ES2208890T3 - Derivados de acido n-(2-oxoacetil o sulfonil)pirrolidin/piperidin-2-carboxilico con actividad de resistencia multifarmaco mejorada. - Google Patents
Derivados de acido n-(2-oxoacetil o sulfonil)pirrolidin/piperidin-2-carboxilico con actividad de resistencia multifarmaco mejorada.Info
- Publication number
- ES2208890T3 ES2208890T3 ES97916231T ES97916231T ES2208890T3 ES 2208890 T3 ES2208890 T3 ES 2208890T3 ES 97916231 T ES97916231 T ES 97916231T ES 97916231 T ES97916231 T ES 97916231T ES 2208890 T3 ES2208890 T3 ES 2208890T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- mmol
- branched
- chosen
- alkenyl
- 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.)
- Expired - Lifetime
Links
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- -1 1-piperazinyl Chemical group 0.000 claims description 117
- 239000000203 mixture Substances 0.000 claims description 97
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- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 25
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
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- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000006040 2-hexenyl group Chemical group 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
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- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
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- CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 1
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- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
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- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
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- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
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- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
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- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
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- 239000001267 polyvinylpyrrolidone Chemical class 0.000 description 1
- 229920000036 polyvinylpyrrolidone Chemical class 0.000 description 1
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- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
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- 230000001953 sensory effect Effects 0.000 description 1
- 210000000413 sensory ganglia Anatomy 0.000 description 1
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- 231100000458 skin sensitization testing Toxicity 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
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- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- LHJCZOXMCGQVDQ-UHFFFAOYSA-N tri(propan-2-yl)silyl trifluoromethanesulfonate Chemical compound CC(C)[Si](C(C)C)(C(C)C)OS(=O)(=O)C(F)(F)F LHJCZOXMCGQVDQ-UHFFFAOYSA-N 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
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- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US626259 | 1996-03-29 | ||
| US08/626,259 US5717092A (en) | 1996-03-29 | 1996-03-29 | Compounds with improved multi-drug resistance activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2208890T3 true ES2208890T3 (es) | 2004-06-16 |
Family
ID=24509627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES97916231T Expired - Lifetime ES2208890T3 (es) | 1996-03-29 | 1997-03-24 | Derivados de acido n-(2-oxoacetil o sulfonil)pirrolidin/piperidin-2-carboxilico con actividad de resistencia multifarmaco mejorada. |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US5717092A (enExample) |
| EP (1) | EP0891331B1 (enExample) |
| JP (1) | JP4759762B2 (enExample) |
| AT (1) | ATE251140T1 (enExample) |
| AU (1) | AU2346597A (enExample) |
| CA (1) | CA2249369A1 (enExample) |
| DE (1) | DE69725293T2 (enExample) |
| DK (1) | DK0891331T3 (enExample) |
| ES (1) | ES2208890T3 (enExample) |
| PT (1) | PT891331E (enExample) |
| WO (1) | WO1997036869A1 (enExample) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6150527A (en) * | 1994-08-18 | 2000-11-21 | Ariad Pharmaceuticals, Inc. | Synthetic multimerizing agents |
| US6133456A (en) * | 1994-08-18 | 2000-10-17 | Ariad Gene Therapeutics, Inc. | Synthetic multimerizing agents |
| US20030036654A1 (en) * | 1994-08-18 | 2003-02-20 | Holt Dennis A. | Synthetic multimerizing agents |
| US5795877A (en) * | 1996-12-31 | 1998-08-18 | Guilford Pharmaceuticals Inc. | Inhibitors of NAALADase enzyme activity |
| US5801187A (en) | 1996-09-25 | 1998-09-01 | Gpi-Nil Holdings, Inc. | Heterocyclic esters and amides |
| US6218424B1 (en) * | 1996-09-25 | 2001-04-17 | Gpi Nil Holdings, Inc. | Heterocyclic ketone and thioester compounds and uses |
| US5786378A (en) * | 1996-09-25 | 1998-07-28 | Gpi Nil Holdings, Inc. | Heterocyclic thioesters |
| JP2002515051A (ja) * | 1996-12-31 | 2002-05-21 | ジーピーアイ エヌアイエル ホールディングス インコーポレイテッド | ヘテロ環式チオエステルのｎ−結合スルホンアミド |
| US5935989A (en) | 1996-12-31 | 1999-08-10 | Gpi Nil Holdings Inc. | N-linked ureas and carbamates of heterocyclic thioesters |
| EP0959882A4 (en) * | 1996-12-31 | 2001-12-05 | N-LINKED UREAS AND CARBAMATES OF HETEROCYCLIC THIOESTERS | |
| US5874449A (en) * | 1996-12-31 | 1999-02-23 | Gpi Nil Holdings, Inc. | N-linked sulfonamides of heterocyclic thioesters |
| US6242468B1 (en) | 1997-02-27 | 2001-06-05 | Jia-He Li | Carbamate and urea compositions and neurotrophic uses |
| US5846979A (en) * | 1997-02-28 | 1998-12-08 | Gpi Nil Holdings, Inc. | N-oxides of heterocyclic esters, amides, thioesters, and ketones |
| US5945441A (en) | 1997-06-04 | 1999-08-31 | Gpi Nil Holdings, Inc. | Pyrrolidine carboxylate hair revitalizing agents |
| US20010049381A1 (en) | 1997-06-04 | 2001-12-06 | Gpl Nil Holdings, Inc., | Pyrrolidine derivative hair growth compositions and uses |
| US6852496B1 (en) * | 1997-08-12 | 2005-02-08 | Oregon Health And Science University | Methods of screening for agents that promote nerve cell growth |
| EP1069897A1 (en) * | 1998-04-08 | 2001-01-24 | Eli Lilly And Company | Methods for inhibiting mrp1 |
| TR200002851T2 (tr) * | 1998-04-08 | 2000-12-21 | Eli Lilly And Company | MRP1'i inhibe etmek için yöntemler. |
| US6410041B1 (en) | 1998-04-28 | 2002-06-25 | Trustees Of Tufts College | Culturing cells in presence of amphipathic weak bases and/or cations and multiple drug resistance inhibitor containing reserpine |
| US20020131972A1 (en) * | 1998-05-21 | 2002-09-19 | Daniel Sem | Multi-partite ligands and methods of identifying and using same |
| CA2333997A1 (en) | 1998-06-02 | 1999-12-09 | Bristol-Myers Squibb Company | Neurotrophic difluoroamide agents |
| US6331537B1 (en) | 1998-06-03 | 2001-12-18 | Gpi Nil Holdings, Inc. | Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds |
| KR20010052503A (ko) | 1998-06-03 | 2001-06-25 | 다니엘 피. 맥컬럼 | Ｎ-헤테로사이클릭 카복실산 또는 카복실산 등입체의ｎ-결합된 설폰아미드 |
| EP1117635A1 (en) * | 1998-09-30 | 2001-07-25 | The Procter & Gamble Company | 2-substituted ketoamides |
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| US4920218A (en) * | 1988-10-12 | 1990-04-24 | Merck & Co., Inc. | Novel hydroxide mediated FK-506 rearrangement process |
| DE4015255A1 (de) * | 1990-05-12 | 1991-11-14 | Hoechst Ag | Oxalyl-aminosaeurederivate, verfahren zu ihrer herstellung und ihrer verwendung als arzneimittel zur inhibierung der prolyl-hydroxylase |
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| AU2152092A (en) * | 1991-06-24 | 1993-01-25 | Erziehungsdirektion Of The Canton Zurich | Neurite growth regulatory factors |
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| NZ314207A (en) * | 1992-09-28 | 2000-12-22 | Vertex Pharma | 1-(2-Oxoacetyl)-piperidine-2-carboxylic acid derivatives as multi drug resistant cancer cell sensitizers |
| ES2245781T3 (es) * | 1994-08-18 | 2006-01-16 | Ariad Gene Therapeutics, Inc. | Nuevos agentes de multimerizacion. |
| US5859031A (en) * | 1995-06-07 | 1999-01-12 | Gpi Nil Holdings, Inc. | Small molecule inhibitors of rotamase enzyme activity |
-
1996
- 1996-03-29 US US08/626,259 patent/US5717092A/en not_active Expired - Lifetime
-
1997
- 1997-03-24 EP EP97916231A patent/EP0891331B1/en not_active Expired - Lifetime
- 1997-03-24 PT PT97916231T patent/PT891331E/pt unknown
- 1997-03-24 DE DE69725293T patent/DE69725293T2/de not_active Expired - Lifetime
- 1997-03-24 AT AT97916231T patent/ATE251140T1/de not_active IP Right Cessation
- 1997-03-24 DK DK97916231T patent/DK0891331T3/da active
- 1997-03-24 CA CA002249369A patent/CA2249369A1/en not_active Abandoned
- 1997-03-24 JP JP53539597A patent/JP4759762B2/ja not_active Expired - Fee Related
- 1997-03-24 AU AU23465/97A patent/AU2346597A/en not_active Abandoned
- 1997-03-24 WO PCT/US1997/004916 patent/WO1997036869A1/en not_active Ceased
- 1997-03-24 ES ES97916231T patent/ES2208890T3/es not_active Expired - Lifetime
- 1997-10-30 US US08/961,551 patent/US5935954A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| PT891331E (pt) | 2004-02-27 |
| CA2249369A1 (en) | 1997-10-09 |
| JP4759762B2 (ja) | 2011-08-31 |
| AU2346597A (en) | 1997-10-22 |
| DE69725293T2 (de) | 2004-07-15 |
| DE69725293D1 (de) | 2003-11-06 |
| EP0891331A1 (en) | 1999-01-20 |
| DK0891331T3 (da) | 2004-02-09 |
| US5935954A (en) | 1999-08-10 |
| JP2000507578A (ja) | 2000-06-20 |
| EP0891331B1 (en) | 2003-10-01 |
| ATE251140T1 (de) | 2003-10-15 |
| WO1997036869A1 (en) | 1997-10-09 |
| US5717092A (en) | 1998-02-10 |
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