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 (enExample) | 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 (enExample) |
| EP (1) | EP1529044B1 (enExample) |
| JP (1) | JP4616649B2 (enExample) |
| KR (2) | KR101184374B1 (enExample) |
| CN (1) | CN100540548C (enExample) |
| AT (1) | ATE374767T1 (enExample) |
| AU (1) | AU2003302721B2 (enExample) |
| BR (2) | BRPI0313363A8 (enExample) |
| CA (1) | CA2494049C (enExample) |
| CO (1) | CO5721010A2 (enExample) |
| DE (1) | DE60316688T2 (enExample) |
| DK (1) | DK1529044T5 (enExample) |
| ES (1) | ES2295695T3 (enExample) |
| IL (2) | IL166628A0 (enExample) |
| MX (1) | MXPA05001217A (enExample) |
| NZ (1) | NZ538433A (enExample) |
| PT (1) | PT1529044E (enExample) |
| WO (1) | WO2004054498A2 (enExample) |
| ZA (1) | ZA200501616B (enExample) |
Families Citing this family (62)
| 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 |
| EP1264831A4 (en) * | 2000-01-18 | 2005-11-23 | Nereus Pharmaceuticals Inc | Cell division inhibitors and a method for fixing the same |
| JP5048201B2 (ja) | 2000-08-04 | 2012-10-17 | ディーエムアイ バイオサイエンシズ インコーポレイテッド | ジケトピペラジン類の使用方法とジケトピペラジン類を含む組成物 |
| US7935704B2 (en) | 2003-08-01 | 2011-05-03 | Nereus Pharmaceuticals, Inc. | Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof |
| US7919497B2 (en) * | 2002-08-02 | 2011-04-05 | Nereus Pharmaceuticals, Inc. | Analogs of dehydrophenylahistins and their therapeutic use |
| AU2003302721B2 (en) | 2002-08-02 | 2009-10-08 | Beyondspring Pharmaceuticals, Inc. | Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof |
| DK1571970T3 (da) | 2002-10-02 | 2011-11-28 | Dmi Biosciences Inc | Diagnose og monitorering af sygdomme |
| CN102210852B (zh) | 2003-05-15 | 2016-10-19 | 安皮奥制药股份有限公司 | T-细胞介导的疾病的治疗 |
| BRPI0506655A (pt) * | 2004-02-04 | 2007-05-08 | Nereus Pharmaceuticals Inc | dehidrofenilahistinas e seus análogos, e sìntese de dehidrofenilahistinas e seus análogos |
| ES2528363T3 (es) * | 2004-12-06 | 2015-02-09 | Pitney Pharmaceuticals Pty Limited | Tratamiento para el cáncer |
| 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 |
| US8129527B2 (en) * | 2006-11-03 | 2012-03-06 | Nereus Pharmacuticals, Inc. | Analogs of dehydrophenylahistins and their therapeutic use |
| JP5856843B2 (ja) | 2008-05-27 | 2016-02-10 | アンピオ ファーマシューティカルズ，インコーポレイテッド | ジケトピペラジンを用いた医薬組成物 |
| AU2009316773A1 (en) * | 2008-11-21 | 2010-05-27 | Isis Pharmaceuticals, Inc. | Anticancer combination comprising docetaxel and an antisense oligonucleotide |
| JP5824511B2 (ja) | 2010-05-03 | 2015-11-25 | テイコク ファーマ ユーエスエー インコーポレーテッド | 非水タキサンプロエマルジョン配合物ならびにそれを調製および使用する方法 |
| EP2613786A4 (en) | 2010-09-07 | 2013-10-23 | Dmi Acquisition Corp | TREATMENT OF DISEASES |
| WO2012035436A1 (en) * | 2010-09-15 | 2012-03-22 | Tokyo University Of Pharmacy And Life Sciences | Plinabulin prodrug analogs and therapeutic uses thereof |
| US8842114B1 (en) | 2011-04-29 | 2014-09-23 | Nvidia Corporation | System, method, and computer program product for adjusting a depth of displayed objects within a region of a display |
| JP2014530063A (ja) | 2011-10-10 | 2014-11-17 | アンピオ ファーマシューティカルズ，インコーポレイテッド | 免疫寛容が高められた埋込み型医療用デバイス、ならびに製造方法および埋込み方法 |
| PH12014500685B1 (en) | 2011-10-10 | 2018-10-03 | Ampio Pharmaceuticals Inc | Treatment of degenerative joint disease |
| HK1198812A1 (en) | 2011-10-28 | 2015-06-12 | Ampio Pharmaceuticals, Inc. | Treatment of rhinitis |
| JO3685B1 (ar) | 2012-10-01 | 2020-08-27 | Teikoku Pharma Usa Inc | صيغ التشتيت الجسيمي للتاكسين غير المائي وطرق استخدامها |
| CA2906864A1 (en) | 2013-03-15 | 2014-09-18 | Ampio Pharmaceuticals, Inc. | Compositions for the mobilization, homing, expansion and differentiation of stem cells and methods of using the same |
| JP6311097B2 (ja) * | 2013-07-31 | 2018-04-18 | 学校法人東京薬科大学 | 微小管脱重合剤 |
| EP3076972B1 (en) | 2013-10-11 | 2021-10-06 | BeyondSpring, Inc. | Cancer treatment with combination of plinabulin and taxane |
| EP4066836A1 (en) | 2014-08-18 | 2022-10-05 | Ampio Pharmaceuticals, Inc. | Treatment of joint conditions |
| MX394865B (es) * | 2015-02-12 | 2025-03-24 | Beyondspring Pharmaceuticals Inc | Uso de plinabulina en combinación con inhibidores de punto de control inmunitario |
| HK1249052A1 (zh) * | 2015-03-06 | 2018-10-26 | BeyondSpring Pharmaceuticals Inc. | 治疗与ras突变相关的癌症的方法 |
| WO2016144636A1 (en) | 2015-03-06 | 2016-09-15 | Beyondspring Pharmaceuticals, Inc. | Method of treating a brain tumor |
| 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 |
| EP3310375A4 (en) | 2015-06-22 | 2019-02-20 | Ampio Pharmaceuticals, Inc. | USE OF LOW-MOLECULAR FRACTIONS OF HUMAN SERUMALBUMINE IN THE TREATMENT OF ILLNESSES |
| EP3334726B1 (en) * | 2015-07-13 | 2022-03-16 | Beyondspring Pharmaceuticals, Inc. | Plinabulin compositions |
| US10912748B2 (en) | 2016-02-08 | 2021-02-09 | Beyondspring Pharmaceuticals, Inc. | Compositions containing tucaresol or its analogs |
| CN109475524A (zh) | 2016-06-06 | 2019-03-15 | 万春药业公司 | 用于减少中性粒细胞减少症的组合物和方法 |
| 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 |
| EP4089085B1 (en) | 2016-08-12 | 2024-04-03 | Shenzhen Huahong Marine Biomedicine Co., Ltd | Manufacturing and purification method of polycrystalline form of dehydrophenylahistin-like compound |
| CN107011331A (zh) * | 2016-08-12 | 2017-08-04 | 青岛海洋生物医药研究院股份有限公司 | 脱氢苯基阿夕斯丁类化合物的多晶型及其制备方法 |
| 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 |
| 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 |
| 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 |
| WO2018129381A1 (en) | 2017-01-06 | 2018-07-12 | Beyondspring Pharmaceuticals, Inc. | Tubulin binding compounds and therapeutic use thereof |
| KR20190109479A (ko) | 2017-02-01 | 2019-09-25 | 비욘드스프링 파마수티컬스, 인코포레이티드. | 호중구감소증의 감소 방법 |
| BR112019018880A2 (pt) | 2017-03-13 | 2020-04-14 | Beyondspring Pharmaceuticals, Inc. | composições de plinabulina e seu uso |
| CN108658945B (zh) * | 2017-03-31 | 2020-11-20 | 深圳海王医药科技研究院有限公司 | 一种微管蛋白抑制剂（vda-1）的a晶型 |
| US11434225B2 (en) | 2017-08-03 | 2022-09-06 | Pliva Hrvatska D.O.O. | Salts and solid state forms of plinabulin |
| 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 |
| CN107698567B (zh) * | 2017-10-25 | 2020-09-15 | 西南大学 | 靛红唑醇类化合物及其制备方法和医药应用 |
| WO2019147615A1 (en) | 2018-01-24 | 2019-08-01 | Beyondspring Pharmaceuticals, Inc. | Composition and method for reducing thrombocytopenia via the administration of plinabulin |
| CN108299399A (zh) * | 2018-02-01 | 2018-07-20 | 深圳海王医药科技研究院有限公司 | 一种小分子免疫化合物的晶型、其制备方法和含有其的药物组合物 |
| US20210161888A1 (en) * | 2018-06-01 | 2021-06-03 | Beyondspring Pharmaceuticals, Inc. | Composition and method of treating cancer associated with egfr mutation |
| CN109030642B (zh) * | 2018-06-26 | 2021-03-09 | 深圳海王医药科技研究院有限公司 | 一种脱氢苯基阿夕斯丁类似物及其异构体的测定方法 |
| 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 |
| EP4319751A4 (en) | 2021-04-09 | 2025-02-26 | Beyondspring Pharmaceuticals, Inc. | THERAPEUTIC COMPOSITIONS AND METHODS FOR THE TREATING OF TUMORS |
| CN115703763A (zh) * | 2021-08-13 | 2023-02-17 | 大连万春布林医药有限公司 | 普那布林或其制剂中的杂质及其用途 |
| WO2023232113A1 (zh) * | 2022-06-02 | 2023-12-07 | 上海旭成医药科技有限公司 | 哌嗪酮类化合物及其制备方法和用途 |
| CN117285516B (zh) * | 2022-06-16 | 2026-06-26 | 大连万众益生大健康有限公司 | 脱氢苯基阿夕斯汀类化合物、其制备方法及其应用 |
| 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 |
| JP2026509292A (ja) | 2023-03-10 | 2026-03-17 | 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 | 腫瘍学的併用療法及びその使用方法 |
| WO2026064520A1 (en) | 2024-09-19 | 2026-03-26 | Tesseract Medicines Us, Llc | Covalent-induced drug conjugates targeting kras and comprising a tubulin inhibitor payload |
| WO2026064527A1 (en) | 2024-09-19 | 2026-03-26 | Tesseract Medicines Us, Llc | Kras-targeting covalent-induced drug conjugates comprising a tubulin inhibitor payload |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU576322B2 (en) | 1983-07-22 | 1988-08-25 | Ici Australia Limited | Alpha-substituted-alpha-cyanomethyl alcohols |
| JPH059164A (ja) | 1991-07-02 | 1993-01-19 | Sumitomo Chem Co Ltd | 光学活性マンデロニトリル誘導体の製造方法 |
| GB9217331D0 (en) | 1992-08-14 | 1992-09-30 | Xenova Ltd | Pharmaceutical compounds |
| CA2149150C (en) * | 1992-11-27 | 2000-08-01 | David R. Carver | Injectable taxol composition with improved stability |
| JPH0725858A (ja) * | 1993-07-13 | 1995-01-27 | Otsuka Pharmaceut Co Ltd | ピペラジン誘導体 |
| GB9402807D0 (en) * | 1994-02-14 | 1994-04-06 | Xenova Ltd | Pharmaceutical compounds |
| GB9402809D0 (en) * | 1994-02-14 | 1994-04-06 | Xenova Ltd | Pharmaceutical compounds |
| GB9426224D0 (en) | 1994-12-23 | 1995-02-22 | Xenova Ltd | Pharmaceutical compounds |
| US5891877A (en) * | 1995-02-14 | 1999-04-06 | Xenova Limited | Pharmaceutical compounds |
| US5874443A (en) * | 1995-10-19 | 1999-02-23 | Trega Biosciences, Inc. | Isoquinoline derivatives and isoquinoline combinatorial libraries |
| US5886210A (en) * | 1996-08-22 | 1999-03-23 | Rohm And Haas Company | Method for preparing aromatic compounds |
| JP3131574B2 (ja) | 1996-09-04 | 2001-02-05 | 新日本製鐵株式会社 | 新規抗腫瘍物質、該物質を製造するための微生物及び方法、並びに該物質を有効成分とする細胞周期阻害剤及び抗腫瘍剤 |
| US5922683A (en) * | 1997-05-29 | 1999-07-13 | Abbott Laboratories | Multicyclic erythromycin derivatives |
| EP2201945B1 (en) * | 1997-11-21 | 2013-03-06 | Purdue Neuroscience Company | Use of substituted 2-aminoacetamides for treating or ameliorating anxiety |
| EP1051397B1 (en) | 1998-01-29 | 2008-12-31 | Aventis Pharmaceuticals Inc. | Method for preparing an n- (aliphatic or aromatic)carbonyl -2-aminoacetamide compound and a cyclyzed compound |
| US6069146A (en) | 1998-03-25 | 2000-05-30 | The Regents Of The University Of California | Halimide, a cytotoxic marine natural product, and derivatives thereof |
| IL137974A0 (en) * | 1998-03-26 | 2001-10-31 | Shionogi & Co | Indole derivatives having antiviral activity |
| US6509331B1 (en) * | 1998-06-22 | 2003-01-21 | Elan Pharmaceuticals, Inc. | Deoxyamino acid compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds |
| FR2784988B1 (fr) * | 1998-10-23 | 2002-09-20 | Adir | Nouveaux composes dihydro et tetrahydroquinoleiniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US6358957B1 (en) * | 1998-11-12 | 2002-03-19 | Nereus Pharmaceuticals, Inc. | Phenylahistin and the phenylahistin analogs, a new class of anti-tumor compounds |
| US7026322B2 (en) * | 1998-11-12 | 2006-04-11 | Nereus Pharmaceuticals, Inc. | Phenylahistin and the phenylahistin analogs, a new class of anti-tumor compounds |
| EP1264831A4 (en) * | 2000-01-18 | 2005-11-23 | Nereus Pharmaceuticals Inc | Cell division inhibitors and a method for fixing the same |
| WO2002064592A1 (en) * | 2000-12-28 | 2002-08-22 | Neurocrine Biosciences, Inc. | Tricyclic crf receptor antagonists |
| US6569556B2 (en) * | 2001-01-29 | 2003-05-27 | General Motors Corporation | Cooling system for a battery pack |
| US7919497B2 (en) * | 2002-08-02 | 2011-04-05 | Nereus Pharmaceuticals, Inc. | Analogs of dehydrophenylahistins and their therapeutic use |
| AU2003302721B2 (en) * | 2002-08-02 | 2009-10-08 | Beyondspring Pharmaceuticals, Inc. | Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof |
| US7935704B2 (en) * | 2003-08-01 | 2011-05-03 | Nereus Pharmaceuticals, Inc. | Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof |
| BRPI0506655A (pt) | 2004-02-04 | 2007-05-08 | Nereus Pharmaceuticals Inc | dehidrofenilahistinas e seus análogos, e sìntese de dehidrofenilahistinas e seus análogos |
| US8129527B2 (en) * | 2006-11-03 | 2012-03-06 | Nereus Pharmacuticals, Inc. | Analogs of dehydrophenylahistins and their therapeutic use |
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2003
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- 2003-08-01 IL IL16662803A patent/IL166628A0/xx unknown
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- 2003-08-01 DE DE60316688T patent/DE60316688T2/de not_active Expired - Lifetime
- 2003-08-01 BR BRPI0313363A patent/BRPI0313363A8/pt unknown
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- 2003-08-01 CN CNB038234645A patent/CN100540548C/zh not_active Expired - Lifetime
- 2003-08-01 BR BR0313363-0A patent/BR0313363A/pt not_active Application Discontinuation
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- 2003-08-01 KR KR1020117006692A patent/KR101184374B1/ko not_active Expired - Lifetime
- 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
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- 2003-08-01 JP JP2004560278A patent/JP4616649B2/ja not_active Expired - Lifetime
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- 2003-08-01 DK DK03811651T patent/DK1529044T5/da active
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2005
- 2005-02-01 IL IL166628A patent/IL166628A/en active IP Right Grant
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2006
- 2006-06-07 US US11/448,924 patent/US7956058B2/en not_active Expired - Lifetime
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- 2006-06-07 US US11/448,283 patent/US20060223822A1/en not_active Abandoned