JP2008500392A5 - - Google Patents
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- Publication number
- JP2008500392A5 JP2008500392A5 JP2007527503A JP2007527503A JP2008500392A5 JP 2008500392 A5 JP2008500392 A5 JP 2008500392A5 JP 2007527503 A JP2007527503 A JP 2007527503A JP 2007527503 A JP2007527503 A JP 2007527503A JP 2008500392 A5 JP2008500392 A5 JP 2008500392A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- optionally substituted
- bis
- compound
- compound according
- 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 53
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- -1 benzenesulfonyloxy Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001475 halogen functional group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 5
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- DALLRVRWWIRXCA-LBPRGKRZSA-N (2r)-2-amino-3-[2-[bis[bis(2-chloroethyl)amino]phosphoryloxy]ethylsulfonyl]propanoic acid Chemical compound OC(=O)[C@@H](N)CS(=O)(=O)CCOP(=O)(N(CCCl)CCCl)N(CCCl)CCCl DALLRVRWWIRXCA-LBPRGKRZSA-N 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 150000008299 phosphorodiamidates Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims 2
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 229940024606 amino acid Drugs 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- JKMGNABLWAMCKC-UHFFFAOYSA-N ethyl 2-[[4-[2-[bis[bis(2-chloroethyl)amino]phosphoryloxy]ethylsulfonylmethyl]benzoyl]amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CC=C(CS(=O)(=O)CCOP(=O)(N(CCCl)CCCl)N(CCCl)CCCl)C=C1 JKMGNABLWAMCKC-UHFFFAOYSA-N 0.000 claims 1
- JOJBPSCYHZWVRG-UHFFFAOYSA-N n-[2-benzylsulfonylethoxy-[bis(2-chloroethyl)amino]phosphoryl]-2-chloro-n-(2-chloroethyl)ethanamine Chemical compound ClCCN(CCCl)P(=O)(N(CCCl)CCCl)OCCS(=O)(=O)CC1=CC=CC=C1 JOJBPSCYHZWVRG-UHFFFAOYSA-N 0.000 claims 1
- OVNNXCTWYLCBTE-UHFFFAOYSA-N n-[bis(2-chloroethyl)amino-(2-butylsulfonylethoxy)phosphoryl]-2-chloro-n-(2-chloroethyl)ethanamine Chemical compound CCCCS(=O)(=O)CCOP(=O)(N(CCCl)CCCl)N(CCCl)CCCl OVNNXCTWYLCBTE-UHFFFAOYSA-N 0.000 claims 1
- SLDJVXONLNUQBT-UHFFFAOYSA-N n-[bis(2-chloroethyl)amino-[2-(thiophen-2-ylmethylsulfonyl)ethoxy]phosphoryl]-2-chloro-n-(2-chloroethyl)ethanamine Chemical compound ClCCN(CCCl)P(=O)(N(CCCl)CCCl)OCCS(=O)(=O)CC1=CC=CS1 SLDJVXONLNUQBT-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229960005190 phenylalanine Drugs 0.000 claims 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims 1
- 125000005496 phosphonium group Chemical group 0.000 claims 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims 1
- 238000001308 synthesis method Methods 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 10
- 239000002246 antineoplastic agent Substances 0.000 description 8
- 238000003556 assay Methods 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 229940041181 antineoplastic drug Drugs 0.000 description 3
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- 206010034133 Pathogen resistance Diseases 0.000 description 2
- 238000002784 cytotoxicity assay Methods 0.000 description 2
- 231100000263 cytotoxicity test Toxicity 0.000 description 2
- ANCLJVISBRWUTR-UHFFFAOYSA-N diaminophosphinic acid Chemical group NP(N)(O)=O ANCLJVISBRWUTR-UHFFFAOYSA-N 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57353204P | 2004-05-21 | 2004-05-21 | |
| US60/573,532 | 2004-05-21 | ||
| US58843604P | 2004-07-16 | 2004-07-16 | |
| US60/588,436 | 2004-07-16 | ||
| PCT/US2005/017880 WO2005118601A2 (en) | 2004-05-21 | 2005-05-20 | Sulfonylethyl phosphorodiamidates for use in the treatment of cancer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008500392A JP2008500392A (ja) | 2008-01-10 |
| JP2008500392A5 true JP2008500392A5 (OSRAM) | 2008-07-10 |
| JP4942653B2 JP4942653B2 (ja) | 2012-05-30 |
Family
ID=35262040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007527503A Expired - Fee Related JP4942653B2 (ja) | 2004-05-21 | 2005-05-20 | スルホニルエチルホスホロジアミデート |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7262182B2 (OSRAM) |
| EP (1) | EP1791549A2 (OSRAM) |
| JP (1) | JP4942653B2 (OSRAM) |
| KR (1) | KR20070029187A (OSRAM) |
| AR (1) | AR049385A1 (OSRAM) |
| AU (1) | AU2005250383B2 (OSRAM) |
| BR (1) | BRPI0511420A (OSRAM) |
| CA (1) | CA2566886A1 (OSRAM) |
| EA (1) | EA200602047A1 (OSRAM) |
| IL (1) | IL178980A0 (OSRAM) |
| MX (1) | MXPA06013373A (OSRAM) |
| NO (1) | NO20065936L (OSRAM) |
| NZ (1) | NZ551270A (OSRAM) |
| TW (1) | TW200600091A (OSRAM) |
| WO (1) | WO2005118601A2 (OSRAM) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0011903D0 (en) * | 2000-05-18 | 2000-07-05 | Astrazeneca Ab | Combination chemotherapy |
| TW200600091A (en) | 2004-05-21 | 2006-01-01 | Telik Inc | Sulfonylethyl phosphorodiamidates |
| DE102005005397B4 (de) * | 2005-02-05 | 2008-08-21 | Lts Lohmann Therapie-Systeme Ag | Isolierung von N-Butylbenzolsulfonamid, Synthese von Benzolsulfonamid-Derivaten sowie Verwendung von N-Butylbenzolsulfonamid und Benzolsulfonamid-Derivaten zur Behandlung der benignen Prostatahyperplasie und/oder des Prostatakarzinoms |
| US8168662B1 (en) | 2006-11-06 | 2012-05-01 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US8168661B2 (en) | 2006-11-06 | 2012-05-01 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US8173686B2 (en) | 2006-11-06 | 2012-05-08 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US8178564B2 (en) | 2006-11-06 | 2012-05-15 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| WO2008066515A1 (en) * | 2006-11-28 | 2008-06-05 | Telik, Inc. | 2-({2-oxo-2-[(pyridin-3-ylmethyl)amino]ethyl}sulfonyl)ethyl n,n,n',n'-tetrakis(2-chloroethyl)phosphorodiamidate |
| US20080125397A1 (en) * | 2006-11-28 | 2008-05-29 | Telik, Inc. | 2 (SULFONYL)ETHYL N,N,N',N' tetrakis(2 chloroethyl)phosphorodia |
| AU2006351255A1 (en) * | 2006-11-29 | 2008-06-05 | Telik, Inc. | 2-{[2-(Substituted amino)ethyl]sulfonyl}ethyl N,N,N',N'-tetrakis(2 -chloroethyl)phosphorodiamidates |
| US7655799B2 (en) * | 2006-11-29 | 2010-02-02 | Telik, Inc. | 2{[2-(substituted amino)ethyl]sulfonyl}ethyl N,N,N',N'-tetrakis(2-chloroethyl)phosphorodiamidates |
| US20110033528A1 (en) * | 2009-08-05 | 2011-02-10 | Poniard Pharmaceuticals, Inc. | Stabilized picoplatin oral dosage form |
| US20100260832A1 (en) * | 2007-06-27 | 2010-10-14 | Poniard Pharmaceuticals, Inc. | Combination therapy for ovarian cancer |
| TW200916094A (en) * | 2007-06-27 | 2009-04-16 | Poniard Pharmaceuticals Inc | Stabilized picoplatin dosage form |
| US20100310661A1 (en) * | 2007-07-16 | 2010-12-09 | Poniard Pharmaceuticals, Inc. | Oral formulations for picoplatin |
| US7872134B2 (en) * | 2007-12-12 | 2011-01-18 | Telik, Inc. | 2-{[2-(substituted amino)ethyl]sulfonyl}ethyl N,N-bis(2-chloroethyl)phosphorodiamidates |
| CN102006875A (zh) * | 2008-02-08 | 2011-04-06 | 帕纳德制药公司 | 吡铂和贝伐单抗治疗结直肠癌的用途 |
| JP6280546B2 (ja) | 2012-06-26 | 2018-02-14 | デル マー ファーマシューティカルズ | ジアンヒドロガラクチトール、ジアセチルジアンヒドロガラクチトール、ジブロモズルシトール、又はこれらの類似体若しくは誘導体を用いた、遺伝子多型又はａｈｉ１の調節不全若しくは変異を有する患者におけるチロシンキナーゼインヒビター抵抗性悪性腫瘍を処置するための方法 |
| EP2983674A4 (en) | 2013-04-08 | 2017-05-10 | Dennis M. Brown | Therapeutic benefit of suboptimally administered chemical compounds |
| US9238620B1 (en) | 2014-07-09 | 2016-01-19 | National Sun Yat-Sen University | Pharmaceutical uses of sulfur-containing compound |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5545621A (en) * | 1991-04-29 | 1996-08-13 | Terrapin Technologies, Inc. | Glutathione S-transferase-activated compounds |
| US5556942A (en) * | 1991-04-29 | 1996-09-17 | Terrapin Technologies, Inc. | Glutathione S-transferase-activated compounds |
| UA74574C2 (en) | 2000-05-02 | 2006-01-16 | Telik Inc | Bis (n,n'-bis(2-halogenethyl)amino)phosphodiamates, a method for producing thereof (variants), a pharmaceutical composition containing them, and a method for the treatment of tumors |
| US6506739B1 (en) * | 2001-05-01 | 2003-01-14 | Telik, Inc. | Bis-(N,N'-bis-(2-haloethyl)amino)phosphoramidates as antitumor agents |
| US6667330B2 (en) * | 2002-01-31 | 2003-12-23 | Galileo Pharmaceuticals, Inc. | Furanone derivatives |
| KR101102384B1 (ko) | 2003-08-14 | 2012-01-05 | 엘지전자 주식회사 | 광디스크, 기록방법, 기록재생장치 및 기록재생시스템 |
| TW200600091A (en) | 2004-05-21 | 2006-01-01 | Telik Inc | Sulfonylethyl phosphorodiamidates |
-
2005
- 2005-05-17 TW TW094115893A patent/TW200600091A/zh unknown
- 2005-05-20 NZ NZ551270A patent/NZ551270A/en unknown
- 2005-05-20 US US11/134,218 patent/US7262182B2/en not_active Expired - Fee Related
- 2005-05-20 AR ARP050102094A patent/AR049385A1/es unknown
- 2005-05-20 AU AU2005250383A patent/AU2005250383B2/en not_active Ceased
- 2005-05-20 CA CA002566886A patent/CA2566886A1/en not_active Abandoned
- 2005-05-20 BR BRPI0511420-9A patent/BRPI0511420A/pt not_active IP Right Cessation
- 2005-05-20 WO PCT/US2005/017880 patent/WO2005118601A2/en not_active Ceased
- 2005-05-20 EA EA200602047A patent/EA200602047A1/ru unknown
- 2005-05-20 MX MXPA06013373A patent/MXPA06013373A/es active IP Right Grant
- 2005-05-20 JP JP2007527503A patent/JP4942653B2/ja not_active Expired - Fee Related
- 2005-05-20 EP EP05804834A patent/EP1791549A2/en not_active Withdrawn
- 2005-05-20 KR KR1020067025574A patent/KR20070029187A/ko not_active Ceased
-
2006
- 2006-11-01 IL IL178980A patent/IL178980A0/en unknown
- 2006-12-20 NO NO20065936A patent/NO20065936L/no not_active Application Discontinuation
-
2007
- 2007-07-17 US US11/779,234 patent/US8093231B2/en not_active Expired - Fee Related
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