JP2018509404A5 - - Google Patents
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- JP2018509404A5 JP2018509404A5 JP2017545239A JP2017545239A JP2018509404A5 JP 2018509404 A5 JP2018509404 A5 JP 2018509404A5 JP 2017545239 A JP2017545239 A JP 2017545239A JP 2017545239 A JP2017545239 A JP 2017545239A JP 2018509404 A5 JP2018509404 A5 JP 2018509404A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- cycloalkyl
- alkyl
- groups
- alkanediyl
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims description 124
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 103
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 92
- 125000003282 alkyl amino group Chemical group 0.000 claims description 76
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 73
- 239000001257 hydrogen Substances 0.000 claims description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims description 70
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 68
- 239000001301 oxygen Substances 0.000 claims description 68
- 229910052760 oxygen Inorganic materials 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000003545 alkoxy group Chemical group 0.000 claims description 61
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 50
- 229910052757 nitrogen Inorganic materials 0.000 claims description 46
- 150000001408 amides Chemical class 0.000 claims description 45
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 41
- -1 amino, hydroxy Chemical group 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 36
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 31
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 26
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 25
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 24
- 125000004104 aryloxy group Chemical group 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000004423 acyloxy group Chemical group 0.000 claims description 18
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 14
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 13
- 125000001769 aryl amino group Chemical group 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 5
- 229940125644 antibody drug Drugs 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 230000001588 bifunctional effect Effects 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 5
- 150000002390 heteroarenes Chemical class 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 description 34
- 238000000034 method Methods 0.000 description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 6
- 230000000699 topical effect Effects 0.000 description 4
- 0 CC(C)C(CC(*)C1(C)SC=C(C(NC(*)CC(C)*)=O)N1)N(C)C(C(NC(*)=O)=*)=O Chemical compound CC(C)C(CC(*)C1(C)SC=C(C(NC(*)CC(C)*)=O)N1)N(C)C(C(NC(*)=O)=*)=O 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 230000036210 malignancy Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010027406 Mesothelioma Diseases 0.000 description 1
- 208000034578 Multiple myelomas Diseases 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 201000010208 Seminoma Diseases 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- 208000000277 Splenic Neoplasms Diseases 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 208000024313 Testicular Neoplasms Diseases 0.000 description 1
- 206010057644 Testis cancer Diseases 0.000 description 1
- 208000024770 Thyroid neoplasm Diseases 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 210000003679 cervix uteri Anatomy 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 210000004696 endometrium Anatomy 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009169 immunotherapy Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 230000002601 intratumoral effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000002429 large intestine Anatomy 0.000 description 1
- 201000011061 large intestine cancer Diseases 0.000 description 1
- 210000000867 larynx Anatomy 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000002200 mouth mucosa Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000002850 nasal mucosa Anatomy 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 210000005000 reproductive tract Anatomy 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 201000002314 small intestine cancer Diseases 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 201000002471 spleen cancer Diseases 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562120613P | 2015-02-25 | 2015-02-25 | |
| US62/120,613 | 2015-02-25 | ||
| US201662275667P | 2016-01-06 | 2016-01-06 | |
| US62/275,667 | 2016-01-06 | ||
| PCT/US2016/019604 WO2016138288A1 (en) | 2015-02-25 | 2016-02-25 | Desacetoxytubulysin h and analogs thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018509404A JP2018509404A (ja) | 2018-04-05 |
| JP2018509404A5 true JP2018509404A5 (https=) | 2019-04-04 |
Family
ID=56789084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017545239A Pending JP2018509404A (ja) | 2015-02-25 | 2016-02-25 | デスアセトキシツブリシンｈおよびその類似体 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US10808007B2 (https=) |
| EP (1) | EP3261443B1 (https=) |
| JP (1) | JP2018509404A (https=) |
| KR (1) | KR20170137725A (https=) |
| CN (1) | CN107529754A (https=) |
| AU (1) | AU2016222575A1 (https=) |
| BR (1) | BR112017018305A2 (https=) |
| CA (1) | CA2977589A1 (https=) |
| CL (1) | CL2017002170A1 (https=) |
| CO (1) | CO2017008600A2 (https=) |
| CR (1) | CR20170438A (https=) |
| DO (1) | DOP2017000202A (https=) |
| EA (1) | EA201791896A1 (https=) |
| EC (1) | ECSP17057131A (https=) |
| GT (1) | GT201700190A (https=) |
| HK (1) | HK1248069A1 (https=) |
| IL (1) | IL254089A0 (https=) |
| MX (1) | MX2017011024A (https=) |
| PE (1) | PE20180355A1 (https=) |
| PH (1) | PH12017501539A1 (https=) |
| SG (1) | SG11201706820RA (https=) |
| WO (1) | WO2016138288A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3350200A4 (en) | 2015-09-18 | 2019-03-27 | Wake Forest University Health Services | ANGIOTENSIN (1 7) ANALOGUE AND ASSOCIATED PROCEDURES |
| CA2914601A1 (en) * | 2015-12-11 | 2017-06-11 | Wake Forest University Health Sciences | Angiotensin-(1-7) analogs and methods relating thereto |
| US20210145771A1 (en) * | 2017-07-03 | 2021-05-20 | Glaxosmithkline Intellectual Property Development Limited | N-(3-(2-(4-chlorophenoxy)acetamido)bicyclo[1.1.1] pentan-1-yl)-2-cyclobutane-1- carboxamide derivatives and related compounds as atf4 inhibitors for treating cancer and other diseases |
| CN118239937A (zh) | 2017-08-09 | 2024-06-25 | 戴纳立制药公司 | 化合物、组合物及方法 |
| DK3676297T3 (da) | 2017-09-01 | 2023-08-14 | Denali Therapeutics Inc | Forbindelser, sammensætninger og fremgangsmåder |
| KR20200051733A (ko) * | 2017-09-08 | 2020-05-13 | 시애틀 지네틱스, 인크. | 튜불리신 및 그 중간물의 제조 공정 |
| WO2019108685A1 (en) * | 2017-11-29 | 2019-06-06 | William March Rice University | Tubulysin analogues as anticancer agents and payloads for antibody-drug conjugates and methods of treatment therewith |
| JP7590328B2 (ja) | 2018-12-21 | 2024-11-26 | レゲネロン ファーマシューティカルス，インコーポレーテッド | ツブリシン及びタンパク質－ツブリシンコンジュゲート |
| MA54953A (fr) | 2019-02-13 | 2021-12-22 | Denali Therapeutics Inc | Composés, compositions et procédés |
| US12091392B2 (en) | 2019-02-13 | 2024-09-17 | Denali Therapeutics Inc. | Compounds, compositions and methods |
| EP3814358B1 (en) * | 2019-07-11 | 2025-09-03 | Ascentage Pharma (Suzhou) Co., Ltd. | Method for preparing 2-indolinospirone compounds and intermediates thereof |
| US11694341B2 (en) | 2019-12-23 | 2023-07-04 | Texas Instmments Incorporated | Cascaded architecture for disparity and motion prediction with block matching and convolutional neural network (CNN) |
| CN112645833A (zh) * | 2021-01-29 | 2021-04-13 | 上海吉奉生物科技有限公司 | 一种(s)-2,6-二氨基-5-氧己酸的合成方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1523493T3 (da) | 2002-07-09 | 2013-12-02 | Alexander Doemling | Nye tubulysinanaloge |
| US7776814B2 (en) * | 2002-07-09 | 2010-08-17 | R&D-Biopharmaceuticals Gmbh | Tubulysin conjugates |
| US20100047841A1 (en) * | 2007-02-27 | 2010-02-25 | University Of Pittsburgh-Of The Commonwealth System Of Higher Education | Synthesis of desacetoxytubulysin h and analogs thereof |
| WO2008138561A1 (en) | 2007-05-10 | 2008-11-20 | R & D Biopharmaceuticals Gmbh | Tubulysine derivatives |
| EP2181101A2 (en) | 2007-07-20 | 2010-05-05 | Helmholtz-Zentrum für Infektionsforschung GmbH | Tubulysin d analogues |
| CN101909441B (zh) * | 2007-10-25 | 2015-05-13 | 恩多塞特公司 | 微管蛋白抑制剂及其制备方法 |
| EP2174947A1 (en) * | 2008-09-25 | 2010-04-14 | Universität des Saarlandes | Bioactive pre-tubulysins and use thereof |
| IT1394860B1 (it) | 2009-07-22 | 2012-07-20 | Kemotech S R L | Composti farmaceutici |
| US8394922B2 (en) | 2009-08-03 | 2013-03-12 | Medarex, Inc. | Antiproliferative compounds, conjugates thereof, methods therefor, and uses thereof |
| EP2322537A1 (en) | 2009-11-12 | 2011-05-18 | R & D Biopharmaceuticals Gmbh | Tubulin inhibitors |
| WO2011069116A1 (en) | 2009-12-04 | 2011-06-09 | Endocyte, Inc. | Binding ligand linked drug delivery conjugates of tubulysins |
| EP2409983A1 (en) | 2010-07-19 | 2012-01-25 | Leibniz-Institut für Pflanzenbiochemie (IPB) | Tubulysin analogues |
| JP2013535220A (ja) * | 2010-08-06 | 2013-09-12 | エンドサイト，インコーポレイテッド | ツブリシンを調製するためのプロセス |
| US20140080175A1 (en) | 2012-03-29 | 2014-03-20 | Endocyte, Inc. | Processes for preparing tubulysin derivatives and conjugates thereof |
| LT2956173T (lt) | 2013-02-14 | 2017-06-26 | Bristol-Myers Squibb Company | Tubulizino junginiai, gavimo ir panaudojimo būdai |
| EA032203B1 (ru) * | 2014-04-11 | 2019-04-30 | МЕДИММЬЮН ЭлЭлСи | Производные тубулизина |
-
2016
- 2016-02-25 US US15/553,674 patent/US10808007B2/en active Active
- 2016-02-25 HK HK18107653.3A patent/HK1248069A1/zh unknown
- 2016-02-25 SG SG11201706820RA patent/SG11201706820RA/en unknown
- 2016-02-25 EP EP16756378.2A patent/EP3261443B1/en active Active
- 2016-02-25 AU AU2016222575A patent/AU2016222575A1/en not_active Abandoned
- 2016-02-25 CR CR20170438A patent/CR20170438A/es unknown
- 2016-02-25 KR KR1020177027116A patent/KR20170137725A/ko not_active Withdrawn
- 2016-02-25 EA EA201791896A patent/EA201791896A1/ru unknown
- 2016-02-25 CA CA2977589A patent/CA2977589A1/en not_active Abandoned
- 2016-02-25 JP JP2017545239A patent/JP2018509404A/ja active Pending
- 2016-02-25 CN CN201680023813.XA patent/CN107529754A/zh active Pending
- 2016-02-25 BR BR112017018305A patent/BR112017018305A2/pt not_active Application Discontinuation
- 2016-02-25 WO PCT/US2016/019604 patent/WO2016138288A1/en not_active Ceased
- 2016-02-25 PE PE2017001465A patent/PE20180355A1/es unknown
- 2016-02-25 MX MX2017011024A patent/MX2017011024A/es unknown
-
2017
- 2017-08-22 IL IL254089A patent/IL254089A0/en unknown
- 2017-08-25 CO CONC2017/0008600A patent/CO2017008600A2/es unknown
- 2017-08-25 DO DO2017000202A patent/DOP2017000202A/es unknown
- 2017-08-25 CL CL2017002170A patent/CL2017002170A1/es unknown
- 2017-08-25 GT GT201700190A patent/GT201700190A/es unknown
- 2017-08-25 PH PH12017501539A patent/PH12017501539A1/en unknown
- 2017-08-30 EC ECIEPI201757131A patent/ECSP17057131A/es unknown
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