JP2002519408A5 - - Google Patents
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- Publication number
- JP2002519408A5 JP2002519408A5 JP2000558073A JP2000558073A JP2002519408A5 JP 2002519408 A5 JP2002519408 A5 JP 2002519408A5 JP 2000558073 A JP2000558073 A JP 2000558073A JP 2000558073 A JP2000558073 A JP 2000558073A JP 2002519408 A5 JP2002519408 A5 JP 2002519408A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- pentanedioic acid
- compound
- sulfanyl
- benzyl
- 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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- 150000001875 compounds Chemical class 0.000 description 13
- -1 R 14 Chemical compound 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- SMGZBRVSYVJHCB-UHFFFAOYSA-N 2-(2-sulfanylethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CCS SMGZBRVSYVJHCB-UHFFFAOYSA-N 0.000 description 2
- XZOBZHOOPYYQLF-UHFFFAOYSA-N 2-(2-sulfanylpropyl)pentanedioic acid Chemical compound CC(S)CC(C(O)=O)CCC(O)=O XZOBZHOOPYYQLF-UHFFFAOYSA-N 0.000 description 2
- FNLNSQHJKVQCBP-UHFFFAOYSA-N 2-(3-sulfanylpropyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CCCS FNLNSQHJKVQCBP-UHFFFAOYSA-N 0.000 description 2
- 102000003958 Glutamate Carboxypeptidase II Human genes 0.000 description 2
- 108090000369 Glutamate Carboxypeptidase II Proteins 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLHDIVLUIDWAEE-UHFFFAOYSA-N 2-(1-sulfanylbutan-2-yl)pentanedioic acid Chemical compound CCC(CS)C(C(O)=O)CCC(O)=O ZLHDIVLUIDWAEE-UHFFFAOYSA-N 0.000 description 1
- ODRDBLPMDUBXIN-UHFFFAOYSA-N 2-(1-sulfanylpropan-2-yl)pentanedioic acid Chemical compound SCC(C)C(C(O)=O)CCC(O)=O ODRDBLPMDUBXIN-UHFFFAOYSA-N 0.000 description 1
- USTZJUOEIVGBAX-UHFFFAOYSA-N 2-(2-benzyl-3-sulfanylpropyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CC(CS)CC1=CC=CC=C1 USTZJUOEIVGBAX-UHFFFAOYSA-N 0.000 description 1
- YVGAHISZPITMEJ-UHFFFAOYSA-N 2-(2-methyl-3-sulfanylpropyl)pentanedioic acid Chemical compound SCC(C)CC(C(O)=O)CCC(O)=O YVGAHISZPITMEJ-UHFFFAOYSA-N 0.000 description 1
- CCYMZXAGFYPCLX-UHFFFAOYSA-N 2-(2-phenyl-2-sulfanylethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CC(S)C1=CC=CC=C1 CCYMZXAGFYPCLX-UHFFFAOYSA-N 0.000 description 1
- BGFCWVUFLJLKGR-UHFFFAOYSA-N 2-(2-phenyl-3-sulfanylpropyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CC(CS)C1=CC=CC=C1 BGFCWVUFLJLKGR-UHFFFAOYSA-N 0.000 description 1
- YXHYMTRLDHMUDB-UHFFFAOYSA-N 2-(2-sulfanylbutyl)pentanedioic acid Chemical compound CCC(S)CC(C(O)=O)CCC(O)=O YXHYMTRLDHMUDB-UHFFFAOYSA-N 0.000 description 1
- UIIGSGCAFJVHAI-UHFFFAOYSA-N 2-(2-sulfanylhexyl)pentanedioic acid Chemical compound CCCCC(S)CC(C(O)=O)CCC(O)=O UIIGSGCAFJVHAI-UHFFFAOYSA-N 0.000 description 1
- VJZDXYDMWPFMRN-UHFFFAOYSA-N 2-(3-sulfanylbutyl)pentanedioic acid Chemical compound CC(S)CCC(C(O)=O)CCC(O)=O VJZDXYDMWPFMRN-UHFFFAOYSA-N 0.000 description 1
- AUDGDJFDXMDNCI-UHFFFAOYSA-N 2-(3-sulfanylpentyl)pentanedioic acid Chemical compound CCC(S)CCC(C(O)=O)CCC(O)=O AUDGDJFDXMDNCI-UHFFFAOYSA-N 0.000 description 1
- PQLHQOMXYWQCET-UHFFFAOYSA-N 2-(4-methyl-3-sulfanylpentyl)pentanedioic acid Chemical compound CC(C)C(S)CCC(C(O)=O)CCC(O)=O PQLHQOMXYWQCET-UHFFFAOYSA-N 0.000 description 1
- IYANJJPQEMIVEW-UHFFFAOYSA-N 2-[2-(sulfanylmethyl)butyl]pentanedioic acid Chemical compound CCC(CS)CC(C(O)=O)CCC(O)=O IYANJJPQEMIVEW-UHFFFAOYSA-N 0.000 description 1
- SOOQDICRKKXBHF-UHFFFAOYSA-N 2-[2-(sulfanylmethyl)pentyl]pentanedioic acid Chemical compound CCCC(CS)CC(C(O)=O)CCC(O)=O SOOQDICRKKXBHF-UHFFFAOYSA-N 0.000 description 1
- IVYRPDPNOXSIGO-UHFFFAOYSA-N 3-(2-sulfanylethyl)pentane-1,3,5-tricarboxylic acid Chemical compound OC(=O)CCC(CCS)(C(O)=O)CCC(O)=O IVYRPDPNOXSIGO-UHFFFAOYSA-N 0.000 description 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000006301 indolyl methyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 1
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11018698A | 1998-07-06 | 1998-07-06 | |
| US09/110,186 | 1998-07-06 | ||
| US09/110,262 | 1998-07-06 | ||
| US09/110,262 US6395718B1 (en) | 1998-07-06 | 1998-07-06 | Pharmaceutical compositions and methods of inhibiting angiogenesis using naaladase inhibitors |
| US09/228,391 US6265609B1 (en) | 1998-07-06 | 1999-01-12 | Thio-substituted pentanedioic acid derivatives |
| US09/228,391 | 1999-01-12 | ||
| PCT/US1999/015128 WO2000001668A2 (en) | 1998-07-06 | 1999-07-02 | Naaladase inhibitors useful as pharmaceutical compounds and compositions |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009228198A Division JP2010001312A (ja) | 1998-07-06 | 2009-09-30 | 医薬化合物及び組成物として有用なＮＡＡＬＡＤａｓｅ阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002519408A JP2002519408A (ja) | 2002-07-02 |
| JP2002519408A5 true JP2002519408A5 (https=) | 2006-08-17 |
| JP4503836B2 JP4503836B2 (ja) | 2010-07-14 |
Family
ID=27380804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000558073A Expired - Fee Related JP4503836B2 (ja) | 1998-07-06 | 1999-07-02 | 医薬化合物及び組成物として有用なＮＡＡＬＡＤａｓｅ阻害剤 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US6458775B1 (https=) |
| EP (2) | EP1093453B1 (https=) |
| JP (1) | JP4503836B2 (https=) |
| KR (1) | KR100672965B1 (https=) |
| CN (1) | CN1314882A (https=) |
| AT (1) | ATE305449T1 (https=) |
| AU (1) | AU770258B2 (https=) |
| BR (1) | BR9912516A (https=) |
| CA (1) | CA2337797C (https=) |
| CZ (1) | CZ200113A3 (https=) |
| DE (1) | DE69927502T2 (https=) |
| ES (1) | ES2251204T3 (https=) |
| HU (1) | HUP0103382A3 (https=) |
| IL (1) | IL140499A0 (https=) |
| MX (1) | MXPA01000144A (https=) |
| NO (1) | NO20010052L (https=) |
| NZ (1) | NZ508978A (https=) |
| PL (1) | PL346762A1 (https=) |
| TR (1) | TR200100025T2 (https=) |
| WO (1) | WO2000001668A2 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6953668B1 (en) | 1992-11-05 | 2005-10-11 | Sloan-Kettering Institute For Cancer Research | Prostate-specific membrane antigen |
| US7070782B1 (en) * | 1992-11-05 | 2006-07-04 | Sloan-Kettering Institute For Cancer Research | Prostate-specific membrane antigen |
| US7105159B1 (en) * | 1992-11-05 | 2006-09-12 | Sloan-Kettering Institute For Cancer Research | Antibodies to prostate-specific membrane antigen |
| US6569432B1 (en) | 1995-02-24 | 2003-05-27 | Sloan-Kettering Institute For Cancer Research | Prostate-specific membrane antigen and uses thereof |
| ATE317435T1 (de) | 1995-02-24 | 2006-02-15 | Sloan Kettering Inst Cancer | Prostataspezifisches membranes antigen und seine anwendungen |
| US20040253246A1 (en) * | 1996-02-23 | 2004-12-16 | Israeli Ron S. | Prostate-specific membrane antigen and uses thereof |
| US6395718B1 (en) * | 1998-07-06 | 2002-05-28 | Guilford Pharmaceuticals Inc. | Pharmaceutical compositions and methods of inhibiting angiogenesis using naaladase inhibitors |
| US6444657B1 (en) * | 1998-12-31 | 2002-09-03 | Guilford Pharmaceuticals Inc. | Methods for treating certain diseases using naaladase inhibitors |
| US6228888B1 (en) * | 1999-07-01 | 2001-05-08 | Guilford Pharmaceuticals Inc. | Methods for treating anxiety, anxiety disorders and memory impairment using naaladase inhibitors |
| WO2001091738A2 (en) * | 2000-05-30 | 2001-12-06 | Guilford Pharmaceuticals Inc. | Naaladase inhibitors for treating amyotrophic lateral sclerosis |
| WO2001092274A2 (en) * | 2000-05-30 | 2001-12-06 | Guilford Pharmaceuticals Inc. | Naaladase inhibitors for treating retinal disorders and glaucoma |
| WO2001092273A2 (en) * | 2000-05-30 | 2001-12-06 | Guilford Pharmaceuticals Inc. | Benzenedicarboxylic acid derivatives |
| US6586623B2 (en) | 2001-01-17 | 2003-07-01 | Guilford Pharmaceuticals Inc. | Thiol-based NAALADase inhibitors |
| WO2002092553A1 (en) * | 2001-05-11 | 2002-11-21 | Guilford Pharmaceuticals Inc. | Hydroxamic acids and acyl hydroxamines as naaladase inhibitors |
| AU2002310202B2 (en) * | 2001-05-30 | 2008-05-15 | Eisai Inc. | Thiolalkyl benzoic acid derivatives |
| US20050215472A1 (en) | 2001-10-23 | 2005-09-29 | Psma Development Company, Llc | PSMA formulations and uses thereof |
| WO2003034903A2 (en) | 2001-10-23 | 2003-05-01 | Psma Development Company, L.L.C. | Psma antibodies and protein multimers |
| WO2003057670A2 (en) * | 2001-12-28 | 2003-07-17 | Guilford Pharmaceuticals Inc. | Indoles as naaladase inhibitors |
| US20040186081A1 (en) * | 2003-03-03 | 2004-09-23 | Guilford Pharmaceuticals Inc. | Naaladase inhibitors for treating opioid tolerance |
| JP4773951B2 (ja) * | 2003-03-03 | 2011-09-14 | エーザイ インコーポレーテッド | チオラクトン |
Family Cites Families (89)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5018886B2 (https=) * | 1971-10-13 | 1975-07-02 | ||
| SU548609A1 (ru) * | 1975-04-19 | 1977-02-28 | Предприятие П/Я Г-4236 | СОЛИ БИС-(у-СУЛЬФОПРОПИОНАТПРОПИЛ-ИЛИ СУЛЬФОИЗОБУТИРАТПРОПИЛ)-ПОЛИДИМЕТИЛ-СИЛОКСАНА, ОБЛАДАЮЩИЕ ПОВЕРХНОСТНО-АКТИВНЫМИСВОЙСТВАМИ1Изобретение относитс к новым химическим соединени м, а именно к сол м бис-(у-сульфо-0нропионатпропил- или сульфонзобутиратпро- пил)-нолидиметилснлоксана общей формулыСНз СНзСН, \КОз5СН2СН(р.)С(о)о(СН2)з-31-0-[81-о]-81-((:Н5,)зО(о)ССН(к)СН2бОзМ\<т\сн, ш,сн3где R = H, СНз; M = Na, К, NH4;m = 4, 8, 12, 16, обладающим поверхност- 5 но-активными свойствами.Соли бис-(•у-сульфопроиионатпропил- н сульфоизобутиратиропил) - нолидиметнлсилок- сана указанной формулы, обладающие повы- щенной поверхностной активностью могут 10 примен тьс в качестве эффективных поверх- ностио-активных веществ (ПАВ).Р1звестны ПАВ на основе кремнийорганнче- ских сульфоэфиров ^[1], сульфатов [2] или сульфонатов [3], снижающие поверхностное 15 нат жение воды до 20—30 дин/см.Наиболее близкими по технической сущности к описываемым соединени м вл ютс Na, К или NH4 соли 1,3-бис-(сульфопропионатал- кил- или сульфоизобутираталкил-1,1,3,3-тетра- 20 метилдисилоксана [4].Однако указанные соединени имеют недостаточную активность на границах фаз: вода — воздух (снижают поверхностное нат жение с 72,5 до 25—30 дин/см) и вода — кремний — органическа жидкость (снижают межфазовое нат жение с 47 до 6—14 дин/см).Целью изобретени вл етс синтез соединений, обладающих высокой эффективностью действи в качестве ПАВ.Дл этого используемые в качестве ПАВ соли бис- (i'-сульфопропионатнроиил- или сульфоизобутнратпропил) - иолидиметилсил- оксана содержат в своем составе удлиненную силоксановую день.Введение солей указанной формулы в концентраци х 1-10~з — 5-10~2 моль/л приводит к резкому снижению поверхностного нат л<е- ни воды (с 72,5 до 17 дин/см) и межфазного нат жени на границе вода — полиднметил- силоксан (с 47,7 до 4,3 дин/см).Соли бис-(у-сульфоироинонатпропнл- и сульфонзобутиратиропил) - полидиметилсил- |
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-
1999
- 1999-07-02 ES ES99932229T patent/ES2251204T3/es not_active Expired - Lifetime
- 1999-07-02 US US09/346,711 patent/US6458775B1/en not_active Expired - Fee Related
- 1999-07-02 HU HU0103382A patent/HUP0103382A3/hu unknown
- 1999-07-02 KR KR1020017000232A patent/KR100672965B1/ko not_active Expired - Fee Related
- 1999-07-02 EP EP99932229A patent/EP1093453B1/en not_active Revoked
- 1999-07-02 CA CA002337797A patent/CA2337797C/en not_active Expired - Fee Related
- 1999-07-02 PL PL99346762A patent/PL346762A1/xx not_active Application Discontinuation
- 1999-07-02 CN CN99810206A patent/CN1314882A/zh active Pending
- 1999-07-02 BR BR9912516-1A patent/BR9912516A/pt not_active IP Right Cessation
- 1999-07-02 NZ NZ508978A patent/NZ508978A/en not_active IP Right Cessation
- 1999-07-02 TR TR2001/00025T patent/TR200100025T2/xx unknown
- 1999-07-02 WO PCT/US1999/015128 patent/WO2000001668A2/en not_active Ceased
- 1999-07-02 JP JP2000558073A patent/JP4503836B2/ja not_active Expired - Fee Related
- 1999-07-02 AU AU48583/99A patent/AU770258B2/en not_active Ceased
- 1999-07-02 AT AT99932229T patent/ATE305449T1/de not_active IP Right Cessation
- 1999-07-02 DE DE69927502T patent/DE69927502T2/de not_active Revoked
- 1999-07-02 EP EP05010637A patent/EP1571141A2/en not_active Withdrawn
- 1999-07-02 IL IL14049999A patent/IL140499A0/xx active IP Right Grant
- 1999-07-02 MX MXPA01000144A patent/MXPA01000144A/es not_active IP Right Cessation
- 1999-07-02 CZ CZ200113A patent/CZ200113A3/cs unknown
-
2001
- 2001-01-04 NO NO20010052A patent/NO20010052L/no not_active Application Discontinuation
-
2002
- 2002-06-10 US US10/164,553 patent/US20030083374A1/en not_active Abandoned
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