JP2008526859A5 - - Google Patents
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- Publication number
- JP2008526859A5 JP2008526859A5 JP2007550441A JP2007550441A JP2008526859A5 JP 2008526859 A5 JP2008526859 A5 JP 2008526859A5 JP 2007550441 A JP2007550441 A JP 2007550441A JP 2007550441 A JP2007550441 A JP 2007550441A JP 2008526859 A5 JP2008526859 A5 JP 2008526859A5
- Authority
- JP
- Japan
- Prior art keywords
- compound according
- glutamyl
- methyl
- phenyl
- cysteinyl
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- -1 L-γ-glutamylglycyl Chemical group 0.000 claims description 11
- 150000005690 diesters Chemical class 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001992 L-gamma-glutamyl group Chemical group N[C@@H](CCC(=O)*)C(=O)O 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- 238000006467 substitution reaction Methods 0.000 claims 3
- 210000001185 bone marrow Anatomy 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 210000004881 tumor cell Anatomy 0.000 claims 2
- YNBWBEDJANIGKO-QSFULLKGSA-N (2S)-2-amino-5-[[(R)-[1-[(2R)-2-amino-3-[(2-phenylphenyl)methylsulfanyl]propanoyl]cyclohexa-2,4-dien-1-yl]-carboxymethyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](CCC(=O)N[C@H](C1(CC=CC=C1)C([C@@H](N)CSCC1=C(C=CC=C1)C1=CC=CC=C1)=O)C(=O)O)C(=O)O YNBWBEDJANIGKO-QSFULLKGSA-N 0.000 claims 1
- ACSONAKGOHBGPL-SBOBVTCZSA-N (2S)-2-amino-5-[[(R)-[1-[(2R)-2-amino-3-[(4-benzoylphenyl)methylsulfanyl]propanoyl]cyclohexa-2,4-dien-1-yl]-carboxymethyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](CCC(=O)N[C@H](C1(CC=CC=C1)C([C@@H](N)CSCC1=CC=C(C=C1)C(C1=CC=CC=C1)=O)=O)C(=O)O)C(=O)O ACSONAKGOHBGPL-SBOBVTCZSA-N 0.000 claims 1
- ANOBOESHEJYLOW-QSFULLKGSA-N (2S)-2-amino-5-[[(R)-[1-[(2R)-2-amino-3-[(4-phenylphenyl)methylsulfanyl]propanoyl]cyclohexa-2,4-dien-1-yl]-carboxymethyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](CCC(=O)N[C@H](C1(CC=CC=C1)C([C@@H](N)CSCC1=CC=C(C=C1)C1=CC=CC=C1)=O)C(=O)O)C(=O)O ANOBOESHEJYLOW-QSFULLKGSA-N 0.000 claims 1
- IEWPLHCQXLDPKO-PRRCYPGKSA-N (2S)-2-amino-5-[[(R)-[1-[(2R)-2-amino-3-[(4-pyridin-2-ylphenyl)methylsulfanyl]propanoyl]cyclohexa-2,4-dien-1-yl]-carboxymethyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](CCC(=O)N[C@H](C1(CC=CC=C1)C([C@@H](N)CSCC1=CC=C(C=C1)C1=NC=CC=C1)=O)C(=O)O)C(=O)O IEWPLHCQXLDPKO-PRRCYPGKSA-N 0.000 claims 1
- RBEHFZUVRVJHCS-HNULWMTKSA-N (2S)-2-amino-5-[[(R)-[1-[(2R)-2-amino-3-[[4-(2-cyanophenyl)phenyl]methylsulfanyl]propanoyl]cyclohexa-2,4-dien-1-yl]-carboxymethyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](CCC(=O)N[C@H](C1(CC=CC=C1)C([C@@H](N)CSCC1=CC=C(C=C1)C1=C(C=CC=C1)C#N)=O)C(=O)O)C(=O)O RBEHFZUVRVJHCS-HNULWMTKSA-N 0.000 claims 1
- FUODYSPTYORQQE-SBOBVTCZSA-N (2S)-2-amino-5-[[(R)-[1-[(2R)-2-amino-3-[[4-(2-methoxyphenyl)phenyl]methylsulfanyl]propanoyl]cyclohexa-2,4-dien-1-yl]-carboxymethyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](CCC(=O)N[C@H](C1(CC=CC=C1)C([C@@H](N)CSCC1=CC=C(C=C1)C1=C(C=CC=C1)OC)=O)C(=O)O)C(=O)O FUODYSPTYORQQE-SBOBVTCZSA-N 0.000 claims 1
- HBWNLLPPJCOXJR-HNULWMTKSA-N (2S)-2-amino-5-[[(R)-[1-[(2R)-2-amino-3-[[4-(4-cyanophenyl)phenyl]methylsulfanyl]propanoyl]cyclohexa-2,4-dien-1-yl]-carboxymethyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](CCC(=O)N[C@H](C1(CC=CC=C1)C([C@@H](N)CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C#N)=O)C(=O)O)C(=O)O HBWNLLPPJCOXJR-HNULWMTKSA-N 0.000 claims 1
- WVXDFTOHKASODW-QSFULLKGSA-N (2S)-2-amino-5-[[(R)-[1-[(2R)-2-amino-3-[[4-[3-(trifluoromethyl)phenyl]phenyl]methylsulfanyl]propanoyl]cyclohexa-2,4-dien-1-yl]-carboxymethyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](CCC(=O)N[C@H](C1(CC=CC=C1)C([C@@H](N)CSCC1=CC=C(C=C1)C1=CC(=CC=C1)C(F)(F)F)=O)C(=O)O)C(=O)O WVXDFTOHKASODW-QSFULLKGSA-N 0.000 claims 1
- IVVVQCXNCNYKIT-ZOYIPQRUSA-N (2S)-2-amino-5-[[(R)-[1-[(2R)-2-amino-3-[[4-[N-(2-aminoethoxy)-C-phenylcarbonimidoyl]phenyl]methylsulfanyl]propanoyl]cyclohexa-2,4-dien-1-yl]-carboxymethyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](CCC(=O)N[C@H](C1(CC=CC=C1)C([C@@H](N)CSCC1=CC=C(C=C1)C(C1=CC=CC=C1)=NOCCN)=O)C(=O)O)C(=O)O IVVVQCXNCNYKIT-ZOYIPQRUSA-N 0.000 claims 1
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- NZOYIRZDBOGWCE-PESIQCSKSA-N 4-[4-[[(2R)-2-amino-3-[1-[(R)-[[(4S)-4-amino-4-carboxybutanoyl]amino]-carboxymethyl]cyclohexa-2,4-dien-1-yl]-3-oxopropyl]sulfanylmethyl]phenyl]benzoic acid Chemical compound N[C@@H](CCC(=O)N[C@H](C1(CC=CC=C1)C([C@@H](N)CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O)=O)C(=O)O)C(=O)O NZOYIRZDBOGWCE-PESIQCSKSA-N 0.000 claims 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 1
- 125000006242 amine protecting group Chemical group 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 210000002798 bone marrow cell Anatomy 0.000 claims 1
- 231100000433 cytotoxic Toxicity 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 230000001472 cytotoxic effect Effects 0.000 claims 1
- 230000004069 differentiation Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000011132 hemopoiesis Effects 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 230000003039 myelosuppressive effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 230000001988 toxicity Effects 0.000 claims 1
- 231100000419 toxicity Toxicity 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64193205P | 2005-01-06 | 2005-01-06 | |
| US60/641,932 | 2005-01-06 | ||
| PCT/US2006/000219 WO2006074249A1 (en) | 2005-01-06 | 2006-01-04 | Tripeptide and tetrapeptide thioethers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008526859A JP2008526859A (ja) | 2008-07-24 |
| JP2008526859A5 true JP2008526859A5 (enExample) | 2009-02-19 |
| JP4903716B2 JP4903716B2 (ja) | 2012-03-28 |
Family
ID=36123437
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007550441A Expired - Fee Related JP4903716B2 (ja) | 2005-01-06 | 2006-01-04 | トリペプチドおよびテトラペプチドチオエーテル |
| JP2007550515A Expired - Fee Related JP4903717B2 (ja) | 2005-01-06 | 2006-01-05 | トリペプチドおよびテトラペプチドスルホン |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007550515A Expired - Fee Related JP4903717B2 (ja) | 2005-01-06 | 2006-01-05 | トリペプチドおよびテトラペプチドスルホン |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US7129215B2 (enExample) |
| EP (2) | EP1833978B1 (enExample) |
| JP (2) | JP4903716B2 (enExample) |
| KR (2) | KR101244609B1 (enExample) |
| CN (2) | CN101090977B (enExample) |
| AR (2) | AR051889A1 (enExample) |
| AT (2) | ATE410520T1 (enExample) |
| AU (2) | AU2006204022B2 (enExample) |
| BR (2) | BRPI0606520A2 (enExample) |
| CA (2) | CA2587284C (enExample) |
| DE (2) | DE602006003064D1 (enExample) |
| DK (2) | DK1833978T3 (enExample) |
| EA (2) | EA200701398A1 (enExample) |
| ES (2) | ES2314890T3 (enExample) |
| HR (2) | HRP20090128T3 (enExample) |
| IL (2) | IL182836A (enExample) |
| MX (2) | MX2007008255A (enExample) |
| NZ (2) | NZ555362A (enExample) |
| PL (2) | PL1833978T3 (enExample) |
| PT (2) | PT1833978E (enExample) |
| SI (2) | SI1833978T1 (enExample) |
| TW (2) | TWI317738B (enExample) |
| WO (2) | WO2006074249A1 (enExample) |
| ZA (2) | ZA200704487B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8198247B2 (en) | 2004-12-21 | 2012-06-12 | Telik, Inc. | Process for and intermediates in the preparation of canfosfamide and its salts |
| JP4903716B2 (ja) * | 2005-01-06 | 2012-03-28 | テリック，インコーポレイテッド | トリペプチドおよびテトラペプチドチオエーテル |
| US20070154963A1 (en) * | 2005-12-30 | 2007-07-05 | Danying Cai | Method to determine whether a compound is a cellular GSTpi inhibitor |
| US20090221703A1 (en) | 2006-07-09 | 2009-09-03 | Chongxi Yu | High penetration composition and uses thereof |
| US20090238763A1 (en) | 2006-07-09 | 2009-09-24 | Chongxi Yu | High penetration compositions and uses thereof |
| AU2016213759B2 (en) * | 2006-11-08 | 2018-03-29 | Chongxi Yu | Transdermal delivery systems of peptides and related compounds |
| AU2006350707A1 (en) | 2006-11-08 | 2008-05-15 | Chongxi Yu | Transdermal delivery systems of peptides and related compounds |
| KR20210103586A (ko) | 2007-06-04 | 2021-08-23 | 테크필즈 인크 | 매우 높은 피부 및 막 침투율을 가지는 비스테로이드성 소염제(ｎｓａｉａ) 약물전구체 및 이들의 새로운 의약적 용도 |
| MX380878B (es) | 2008-12-04 | 2025-03-12 | Chongxi Yu | Composiciones de alta penetracion y sus aplicaciones. |
| DE102008060888A1 (de) | 2008-12-09 | 2010-06-10 | Evonik Stockhausen Gmbh | Verfahren zur Herstellung von Acrolein umfassend die Aufarbeitung einer Rohglycerin-Phase |
| KR20180110187A (ko) | 2009-05-08 | 2018-10-08 | 테크필즈 바이오켐 코., 엘티디. | 펩티드 및 펩티드관련 화합물의 고침투성 전구약물 조성물 |
| CN102939300A (zh) | 2010-06-07 | 2013-02-20 | 泰立克公司 | 无溶剂化晶体依泽替米贝盐酸盐d型的制备 |
| CN102917694A (zh) * | 2010-06-07 | 2013-02-06 | 泰立克公司 | 依泽替米贝的片剂制剂 |
| US20130035389A1 (en) * | 2011-08-05 | 2013-02-07 | Telik, Inc. | Methods for treating myelodysplastic syndrome with ezatiostat |
| JP5970439B2 (ja) * | 2013-09-20 | 2016-08-17 | チョンシー ユー | ペプチド及び関連化合物の経皮送達システム |
| CN106146616A (zh) * | 2015-04-03 | 2016-11-23 | 浙江海正药业股份有限公司 | 环肽类化合物及其制备和用途 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5599903A (en) * | 1992-04-03 | 1997-02-04 | Terrapin Technologies, Inc. | Glutathione analogs and paralog panels comprising glutathione mimics |
| US5556942A (en) | 1991-04-29 | 1996-09-17 | Terrapin Technologies, Inc. | Glutathione S-transferase-activated compounds |
| US5786336A (en) * | 1991-04-29 | 1998-07-28 | Terrapin Technologies, Inc. | Target-selective protocols based on mimics |
| US5767086A (en) * | 1992-04-03 | 1998-06-16 | Terrapin Technologies, Inc. | Bone marrow stimulation by certain glutathione analogs |
| US5955432A (en) * | 1992-04-03 | 1999-09-21 | Terrapin Technologies, Inc. | Metabolic effects of certain glutathione analogs |
| CA2105492C (en) | 1993-09-03 | 2000-02-01 | Lawrence M. Kauvar | Glutathione analogs and paralog panels comprising glutathione mimics |
| US5908919A (en) * | 1993-10-01 | 1999-06-01 | Terrapin Technologies | Urethane mediated, GST specific molecular release systems |
| DE69633722T2 (de) | 1995-06-07 | 2005-11-03 | TELIK, INC., Palo Alto | Stoffwechseleffekt von bestimmten glutation analogen |
| AU4124697A (en) * | 1996-09-02 | 1998-03-26 | Manchester Metropolitan University, The | S-blocked glutathiones |
| CA2328731A1 (en) * | 1998-04-16 | 1999-10-28 | Atsushi Imaizumi | Glutathione derivatives and dosage forms thereof |
| WO2000044366A2 (en) * | 1999-01-27 | 2000-08-03 | Telik, Inc. | Therapeutic compositions containing glutathione analogs |
| US7029695B2 (en) * | 2001-07-10 | 2006-04-18 | Telik, Inc. | Therapeutic compositions containing glutathione analogs |
| TWI323662B (en) * | 2002-11-15 | 2010-04-21 | Telik Inc | Combination cancer therapy with a gst-activated anticancer compound and another anticancer therapy |
| JP4903716B2 (ja) * | 2005-01-06 | 2012-03-28 | テリック，インコーポレイテッド | トリペプチドおよびテトラペプチドチオエーテル |
-
2006
- 2006-01-04 JP JP2007550441A patent/JP4903716B2/ja not_active Expired - Fee Related
- 2006-01-04 DK DK06717426T patent/DK1833978T3/da active
- 2006-01-04 TW TW095100277A patent/TWI317738B/zh not_active IP Right Cessation
- 2006-01-04 US US11/325,846 patent/US7129215B2/en not_active Expired - Fee Related
- 2006-01-04 CA CA2587284A patent/CA2587284C/en not_active Expired - Fee Related
- 2006-01-04 DE DE602006003064T patent/DE602006003064D1/de active Active
- 2006-01-04 HR HR20090128T patent/HRP20090128T3/xx unknown
- 2006-01-04 EA EA200701398A patent/EA200701398A1/ru unknown
- 2006-01-04 SI SI200630153T patent/SI1833978T1/sl unknown
- 2006-01-04 NZ NZ555362A patent/NZ555362A/en not_active IP Right Cessation
- 2006-01-04 CN CN2006800014949A patent/CN101090977B/zh not_active Expired - Fee Related
- 2006-01-04 MX MX2007008255A patent/MX2007008255A/es active IP Right Grant
- 2006-01-04 ES ES06717426T patent/ES2314890T3/es active Active
- 2006-01-04 TW TW095100278A patent/TWI317739B/zh not_active IP Right Cessation
- 2006-01-04 AU AU2006204022A patent/AU2006204022B2/en not_active Ceased
- 2006-01-04 WO PCT/US2006/000219 patent/WO2006074249A1/en not_active Ceased
- 2006-01-04 PT PT06717426T patent/PT1833978E/pt unknown
- 2006-01-04 BR BRPI0606520-1A patent/BRPI0606520A2/pt not_active IP Right Cessation
- 2006-01-04 PL PL06717426T patent/PL1833978T3/pl unknown
- 2006-01-04 AT AT06717426T patent/ATE410520T1/de active
- 2006-01-04 KR KR1020077018022A patent/KR101244609B1/ko not_active Expired - Fee Related
- 2006-01-04 EP EP06717426A patent/EP1833978B1/en active Active
- 2006-01-05 AU AU2006203901A patent/AU2006203901B2/en not_active Ceased
- 2006-01-05 HR HR20090134T patent/HRP20090134T3/xx unknown
- 2006-01-05 US US11/326,975 patent/US7192918B2/en not_active Expired - Fee Related
- 2006-01-05 NZ NZ555361A patent/NZ555361A/en not_active IP Right Cessation
- 2006-01-05 SI SI200630154T patent/SI1833842T1/sl unknown
- 2006-01-05 EA EA200701399A patent/EA200701399A1/ru unknown
- 2006-01-05 DE DE602006003063T patent/DE602006003063D1/de active Active
- 2006-01-05 MX MX2007008254A patent/MX2007008254A/es active IP Right Grant
- 2006-01-05 CN CNA2006800013664A patent/CN101080418A/zh active Pending
- 2006-01-05 EP EP06717699A patent/EP1833842B1/en active Active
- 2006-01-05 AR ARP060100041A patent/AR051889A1/es not_active Application Discontinuation
- 2006-01-05 AT AT06717699T patent/ATE410440T1/de active
- 2006-01-05 JP JP2007550515A patent/JP4903717B2/ja not_active Expired - Fee Related
- 2006-01-05 BR BRPI0606396-9A patent/BRPI0606396A2/pt not_active IP Right Cessation
- 2006-01-05 AR ARP060100042A patent/AR051890A1/es not_active Application Discontinuation
- 2006-01-05 CA CA2587310A patent/CA2587310C/en not_active Expired - Fee Related
- 2006-01-05 KR KR1020077012531A patent/KR20070091611A/ko not_active Ceased
- 2006-01-05 ES ES06717699T patent/ES2314891T3/es active Active
- 2006-01-05 WO PCT/US2006/000532 patent/WO2006074409A1/en not_active Ceased
- 2006-01-05 DK DK06717699T patent/DK1833842T3/da active
- 2006-01-05 PT PT06717699T patent/PT1833842E/pt unknown
- 2006-01-05 PL PL06717699T patent/PL1833842T3/pl unknown
-
2007
- 2007-04-26 IL IL182836A patent/IL182836A/en not_active IP Right Cessation
- 2007-05-10 IL IL183107A patent/IL183107A/en not_active IP Right Cessation
- 2007-05-20 ZA ZA200704487A patent/ZA200704487B/xx unknown
- 2007-05-30 ZA ZA200704488A patent/ZA200704488B/xx unknown
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