JP2020503363A5 - - Google Patents
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- JP2020503363A5 JP2020503363A5 JP2019536967A JP2019536967A JP2020503363A5 JP 2020503363 A5 JP2020503363 A5 JP 2020503363A5 JP 2019536967 A JP2019536967 A JP 2019536967A JP 2019536967 A JP2019536967 A JP 2019536967A JP 2020503363 A5 JP2020503363 A5 JP 2020503363A5
- Authority
- JP
- Japan
- Prior art keywords
- atom
- tubulin
- pharmaceutical composition
- composition according
- alkyl
- 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.)
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- 125000004429 atom Chemical group 0.000 claims 53
- 239000008194 pharmaceutical composition Substances 0.000 claims 38
- 102000004243 Tubulin Human genes 0.000 claims 37
- 108090000704 Tubulin Proteins 0.000 claims 37
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 239000001257 hydrogen Substances 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 125000003118 aryl group Chemical group 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- -1 natiflu Chemical compound 0.000 claims 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 230000003993 interaction Effects 0.000 claims 5
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 2
- STWMVDMOJPLMPX-UHFFFAOYSA-N 1-piperidin-1-yl-3,4-dihydro-2h-quinoline Chemical compound C1CCCCN1N1C2=CC=CC=C2CCC1 STWMVDMOJPLMPX-UHFFFAOYSA-N 0.000 claims 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims 2
- SAKJVQIASONOAF-UHFFFAOYSA-N 4-(azepan-1-yl)morpholine Chemical compound C1COCCN1N1CCCCCC1 SAKJVQIASONOAF-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- 102100021707 Rho guanine nucleotide exchange factor 2 Human genes 0.000 claims 2
- 101710128399 Rho guanine nucleotide exchange factor 2 Proteins 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 2
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 2
- 125000005110 aryl thio group Chemical group 0.000 claims 2
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 150000001540 azides Chemical class 0.000 claims 2
- 125000004452 carbocyclyl group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- 150000003852 triazoles Chemical class 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- GWMHBVLPNWHWGW-CNYBTUBUSA-N (3s,6z)-3-benzyl-6-[[5-(2-methylbut-3-en-2-yl)-1h-imidazol-4-yl]methylidene]piperazine-2,5-dione Chemical compound N1C=NC(\C=C/2C(N[C@@H](CC=3C=CC=CC=3)C(=O)N\2)=O)=C1C(C)(C=C)C GWMHBVLPNWHWGW-CNYBTUBUSA-N 0.000 claims 1
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 1
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical group C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims 1
- MQLACMBJVPINKE-UHFFFAOYSA-N 10-[(3-hydroxy-4-methoxyphenyl)methylidene]anthracen-9-one Chemical compound C1=C(O)C(OC)=CC=C1C=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MQLACMBJVPINKE-UHFFFAOYSA-N 0.000 claims 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- RELAJOWOFXGXHI-UHFFFAOYSA-N 3h-oxathiole Chemical group C1SOC=C1 RELAJOWOFXGXHI-UHFFFAOYSA-N 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 206010052360 Colorectal adenocarcinoma Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- 125000005237 alkyleneamino group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 108010054981 dehydrophenylahistin Proteins 0.000 claims 1
- 150000002013 dioxins Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 150000004662 dithiols Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 230000002209 hydrophobic effect Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 229910052757 nitrogen Chemical group 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- SFLGSKRGOWRGBR-UHFFFAOYSA-N phthalane Chemical compound C1=CC=C2COCC2=C1 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 208000015347 renal cell adenocarcinoma Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022206294A JP2023027366A (ja) | 2017-01-06 | 2022-12-23 | チューブリン結合化合物およびその治療的使用 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762443247P | 2017-01-06 | 2017-01-06 | |
| US62/443,247 | 2017-01-06 | ||
| PCT/US2018/012668 WO2018129381A1 (en) | 2017-01-06 | 2018-01-05 | Tubulin binding compounds and therapeutic use thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022206294A Division JP2023027366A (ja) | 2017-01-06 | 2022-12-23 | チューブリン結合化合物およびその治療的使用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2020503363A JP2020503363A (ja) | 2020-01-30 |
| JP2020503363A5 true JP2020503363A5 (https=) | 2021-04-30 |
Family
ID=62790877
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019536967A Pending JP2020503363A (ja) | 2017-01-06 | 2018-01-05 | チューブリン結合化合物およびその治療的使用 |
| JP2022206294A Pending JP2023027366A (ja) | 2017-01-06 | 2022-12-23 | チューブリン結合化合物およびその治療的使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022206294A Pending JP2023027366A (ja) | 2017-01-06 | 2022-12-23 | チューブリン結合化合物およびその治療的使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US11633393B2 (https=) |
| EP (1) | EP3565812B1 (https=) |
| JP (2) | JP2020503363A (https=) |
| CN (1) | CN110431135A (https=) |
| WO (1) | WO2018129381A1 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2016229294B2 (en) | 2015-03-06 | 2021-11-04 | Beyondspring Pharmaceuticals, Inc. | Method of treating cancer associated with a RAS mutation |
| SG11201707128TA (en) | 2015-03-06 | 2017-09-28 | Beyondspring Pharmaceuticals Inc | Method of treating a brain tumor |
| JP6969848B2 (ja) | 2015-07-13 | 2021-11-24 | ビヨンドスプリング ファーマシューティカルズ，インコーポレイテッド | プリナブリン組成物 |
| KR20180105685A (ko) | 2016-02-08 | 2018-09-28 | 비욘드스프링 파마수티컬스, 인코포레이티드. | 투카레솔 또는 이의 유사체를 함유하는 조성물 |
| JP7025416B2 (ja) | 2016-06-06 | 2022-02-24 | ビヨンドスプリング ファーマシューティカルズ，インコーポレイテッド | 好中球減少症を低減させるための組成物および方法 |
| WO2018129381A1 (en) * | 2017-01-06 | 2018-07-12 | Beyondspring Pharmaceuticals, Inc. | Tubulin binding compounds and therapeutic use thereof |
| BR112019015974A2 (pt) | 2017-02-01 | 2020-03-31 | Beyondspring Pharmaceuticals, Inc. | Método para reduzir neutropenia |
| KR20200112881A (ko) | 2018-01-24 | 2020-10-05 | 비욘드스프링 파마수티컬스, 인코포레이티드. | 플리나불린의 투여를 통해 혈소판감소증을 감소시키는 조성물 및 방법 |
| CN111954532A (zh) * | 2018-04-13 | 2020-11-17 | 上海交通大学医学院附属瑞金医院 | 杂芳基酰胺类化合物的抗肿瘤多药耐药性、治疗癌症的用途和蛋白质-药物分子复合物 |
| MX2021001762A (es) * | 2018-08-16 | 2021-04-19 | Beyondspring Pharmaceuticals Inc | Metodo y composicion para estimular la respuesta inmunitaria. |
| CA3137193A1 (en) * | 2019-04-24 | 2020-10-29 | The Governors Of The University Of Alberta | Non-peptidic heterocycle-containing compounds for the treatment of alzheimer's disease |
| KR20220058553A (ko) * | 2019-09-05 | 2022-05-09 | 루난 파마슈티컬 그룹 코퍼레이션 | Magl 억제제 및 이의 제조 방법, 용도 |
| KR102304026B1 (ko) * | 2020-02-03 | 2021-09-23 | 순천대학교 산학협력단 | 세포자멸사를 유도하는 치환된 아릴사이클로프로필우레아 화합물 및 이를 포함하는 항암용 조성물 |
| TWI879949B (zh) | 2020-04-27 | 2025-04-11 | 南韓商奧土擇破利悟股份有限公司 | 用於ｕｂｒ盒結構域配體之化合物、組成物以及醫藥組成物 |
| AU2021359129A1 (en) * | 2020-10-16 | 2023-06-01 | Proxygen Gmbh | Heterocyclic cullin ring ubiquitin ligase compounds and uses thereof |
| CA3215047A1 (en) | 2021-04-09 | 2022-10-13 | Lan Huang | Therapeutic compositions and methods for treating tumors |
| CN113750088B (zh) * | 2021-09-16 | 2024-05-28 | 中国人民解放军海军特色医学中心 | 杂环化合物在制备治疗溃疡性结肠炎药物中的应用 |
| WO2023203174A1 (en) * | 2022-04-20 | 2023-10-26 | Proxygen Gmbh | Heterocyclic cullin ring ubiquitin ligase compounds and uses thereof |
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2022
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