JP2006511534A5 - - Google Patents
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- Publication number
- JP2006511534A5 JP2006511534A5 JP2004560278A JP2004560278A JP2006511534A5 JP 2006511534 A5 JP2006511534 A5 JP 2006511534A5 JP 2004560278 A JP2004560278 A JP 2004560278A JP 2004560278 A JP2004560278 A JP 2004560278A JP 2006511534 A5 JP2006511534 A5 JP 2006511534A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- group
- nitro
- heteroaryl
- amino
- 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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- -1 amino, substituted amino Chemical group 0.000 claims description 77
- 125000001072 heteroaryl group Chemical group 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 229920006395 saturated elastomer Polymers 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 30
- 125000003107 substituted aryl group Chemical group 0.000 claims description 27
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 26
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000004434 sulfur atom Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 150000001299 aldehydes Chemical class 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical compound [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims description 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 150000002829 nitrogen Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 claims description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 4
- TYHOSUCCUICRLM-UHFFFAOYSA-N 1,3-oxazole-2-carbaldehyde Chemical compound O=CC1=NC=CO1 TYHOSUCCUICRLM-UHFFFAOYSA-N 0.000 claims description 2
- 150000003935 benzaldehydes Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims 17
- 239000003795 chemical substances by application Substances 0.000 claims 17
- 201000011510 cancer Diseases 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 206010017533 Fungal infection Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 208000031888 Mycoses Diseases 0.000 claims 2
- 230000000843 anti-fungal effect Effects 0.000 claims 2
- HUMNYLRZRPPJDN-KWCOIAHCSA-N benzaldehyde Chemical group O=[11CH]C1=CC=CC=C1 HUMNYLRZRPPJDN-KWCOIAHCSA-N 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 229940123587 Cell cycle inhibitor Drugs 0.000 claims 1
- 206010052360 Colorectal adenocarcinoma Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 229930012538 Paclitaxel Natural products 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 claims 1
- 229940121375 antifungal agent Drugs 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000001472 cytotoxic effect Effects 0.000 claims 1
- 208000032839 leukemia 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
- 238000004519 manufacturing process Methods 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical group O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims 1
- 229960001156 mitoxantrone Drugs 0.000 claims 1
- 230000001613 neoplastic effect Effects 0.000 claims 1
- 229960001592 paclitaxel Drugs 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 201000005825 prostate adenocarcinoma Diseases 0.000 claims 1
- 125000002456 taxol group Chemical group 0.000 claims 1
- 208000037965 uterine sarcoma Diseases 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 0 C*C(*C)C=C(C(N(*)C1=CC2=C(*)*C(*)=N2)=*)N(C)C1=* Chemical compound C*C(*C)C=C(C(N(*)C1=CC2=C(*)*C(*)=N2)=*)N(C)C1=* 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40107402P | 2002-08-02 | 2002-08-02 | |
| US41112802P | 2002-09-16 | 2002-09-16 | |
| US45006303P | 2003-02-24 | 2003-02-24 | |
| PCT/US2003/024232 WO2004054498A2 (en) | 2002-08-02 | 2003-08-01 | Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006511534A JP2006511534A (ja) | 2006-04-06 |
| JP2006511534A5 true JP2006511534A5 (https=) | 2006-09-21 |
| JP4616649B2 JP4616649B2 (ja) | 2011-01-19 |
Family
ID=32600863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004560278A Expired - Lifetime JP4616649B2 (ja) | 2002-08-02 | 2003-08-01 | デヒドロフェニラヒスチンおよびそれらの類似体、ならびにデヒドロフェニラヒスチンおよびそれらの類似体の合成 |
Country Status (19)
| Country | Link |
|---|---|
| US (4) | US7064201B2 (https=) |
| EP (1) | EP1529044B1 (https=) |
| JP (1) | JP4616649B2 (https=) |
| KR (2) | KR101049100B1 (https=) |
| CN (1) | CN100540548C (https=) |
| AT (1) | ATE374767T1 (https=) |
| AU (1) | AU2003302721B2 (https=) |
| BR (2) | BR0313363A (https=) |
| CA (1) | CA2494049C (https=) |
| CO (1) | CO5721010A2 (https=) |
| DE (1) | DE60316688T2 (https=) |
| DK (1) | DK1529044T5 (https=) |
| ES (1) | ES2295695T3 (https=) |
| IL (2) | IL166628A0 (https=) |
| MX (1) | MXPA05001217A (https=) |
| NZ (1) | NZ538433A (https=) |
| PT (1) | PT1529044E (https=) |
| WO (1) | WO2004054498A2 (https=) |
| ZA (1) | ZA200501616B (https=) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7026322B2 (en) | 1998-11-12 | 2006-04-11 | Nereus Pharmaceuticals, Inc. | Phenylahistin and the phenylahistin analogs, a new class of anti-tumor compounds |
| BRPI0017067B8 (pt) * | 2000-01-18 | 2021-05-25 | Beyondspring Pharmaceuticals Inc | inibidor de divisão de célula, desidrogenase, método para a produção de um inibidor de divisão de célula e composto |
| WO2002011676A2 (en) | 2000-08-04 | 2002-02-14 | Dmi Biosciences, Inc. | Method of using diketopiperazines and composition containing them |
| US7919497B2 (en) | 2002-08-02 | 2011-04-05 | Nereus Pharmaceuticals, Inc. | Analogs of dehydrophenylahistins and their therapeutic use |
| BR0313363A (pt) | 2002-08-02 | 2005-08-09 | Nereus Pharmaceuticals Inc | Deidrofenilahistinas e seus análogos, e sua sìntese |
| US7935704B2 (en) | 2003-08-01 | 2011-05-03 | Nereus Pharmaceuticals, Inc. | Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof |
| NZ539735A (en) | 2002-10-02 | 2009-07-31 | Dmi Biosciences Inc | Diagnosis and monitoring of diseases using markers, such as diketopiperazines |
| EP1622633B1 (en) | 2003-05-15 | 2016-02-24 | Ampio Pharmaceuticals, Inc. | Treatment of t-cell mediated diseases |
| EP1711487A1 (en) * | 2004-02-04 | 2006-10-18 | Nereus Pharmaceuticals, Inc. | Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof |
| US20090286838A1 (en) * | 2004-12-06 | 2009-11-19 | Newsouth Innovations Pty Limited | Treatment for cancer |
| WO2006105051A2 (en) | 2005-03-29 | 2006-10-05 | Nereus Pharmaceuticals, Inc. | Synthesis of diketopiperazines |
| JP2008024871A (ja) * | 2006-07-24 | 2008-02-07 | Fujifilm Corp | インク組成物、インクジェット記録方法、印刷物、平版印刷版の製造方法、及び平版印刷版 |
| KR100932093B1 (ko) | 2006-09-27 | 2009-12-16 | 주식회사종근당 | 미세소관 형성 저해제로서 유용한 벤조페논 유도체 |
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| JP2012509878A (ja) * | 2008-11-21 | 2012-04-26 | アイシス ファーマシューティカルズ， インコーポレーテッド | ドセタキセルおよびアンチセンスオリゴヌクレオチドを含む、抗腫瘍併用療法 |
| EA027666B1 (ru) | 2010-05-03 | 2017-08-31 | ТЕИКОКУ ФАРМА ЮСЭй, ИНК. | Неводные лекарственные средства в форме проэмульсии на основе таксанов и способы их приготовления и использования |
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| WO2012035436A1 (en) * | 2010-09-15 | 2012-03-22 | Tokyo University Of Pharmacy And Life Sciences | Plinabulin prodrug analogs and therapeutic uses thereof |
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| AU2016219204B2 (en) * | 2015-02-12 | 2021-01-21 | Beyondspring Pharmaceuticals, Inc. | Use of Plinabulin in combination with immune checkpoint inhibitors |
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| HK1249051A1 (zh) | 2015-03-06 | 2018-10-26 | BeyondSpring Pharmaceuticals Inc. | 治疗脑肿瘤的方法 |
| CN106279039B (zh) * | 2015-06-02 | 2019-01-11 | 青岛海洋生物医药研究院股份有限公司 | 氘代脱氢苯基阿夕斯丁类化合物及其制备方法和在制备抗肿瘤的药物中的应用 |
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| US10155748B2 (en) | 2015-07-13 | 2018-12-18 | Beyondspring Pharmaceuticals, Inc. | Plinabulin compositions |
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| CN107778297B (zh) * | 2016-08-12 | 2021-11-19 | 深圳华大海洋科技有限公司 | 氘代脱氢苯基阿夕斯丁类化合物的多晶型及其制备方法和应用 |
| CN107011322B (zh) * | 2016-08-12 | 2020-02-18 | 青岛海洋生物医药研究院股份有限公司 | 一种脱氢苯基阿夕斯丁类化合物的制备纯化方法 |
| CN109563079B (zh) * | 2016-08-12 | 2021-10-26 | 深圳华大海洋科技有限公司 | 脱氢苯基阿夕斯丁类化合物的多晶型及其制备纯化方法和应用 |
| CN106565685B (zh) * | 2016-10-11 | 2019-03-01 | 深圳海王医药科技研究院有限公司 | 微管蛋白抑制剂 |
| CN106565686B (zh) | 2016-10-11 | 2019-03-01 | 深圳海王医药科技研究院有限公司 | 微管蛋白抑制剂 |
| JP2020503363A (ja) | 2017-01-06 | 2020-01-30 | 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 | チューブリン結合化合物およびその治療的使用 |
| BR112019015974A2 (pt) | 2017-02-01 | 2020-03-31 | Beyondspring Pharmaceuticals, Inc. | Método para reduzir neutropenia |
| AU2018236168B2 (en) | 2017-03-13 | 2024-02-29 | Beyondspring Pharmaceuticals, Inc. | Compositions of plinabulin and use thereof |
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| CN109498627B (zh) * | 2017-09-15 | 2021-06-04 | 深圳华大海洋科技有限公司 | 一种治疗肿瘤的药物组合物及其应用 |
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| CN111840291B (zh) * | 2020-07-14 | 2021-12-21 | 深圳海王医药科技研究院有限公司 | 一种在肿瘤治疗中具有增效作用的化合物的应用 |
| CA3215047A1 (en) | 2021-04-09 | 2022-10-13 | Lan Huang | Therapeutic compositions and methods for treating tumors |
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| CN117860672A (zh) | 2022-10-11 | 2024-04-12 | 大连万春布林医药有限公司 | 一种普那布林胶束组合物及其制备方法 |
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-
2003
- 2003-08-01 BR BR0313363-0A patent/BR0313363A/pt not_active Application Discontinuation
- 2003-08-01 WO PCT/US2003/024232 patent/WO2004054498A2/en not_active Ceased
- 2003-08-01 EP EP03811651A patent/EP1529044B1/en not_active Expired - Lifetime
- 2003-08-01 JP JP2004560278A patent/JP4616649B2/ja not_active Expired - Lifetime
- 2003-08-01 CN CNB038234645A patent/CN100540548C/zh not_active Expired - Lifetime
- 2003-08-01 KR KR1020057001947A patent/KR101049100B1/ko not_active Expired - Lifetime
- 2003-08-01 ES ES03811651T patent/ES2295695T3/es not_active Expired - Lifetime
- 2003-08-01 IL IL16662803A patent/IL166628A0/xx unknown
- 2003-08-01 KR KR1020117006692A patent/KR101184374B1/ko not_active Expired - Lifetime
- 2003-08-01 CA CA2494049A patent/CA2494049C/en not_active Expired - Lifetime
- 2003-08-01 BR BRPI0313363A patent/BRPI0313363A8/pt unknown
- 2003-08-01 AU AU2003302721A patent/AU2003302721B2/en not_active Expired
- 2003-08-01 DE DE60316688T patent/DE60316688T2/de not_active Expired - Lifetime
- 2003-08-01 MX MXPA05001217A patent/MXPA05001217A/es active IP Right Grant
- 2003-08-01 NZ NZ538433A patent/NZ538433A/en not_active IP Right Cessation
- 2003-08-01 US US10/632,531 patent/US7064201B2/en not_active Expired - Lifetime
- 2003-08-01 AT AT03811651T patent/ATE374767T1/de active
- 2003-08-01 PT PT03811651T patent/PT1529044E/pt unknown
- 2003-08-01 DK DK03811651T patent/DK1529044T5/da active
-
2005
- 2005-02-01 IL IL166628A patent/IL166628A/en active IP Right Grant
- 2005-02-24 ZA ZA2005/01616A patent/ZA200501616B/en unknown
- 2005-02-28 CO CO05018564A patent/CO5721010A2/es active IP Right Grant
-
2006
- 2006-06-07 US US11/448,948 patent/US7674903B2/en not_active Expired - Lifetime
- 2006-06-07 US US11/448,924 patent/US7956058B2/en not_active Expired - Lifetime
- 2006-06-07 US US11/448,283 patent/US20060223822A1/en not_active Abandoned
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