KR20220024629A

KR20220024629A - 엑토뉴클레오티다제 억제제 및 이의 사용 방법

엑토뉴클레오티다제 억제제 및 이의 사용 방법 Download PDF

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Publication number: KR20220024629A
Authority: KR; South Korea
Prior art keywords: compound; amino; cancer; alkyl; chloro
Prior art date: 2019-06-20
Legal status : Withdrawn

Application number

KR1020227001589A

Other languages

English (en)

Korean (ko)

Inventor

리징 첸

롤란드 조세프 빌도

짐 리

티모시 프렌드 스탄톤

Original Assignee

칼리테라 바이오사이언시즈, 인코포레이티드

Priority date

2019-06-20

Filing date

2020-06-18

Publication date

2022-03-03

2020-06-18 Application filed by 칼리테라 바이오사이언시즈, 인코포레이티드 filed Critical 칼리테라 바이오사이언시즈, 인코포레이티드

2022-03-03 Publication of KR20220024629A publication Critical patent/KR20220024629A/ko

Status Withdrawn legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 51
239000003112 inhibitor Substances 0.000 title description 12
108010047482 ectoATPase Proteins 0.000 title description 3
206010028980 Neoplasm Diseases 0.000 claims abstract description 48
201000011510 cancer Diseases 0.000 claims abstract description 36
150000001875 compounds Chemical class 0.000 claims description 209
-1 cyano, azido, amino Chemical group 0.000 claims description 92
125000000217 alkyl group Chemical group 0.000 claims description 80
125000003118 aryl group Chemical group 0.000 claims description 54
125000001072 heteroaryl group Chemical group 0.000 claims description 50
125000000623 heterocyclic group Chemical group 0.000 claims description 43
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
102100022464 5'-nucleotidase Human genes 0.000 claims description 32
101000678236 Homo sapiens 5'-nucleotidase Proteins 0.000 claims description 31
125000001424 substituent group Chemical group 0.000 claims description 31
125000003710 aryl alkyl group Chemical group 0.000 claims description 27
125000000753 cycloalkyl group Chemical group 0.000 claims description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
239000002246 antineoplastic agent Substances 0.000 claims description 21
229940127089 cytotoxic agent Drugs 0.000 claims description 21
201000010099 disease Diseases 0.000 claims description 21
125000004475 heteroaralkyl group Chemical group 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 21
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AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 18
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229910052739 hydrogen Inorganic materials 0.000 claims description 14
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125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 13
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239000000546 pharmaceutical excipient Substances 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
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REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
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125000002619 bicyclic group Chemical group 0.000 claims description 7
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ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
ZCQMYMXRGJWSHH-UHFFFAOYSA-N 1-amino-4-(4-aminoanilino)-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC(N)=CC=C1NC1=CC(S(O)(=O)=O)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O ZCQMYMXRGJWSHH-UHFFFAOYSA-N 0.000 claims description 5
KFBGXLCLNATBFL-UHFFFAOYSA-N 1-amino-4-(4-hydroxyanilino)-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=C(O)C=C1 KFBGXLCLNATBFL-UHFFFAOYSA-N 0.000 claims description 5
JXFRJOYKTCEJDG-UHFFFAOYSA-N 1-amino-4-(anthracen-2-ylamino)-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=CC2=CC3=CC(NC4=C5C(=O)C6=CC=CC=C6C(=O)C5=C(C(=C4)S(O)(=O)=O)N)=CC=C3C=C21 JXFRJOYKTCEJDG-UHFFFAOYSA-N 0.000 claims description 5
OPBOOIFXQHPAPJ-UHFFFAOYSA-N 1-amino-4-anilino-9,10-dioxoanthracene-2-sulfonic acid Chemical group C1=C(S(O)(=O)=O)C(N)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC=C1 OPBOOIFXQHPAPJ-UHFFFAOYSA-N 0.000 claims description 5
OBFSYBSKXOCXQH-UHFFFAOYSA-N 2-[(4-amino-9,10-dioxo-3-sulfoanthracen-1-yl)amino]-5-fluorobenzoic acid Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S(O)(=O)=O)C=C1NC1=CC=C(F)C=C1C(O)=O OBFSYBSKXOCXQH-UHFFFAOYSA-N 0.000 claims description 5
PNFZSRRRZNXSMF-UHFFFAOYSA-N 5'-phosphopyridoxal-6-azobenzene-2,4-disulfonic acid Chemical compound O=CC1=C(O)C(C)=NC(N=NC=2C(=CC(=CC=2)S(O)(=O)=O)S(O)(=O)=O)=C1COP(O)(O)=O PNFZSRRRZNXSMF-UHFFFAOYSA-N 0.000 claims description 5
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GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims description 5
GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 claims description 5
PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 claims description 5
UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims description 5
201000008808 Fibrosarcoma Diseases 0.000 claims description 5
206010016654 Fibrosis Diseases 0.000 claims description 5
ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 claims description 5
HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 claims description 5
LIKZXCROQGHXTI-UHFFFAOYSA-M acid blue 25 Chemical compound [Na+].C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S([O-])(=O)=O)C=C1NC1=CC=CC=C1 LIKZXCROQGHXTI-UHFFFAOYSA-M 0.000 claims description 5
125000003368 amide group Chemical group 0.000 claims description 5
229960004117 capecitabine Drugs 0.000 claims description 5
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230000004761 fibrosis Effects 0.000 claims description 5
229960000390 fludarabine Drugs 0.000 claims description 5
GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 claims description 5
SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims description 5
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MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims description 5
125000002950 monocyclic group Chemical group 0.000 claims description 5
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GSBYVRKLPCSLNV-UHFFFAOYSA-M sodium 2,4-dinitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C([N+]([O-])=O)=C1 GSBYVRKLPCSLNV-UHFFFAOYSA-M 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
VZPXDCIISFTYOM-UHFFFAOYSA-K trisodium;1-amino-4-[4-[[4-chloro-6-(3-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-3-sulfonatoanilino]-9,10-dioxoanthracene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S([O-])(=O)=O)C=C1NC(C=C1S([O-])(=O)=O)=CC=C1NC(N=1)=NC(Cl)=NC=1NC1=CC=CC(S([O-])(=O)=O)=C1 VZPXDCIISFTYOM-UHFFFAOYSA-K 0.000 claims description 5
IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 claims description 4
ZHQRPIRGSWEALJ-UHFFFAOYSA-N 1-amino-4-(1-naphthalenylamino)-9,10-dioxo-2-anthracenesulfonic acid Chemical compound C1=CC=C2C(NC3=C4C(=O)C5=CC=CC=C5C(=O)C4=C(C(=C3)S(O)(=O)=O)N)=CC=CC2=C1 ZHQRPIRGSWEALJ-UHFFFAOYSA-N 0.000 claims description 4
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
208000000461 Esophageal Neoplasms Diseases 0.000 claims description 4
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MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims description 4
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