JP2012505213A - スピカマイシン誘導体を用いて疼痛を治療又は予防する方法 - Google Patents
スピカマイシン誘導体を用いて疼痛を治療又は予防する方法 Download PDFInfo
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- JP2012505213A JP2012505213A JP2011531024A JP2011531024A JP2012505213A JP 2012505213 A JP2012505213 A JP 2012505213A JP 2011531024 A JP2011531024 A JP 2011531024A JP 2011531024 A JP2011531024 A JP 2011531024A JP 2012505213 A JP2012505213 A JP 2012505213A
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- UPGGKUQISSWRJJ-UHFFFAOYSA-N thiocoraline Natural products CN1C(=O)CNC(=O)C(NC(=O)C=2C(=CC3=CC=CC=C3N=2)O)CSC(=O)C(CSC)N(C)C(=O)C(N(C(=O)CNC2=O)C)CSSCC1C(=O)N(C)C(CSC)C(=O)SCC2NC(=O)C1=NC2=CC=CC=C2C=C1O UPGGKUQISSWRJJ-UHFFFAOYSA-N 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- 229960000874 thyrotropin Drugs 0.000 description 1
- 230000001748 thyrotropin Effects 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 description 1
- 229960003087 tioguanine Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 125000002640 tocopherol group Chemical class 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 229960002905 tolfenamic acid Drugs 0.000 description 1
- YEZNLOUZAIOMLT-UHFFFAOYSA-N tolfenamic acid Chemical compound CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O YEZNLOUZAIOMLT-UHFFFAOYSA-N 0.000 description 1
- 229960001017 tolmetin Drugs 0.000 description 1
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 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
- 210000003014 totipotent stem cell Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- 229960004380 tramadol Drugs 0.000 description 1
- TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 description 1
- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 238000011277 treatment modality Methods 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229950003873 triciribine Drugs 0.000 description 1
- HOGVTUZUJGHKPL-HTVVRFAVSA-N triciribine Chemical compound C=12C3=NC=NC=1N(C)N=C(N)C2=CN3[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O HOGVTUZUJGHKPL-HTVVRFAVSA-N 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- FEZBIKUBAYAZIU-UHFFFAOYSA-N trimethobenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NCC=2C=CC(OCCN(C)C)=CC=2)=C1 FEZBIKUBAYAZIU-UHFFFAOYSA-N 0.000 description 1
- 229960004161 trimethobenzamide Drugs 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical group [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- WMPQMBUXZHMEFZ-YJPJVVPASA-N turosteride Chemical compound CN([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)N(C(C)C)C(=O)NC(C)C)[C@@]2(C)CC1 WMPQMBUXZHMEFZ-YJPJVVPASA-N 0.000 description 1
- 229950007816 turosteride Drugs 0.000 description 1
- 229920001664 tyloxapol Polymers 0.000 description 1
- MDYZKJNTKZIUSK-UHFFFAOYSA-N tyloxapol Chemical compound O=C.C1CO1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 MDYZKJNTKZIUSK-UHFFFAOYSA-N 0.000 description 1
- 229960004224 tyloxapol Drugs 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 description 1
- 229950009811 ubenimex Drugs 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 229960001055 uracil mustard Drugs 0.000 description 1
- SPDZFJLQFWSJGA-UHFFFAOYSA-N uredepa Chemical compound C1CN1P(=O)(NC(=O)OCC)N1CC1 SPDZFJLQFWSJGA-UHFFFAOYSA-N 0.000 description 1
- 229950006929 uredepa Drugs 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- AUFUWRKPQLGTGF-FMKGYKFTSA-N uridine triacetate Chemical compound CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](COC(=O)C)O[C@H]1N1C(=O)NC(=O)C=C1 AUFUWRKPQLGTGF-FMKGYKFTSA-N 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 229960002730 vapreotide Drugs 0.000 description 1
- 108700029852 vapreotide Proteins 0.000 description 1
- XLQGICHHYYWYIU-UHFFFAOYSA-N veramine Natural products O1C2CC3C4CC=C5CC(O)CCC5(C)C4CC=C3C2(C)C(C)C21CCC(C)CN2 XLQGICHHYYWYIU-UHFFFAOYSA-N 0.000 description 1
- KDQAABAKXDWYSZ-PNYVAJAMSA-N vinblastine sulfate Chemical compound OS(O)(=O)=O.C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 KDQAABAKXDWYSZ-PNYVAJAMSA-N 0.000 description 1
- 229960004982 vinblastine sulfate Drugs 0.000 description 1
- AQTQHPDCURKLKT-JKDPCDLQSA-N vincristine sulfate Chemical compound OS(O)(=O)=O.C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C=O)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 AQTQHPDCURKLKT-JKDPCDLQSA-N 0.000 description 1
- 229960002110 vincristine sulfate Drugs 0.000 description 1
- 229960005212 vindesine sulfate Drugs 0.000 description 1
- BCXOZISMDZTYHW-IFQBWSDRSA-N vinepidine sulfate Chemical compound OS(O)(=O)=O.C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C=O)C=2)OC)C[C@@H](C2)CC)N2CCC2=C1NC1=CC=CC=C21 BCXOZISMDZTYHW-IFQBWSDRSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 229960003414 zomepirac Drugs 0.000 description 1
- ZXVNMYWKKDOREA-UHFFFAOYSA-N zomepirac Chemical compound C1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZXVNMYWKKDOREA-UHFFFAOYSA-N 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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Abstract
【選択図】なし
Description
又はその薬学的に許容可能な塩、プロドラッグ若しくは光学異性体を投与することを含む方法を提供する。
又はその薬学的に許容可能な塩、プロドラッグ若しくは光学異性体を投与することを含む方法も提供する。
各R’’基は独立して、H又は1個〜3個の独立したR3若しくはR4で置換された炭素数1〜5のアルキル基、アルケニル基、アルキニル基若しくはシクロアルキル基である場合があり、
各R3は独立して、1個〜3個の独立したR5で置換されていてもよいヘテロシクリル又はヘテロアリールであり、
各R4は独立して、ハロゲン、酸素、硫黄、CF3、SR6、OR6、OC(O)R6、NR6R6、NR6R7、COOR6、C(O)R6又はC(O)NR6R6であり、
各R5は独立して、C1〜C10アルキル、ハロ、ハロアルキル、SR6、OR6、NR6R6、COOR6、NO2、CN、C(O)R6、C(O)NR6R6、OC(O)R6、S(O)2R6、S(O)2NR6R6、NR6C(O)NR6R6、NR6C(O)R6、NR6(COOR6)、NR6C(O)R8、NR6S(O)2NR6R6、NR6S(O)2R6、NR6S(O)2R8又はR4若しくはR8で置換されたC1〜C10アルキルであり、
各R6は独立して、H、C1〜C10アルキル、C2〜C10アルケニル、C2〜C10アルキニル、C3〜C10シクロアルキル、R8又はR8で置換されたC1〜C10アルキルであり、
各R7は独立して、COOR9、C(O)NR9R9、S(O)2R9又はS(O)2NR9R9であり、
各R8は独立して、アリール、ヘテロアリール又はヘテロシクリルであり、
各R9は独立して、H、C1〜C10アルキル、アリール、ヘテロアリール又はヘテロシクリルである)
又はその薬学的に許容可能な塩、プロドラッグ若しくは光学異性体を投与することを含む、方法を提供する。
本明細書で用いられる場合、「a」、「an」又は「the」は1又は1超を意味し得る。例えば、「a」細胞は単一の細胞又は複数の細胞を意味し得る。
又はその薬学的に許容可能な塩、プロドラッグ若しくは光学異性体を投与することを含む、方法を提供する。
(1)炭素数11〜13の直鎖アルケニル、
(2)二重結合又は三重結合を有しない炭素数11〜13の直鎖非置換アルキル、
(3)炭素数10〜15の直鎖ハロアルキル、
(4)CH3(CH2)nCH(OH)−又はCH3(CH2)n−1CH(OH)CH2−(式中、nは9〜13の整数を示す)、
(5)アジド基又はシアノ基で置換された炭素数10〜15のアルキル、
(6)フェノキシ基又はハロゲン置換フェノキシ基で置換された炭素数10〜13の直鎖アルキル、
(7)
(8)
(9)
(10)CH3(CH2)mSO2O(CH2)p−(式中、mは0〜3の整数を示し、pは9〜14の整数を示す)、
(11)
(12)CH3Si(CH2)10−又はCH3Si−C=C−(CH2)8−、
(13)
(16)炭素数11〜13の直鎖アルカジエニル、
からなる群から選択される。
(1)炭素数11〜13の直鎖アルケニル、
(2)二重結合又は三重結合を有しない炭素数11〜13の直鎖非置換アルキル、及び
(3)CH3(CH2)nCH(OH)−又はCH3(CH2)nCH(OH)CH2−(式中、nは9〜13の整数を示す)、
からなる群から選択される。
6−[4’−N−(N’−トリデカノイルグリシル)スピカミニル−アミノ]プリン(SPM9)、
6−[4’−N−(N’−テトラデカノイルグリシル)スピカミニル−アミノ]プリン(SPM10)、
6−[4’−N−(N’−10−メチルウンデカノイルグリシル)スピカミニル−アミノ]プリン(SPK9)、
6−[4’−N−(N’−11−メチルドデカノイルグリシル)スピカミニル−アミノ]プリン(SPK251)、
6−[4’−N−(N’−12−メチルトリデカノイルグリシル)スピカミニル−アミノ]プリン(SPK136)、
6−[4’−N−(N’−11−ドデセノイルグリシル)スピカミニル−アミノ]プリン(SPK44)、
6−[4’−N−(N’−12−トリデセノイルグリシル)スピカミニル−アミノ]プリン(SPK142)、
6−[4’−N−(N’−シス−9−テトラデセノイルグリシル)スピカミニル−アミノ]プリン(SPK231)、
6−[4’−N−(N’−シス−9−ヘキサデセノイルグリシル)スピカミニル−アミノ]プリン(SPK148)、
6−[4’−N−(N’−トランス−2−ドデセノイルグリシル)スピカミニル−アミノ]プリン(SPK86)、
6−[4’−N−(N’−トランス−2−テトラデセノイルグリシル)スピカミニル−アミノ]プリン(SPK156)、
6−[4’−N−(N’−トランス−2−ヘキサデセノイルグリシル)スピカミニル−アミノ]プリン(SPK188)、
6−[4’−N−(N’−トランス,トランス−2,4−ドデカジエノイル−グリシル)スピカミニル−アミノ]プリン(SPK282)、
6−[4’−N−(N’−トランス,トランス−2,4−トリデカジエノイル−グリシル)スピカミニル−アミノ]プリン(SPK281)、
6−[4’−N−(N’−トランス,トランス−2,4−テトラデカジエノイル−グリシル)スピカミニル−アミノ]プリン(SPK241)、
6−[4’−N−(N’−11−ブロモウンデカノイルグリシル)スピカミニル−アミノ]プリン(SPK64)、
6−[4’−N−(N’−12−ブロモドデカノイルグリシル)スピカミニル−アミノ]プリン(SPK152)、
6−[4’−N−(N’−13−ブロモトリデカノイルグリシル)スピカミニル−アミノ]プリン(SPK276)、
6−[4’−N−(N’−14−ブロモテトラデカノイルグリシル)スピカミニル−アミノ]プリン(SPK273)、
6−[4’−N−(N’−12−クロロドデカノイルグリシル)スピカミニル−アミノ]プリン(SPK132)、
6−[4’−N−(N’−13−クロロトリデカノイルグリシル)スピカミニル−アミノ)プリン(SPK278)、
6−[4’−N−(N’−14−クロロテトラデカノイルグリシル)スピカミニル−アミノ]プリン(SPK280)、
6−[4’−N−(N’−14−フルオロテトラデカノイルグリシル)スピカミニル−アミノ]プリン(SPK279)、
6−[4’−N−(N’−15−フルオロペンタデカノイルグリシル)スピカミニル−アミノ]プリン(SPK247)、
6−[4’−N−(N’−16−フルオロヘキサデカノイルグリシル)スピカミニル−アミノ]プリン(SPK157)、
6−[4’−N−(N’−11−ヨードウンデカノイルグリシル)スピカミニル−アミノ]プリン(SPK165)、
6−[4’−N−(N’−2−クロロヘキサデカノイルグリシル)スピカミニル−アミノ]プリン(SPK135)、
6−[4’−N−(N’−2−フルオロドデカノイルグリシル)スピカミニル−アミノ]プリン(SPK159)、
6−[4’−N−(N’−2−フルオロヘキサデカノイルグリシル)スピカミニル−アミノ]プリン(SPK233)、
6−[4’−N−(N’−2,2−ジフルオロテトラデカノイルグリシル)−スピカミニル−アミノ]プリン(SPK182)、
6−[4’−N−(N’−2−ヒドロキシヘキサデカノイルグリシル)スピカミニル−アミノ]プリン(SPK112)、
6−[4’−N−(N’−(S)−2−ヒドロキシヘキサデカノイルグリシル)−スピカミニル−アミノ]プリン(SPK271)、
6−[4’−N−(N’−(R)−3−ヒドロキシテトラデカノイルグリシル)−スピカミニル−アミノ]プリン(SPK270)、
6−[4’−N−(N’−(S)−3−ヒドロキシテトラデカノイルグリシル)−スピカミニル−アミノ]プリン(SPK274)、
6−[4’−N−(N’−3−ヒドロキシヘキサデカノイルグリシル)−スピカミニル−アミノ]プリン(SPK115)、
6−[4’−N−(N’−16−シアノヘキサデカノイルグリシル)−スピカミニル−アミノ]プリン(SPK177)、
6−[4’−N−(N’−11−フェノキシウンデカノイルグリシル)−スピカミニル−アミノ]プリン(SPK422)、
6−[4’−N−(N’−12−フェノキシドデカノイルグリシル)−スピカミニル−アミノ]プリン(SPK249)、
6−[4’−N−(N’−(R)−2−アセトキシヘキサデカノイルグリシル)−スピカミニル−アミノ]プリン(SPK198)、
6−[4’−N−(N’−3−アセトキシヘキサデカノイルグリシル)−スピカミニル−アミノ]プリン(SPK189)、
6−[4’−N−(N’−12−ブタンスルホニルオキシドデカノイルグリシル)−スピカミニル−アミノ]プリン(SPK232)、
6−{4’−N−[N’−11−(2’−チエニル)−10−ウンデシノイルグリシル]−スピカミニル−アミノ}プリン(SPK262)、
6−{4’−N−[N’−11−(3’−チエニル)−10−ウンデシノイルグリシル]−スピカミニル−アミノ}プリン(SPK263)及び
6−{4’−N−[N’−11−(3’−フリル)−10−ウンデシノイルグリシル]−スピカミニル−アミノ}プリン(SPK266)。
R’は(1)炭素数1若しくは2の置換若しくは非置換アルキル若しくはアルケニル又は(2)Hを表す)
又はその薬学的に許容可能な塩、プロドラッグ若しくは光学異性体を投与することを含む、方法を提供する。
各R’’基は独立して、H又は1個〜3個の独立したR3若しくはR4で置換された炭素数1〜5のアルキル基、アルケニル基、アルキニル基若しくはシクロアルキル基であり、
各R3は独立して、1個〜3個の独立したR5で置換されていてもよいヘテロシクリル又はヘテロアリールであり、
各R4は独立して、ハロゲン、酸素、硫黄、CF3、SR6、OR6、OC(O)R6、NR6R6、NR6R7、COOR6、C(O)R6又はC(O)NR6R6であり、
各R5は独立して、C1〜C10アルキル、C2〜C10アルケニル、C2〜C10アルキニル、C3〜C10シクロアルキル、ハロ、ハロアルキル、SR6、OR6、NR6R6、COOR6、NO2、CN、C(O)R6、C(O)NR6R6、OC(O)R6、S(O)2R6、S(O)2NR6R6、NR6C(O)NR6R6、NR6C(O)R6、NR6(COOR6)、NR6C(O)R8、NR6S(O)2NR6R6、NR6S(O)2R6、NR6S(O)2R8又はR4若しくはR8で置換されたC1〜C10アルキル、C2〜C10アルケニル、C2〜C10アルキニル若しくはC3〜C10シクロアルキルであり、
各R6は独立して、H、C1〜C10アルキル、C2〜C10アルケニル、C2〜C10アルキニル、C3〜C10シクロアルキル、R8又はR8で置換されたC1〜C10アルキル、C2〜C10アルケニル、C2〜C10アルキニル若しくはC3〜C10シクロアルキルであり、
各R7は独立して、COOR9、C(O)NR9R9、S(O)2R9又はS(O)2NR9R9であり、
各R8は独立して、アリール、ヘテロアリール又はヘテロシクリルであり、
各R9は独立して、H、C1〜C10アルキル、C2〜C10アルケニル、C2〜C10アルキニル、C3〜C10シクロアルキル、アリール、ヘテロアリール又はヘテロシクリルである)
又はその薬学的に許容可能な塩、プロドラッグ若しくは光学異性体を投与することを含む、方法を提供する。
癌患者における神経障害性疼痛の試験:
第2相多施設プラセボ対照無作為並行群間試験を実施して、神経障害性疼痛を伴う末期の癌を有する患者におけるKRN5500の安全性、有効性及び用量応答を評価した。19名の患者が、試験に参加した。13名をKRN5500の投与を受けるように無作為化し、6名をプラセボの投与を受けるように無作為化した。調査場所(investigative site)における無作為化誤差(randomization error)により、KRN5500の投与を受けるように無作為化した1名の患者は、実際にはプラセボの投与を受けた。KRN5500の投与を受けた12名の患者のうち、3名(25%)が、投与のための来院(dosing visits)を全て完了した。プラセボの投与を受けた患者のうち2名(28.6%)が、投与のための来院を全て完了した。追跡不能となった患者はおらず、死亡した患者もいなかった。
臨床的な数値評価スケール(NRS)スコアに基づいて、疼痛強度をIntent−to−treat(ITT)集団及びmodified efficacy(ME)集団の両方に対して解析した。結果は両解析とも同様であり、KRN5500群が示すベースラインからの低下の中央値が22%(ITT)及び23.6%(ME)であったのに対し、プラセボ群における変化の中央値は両解析とも0であった。中央値のウィルコクソン順位和検定に基づいて、ME解析では疼痛強度の低下が統計的に有意であった(p=0.03)。患者の80%超がベースライン特性としてアロディニアを有し、ベースラインでアロディニアを呈する患者のサブセットについての解析結果は全体解析と一致した。ベースラインでアロディニアを呈さない患者はほとんどおらず、本サブセットにおける結論が適切に導かれた。全ての用量に対して診療所で記録された最良の疼痛強度応答(疼痛の最大低下)についての解析からは、KRN5500治療患者の低下の中央値が29.3%であったのに対し、プラセボ治療患者は全く低下を示さなかったことが示される。日記の(diary)データに基づく疼痛強度の低下は診療所で観察されたものと同様であり、KRN5500治療群が示す低下の中央値が16.4%であったのに対し、プラセボ治療群は低下を示さなかった。全体的に見ると、KRN5500治療患者では5名(42%)が、日記のエンドポイントに基づいて、20%以上の疼痛強度低減を示したのに対し、プラセボ治療患者では1名(14%)しかこのレベルを達成しなかった。KRN5500治療患者では3名(25%)が33%以上の疼痛低下を達成したが、プラセボ患者は誰もこのレベルを達成しなかった。投与された最後の用量(エンドポイント)について評価すると、ITT集団解析又はME集団解析のいずれにおいてもKRN5500の用量応答の傾向はなかった。
KRN5500治療患者全て(100%)において、プラセボ治療群における86%(7名中6名の患者)と比較して少なくとも1つの治療中に発生した有害事象があった。KRN5500患者によって記録された事象はより重篤である傾向があった(KRN5500では84%が中等度又は重篤であったのに対し、プラセボでは71%)。事象は典型的には悪心又は嘔吐等の胃腸障害であり、KRN5500群の方がプラセボ群よりも治療に関連すると考えられるものが多かった(92%対14%)。KRN5500群の患者3名(25%)及びプラセボ群の患者1名(14%)が深刻な有害事象(AE)を経験した。試験薬に関連すると考えられるものはなかった。KRN5500治療患者2名を試験薬に関連するとは考えられない悪心及び嘔吐のために試験から除外した。KRN5500治療患者1名を試験薬に関連するとは考えられない痙攣のために除外した。プラセボ治療患者1名を試験薬に関連しない卒中のために試験から除外した。死亡は観察されなかった。
KRN5500は診療所でNRSによって測定されたように疼痛強度の統計的に有意な低下を示した。患者の日記の結果は臨床評価と一致した。NPQは有効性の尺度として鋭敏でなかった。さらに、SPQの「低温誘発疼痛」項目からは治療効果が示されなかった一方、SPQのBPI及び「ブラシ/接触」項目は臨床的NRS測定結果と一致した。
KRN5500の製剤:
静脈内投与用のナノエマルジョン製剤をKRN5500について開発した。製剤の構成成分を表1に重量%表示で列記する。この製剤は以前に使用したKRN5500製剤と比較して胃腸障害の形で引き起こす副作用が少ないことが期待される。
Claims (67)
- Rが
(1)炭素数11〜13の直鎖アルケニル、
(2)二重結合又は三重結合を有しない炭素数11〜13の直鎖非置換アルキル、
(3)炭素数10〜15の直鎖ハロアルキル、
(4)CH3(CH2)nCH(OH)−又はCH3(CH2)n−1CH(OH)CH2−(式中、nは9〜13の整数を示す)、
(5)アジド基又はシアノ基で置換された炭素数10〜15のアルキル、
(6)フェノキシ基又はハロゲン置換フェノキシ基で置換された炭素数10〜13の直鎖アルキル、
(7)
(8)
(9)
(10)CH3(CH2)mSO2O(CH2)p−(式中、mは0〜3の整数を示し、pは9〜14の整数を示す)、
(11)
(12)CH3Si(CH2)10−又はCH3Si−C=C−(CH2)8−、
(13)
(16)炭素数11〜13の直鎖アルカジエニル
からなる群から選択される、請求項1に記載の方法。 - Rが
(1)炭素数11〜13の直鎖アルケニル、
(2)二重結合又は三重結合を有しない炭素数11〜13の直鎖非置換アルキル及び
(3)CH3(CH2)nCH(OH)−又はCH3(CH2)nCH(OH)CH2−(式中、nは9〜13の整数を示す)、
からなる群から選択される、請求項1に記載の方法。 - Rが炭素数11のアルカジエニルである、請求項1に記載の方法。
- Rが炭素数12のアルカジエニルである、請求項1に記載の方法。
- Rが炭素数13のアルカジエニルである、請求項1に記載の方法。
- R1がHであり、R2がOHである、請求項1に記載の方法。
- R1がHであり、R2がOHである、請求項6に記載の方法。
- 前記化合物が6−[4−デオキシ−4−[(2E,4E)−テトラデカジエノイルグリシル]アミノ−L−グリセロ−β−L−マンノヘプトピラノシル]アミノ−9H−プリン(KRN5500)である、請求項1に記載の方法。
- R’が置換アルキルである、請求項10に記載の方法。
- R’の炭素数が2である、請求項10に記載の方法。
- R’がペプチド結合を含む、請求項10に記載の方法。
- R’がアミノ基を含む、請求項10に記載の方法。
- 前記アミノ基が第一級アミノ基である、請求項14に記載の方法。
- R’が−COCH2NH2である、請求項10に記載の方法。
- R1がHであり、R2がOHである、請求項16に記載の方法。
- R’がHであり、R1がHであり、R2がOHである、請求項10に記載の方法。
- 被験体における疼痛を治療又は予防する方法であって、それらを必要とする被験体に対し、治療有効量又は予防有効量の式IVの化合物:
各R’’基は独立して、H又は1個〜3個の独立したR3若しくはR4で置換された炭素数1〜5のアルキル基、アルケニル基、アルキニル基若しくはシクロアルキル基である場合があり、
各R3は独立して、1個〜3個の独立したR5で置換されていてもよいヘテロシクリル又はヘテロアリールであり、
各R4は独立して、ハロゲン、酸素、硫黄、CF3、SR6、OR6、OC(O)R6、NR6R6、NR6R7、COOR6、C(O)R6又はC(O)NR6R6であり、
各R5は独立して、C1〜C10アルキル、ハロ、ハロアルキル、SR6、OR6、NR6R6、COOR6、NO2、CN、C(O)R6、C(O)NR6R6、OC(O)R6、S(O)2R6、S(O)2NR6R6、NR6C(O)NR6R6、NR6C(O)R6、NR6(COOR6)、NR6C(O)R8、NR6S(O)2NR6R6、NR6S(O)2R6、NR6S(O)2R8又はR4若しくはR8で置換されたC1〜C10アルキルであり、
各R6は独立して、H、C1〜C10アルキル、C2〜C10アルケニル、C2〜C10アルキニル、C3〜C10シクロアルキル、R8又はR8で置換されたC1〜C10アルキルであり、
各R7は独立して、COOR9、C(O)NR9R9、S(O)2R9又はS(O)2NR9R9であり、
各R8は独立して、アリール、ヘテロアリール又はヘテロシクリルであり、
各R9は独立して、H、C1〜C10アルキル、アリール、ヘテロアリール又はヘテロシクリルである)
又はその薬学的に許容可能な塩、プロドラッグ若しくは光学異性体を投与することを含む方法。 - R1及びR2が互いに異なり、H又はOHを表し、R’’が(1)炭素数1若しくは2の置換若しくは非置換のアルキル若しくはアルケニル又は(2)Hを表す、請求項19に記載の方法。
- 各R’’基が独立して、H又は1個〜3個の独立したR3若しくはR4で置換された炭素数1〜2のアルキル基若しくはアルケニル基である場合がある、請求項19に記載の方法。
- 前記疼痛が神経障害性疼痛である、請求項1、10又は19のいずれか一項に記載の方法。
- 前記神経障害性疼痛が、化学療法誘発性神経障害、癌関連神経障害、HIV関連末梢神経障害、ヘルペス後神経痛、糖尿病性神経障害、坐骨神経痛、線維筋痛、慢性疲労症候群による疼痛、多発性硬化症による疼痛、複合性局所疼痛症候群I型、複合性局所疼痛症候群II型、中枢性疼痛症候群、有痛性外傷性単神経障害、術後疼痛症候群、乳房切除後症候群、開胸術後症候群、幻肢痛、神経根引き抜き損傷、放射線照射後神経障害、反復運動神経損傷、反復運動過多損傷及び受傷後神経障害からなる群から選択される神経障害に起因するものである、請求項22に記載の方法。
- 前記化合物を1週間に1回を超えない頻度で投与する、請求項1、10又は19のいずれか一項に記載の方法。
- 前記化合物を2週間に1回を超えない頻度で投与する、請求項24に記載の方法。
- 前記化合物を1ヶ月に1回を超えない頻度で投与する、請求項25に記載の方法。
- 前記化合物を6ヶ月に1回を超えない頻度で投与する、請求項26に記載の方法。
- 前記化合物が、該化合物と薬学的に許容可能な担体とを含む医薬組成物の形態である、請求項1、10又は19のいずれか一項に記載の方法。
- 前記医薬組成物がナノ粒子を含む、請求項29に記載の方法。
- 前記医薬組成物がナノエマルジョンを含む、請求項29に記載の方法。
- 前記化合物を静脈内投与する、請求項1、10又は19のいずれか一項に記載の方法。
- 前記化合物を筋肉内投与する、請求項1、10又は19のいずれか一項に記載の方法。
- 前記化合物を皮下内投与する、請求項1、10又は19のいずれか一項に記載の方法。
- 前記化合物を局所投与する、請求項1、10又は19のいずれか一項に記載の方法。
- 前記化合物を約0.6mg/m2〜約4.0mg/m2の用量で投与する、請求項1、10又は19のいずれか一項に記載の方法。
- 前記化合物を約1.0mg/m2〜約3.0mg/m2の用量で投与する、請求項35に記載の方法。
- 前記被験体における神経障害の発症後に、前記化合物を該被験体に投与する、請求項1、10又は19のいずれか一項に記載の方法。
- 前記被験体における神経障害の発症前に、前記化合物を該被験体に投与する、請求項1、10又は19のいずれか一項に記載の方法。
- 前記被験体における神経障害の発症を引き起こす可能性がある事象の前に又は該事象と同時に、前記化合物を該被験体に投与する、請求項1、10又は19のいずれか一項に記載の方法。
- 前記事象が手術である、請求項39に記載の方法。
- 前記事象が放射線治療である、請求項39に記載の方法。
- 前記事象が化学療法の投与である、請求項39に記載の方法。
- 前記化学療法が、神経障害を誘発することが知られている化学療法剤の投与を包む、請求項42に記載の方法。
- 前記化学療法がビンカアルカロイド、タキサン、白金系化合物及びVELCADE(ボルテゾミブ)からなる群から選択される化学療法剤の投与を含む、請求項42に記載の方法。
- 前記ビンカアルカロイドがビンブラスチン、ビンクリスチン、ビンデシン又はビノレルビンである、請求項44に記載の方法。
- 前記タキサンがパクリタキセル又はドセタキセルである、請求項44に記載の方法。
- 前記白金系化合物がシスプラチン、カルボプラチン、ネダプラチン、四硝酸トリプラチン、サトラプラチン又はオキサリプラチンである、請求項44に記載の方法。
- 前記化合物をさらなる薬剤と同時に投与する、請求項1、10又は19のいずれか一項に記載の方法。
- 前記化合物を前記さらなる薬剤と同一の医薬組成物で投与する、請求項48に記載の方法。
- 前記化合物を前記さらなる薬剤と異なる医薬組成物で投与する、請求項48に記載の方法。
- 前記さらなる薬剤が化学療法剤である、請求項48に記載の方法。
- 前記さらなる薬剤が制吐剤である、請求項48に記載の方法。
- 前記さらなる薬剤が鎮痛剤である、請求項48に記載の方法。
- 前記さらなる薬剤が抗炎症剤である、請求項48に記載の方法。
- 前記さらなる薬剤がPPARアゴニストである、請求項48に記載の方法。
- 前記PPARアゴニストがPPARδアゴニストである、請求項55に記載の方法。
- 治療有効量又は予防有効量の
式IIの化合物:
若しくはその薬学的に許容可能な塩、プロドラッグ若しくは光学異性体、
式IIIの化合物:
若しくはその薬学的に許容可能な塩、プロドラッグ若しくは光学異性体又は
式IVの化合物:
各R’’基は独立して、H又は1個〜3個の独立したR3又はR4で置換された炭素数1〜5のアルキル基、アルケニル基、アルキニル基又はシクロアルキル基である場合があり、
各R3は独立して、1個〜3個の独立したR5で置換されていてもよいヘテロシクリル又はヘテロアリールであり、
各R4は独立して、ハロゲン、酸素、硫黄、CF3、SR6、OR6、OC(O)R6、NR6R6、NR6R7、COOR6、C(O)R6又はC(O)NR6R6であり、
各R5は独立して、C1〜C10アルキル、ハロ、ハロアルキル、SR6、OR6、NR6R6、COOR6、NO2、CN、C(O)R6、C(O)NR6R6、OC(O)R6、S(O)2R6、S(O)2NR6R6、NR6C(O)NR6R6、NR6C(O)R6、NR6(COOR6)、NR6C(O)R8、NR6S(O)2NR6R6、NR6S(O)2R6、NR6S(O)2R8又はR4若しくはR8で置換されたC1〜C10アルキルであり、
各R6は独立して、H、C1〜C10アルキル、C2〜C10アルケニル、C2〜C10アルキニル、C3〜C10シクロアルキル、R8又はR8で置換されたC1〜C10アルキルであり、
各R7は独立して、COOR9、C(O)NR9R9、S(O)2R9又はS(O)2NR9R9であり、
各R8は独立して、アリール、ヘテロアリール又はヘテロシクリルであり、
各R9は独立して、H、C1〜C10アルキル、アリール、ヘテロアリール又はヘテロシクリルである)
若しくはその薬学的に許容可能な塩、プロドラッグ若しくは光学異性体と、
薬学的に許容可能な担体と、
を含む、医薬組成物。 - ナノ粒子を含む、請求項57に記載の医薬組成物。
- ナノエマルジョンを含む、請求項57に記載の医薬組成物。
- さらなる薬剤を含む、請求項57に記載の医薬組成物。
- 約10重量%〜約15重量%の油相、約5重量%〜約10重量%の界面活性剤及び約50重量%〜約70重量%の水相を含む、請求項57に記載の医薬組成物。
- 約13重量%〜約15重量%の油相、約6重量%〜約8重量%の界面活性剤及び約55重量%〜約65重量%の水相を含む、請求項61に記載の医薬組成物。
- 約7重量%の大豆油、約7重量%のMIGLYOL 812、約7重量%の大豆レシチン、約0.3重量%のオレイン酸ナトリウム及び約62重量%の水を含む、請求項62に記載の医薬組成物。
- 約7重量%の大豆油、約7重量%のMIGLYOL 812、約7重量%の大豆レシチン、約0.3重量%のオレイン酸ナトリウム、約0.006重量%のEDTA、約17重量%のスクロース及び約62重量%の水を含む、請求項63に記載の医薬組成物。
- pHが約5〜約7である、請求項61に記載の医薬組成物。
- pHが約6.2である、請求項65に記載の医薬組成物。
- 前記化合物を、請求項61〜66のいずれか一項に記載の医薬組成物で投与する、請求項1、10又は19のいずれか一項に記載の方法。
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US20110237536A1 (en) | 2011-09-29 |
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CN102202672A (zh) | 2011-09-28 |
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