JP2020533288A5 - - Google Patents
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- Publication number
- JP2020533288A5 JP2020533288A5 JP2020513331A JP2020513331A JP2020533288A5 JP 2020533288 A5 JP2020533288 A5 JP 2020533288A5 JP 2020513331 A JP2020513331 A JP 2020513331A JP 2020513331 A JP2020513331 A JP 2020513331A JP 2020533288 A5 JP2020533288 A5 JP 2020533288A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- heterocycle
- inhibitor
- alkoxy
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 50
- 239000003112 inhibitor Substances 0.000 claims description 33
- 101000812677 Homo sapiens Nucleotide pyrophosphatase Proteins 0.000 claims description 25
- 102100039306 Nucleotide pyrophosphatase Human genes 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- -1 phosphonate ester Chemical class 0.000 claims description 18
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 18
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 239000000651 prodrug Substances 0.000 claims description 14
- 229940002612 prodrug Drugs 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 201000011510 cancer Diseases 0.000 claims description 10
- 239000000523 sample Substances 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 10
- 229910019142 PO4 Inorganic materials 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 239000010452 phosphate Substances 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- RFCBNSCSPXMEBK-INFSMZHSSA-N c-GMP-AMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]3[C@@H](O)[C@H](N4C5=NC=NC(N)=C5N=C4)O[C@@H]3COP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 RFCBNSCSPXMEBK-INFSMZHSSA-N 0.000 claims description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical class C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 4
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical class N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 2
- KDCGOANMDULRCW-HQMMCQRPSA-N 7H-purine Chemical class N1=[14CH]N=C2N=CNC2=C1 KDCGOANMDULRCW-HQMMCQRPSA-N 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 239000013068 control sample Substances 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 150000002537 isoquinolines Chemical class 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 150000004885 piperazines Chemical class 0.000 claims description 2
- 150000003053 piperidines Chemical class 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims description 2
- 150000003248 quinolines Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 2
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023089900A JP7607969B2 (ja) | 2017-09-08 | 2023-05-31 | Ｅｎｐｐ１阻害剤及びがんの治療のためのそれらの使用 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762556117P | 2017-09-08 | 2017-09-08 | |
| US62/556,117 | 2017-09-08 | ||
| PCT/US2018/050018 WO2019051269A1 (en) | 2017-09-08 | 2018-09-07 | ENPP1 INHIBITORS AND THEIR USE FOR THE TREATMENT OF CANCER |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023089900A Division JP7607969B2 (ja) | 2017-09-08 | 2023-05-31 | Ｅｎｐｐ１阻害剤及びがんの治療のためのそれらの使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020533288A JP2020533288A (ja) | 2020-11-19 |
| JP2020533288A5 true JP2020533288A5 (enExample) | 2021-10-14 |
| JP7292740B2 JP7292740B2 (ja) | 2023-06-19 |
Family
ID=63714052
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020513331A Active JP7292740B2 (ja) | 2017-09-08 | 2018-09-07 | Ｅｎｐｐ１阻害剤及びがんの治療のためのそれらの使用 |
| JP2023089900A Active JP7607969B2 (ja) | 2017-09-08 | 2023-05-31 | Ｅｎｐｐ１阻害剤及びがんの治療のためのそれらの使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023089900A Active JP7607969B2 (ja) | 2017-09-08 | 2023-05-31 | Ｅｎｐｐ１阻害剤及びがんの治療のためのそれらの使用 |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US11701371B2 (enExample) |
| EP (2) | EP4327882A3 (enExample) |
| JP (2) | JP7292740B2 (enExample) |
| KR (2) | KR102715420B1 (enExample) |
| CN (2) | CN117883449A (enExample) |
| AU (2) | AU2018330188C1 (enExample) |
| BR (1) | BR112020004559A2 (enExample) |
| CA (1) | CA3074268A1 (enExample) |
| DK (1) | DK3678668T3 (enExample) |
| EA (1) | EA202090595A1 (enExample) |
| ES (1) | ES2975183T3 (enExample) |
| HU (1) | HUE066413T2 (enExample) |
| IL (3) | IL311010A (enExample) |
| MA (1) | MA50082A (enExample) |
| MX (2) | MX2020002646A (enExample) |
| PL (1) | PL3678668T3 (enExample) |
| SG (1) | SG11202001728YA (enExample) |
| WO (1) | WO2019051269A1 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2020140001A1 (en) * | 2018-12-28 | 2020-07-02 | Riboscience Llc | Quinazoline derivatives as ectonucleotide pyrophosphatase phosphodiesterase 1 inhibitors |
| ES2960987T3 (es) | 2019-04-12 | 2024-03-07 | Riboscience Llc | Derivados de heteroarilo bicíclicos como inhibidores de la ectonucleótido pirofosfatasa fosfodiesterasa 1 |
| CN114728971B (zh) | 2019-09-16 | 2025-05-13 | 阿托恩波罗斯生命科学私人有限公司 | 作为enpp1蛋白的抑制剂的2-氨基-s6-取代的硫嘌呤化合物 |
| KR20220068243A (ko) * | 2019-09-23 | 2022-05-25 | 난징 젱시앙 파마슈티칼스 컴퍼니 리미티드 | 포스포디에스테라제 억제제 및 용도 |
| CN115362145B (zh) * | 2020-02-04 | 2025-05-02 | 斯汀格瑞治疗股份有限公司 | 外核苷酸焦磷酸酶/磷酸二酯酶1(enpp1)抑制剂及其使用方法 |
| AU2021224588B2 (en) | 2020-02-18 | 2024-07-18 | Gilead Sciences, Inc. | Antiviral compounds |
| TWI775313B (zh) | 2020-02-18 | 2022-08-21 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| TWI883391B (zh) | 2020-02-18 | 2025-05-11 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| WO2021203772A1 (en) * | 2020-04-09 | 2021-10-14 | Betta Pharmaceuticals Co., Ltd | Ectonucleotide pyrophosphatase-phosphodiesterase 1 inhibitors,compositions and uses thereof |
| WO2021225969A1 (en) * | 2020-05-04 | 2021-11-11 | Volastra Therapeutics, Inc. | Imino sulfanone inhibitors of enpp1 |
| KR102682428B1 (ko) | 2020-05-08 | 2024-07-05 | 주식회사 티씨노바이오사이언스 | 엑토뉴클레오티드 피로포스파타아제-포스포디에스터라아제의 저해 활성을 갖는 신규한 프탈라진 유도체 및 이들의 용도 |
| EP4148046A4 (en) | 2020-05-08 | 2024-07-24 | Txinno Bioscience Inc. | NEW PHTHALAZINE DERIVATIVE WITH ECTONUCLEOTIDE PYROPHOSPHATASE/PHOSPHODIESTERASE INHIBITING ACTIVITY AND USE THEREOF |
| WO2021257614A1 (en) * | 2020-06-16 | 2021-12-23 | Volastra Therapeutics, Inc. | Heterocyclic inhibitors of enpp1 |
| CN116234802A (zh) | 2020-09-03 | 2023-06-06 | 免疫传感器治疗股份有限公司 | 喹啉cgas拮抗剂化合物 |
| JP2023549738A (ja) * | 2020-10-30 | 2023-11-29 | １シーバイオ， インコーポレイテッド | エクトヌクレオチドピロホスファターゼ－ホスホジエステラーゼ－１（ｅｎｐｐ１）阻害物質及びそれらの使用 |
| US20250099493A1 (en) * | 2020-12-09 | 2025-03-27 | Stingray Therapeutics, Inc. | Phosphonates as inhibitors of enpp1 and cdnp |
| CN116600813A (zh) * | 2020-12-09 | 2023-08-15 | 斯汀格瑞治疗股份有限公司 | 作为enpp1和cdnp抑制剂的膦酸盐 |
| KR102720206B1 (ko) | 2020-12-29 | 2024-10-21 | 주식회사 티씨노바이오사이언스 | 엑토뉴클레오티드 피로포스파타아제-포스포디에스터라아제의 저해 활성을 갖는 신규한 나프티리딘온 유도체 및 이들의 용도 |
| WO2022146022A1 (ko) | 2020-12-29 | 2022-07-07 | 주식회사 티씨노바이오사이언스 | 엑토뉴클레오티드 피로포스파타아제-포스포디에스터라아제의 저해 활성을 갖는 신규한 나프티리딘온 유도체 및 이들의 용도 |
| KR102686866B1 (ko) | 2021-01-29 | 2024-07-19 | 주식회사 티씨노바이오사이언스 | 엑토뉴클레오티드 피로포스파타아제-포스포디에스터라아제의 저해 활성을 갖는 신규한 벤조트리아졸 유도체 및 이들의 용도 |
| CA3204409A1 (en) | 2021-01-29 | 2022-08-04 | Chan Sun Park | Novel benzotriazole derivative having inhibitory activity against ectonucleotide pyrophosphatase-phosphodiesterase, and use thereof |
| US20240209005A1 (en) * | 2021-03-16 | 2024-06-27 | Riboscience Llc | Bicyclic heteroaryl boronate derivatives as ectonucleotide pyrophosphatase phosphodiesterase 1 inhibitors |
| KR20230170745A (ko) | 2021-04-16 | 2023-12-19 | 길리애드 사이언시즈, 인코포레이티드 | 아미드를 사용한 카르바뉴클레오시드를 제조하는 방법 |
| CN115536696B (zh) * | 2021-06-29 | 2023-07-14 | 上海齐鲁制药研究中心有限公司 | Enpp1抑制剂 |
| US12116380B2 (en) | 2021-08-18 | 2024-10-15 | Gilead Sciences, Inc. | Phospholipid compounds and methods of making and using the same |
| WO2023035001A1 (en) * | 2021-09-03 | 2023-03-09 | Angarus Therapeutics, Inc. | Enpp1 inhibitors and immune cells expressing chimeric antigen receptors |
| WO2023077083A1 (en) * | 2021-10-29 | 2023-05-04 | Angarus Therapeutics, Inc. | Enpp1 inhibitors as inhibitors of metastasis |
| AU2023228915A1 (en) | 2022-03-02 | 2024-09-19 | Immunesensor Therapeutics, Inc. | QUINOLINE cGAS ANTAGONIST COMPOUNDS |
| WO2023197987A1 (zh) * | 2022-04-11 | 2023-10-19 | 上海齐鲁制药研究中心有限公司 | Enpp1抑制剂 |
| US20230346771A1 (en) | 2022-04-29 | 2023-11-02 | Petragen, Inc. | Inhibitors of enpp1 and modulation of bone growth |
| CN114767863B (zh) * | 2022-04-29 | 2024-01-30 | 西北工业大学 | 一种enpp2基因或蛋白在调控结直肠癌细胞中的应用 |
| WO2024028727A1 (en) * | 2022-08-01 | 2024-02-08 | Sravathi Ai Technology Private Limited | Novel ectonucleotide pyrophosphatase / phosphodiesterase 1 (enpp-1) inhibitors and uses thereof |
| CN120981233A (zh) * | 2023-04-11 | 2025-11-18 | 香港科技大学 | 由新型enpp1抑制剂使轴突再生 |
| WO2024216211A2 (en) * | 2023-04-14 | 2024-10-17 | The Board Of Trustees Of The Leland Stanford Junior University | Methods of inhibiting tumor progression and metastasis by inhibition of enpp1 |
| WO2025207514A1 (en) * | 2024-03-25 | 2025-10-02 | Riboscience Llc | Bicyclic heteroaryl sulfanediimine derivatives as ectonucleotide pyrophosphatase phosphodiesterase 1 inhibitors |
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| CN114437128B (zh) * | 2022-01-28 | 2023-12-19 | 中国科学院长春应用化学研究所 | 一种胆碱磷酸修饰的紫杉醇药物及其制备方法和应用 |
-
2018
- 2018-09-07 ES ES18779884T patent/ES2975183T3/es active Active
- 2018-09-07 AU AU2018330188A patent/AU2018330188C1/en active Active
- 2018-09-07 CA CA3074268A patent/CA3074268A1/en active Pending
- 2018-09-07 EP EP24150802.7A patent/EP4327882A3/en not_active Withdrawn
- 2018-09-07 SG SG11202001728YA patent/SG11202001728YA/en unknown
- 2018-09-07 HU HUE18779884A patent/HUE066413T2/hu unknown
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