07-26 |
US8952162B2 (en) | 2015-02-10 |
CN102317287A (zh) | 2012-01-11 |
EP2379548B1 (en) | 2016-03-09 |
BRPI0922452A2 (pt) | 2015-12-15 |
SG172206A1 (en) | 2011-07-28 |
ZA201104422B (en) | 2012-09-26 |
JP2012512192A (ja) | 2012-05-31 |
HK1165791A1 (en) | 2012-10-12 |
CY1117562T1 (el) | 2017-04-26 |
US20120028974A1 (en) | 2012-02-02 |
AU2009328752B2 (en) | 2015-07-16 |
NO20110871A1 (no) | 2011-09-19 |
JP2015096535A (ja) | 2015-05-21 |
JP5743901B2 (ja) | 2015-07-01 |
IL213570A0 (en) | 2011-07-31 |
EP2379548A1 (en) | 2011-10-26 |
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