HRP20240935T1 - Heterociklični i heteroaril spojevi za liječenje huntingtonove bolesti - Google Patents

Heterociklični i heteroaril spojevi za liječenje huntingtonove bolesti Download PDF

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Publication number: HRP20240935T1
Authority: HR; Croatia
Prior art keywords: pyridazin; tetramethylpiperidin; triazolo; phenol; pyrazol
Prior art date: 2018-06-27

Application number

HRP20240935TT

Other languages

English (en)

Croatian (hr)

Inventor

Nadiya Sydorenko

Md Rauful ALAM

Michael A. Arnold

Suresh Babu

Anuradha Bhattacharyya

Guangming Chen

Aleksey I. Gerasyuto

Gary Mitchell Karp

Andrew J. Kassick

Anthony R. Mazzotti

Young-Choon Moon

Jana Narasimhan

Jigar Patel

Anthony Turpoff

Matthew G. Woll

Wuming YAN

Nanjing Zhang

Original Assignee

Ptc Therapeutics, Inc.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2018-06-27

Filing date

2019-06-25

Publication date

2024-11-22

2019-06-25 Application filed by Ptc Therapeutics, Inc. filed Critical Ptc Therapeutics, Inc.

2024-11-22 Publication of HRP20240935T1 publication Critical patent/HRP20240935T1/hr

Links

150000001875 compounds Chemical class 0.000 title claims 52
208000023105 Huntington disease Diseases 0.000 title claims 3
-1 5-(1H-pyrazol-4-yl)-2-[7-(2,2,6,6-tetramethylpiperidin-4-yl)-7H-imidazo[4,5-c]pyridazin-3-yl]phenol hydrochloride Chemical compound 0.000 claims 190
125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 claims 33
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 21
239000000825 pharmaceutical preparation Substances 0.000 claims 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
ZXRCAYWYTOIRQS-UHFFFAOYSA-N hydron;phenol;chloride Chemical compound Cl.OC1=CC=CC=C1 ZXRCAYWYTOIRQS-UHFFFAOYSA-N 0.000 claims 9
238000000034 method Methods 0.000 claims 8
239000000546 pharmaceutical excipient Substances 0.000 claims 8
JELQZSVKOONUKD-UHFFFAOYSA-N phenol dihydrochloride Chemical compound Cl.Cl.OC1=CC=CC=C1.OC1=CC=CC=C1 JELQZSVKOONUKD-UHFFFAOYSA-N 0.000 claims 8
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 8
150000003839 salts Chemical group 0.000 claims 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 6
201000010099 disease Diseases 0.000 claims 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
239000012453 solvate Substances 0.000 claims 5
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
ICZNVPJUHBURBG-UHFFFAOYSA-N 2-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]-5-(triazol-2-yl)phenol Chemical compound N1C(CC(CC1(C)C)N1C2=C(N=N1)C=C(C1=CC=C(N3N=CC=N3)C=C1O)N=N2)(C)C ICZNVPJUHBURBG-UHFFFAOYSA-N 0.000 claims 3
ORXRRLUUTYHCNI-UHFFFAOYSA-N CC1(CC(CC(N1)(C)C)N2C3=NN=C(C=C3N=N2)C4=C(C=C(C=C4)N5N=CC=N5)O)C.Cl Chemical compound CC1(CC(CC(N1)(C)C)N2C3=NN=C(C=C3N=N2)C4=C(C=C(C=C4)N5N=CC=N5)O)C.Cl ORXRRLUUTYHCNI-UHFFFAOYSA-N 0.000 claims 3
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 3
YOUQXTMNMLEWCM-UHFFFAOYSA-N 2-(1-piperidin-4-ylpyrazolo[3,4-c]pyridazin-5-yl)-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=NN=C2N(N=CC2=C1)C1CCNCC1 YOUQXTMNMLEWCM-UHFFFAOYSA-N 0.000 claims 2
FVXQGVZLCVMFLE-UHFFFAOYSA-N 2-(1-piperidin-4-ylpyrazolo[3,4-c]pyridazin-5-yl)-5-(1H-pyrazol-4-yl)phenol hydrochloride Chemical compound Cl.Oc1cc(ccc1-c1cc2cnn(C3CCNCC3)c2nn1)-c1cn[nH]c1 FVXQGVZLCVMFLE-UHFFFAOYSA-N 0.000 claims 2
NJYKXOJRBBASGJ-UHFFFAOYSA-N 2-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]-5-(1,2,4-thiadiazol-5-yl)phenol Chemical compound CC1(NC(CC(C1)N1N=NC2=C1N=NC(=C2)C1=C(C=C(C=C1)C1=NC=NS1)O)(C)C)C NJYKXOJRBBASGJ-UHFFFAOYSA-N 0.000 claims 2
NDQVGHCUUVQCTH-UHFFFAOYSA-N 2-[6-(methylamino)-7-(2,2,6,6-tetramethylpiperidin-4-yl)imidazo[4,5-c]pyridazin-3-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C1(NC(CC(C1)N1C2=C(N=C1NC)C=C(C1=CC=C(C=3C=NNC=3)C=C1O)N=N2)(C)C)(C)C NDQVGHCUUVQCTH-UHFFFAOYSA-N 0.000 claims 2
WYXAJJZBFJBRKP-UHFFFAOYSA-N 2-fluoro-3-(1H-pyrazol-4-yl)-6-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]phenol Chemical compound N1C(CC(CC1(C)C)N1C2=C(N=N1)C=C(C1=CC=C(C=3C=NNC=3)C(F)=C1O)N=N2)(C)C WYXAJJZBFJBRKP-UHFFFAOYSA-N 0.000 claims 2
QFFQDEGMTBBEMV-UHFFFAOYSA-N 2-methyl-6-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]-1H-benzimidazol-5-ol Chemical compound C1(NC(CC(N2C3=NN=C(C4=C(O)C=C5NC(=NC5=C4)C)C=C3N=N2)C1)(C)C)(C)C QFFQDEGMTBBEMV-UHFFFAOYSA-N 0.000 claims 2
VTBHBWBXALXSJK-UHFFFAOYSA-N 3-methyl-6-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]benzimidazol-5-ol Chemical compound N1C(CC(CC1(C)C)N1C2=C(N=N1)C=C(C1=C(O)C=C3N(C=NC3=C1)C)N=N2)(C)C VTBHBWBXALXSJK-UHFFFAOYSA-N 0.000 claims 2
NKDRVWDDKGMPCZ-UHFFFAOYSA-N 4-fluoro-2-(1H-pyrazol-4-yl)-5-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]phenol Chemical compound FC1=CC(=C(C=C1C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C)O)C=1C=NNC=1 NKDRVWDDKGMPCZ-UHFFFAOYSA-N 0.000 claims 2
WGGHKOLLPVNZPN-UHFFFAOYSA-N 5-(1-methylpyrazol-4-yl)-2-[1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazolo[3,4-c]pyridazin-5-yl]phenol Chemical compound C1(C)(CC(N2C3=C(C=N2)C=C(C2=CC=C(C4=CN(N=C4)C)C=C2O)N=N3)CC(C)(C)N1)C WGGHKOLLPVNZPN-UHFFFAOYSA-N 0.000 claims 2
JYDWYIQQANSETH-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[1-(2,2,6,6-tetramethylpiperidin-4-yl)imidazo[4,5-b]pyrazin-5-yl]phenol Chemical compound C1(NC(CC(C1)N1C2=NC=C(N=C2N=C1)C1=CC=C(C=2C=NNC=2)C=C1O)(C)C)(C)C JYDWYIQQANSETH-UHFFFAOYSA-N 0.000 claims 2
YFWCCAXUEVEWBF-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazolo[3,4-c]pyridazin-5-yl]phenol Chemical compound CC1(NC(CC(C1)N1C2=C(C=N1)C=C(C1=CC=C(C=3C=NNC=3)C=C1O)N=N2)(C)C)C YFWCCAXUEVEWBF-UHFFFAOYSA-N 0.000 claims 2
UMAYQOIOMNDPOE-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]phenol Chemical compound C1(NC(CC(N2C3=NN=C(C=C3N=N2)C2=C(C=C(C=3C=NNC=3)C=C2)O)C1)(C)C)(C)C UMAYQOIOMNDPOE-UHFFFAOYSA-N 0.000 claims 2
HODKQVFXRRLNPJ-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[5-(2,2,6,6-tetramethyl-1,3-dihydropyridin-4-yl)pyrrolo[2,3-b]pyrazin-2-yl]phenol Chemical compound N1C(CC(=CC1(C)C)N1C2=NC=C(N=C2C=C1)C1=CC=C(C2=CNN=C2)C=C1O)(C)C HODKQVFXRRLNPJ-UHFFFAOYSA-N 0.000 claims 2
JECMMGGVMZYOIW-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[5-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolo[2,3-b]pyrazin-2-yl]phenol Chemical compound CC1(CC(N2C3=C(C=C2)N=C(C2=CC=C(C4=CNN=C4)C=C2O)C=N3)CC(C)(C)N1)C JECMMGGVMZYOIW-UHFFFAOYSA-N 0.000 claims 2
GTKDDLZJVSMISF-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[7-(1,2,3,6-tetrahydropyridin-4-yl)-5H-pyrrolo[3,2-c]pyridazin-3-yl]phenol Chemical compound N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)C(=CN2)C=1CCNCC=1 GTKDDLZJVSMISF-UHFFFAOYSA-N 0.000 claims 2
ZEZSKTLJQHOQSU-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[7-(2,2,6,6-tetramethyl-1,3-dihydropyridin-4-yl)thieno[3,2-c]pyridazin-3-yl]phenol Chemical compound N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)C(=CS2)C=1CC(NC(C=1)(C)C)(C)C ZEZSKTLJQHOQSU-UHFFFAOYSA-N 0.000 claims 2
DTSRPRILCQRTJV-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[7-(2,2,6,6-tetramethylpiperidin-4-yl)-5,6-dihydropyrrolo[2,3-c]pyridazin-3-yl]phenol Chemical compound C1(C)(CC(N2CCC3=CC(C4=CC=C(C=5C=NNC=5)C=C4O)=NN=C23)CC(C)(C)N1)C DTSRPRILCQRTJV-UHFFFAOYSA-N 0.000 claims 2
CZWBOKNESMYJDW-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[7-(2,2,6,6-tetramethylpiperidin-4-yl)imidazo[4,5-c]pyridazin-3-yl]phenol Chemical compound C1(NC(CC(C1)N1C2=C(N=C1)C=C(C1=CC=C(C=3C=NNC=3)C=C1O)N=N2)(C)C)(C)C CZWBOKNESMYJDW-UHFFFAOYSA-N 0.000 claims 2
BRXVPPNQNVMBRK-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[7-(2,2,6,6-tetramethylpiperidin-4-yl)imidazo[4,5-c]pyridazin-3-yl]pyridin-3-ol Chemical compound C1(NC(CC(C1)N1C2=C(N=C1)C=C(C1=C(O)C=C(C3=CNN=C3)C=N1)N=N2)(C)C)(C)C BRXVPPNQNVMBRK-UHFFFAOYSA-N 0.000 claims 2
XGLPDROYXHTXMK-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[7-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolo[2,3-c]pyridazin-3-yl]phenol Chemical compound C1(C)(NC(C)(C)CC(N2C=CC3=CC(C4=CC=C(C=5C=NNC=5)C=C4O)=NN=C23)C1)C XGLPDROYXHTXMK-UHFFFAOYSA-N 0.000 claims 2
WBDSEOVLSQMPDX-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[7-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolo[2,3-c]pyridazin-3-yl]pyridin-3-ol Chemical compound N1C(CC(CC1(C)C)N1C2=C(C=C1)C=C(C1=C(O)C=C(C3=CNN=C3)C=N1)N=N2)(C)C WBDSEOVLSQMPDX-UHFFFAOYSA-N 0.000 claims 2
FKTKNHQDCOLWNI-UHFFFAOYSA-N 5-(2-methyl-1,3-thiazol-5-yl)-2-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]phenol Chemical compound CC=1SC(=CN=1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C FKTKNHQDCOLWNI-UHFFFAOYSA-N 0.000 claims 2
GIYSUKBTCIPXND-UHFFFAOYSA-N 5-(4-methylpyrazol-1-yl)-2-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]phenol Chemical compound C1(C)(CC(N2C3=C(N=N2)C=C(C2=C(C=C(N4C=C(C=N4)C)C=C2)O)N=N3)CC(C)(C)N1)C GIYSUKBTCIPXND-UHFFFAOYSA-N 0.000 claims 2
GXDFXOVBSJEHBS-UHFFFAOYSA-N 5-imidazol-1-yl-2-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]phenol Chemical compound N1C(CC(CC1(C)C)N1C2=C(N=N1)C=C(C1=CC=C(N3C=NC=C3)C=C1O)N=N2)(C)C GXDFXOVBSJEHBS-UHFFFAOYSA-N 0.000 claims 2
XBRAKTVAHFZAIT-UHFFFAOYSA-N 5-pyrazol-1-yl-2-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]phenol Chemical compound N1(N=CC=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C XBRAKTVAHFZAIT-UHFFFAOYSA-N 0.000 claims 2
BQSBAHQXPBCOHL-UHFFFAOYSA-N 6-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]quinolin-7-ol Chemical compound N1C(CC(CC1(C)C)N1C2=C(N=N1)C=C(C1=C(O)C=C3N=CC=CC3=C1)N=N2)(C)C BQSBAHQXPBCOHL-UHFFFAOYSA-N 0.000 claims 2
HCHBPWYLYODRFT-UHFFFAOYSA-N 6-[3-hydroxy-4-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]phenyl]pyridin-3-ol Chemical compound CC1(NC(C)(C)CC(N2C3=C(N=N2)C=C(C2=CC=C(C4=CC=C(O)C=N4)C=C2O)N=N3)C1)C HCHBPWYLYODRFT-UHFFFAOYSA-N 0.000 claims 2
FWZMSKSFXHUBSW-UHFFFAOYSA-N 6-[3-hydroxy-4-[3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazin-6-yl]phenyl]pyridin-3-ol dihydrochloride Chemical compound CC1(CC(CC(N1)(C)C)N2C3=NN=C(C=C3N=N2)C4=C(C=C(C=C4)C5=NC=C(C=C5)O)O)C.Cl.Cl FWZMSKSFXHUBSW-UHFFFAOYSA-N 0.000 claims 2
KANAKZDOZBCHQI-UHFFFAOYSA-N 6-[7-(1H-pyrazol-4-yl)-2H-benzotriazol-4-yl]-3-(2,2,6,6-tetramethylpiperidin-4-yl)triazolo[4,5-c]pyridazine Chemical compound N1C(CC(CC1(C)C)N1C2=C(N=N1)C=C(C1=CC=C(C=3C=NNC=3)C=3N=NNC1=3)N=N2)(C)C KANAKZDOZBCHQI-UHFFFAOYSA-N 0.000 claims 2
LKKVVUAIJFFYKR-UHFFFAOYSA-N Br.CC1(NC(CC(C1)N1N=NC2=C1N=NC(=C2)C=1C=C2C=CC=NC2=CC=1O)(C)C)C Chemical compound Br.CC1(NC(CC(C1)N1N=NC2=C1N=NC(=C2)C=1C=C2C=CC=NC2=CC=1O)(C)C)C LKKVVUAIJFFYKR-UHFFFAOYSA-N 0.000 claims 2
WLVVXZGHMCKLHT-UHFFFAOYSA-N Br.FC1=CC(=C(C=C1C1=CC=C(C=C1)O)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C Chemical compound Br.FC1=CC(=C(C=C1C1=CC=C(C=C1)O)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C WLVVXZGHMCKLHT-UHFFFAOYSA-N 0.000 claims 2
PXVVRAVHOUCNOQ-UHFFFAOYSA-N BrC1=NNC=C1C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C Chemical compound BrC1=NNC=C1C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C PXVVRAVHOUCNOQ-UHFFFAOYSA-N 0.000 claims 2
RMBKEKVHYKCBQU-UHFFFAOYSA-N C(=O)OC1=C(C=CC(=C1)C1=NC=C(C=C1)OC(F)F)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C Chemical compound C(=O)OC1=C(C=CC(=C1)C1=NC=C(C=C1)OC(F)F)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C RMBKEKVHYKCBQU-UHFFFAOYSA-N 0.000 claims 2
KTAQHPPSQLMJJW-UHFFFAOYSA-N C(=O)OC1=C(C=CC(=C1)C=1OC=CN=1)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C Chemical compound C(=O)OC1=C(C=CC(=C1)C=1OC=CN=1)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C KTAQHPPSQLMJJW-UHFFFAOYSA-N 0.000 claims 2
IETUBBFAMCEKDY-UHFFFAOYSA-N C(C)N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C Chemical compound C(C)N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C IETUBBFAMCEKDY-UHFFFAOYSA-N 0.000 claims 2
NRAVMEBVFBHKNZ-UHFFFAOYSA-N C(C)N1N=CC(=C1F)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C Chemical compound C(C)N1N=CC(=C1F)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C NRAVMEBVFBHKNZ-UHFFFAOYSA-N 0.000 claims 2
KHTWIGWWVCHDGM-UHFFFAOYSA-N C(C)NC1=NC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N1C1CC(NC(C1)(C)C)(C)C Chemical compound C(C)NC1=NC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N1C1CC(NC(C1)(C)C)(C)C KHTWIGWWVCHDGM-UHFFFAOYSA-N 0.000 claims 2
JHDYRZFBNRBQPV-UHFFFAOYSA-N C(C)OC1=CC(=NC=N1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C Chemical compound C(C)OC1=CC(=NC=N1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C JHDYRZFBNRBQPV-UHFFFAOYSA-N 0.000 claims 2
KHAZRTSCDAEECH-UHFFFAOYSA-N C(C)OC1=NC=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C Chemical compound C(C)OC1=NC=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C KHAZRTSCDAEECH-UHFFFAOYSA-N 0.000 claims 2
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AQEDLCXPALRUPH-VPYROQPTSA-N C(N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C)([2H])([2H])[2H] Chemical compound C(N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C)([2H])([2H])[2H] AQEDLCXPALRUPH-VPYROQPTSA-N 0.000 claims 2
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WEDZOCIMYALXKQ-UHFFFAOYSA-N OC=1C=C(C=CC=1C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C)C=1C(=NN(C=1)C)C#N Chemical compound OC=1C=C(C=CC=1C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C)C=1C(=NN(C=1)C)C#N WEDZOCIMYALXKQ-UHFFFAOYSA-N 0.000 claims 2
MAEXIMRWSQWRSA-UHFFFAOYSA-N OC=1C=C(C=CC=1C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C)C=1C(=NNC=1)C#N Chemical compound OC=1C=C(C=CC=1C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C)C=1C(=NNC=1)C#N MAEXIMRWSQWRSA-UHFFFAOYSA-N 0.000 claims 2
GHGGQGHLUNPXIO-UHFFFAOYSA-N OC=1C=C(C=CC=1C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C)C=1SC(=CN=1)C#N Chemical compound OC=1C=C(C=CC=1C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C)C=1SC(=CN=1)C#N GHGGQGHLUNPXIO-UHFFFAOYSA-N 0.000 claims 2
GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 claims 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
HGNVKFMIZLRXNG-UHFFFAOYSA-N C1(NC(CC(C2=CSC3=CC(C4=CC=C(C=5C=NNC=5)C=C4O)=NN=C23)C1)(C)C)(C)C Chemical compound C1(NC(CC(C2=CSC3=CC(C4=CC=C(C=5C=NNC=5)C=C4O)=NN=C23)C1)(C)C)(C)C HGNVKFMIZLRXNG-UHFFFAOYSA-N 0.000 claims 1
UDAKOGRSNZDUHN-UHFFFAOYSA-N C12CC(CC(CC1)N2)C1=CNC2=C1N=NC(=C2)C1=C(C=C(C=C1)C=1C=NNC=1)O Chemical compound C12CC(CC(CC1)N2)C1=CNC2=C1N=NC(=C2)C1=C(C=C(C=C1)C=1C=NNC=1)O UDAKOGRSNZDUHN-UHFFFAOYSA-N 0.000 claims 1
AWMVRQRPJPJTOJ-UHFFFAOYSA-N CC1(CC(CC(N1)(C)C)N2C3=NN=C(C=C3C=N2)C4=C(C=C(C=C4)C5=CN=CN=C5)O)C.Cl Chemical compound CC1(CC(CC(N1)(C)C)N2C3=NN=C(C=C3C=N2)C4=C(C=C(C=C4)C5=CN=CN=C5)O)C.Cl AWMVRQRPJPJTOJ-UHFFFAOYSA-N 0.000 claims 1
ARPRJAMVDNNOMT-UHFFFAOYSA-N CC1(CC(CC(N1)(C)C)N2C3=NN=C(C=C3N=N2)C4=C(C=C(C=C4)C5=NC(=NC=N5)OC)O)C.Cl.Cl Chemical compound CC1(CC(CC(N1)(C)C)N2C3=NN=C(C=C3N=N2)C4=C(C=C(C=C4)C5=NC(=NC=N5)OC)O)C.Cl.Cl ARPRJAMVDNNOMT-UHFFFAOYSA-N 0.000 claims 1
DOHWIWKJZVGRLO-UHFFFAOYSA-N CC1=CN=C(S1)C2=CC(=C(C=C2)C3=NN=C4C(=C3)N=NN4C5CC(NC(C5)(C)C)(C)C)O.Cl Chemical compound CC1=CN=C(S1)C2=CC(=C(C=C2)C3=NN=C4C(=C3)N=NN4C5CC(NC(C5)(C)C)(C)C)O.Cl DOHWIWKJZVGRLO-UHFFFAOYSA-N 0.000 claims 1
XZMKNTZTVAGYFH-UHFFFAOYSA-N CN(C1=CC=C(C=N1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C)C Chemical compound CN(C1=CC=C(C=N1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C)C XZMKNTZTVAGYFH-UHFFFAOYSA-N 0.000 claims 1
NMLSGBBRNRYDPQ-UHFFFAOYSA-N COC1=CC(=NC=N1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C Chemical compound COC1=CC(=NC=N1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C NMLSGBBRNRYDPQ-UHFFFAOYSA-N 0.000 claims 1
AGMDABBTPJPSBL-UHFFFAOYSA-N Cl.CC1=NC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N1C1CC(NC(C1)(C)C)(C)C Chemical compound Cl.CC1=NC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N1C1CC(NC(C1)(C)C)(C)C AGMDABBTPJPSBL-UHFFFAOYSA-N 0.000 claims 1
HFBKNGRWUHFVPQ-UGKGYDQZSA-N F[C@@H]1C(NC(C[C@@H]1N1N=NC2=C1N=NC(=C2)C1=C(C=C(C=C1)C1=CC(N(C=C1)C)=O)O)(C)C)(C)C Chemical compound F[C@@H]1C(NC(C[C@@H]1N1N=NC2=C1N=NC(=C2)C1=C(C=C(C=C1)C1=CC(N(C=C1)C)=O)O)(C)C)(C)C HFBKNGRWUHFVPQ-UGKGYDQZSA-N 0.000 claims 1
DKNQRBOACKPKCF-RXVVDRJESA-N F[C@@H]1C(NC(C[C@@H]1N1N=NC2=C1N=NC(=C2)C1=C(C=C(C=C1)C1=CC(N(C=N1)C)=O)O)(C)C)(C)C Chemical compound F[C@@H]1C(NC(C[C@@H]1N1N=NC2=C1N=NC(=C2)C1=C(C=C(C=C1)C1=CC(N(C=N1)C)=O)O)(C)C)(C)C DKNQRBOACKPKCF-RXVVDRJESA-N 0.000 claims 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
BHNGOLBLNBLFDX-UHFFFAOYSA-N N1N=C(C=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C Chemical compound N1N=C(C=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C BHNGOLBLNBLFDX-UHFFFAOYSA-N 0.000 claims 1
OYUZGZPXJAMKJN-UHFFFAOYSA-N N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)C(=CN2)C1CC(NC(C1)(C)C)(C)C Chemical compound N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)C(=CN2)C1CC(NC(C1)(C)C)(C)C OYUZGZPXJAMKJN-UHFFFAOYSA-N 0.000 claims 1
MJTJPEAXZOVPOK-UHFFFAOYSA-N OC1=C(C=CC(=C1)C=1C=NNC=1)C1=CC2=C(N=N1)N(C(=N2)O)C1CC(NC(C1)(C)C)(C)C Chemical compound OC1=C(C=CC(=C1)C=1C=NNC=1)C1=CC2=C(N=N1)N(C(=N2)O)C1CC(NC(C1)(C)C)(C)C MJTJPEAXZOVPOK-UHFFFAOYSA-N 0.000 claims 1
LNAFRHAHLZMSDN-WGOQTCKBSA-N O\N=C\1/CCC2=CC(=C(C=C/12)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C Chemical compound O\N=C\1/CCC2=CC(=C(C=C/12)O)C1=CC2=C(N=N1)N(N=N2)C1CC(NC(C1)(C)C)(C)C LNAFRHAHLZMSDN-WGOQTCKBSA-N 0.000 claims 1
125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 claims 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

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Chemical & Material Sciences (AREA)
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Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Plural Heterocyclic Compounds (AREA)

HRP20240935TT 2018-06-27 2019-06-25 Heterociklični i heteroaril spojevi za liječenje huntingtonove bolesti HRP20240935T1 (hr)

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US201862690653P	2018-06-27	2018-06-27
EP19736566.1A EP3814357B1 (en)	2018-06-27	2019-06-25	Heterocyclic and heteroaryl compounds for treating huntington's disease
PCT/US2019/038889 WO2020005873A1 (en)	2018-06-27	2019-06-25	Heterocyclic and heteroaryl compounds for treating huntington's disease

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AR (1)	AR119651A1 (2)
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PT3814357T (pt)	2024-07-11
HUE068060T2 (hu)	2024-12-28
US20210238186A1 (en)	2021-08-05
CO2020016285A2 (es)	2021-01-18
JP7421507B2 (ja)	2024-01-24
CL2022003434A1 (es)	2023-06-02
CL2021003022A1 (es)	2022-07-01
CA3103976A1 (en)	2020-01-02
MX2020014098A (es)	2021-05-27
EP3814357B1 (en)	2024-05-01
ES2983003T3 (es)	2024-10-21
PL3814357T3 (pl)	2024-09-16
UA129258C2 (uk)	2025-03-05
KR102823158B1 (ko)	2025-06-20
US11858941B2 (en)	2024-01-02
IL279688B1 (en)	2024-09-01
AU2019294478A1 (en)	2021-01-21
CL2020003378A1 (es)	2021-06-18
CN112654625A (zh)	2021-04-13
BR112020026545A2 (pt)	2021-03-23
KR20210042265A (ko)	2021-04-19
JP2021528467A (ja)	2021-10-21
IL279688B2 (en)	2025-01-01
US20260028347A1 (en)	2026-01-29
FI3814357T3 (fi)	2024-07-26
SI3814357T1 (sl)	2024-09-30
PE20211378A1 (es)	2021-07-27
AR119651A1 (es)	2022-01-05
AU2023203241A1 (en)	2023-06-15
EP3814357A1 (en)	2021-05-05
WO2020005873A1 (en)	2020-01-02
DK3814357T3 (da)	2024-07-22
SMT202400286T1 (it)	2024-09-16
AU2019294478B2 (en)	2023-03-23
CN112654625B (zh)	2024-08-06
RS65727B1 (sr)	2024-08-30
SG11202012674PA (en)	2021-01-28
EA202092896A1 (ru)	2021-04-13
AU2023203241B2 (en)	2025-01-02
EP4434990A1 (en)	2024-09-25
IL279688A (en)	2021-03-01
ZA202100208B (en)	2025-05-28
LT3814357T (lt)	2024-06-25

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