JP2012519691A - ホスホチオフェン及びホスホチアゾールhcvポリメラーゼ阻害剤 - Google Patents
ホスホチオフェン及びホスホチアゾールhcvポリメラーゼ阻害剤 Download PDFInfo
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- JP2012519691A JP2012519691A JP2011553059A JP2011553059A JP2012519691A JP 2012519691 A JP2012519691 A JP 2012519691A JP 2011553059 A JP2011553059 A JP 2011553059A JP 2011553059 A JP2011553059 A JP 2011553059A JP 2012519691 A JP2012519691 A JP 2012519691A
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- JCVUDCBIOSOBRZ-UHFFFAOYSA-N oxido-oxo-thiophen-2-ylphosphanium Chemical compound O=P(=O)C1=CC=CS1 JCVUDCBIOSOBRZ-UHFFFAOYSA-N 0.000 title abstract description 13
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- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
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- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000004954 trialkylamino group Chemical group 0.000 description 1
- 229960005294 triamcinolone Drugs 0.000 description 1
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- 229960001288 triamterene Drugs 0.000 description 1
- 150000004654 triazenes Chemical class 0.000 description 1
- LMJSLTNSBFUCMU-UHFFFAOYSA-N trichlormethiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(C(Cl)Cl)NS2(=O)=O LMJSLTNSBFUCMU-UHFFFAOYSA-N 0.000 description 1
- 229960004813 trichlormethiazide Drugs 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- FQCQGOZEWWPOKI-UHFFFAOYSA-K trisalicylate-choline Chemical compound [Mg+2].C[N+](C)(C)CCO.OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O FQCQGOZEWWPOKI-UHFFFAOYSA-K 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
- 229960005041 troleandomycin Drugs 0.000 description 1
- LQCLVBQBTUVCEQ-QTFUVMRISA-N troleandomycin Chemical compound O1[C@@H](C)[C@H](OC(C)=O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](OC(C)=O)[C@@H](C)C(=O)[C@@]2(OC2)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)OC(C)=O)[C@H]1C LQCLVBQBTUVCEQ-QTFUVMRISA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- WVPSKSLAZQPAKQ-CDMJZVDBSA-N trovafloxacin Chemical compound C([C@H]1[C@@H]([C@H]1C1)N)N1C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=NC=1N2C1=CC=C(F)C=C1F WVPSKSLAZQPAKQ-CDMJZVDBSA-N 0.000 description 1
- 229960000497 trovafloxacin Drugs 0.000 description 1
- 229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 description 1
- 239000002452 tumor necrosis factor alpha inhibitor Substances 0.000 description 1
- 102000003298 tumor necrosis factor receptor Human genes 0.000 description 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 229920011532 unplasticized polyvinyl chloride Polymers 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 239000006217 urethral suppository Substances 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 229940120293 vaginal suppository Drugs 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- 229960002381 vardenafil Drugs 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 201000001862 viral hepatitis Diseases 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- ZXIBCJHYVWYIKI-PZJWPPBQSA-N ximelagatran Chemical compound C1([C@@H](NCC(=O)OCC)C(=O)N2[C@@H](CC2)C(=O)NCC=2C=CC(=CC=2)C(\N)=N\O)CCCCC1 ZXIBCJHYVWYIKI-PZJWPPBQSA-N 0.000 description 1
- 229960001522 ximelagatran Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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- A—HUMAN NECESSITIES
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
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Abstract
【選択図】 なし
Description
ホスホチオフェン及びホスホチアゾール化合物、該化合物を含有する医薬組成物、及びそれらの製造方法が本明細書に提供される。また、HCV感染の治療を必要とする宿主における該治療のためのそれらの使用方法が提供される。
C型肝炎ウイルス(HCV)は、輸血後肝炎の少なくとも80%及び実質的な割合の散発性急性肝炎の原因となることが公知である(Houghtonらの文献(Science 1989,244,362-364);Thomasの文献(Curr.Top.Microbiol.Immunol.2000,25-41))。また、予備試験の証拠によって、「特発性」慢性肝炎、「原因不明の」硬変症、及びおそらくB型肝炎ウイルスのような他の肝炎ウイルスと関連していない肝細胞癌の多くの症例においてHCVが関係しているとみなされている(Di Besceglieらの文献(Scientific American,1999,October, 80‐85);Boyerらの文献(J.Hepatol.2000,32,98-112))。
ホスホチオフェン及びホスホチアゾール化合物、該化合物を含有する医薬組成物、及びそれらの調製方法が本明細書に提供される。また、HCV感染した宿主の治療のための該化合物の使用方法が提供される。
R1及びR2の各々は独立して、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R3は、H、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-P(O)(OR6)2、又は-C(O)NHSO2R21であり;
Xは、N又はCR4であり;
R4及びR5の各々は独立して、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であるか、又はR4及びR5はそれらが結合した2個の炭素原子と一緒に、環(例えば、5-、6-又は7-員環)を形成し;
Lは、結合、又はO、S、NR16、若しくはCR19R20などの任意の二価の基であり;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20及びR21の各々は、独立して、水素、アルキル(例えば、C1-6アルキル)、アルケニル(例えば、C2-6アルケニル)、アルキニル(例えば、C2-6アルキニル)、シクロアルキル(例えば、C3-7シクロアルキル)、アリール(例えば、C6-14アリール)、ヘテロアリール(例えば、5-、6-又は7-員のヘテロアリール)、ヘテロシクリル(例えば、3-7員のヘテロシクリル)、アルキル-シクロアルキレン(例えば、C1-6アルキル-C3-7シクロアルキレン)、又はシクロアルキル-アルキレンである。)。一部の実施態様において、アルキル、アリール、アリールアルキル、アルカリル、ヘテロアリール、アルケニル、アルキニル、シクロアルキル、ヘテロシクリル、アルキル-シクロアルキレン又はシクロアルキル-アルキレンの各々は、任意に置換されている。
(式中、R1、R2、R3、R4、R5及びLは、本明細書において定義されたものである。)。
(式中、R1、R2、R3、R5及びLは、本明細書において定義されたものである。)。
本明細書に示される開示の理解を容易にするために、いくつかの用語を以下に定義する。
一部の実施態様において、HCVポリメラーゼ阻害剤としての活性を有することができる、HCV感染の治療に有用であるリン-含有複素環式化合物(例えばホスホチオフェン化合物、ホスホチアゾール化合物及びホスホピラゾール化合物)が、本明細書に提供される。また、該化合物を含む医薬組成物、該化合物の製造方法、及び治療を必要とする宿主におけるHCV感染の治療のための該化合物の使用方法が、本明細書に提供される。
R1及びR2の各々は独立して、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
Lは、結合、又はO、S、NR16、若しくはCR19R20などの任意の二価の基であり;
R6、R16、R19、及びR20の各々は、本明細書に定義されており;かつ
Yは、アリール、ヘテロシクリル又はヘテロアリールである。)。
Aは、CRa、N、NRb、O又はSであり;
Bは、CRc、N、NRd、O又はSであり;
Cは、CRe、N、NRf、O又はSであり;
Dは、CRg、N、NRh、O又はSであり、但しA、B、C又はDの少なくとも1つは、N、NRb、NRd、NRf、NRh、O又はSであることを条件とし;
Ra、Rb、Rc、Rd、Re、Rf、Rg及びRhの各々は、独立してH、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、-SO2R18-C(O)又はNSO2R21であり;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R17、R18及びR21の各々は独立して、水素、アルキル(例えばC1-6アルキル)、アルケニル(例えばC2-6アルケニル)、アルキニル(例えばC2-6アルキニル)、シクロアルキル(例えばC3-7シクロアルキル)、アリール(例えばC6-14アリール)、ヘテロアリール(例えば5-、6-又は7-員のヘテロアリール)、ヘテロシクリル(例えば3〜7員のヘテロシクリル)、アルキル-シクロアルキレン(例えばC1-6アルキル-C3-7シクロアルキレン)、又はシクロアルキル-アルキレンである。一部の実施態様において、アルキル、アリール、アリールアルキル、アルカリル、ヘテロアリール、アルケニル、アルキニル、シクロアルキル、ヘテロシクリル、アルキル-シクロアルキレン又はシクロアルキル-アルキレンの各々は、任意に置換されている。
各R3は独立して、H、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-P(O)(OR6)2、又は-C(O)NHSO2R21であり;
R4及びR5の各々は独立して、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18 であるか、又はR4及びR5はそれらが結合した2個の炭素原子と一緒に、環(例えば、5-、6-又は7-員の環)を形成し;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R17、R18、及びR21の各々は独立して、水素、アルキル(例えばC1-6アルキル)、アルケニル(例えばC2-6アルケニル)、アルキニル(例えばC2-6アルキニル)、シクロアルキル(例えばC3-7シクロアルキル)、アリール(例えばC6-14アリール)、ヘテロアリール(例えば5-、6-又は7-員のヘテロアリール)、ヘテロシクリル(例えば3〜7員のヘテロシクリル)、アルキル-シクロアルキレン(例えばC1-6アルキル-C3-7シクロアルキレン)、又はシクロアルキル-アルキレンである。一部の実施態様において、アルキル、アリール、アリールアルキル、アルカリル、ヘテロアリール、アルケニル、アルキニル、シクロアルキル、ヘテロシクリル、アルキル-シクロアルキレン又はシクロアルキル-アルキレンの各々は、任意に置換されている。
R1及びR2の各々は独立して、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R3は、H、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-P(O)(OR6)2、又は-C(O)NHSO2R21であり;
Xは、N又はCR4であり;
R4及びR5の各々は独立して、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であるか、又はR4及びR5はそれらが結合した2個の炭素原子と一緒に、環(例えば5-、6-又は7-員の環)を形成し;
Lは、結合、又はO、S、NR16、若しくはCR19R20などの任意の二価の基であり;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20及びR21の各々は、独立して水素、アルキル(例えばC1-6アルキル)、アルケニル(例えばC2-6アルケニル)、アルキニル(例えばC2-6アルキニル)、シクロアルキル(例えばC3-7シクロアルキル)、アリール(例えばC6-14アリール)、ヘテロアリール(例えば5-、6-又は7-員のヘテロアリール)、ヘテロシクリル(例えば3〜7員のヘテロシクリル)、アルキル-シクロアルキレン(例えばC1-6アルキル-C3-7シクロアルキレン)又はシクロアルキル-アルキレンである。)。一部の実施態様において、アルキル、アリール、アリールアルキル、アルカリル、ヘテロアリール、アルケニル、アルキニル、シクロアルキル、ヘテロシクリル、アルキル-シクロアルキレン又はシクロアルキル-アルキレンの各々は、任意に置換されている。
R3は、H、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-P(O)(OR6)2、又は-C(O)NHSO2R21であり;
R4及びR5の各々は独立して、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であるか、又はR4及びR5はそれらが結合した2個の炭素原子と一緒に、環(例えば5-、6-又は7-員の環)を形成し;
Lは、結合、又はO、S、NR16、若しくはCR19R20などの任意の二価の基であり;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20及びR21の各々は、独立して水素、アルキル(例えばC1-6アルキル)、アルケニル(例えばC2-6アルケニル)、アルキニル(例えばC2-6アルキニル)、シクロアルキル(例えばC3-7シクロアルキル)、アリール(例えばC6-14アリール)、ヘテロアリール(例えば5-、6-又は7-員のヘテロアリール)、ヘテロシクリル(例えば3〜7員のヘテロシクリル)、アルキル-シクロアルキレン(例えばC1-6アルキル-C3-7シクロアルキレン)又はシクロアルキル-アルキレンである。)。
R1及びR2の各々は独立して、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R3は、H、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-P(O)(OR6)2、又は-C(O)NHSO2R21であり;
R4及びR5の各々は独立して、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であるか、又はR4及びR5はそれらが結合した2個の炭素原子と一緒に、環(例えば5-、6-又は7-員の環)を形成し;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R17、R18、R19、R20及びR21の各々は独立して、水素、アルキル(例えばC1-6アルキル)、アルケニル(例えばC2-6アルケニル)、アルキニル(例えばC2-6アルキニル)、シクロアルキル(例えばC3-7シクロアルキル)、アリール(例えばC6-14アリール)、ヘテロアリール(例えば5-、6-又は7-員のヘテロアリール)、ヘテロシクリル(例えば3〜7員のヘテロシクリル)、アルキル-シクロアルキレン(例えばC1-6アルキル-C3-7シクロアルキレン)又はシクロアルキル-アルキレンである。)。
R1及びR2の各々は独立して、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R3は、H、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-P(O)(OR6)2、又は-C(O)NHSO2R21であり;
R4及びR5の各々は独立して、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であるか、又はR4及びR5はそれらが結合した2個の炭素原子と一緒に、環(例えば5-、6-又は7-員の環)を形成し;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R17、R18、R19、R20及びR21の各々は独立して、水素、アルキル(例えばC1-6アルキル)、アルケニル(例えばC2-6アルケニル)、アルキニル(例えばC2-6アルキニル)、シクロアルキル(例えばC3-7シクロアルキル)、アリール(例えばC6-14アリール)、ヘテロアリール(例えば5-、6-又は7-員のヘテロアリール)、ヘテロシクリル(例えば3〜7員のヘテロシクリル)、アルキル-シクロアルキレン(例えばC1-6アルキル-C3-7シクロアルキレン)又はシクロアルキル-アルキレンである。)。
R1及びR2の各々は独立して、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R4及びR5の各々は独立して、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であるか、又はR4及びR5はそれらが結合した2個の炭素原子と一緒に、環(例えば5-、6-又は7-員の環)を形成し;
Lは、結合、又はO、S、NR16、若しくはCR19R20などの任意の二価の基であり;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、及びR20の各々は独立して、水素、アルキル(例えばC1-6アルキル)、アルケニル(例えばC2-6アルケニル)、アルキニル(例えばC2-6アルキニル)、シクロアルキル(例えばC3-7シクロアルキル)、アリール(例えばC6-14アリール)、ヘテロアリール(例えば5-、6-又は7-員のヘテロアリール)、ヘテロシクリル(例えば3〜7員のヘテロシクリル)、アルキル-シクロアルキレン(例えばC1-6アルキル-C3-7シクロアルキレン)又はシクロアルキル-アルキレンである。)。
R2は、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R4及びR5の各々は独立して、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であるか、又はR4及びR5はそれらが結合した2個の炭素原子と一緒に、環(例えば5-、6-又は7-員の環)を形成し;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、及びR18の各々は独立して、水素、アルキル(例えばC1-6アルキル)、アルケニル(例えばC2-6アルケニル)、アルキニル(例えばC2-6アルキニル)、シクロアルキル(例えばC3-7シクロアルキル)、アリール(例えばC6-14アリール)、ヘテロアリール(例えば5-、6-又は7-員のヘテロアリール)、ヘテロシクリル(例えば3〜7員のヘテロシクリル)、アルキル-シクロアルキレン(例えばC1-6アルキル-C3-7シクロアルキレン)又はシクロアルキル-アルキレンである。)。
R2は、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R4及びR5の各々は独立して、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であるか、又はR4及びR5はそれらが結合した2個の炭素原子と一緒に、環(例えば5-、6-又は7-員の環)を形成し;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R17、R18、及びR19の各々は独立して、水素、アルキル(例えばC1-6アルキル)、アルケニル(例えばC2-6アルケニル)、アルキニル(例えばC2-6アルキニル)、シクロアルキル(例えばC3-7シクロアルキル)、アリール(例えばC6-14アリール)、ヘテロアリール(例えば5-、6-又は7-員のヘテロアリール)、ヘテロシクリル(例えば3〜7員のヘテロシクリル)、アルキル-シクロアルキレン(例えばC1-6アルキル-C3-7シクロアルキレン)又はシクロアルキル-アルキレンである。)。
R2は、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R3は、H、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-P(O)(OR6)2、又は-C(O)NHSO2R21であり;
R5は、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であり;
Lは、結合、又はO、S、NR16、若しくはCR19R20などの任意の二価の基であり;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、及びR21の各々は独立して、水素、アルキル(例えばC1-6アルキル)、アルケニル(例えばC2-6アルケニル)、アルキニル(例えばC2-6アルキニル)、シクロアルキル(例えばC3-7シクロアルキル)、アリール(例えばC6-14アリール)、ヘテロアリール(例えば5-、6-又は7-員のヘテロアリール)、ヘテロシクリル(例えば3〜7員のヘテロシクリル)、アルキル-シクロアルキレン(例えばC1-6アルキル-C3-7シクロアルキレン)又はシクロアルキル-アルキレンである。)。
R1及びR2の各々は独立して、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R3は、H、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-P(O)(OR6)2、又は-C(O)NHSO2R21であり;
R5は、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であり;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R17、R18、R19、R20、及びR21の各々は独立して、水素、アルキル(例えばC1-6アルキル)、アルケニル(例えばC2-6アルケニル)、アルキニル(例えばC2-6アルキニル)、シクロアルキル(例えばC3-7シクロアルキル)、アリール(例えばC6-14アリール)、ヘテロアリール(例えば5-、6-又は7-員のヘテロアリール)、ヘテロシクリル(例えば3〜7員のヘテロシクリル)、アルキル-シクロアルキレン(例えばC1-6アルキル-C3-7シクロアルキレン)又はシクロアルキル-アルキレンである。)。
R1及びR2の各々は独立して、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R3は、H、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-P(O)(OR6)2、又は-C(O)NHSO2R21であり;
R5は、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であり;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R17、R18、R19、R20、及びR21の各々は独立して、水素、アルキル(例えばC1-6アルキル)、アルケニル(例えばC2-6アルケニル)、アルキニル(例えばC2-6アルキニル)、シクロアルキル(例えばC3-7シクロアルキル)、アリール(例えばC6-14アリール)、ヘテロアリール(例えば5-、6-又は7-員のヘテロアリール)、ヘテロシクリル(例えば3〜7員のヘテロシクリル)、アルキル-シクロアルキレン(例えばC1-6アルキル-C3-7シクロアルキレン)又はシクロアルキル-アルキレンである。)。
R1及びR2の各々は独立して、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R5は、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であり;
Lは、結合、又はO、S、NR16、若しくはCR19R20などの任意の二価の基であり;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R17、R18、R19、及びR20の各々は独立して、水素、アルキル(例えばC1-6アルキル)、アルケニル(例えばC2-6アルケニル)、アルキニル(例えばC2-6アルキニル)、シクロアルキル(例えばC3-7シクロアルキル)、アリール(例えばC6-14アリール)、ヘテロアリール(例えば5-、6-又は7-員のヘテロアリール)、ヘテロシクリル(例えば3〜7員のヘテロシクリル)、アルキル-シクロアルキレン(例えばC1-6アルキル-C3-7シクロアルキレン)又はシクロアルキル-アルキレンである。)。
R2は、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R5は、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であり;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R17、及びR18の各々は独立して、水素、アルキル(例えばC1-6アルキル)、アルケニル(例えばC2-6アルケニル)、アルキニル(例えばC2-6アルキニル)、シクロアルキル(例えばC3-7シクロアルキル)、アリール(例えばC6-14アリール)、ヘテロアリール(例えば5-、6-又は7-員のヘテロアリール)、ヘテロシクリル(例えば3〜7員のヘテロシクリル)、アルキル-シクロアルキレン(例えばC1-6アルキル-C3-7シクロアルキレン)又はシクロアルキル-アルキレンである。)。
R2は、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R3は、H、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-P(O)(OR6)2、又は-C(O)NHSO2R21であり;
R5は、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であり;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R17、R18、R19、R20、及びR21の各々は独立して、水素、アルキル(例えばC1-6アルキル)、アルケニル(例えばC2-6アルケニル)、アルキニル(例えばC2-6アルキニル)、シクロアルキル(例えばC3-7シクロアルキル)、アリール(例えばC6-14アリール)、ヘテロアリール(例えば5-、6-又は7-員のヘテロアリール)、ヘテロシクリル(例えば3〜7員のヘテロシクリル)、アルキル-シクロアルキレン(例えばC1-6アルキル-C3-7シクロアルキレン)又はシクロアルキル-アルキレンである。)。
R1'、R2'、R3'、R4'、及びR5'の各々は独立して、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であるか、又はR1'及びR2'、又はR2'及びR3'、又はR3'及びR4'、又はR4'及びR5'は、それらが結合した2個の炭素原子と一緒に、環(例えば5-、6-又は7-員の環)を形成している。
本明細書に提供される化合物は、当業者に明らかな任意の方法により調製、単離、又は入手することができる。例えば式IAの化合物は、スキーム1に示されたように調製することができる。ある実施態様において、R1、R2、R3、R4、R5、及びLは、本明細書において定義されたものである。
医薬として許容し得る媒体、担体、希釈剤、若しくは賦形剤、又はそれらの混合物中の、本明細書に提供される化合物の単一の鏡像異性体、鏡像異性体対の混合物、個別のジアステレオマー、若しくはジアステレオマーの混合物;又は、それらの医薬として許容し得る塩、溶媒和物、若しくはプロドラッグを含む該化合物を活性成分として、1種以上の医薬として許容し得る希釈剤、賦形剤、又は担体との組み合わせで含有する医薬組成物が、本明細書に提供される。ある実施態様において、医薬組成物は、少なくとも1つの放出制御性の賦形剤又は担体を含有する。ある実施態様において、医薬組成物は、少なくとも1つの非放出制御性の賦形剤又は担体を含有する。ある実施態様において、医薬組成物は、少なくとも1つの放出制御性の賦形剤又は担体と、少なくとも1つの非放出制御性の賦形剤又は担体とを含有する。
本明細書に提供される医薬組成物は、経口投与のために固体、半固体、又は液体の剤形で提供され得る。本明細書で使用されるように、経口投与はまた、口腔内、舌側、及び舌下への投与を含む。適切な経口剤形には、錠剤、カプセル剤、丸剤、トローチ剤、ロゼンジ剤、パステル剤、カシェ剤、ペレット剤、薬用チューインガム、顆粒剤、バルク散剤、発泡性又は非発泡性の散剤又は顆粒剤、液剤、乳剤、懸濁剤、溶液、ウェーハー、スプリンクル(sprinkle)、エリキシル剤、及びシロップ剤が含まれるが、これらに限定されるわけではない。活性成分に加えて、医薬組成物は、結合剤、充填剤、希釈剤、崩壊剤、湿潤剤、滑沢剤、流動促進剤、着色剤、色素遊走阻害剤、甘味剤、及び香味剤を含むがこれらに限定されるわけではない1つ以上の医薬として許容し得る担体又は賦形剤を含有し得る。
本明細書で提供される医薬組成物は、局所投与又は全身投与のために、注射、注入、又は植え込みによって非経口的に投与され得る。本明細書で使用されるように、非経口投与には、静脈内投与、動脈内投与、腹腔内投与、髄腔内投与、心室内投与、尿管内投与、胸骨内投与、頭蓋内投与、筋肉内投与、滑液内投与、並びに皮下投与が含まれる。
本明細書に提供される医薬組成物は、皮膚、開口部又は粘膜へ局所的に投与され得る。本明細書で使用されるように、局所投与には、真皮(内)投与、結膜投与、角膜内投与、眼内投与、点眼投与、耳介投与、経皮投与、点鼻投与、膣投与、尿道投与、呼吸器系投与、及び直腸投与が含まれる。
本明細書に提供される医薬組成物は、改変された放出の剤形として製剤され得る。本明細書で使用されるように、「改変された放出」という用語は、活性成分の放出の速度又は場所が、同一の経路によって投与される場合の即時剤形の活性成分の放出の速度又は場所とは異なる剤形をいう。改変された放出の剤形には、遅延性の、拡大性の、持続性の、持効性の、間欠性の、制御性の、加速性のかつ迅速な、標的とされた、プログラムされた放出、及び胃滞留の剤形が含まれる。改変された放出の剤形における医薬組成物は、マトリックス放出制御装置、浸透圧性放出制御装置、多粒子放出制御装置、イオン交換樹脂、腸溶性コーティング、多層状コーティング、ミクロスフェア、リポソーム、及びそれらの組み合わせを含むがこれらに限定されるわけではない当業者に公知の多様な改変された放出装置及び方法を使用して調製できる。また、活性成分の放出速度は、活性成分の粒子の大きさ及び多形(polymorphorism)を変動させることによって改変できる。
改変された放出の剤形における本明細書に提供される医薬組成物は、当業者に公知のマトリックス放出制御装置を使用して作製され得る(Takadaらの文献「制御された薬物送達の事典(Encyclopedia of Controlled Drug Delivery)」(第2巻,Mathiowitz編,Wiley,1999)参照)。
改変された放出の剤形における本明細書に提供される医薬組成物は、1チャンバーシステム、2チャンバーシステム、非対称性メンブレン技術(AMT)、及び押し出しコアシステム(ECS)を含む浸透圧性放出制御装置を使用して作製され得る。一般に、このような装置は少なくとも2つの構成要素を有する:(a)活性成分を含有するコア;及び(b)コアを封入する少なくとも1つの送達ポートを有する半透性メンブレン。この半透性メンブレンは、送達ポートを通じての押し出しによって薬物放出を生じるよう、水性の使用環境からコアへの水の流入を制御する。
改変された放出の剤形における本明細書に提供される医薬組成物は、直径約10μm〜約3mm、約50μm〜約2.5mm、又は約100μm〜約1mmの範囲の多数の粒子、顆粒、又はペレットを含む、多粒子放出制御装置を作製され得る。このような多粒子は、湿式及び乾式造粒、押し出し成形/球状化(spheronization)、ローラー圧縮、融解−凍結を含む当業者に公知の過程によって、及び種晶(seed core)をスプレーコーティングすることによって作られ得る。例えば、「多粒子経口薬剤送達(Multiparticulate Oral Drug Delivery)」;Marcel Dekker: 1994;及び「医薬造粒技術(Pharmaceutical Pelletization Technology)」;Marcel Dekker: 1989を参照されたい。
また、本明細書に提供される医薬組成物は、治療されるべき対象の身体の特定の組織、受容体、又は他の領域を標的とするよう製剤され得、リポソーム、再封入赤血球、及び抗体をベースとした送達系を含む。例には、米国特許第6,316,652号;第6,274,552号;第6,271,359号;第6,253,872号;第6,139,865号;第6,131,570号;第6,120,751号;第6,071,495号;第6,060,082号;第6,048,736号;第6,039,975号;第6,004,534号;第5,985,307号;第5,972,366号;第5,900,252号;第5,840,674号;第5,759,542号;及び第5,709,874号が含まれるが、これらに限定されるわけではない。
本明細書に提供される化合物の単一の鏡像異性体、鏡像異性体対の混合物、個別のジアステレオマー、若しくはジアステレオマーの混合物;又は、それらの医薬として許容し得る塩、溶媒和物、若しくはプロドラッグを含む、該化合物の治療的有効量をHCVに感染した対象へ投与することを含む、対象におけるC型肝炎ウイルス感染を治療し又は予防する方法が本明細書に提供される。一部の実施態様において、対象は哺乳動物である。別の実施態様において、対象はヒトである。
また、本明細書に提供される化合物は、HCV感染の治療及び/又は予防において有用な他の治療薬との組み合わせられるか又は組み合わせで使用され得る。
本明細書で使用されるように、特定の略記が具体的に定義されているかどうかにかかわらず、これらの方法、スキーム及び実施例において使用される記号及び慣例は、現代の科学文献、例えば、Journal of the American Chemical Society又はJournal of Biological Chemistryにおいて使用されるものと一致している。具体的には、制限するものではないが、下記の略記が、実施例において及び明細書を通じて使用され得る:g(グラム);mg(ミリグラム);mL(ミリリットル);μL(マイクロリットル);mM(ミリモラー);μM(マイクロモラー);Hz(ヘルツ);MHz(メガヘルツ);mmol(ミリモル);hr(時);min(分);TLC(薄層クロマトグラフィー);HPLC(高速液体クロマトグラフィー);SCX(強陽イオン交換体);MS(質量分析);ESI(エレクトロスプレーイオン化);Rt(保持時間);SiO2(シリカ);THF(テトラヒドロフラン);CD3OD(重水素化メタノール);CDCl3(重水素化クロロホルム);DCE(ジクロロエタン);DCM(ジクロロメタン);DMF(ジメチルホルムアミド);DMSO(ジメチルスルホキシド);EtOAc(酢酸エチル);CHCl3(クロロホルム);DMF(N,N-ジメチルホルムアミド);DMA(N,N-ジメチルアセトアミド);MeOH(メタノール);EtOH(エタノール);HCl(塩酸);LiOH(水酸化リチウム);NaOH(水酸化ナトリウム);KOH(水酸化カリウム);Cs2CO3(炭酸セシウム);DIPEA(N,N-ジイソプロピルエチルアミン);TEA(トリエチルアミン);DBU(1,8-ジアザビシクロ[5.4.0]ウンデセ-7-エン);CDI(カルボニルジイミダゾール);TBTU(テトラフルオロホウ酸O-(ベンゾトリアゾール-1-イル)-N,N,N',N'-テトラメチルウロニウム);Ac(アセチル);Me(メチル);Et(エチル);tBu(tert-ブチル);Boc(tert-ブトキシルカルボニ(butoxylcarbony));Bn(ベンジル);及び、Ts(トシレート)。
((2,4-ジメチル-フェニル)-ホスホン酸ジエチルエステル)
((2,4-ジメチル-フェニル)-ホスホン酸エチルエステル)
(2-チオフェンカルボキシリックメチルエステル, 3-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートエチルエステル]-5-(4-フルオロフェニル))
(2-チオフェンカルボン酸, 3-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートエチルエステル]-5-(4-フルオロフェニル)(化合物22))
((2,4-ジメチル-フェニル)-ホスホン酸ジメチルエステル)
((2,4-ジメチル-フェニル)-ホスホン酸メチルエステル)
(2-チオフェンカルボキシリックメチルエステル, 3-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-5-(4-フルオロフェニル))
(2-チオフェンカルボン酸, 3-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-5-(4-フルオロフェニル)(化合物 21))
(フェニル-ホスホン酸ジメチルエステル)
(フェニルホスホン酸メチルエステル)
(2-チオフェンカルボキシリックメチルエステル, 3-N-(フェニル-ホスホンアミデートメチルエステル)-5-フェニル)
(2-チオフェンカルボン酸, 3-N-(フェニル-ホスホンアミデートメチルエステル)-5-フェニル(化合物25))
((2,4-ジクロロ-フェニル)-ホスホン酸ジエチルエステル)
((2,4-ジメチル-フェニル)-ホスホン酸エチルエステル)
(2-チオフェンカルボキシリックメチルエステル, 3-N-[(2,4-ジクロロ-フェニル)-ホスホンアミデートメチルエステル]-5-(4-フルオロフェニル))
(2-チオフェンカルボン酸, 3-N-[(2,4-ジクロロ-フェニル)-ホスホンアミデートメチルエステル]-5-(4-フルオロフェニル)(化合物23))
(メチル 3-N-[(2,4-ジクロロ-フェニル)-ホスホンアミデートエチルエステル]-5-(4-ピラゾロ[1,5-a]ピリミジン-2-イルフェニル)-2-チオフェンカルボキシラート)
(3-N-[(2,4-ジクロロ-フェニル)-ホスホンアミデートエチルエステル]-5-(4-ピラゾロ[1,5-a]ピリミジン-2-イルフェニル)-2-チオフェンカルボン酸(化合物11))
(メチル 3-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートエチルエステル]-5-(4-ピラゾロ[1,5-a]ピリミジン-2-イルフェニル)-2-チオフェンカルボキシラート)
(3-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートエチルエステル]-5-(4-ピラゾロ[1,5-a]ピリミジン-2-イルフェニル)-2-チオフェンカルボン酸(化合物26))
(メチル 3-N-[(2,4-ジクロロ-フェニル)-ホスホンアミデートエチルエステル]-5-(4-フェニル-エチニル-1,3-チアゾール)-2-チオフェンカルボキシラート)
(3-N-[(2,4-ジクロロ-フェニル)-ホスホンアミデートエチルエステル]-5-(4-フェニル-エチニル-1,3-チアゾール)-2-チオフェンカルボン酸(化合物24))
(2-チオフェンカルボキシリックメチルエステル, 3-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-5-フェニル)
(2-チオフェンカルボン酸, 3-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-5-フェニル(化合物27))
(2-チオフェンカルボキシリックメチルエステル, 5-ヨード-3-N-[(2,4-ジクロロフェニル)-ホスホンアミデートエチルエステル])
(2-チオフェンカルボキシリックメチルエステル, 3-N-[(2,4-ジクロロフェニル)-ホスホンアミデートエチルエステル]-5-フェニル)
(2-チオフェンカルボン酸, 3-N-[(2,4-ジクロロフェニル)-ホスホンアミデートエチルエステル]-5-フェニル(化合物28))
(2-チオフェンカルボキシリックメチルエステル, 3-N-[(2,4-ジクロロフェニル)-ホスホンアミデートメチルエステル]-5-(4-シアノフェニル))
(2-チオフェンカルボン酸, 3-N-[(2,4-ジクロロフェニル)-ホスホンアミデートエチルエステル]-5-(4-シアノフェニル)(化合物29))
(2-チオフェンカルボン酸, 3-N-[(2,4-ジクロロフェニル)-ホスホンアミデートエチルエステル]-5-(4-クロロフェニル)(化合物30))
(2-チオフェンカルボン酸, 3-N-[(2,4-ジクロロフェニル)-ホスホンアミデートエチルエステル]-5-(3,4-ジクロロフェニル)(化合物31))
(2-チオフェンカルボン酸, 3-N-[(2,4-ジクロロフェニル)-ホスホンアミデートエチルエステル]-5-(4-ベンジルオキシフェニル))
(2-チオフェンカルボン酸, 3-N-[(2,4-ジクロロフェニル)-ホスホンアミデートエチルエステル]-5-[4-ベンゾ[b]チオフェン-2-イル]-フェニル))
((2-フルオロ-4-クロロ-フェニル)-ホスホン酸ジエチルエステル)
(2-チオフェンカルボキシリックメチルエステル, 3-N-[(2-フルオロ-4-クロロフェニル)-ホスホンアミデートエチルエステル]-5-[4-(フロ[3,2-b]ピリジン-2-イルフェニル)])
(2-チオフェンカルボン酸, 3-N-[(2-フルオロ-4-クロロフェニル)-ホスホンアミデートエチルエステル]-5-[4-(フロ[3,2-b]ピリジン-2-イルフェニル)])
(2-チオフェンカルボキシリックメチルエステル, 3-N-メチル-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-5-(4-フルオロフェニル))
(2-チオフェンカルボン酸, 3-N-メチル-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-5-(4-フルオロフェニル)(化合物32))
(2-チオフェンカルボキシリックメチルエステル, 3-N-イソプロピル-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートエチルエステル]-5-(4-フルオロフェニル))
(2-チオフェンカルボン酸, 3-N-イソプロピル-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートエチルエステル]-5-(4-フルオロフェニル)(化合物33))
(2-チオフェンカルボキシリックメチルエステル, 3-N-[(2,4-ジメチル-フェニル)-ホスホンアミデート]-5-(4-フルオロフェニル))
(2-チオフェンカルボン酸, 3-N-[(2,4-ジメチル-フェニル)-ホスホンアミデート]-5-(4-フルオロフェニル))
(メチル3-(ブロモメチル)チオフェン-2-カルボキシラート)
(メチル 3-メチレン[(2,4-ジメチル-フェニル)-ホスフィン酸エチルエステル]チオフェン-2-カルボキシラート)
(メチル 3-メチレン[(2,4-ジメチル-フェニル)-ホスフィン酸エチルエステル]-5-(4-フルオロフェニル)チオフェン-2-カルボキシラート)
(3-メチレン[(2,4-ジメチル-フェニル)-ホスフィン酸エチルエステル]-5-(4-フルオロフェニル)チオフェン-2-カルボン酸)
(メチル 3-メチル-5-フェニル-チオフェン-2-カルボキシラート)
(メチル 3-(ブロモメチル)-5-フェニル-チオフェン-2-カルボキシラート)
(メチル 3-メチレン[(2,4-ジメチル-フェニル)-ホスフィン酸エチルエステル]-5-フェニル-チオフェン-2-カルボキシラート)
(3-メチレン[(2,4-ジメチル-フェニル)-ホスフィン酸エチルエステル]-5-フェニル-チオフェン-2-カルボン酸)
(メチル 3-メチレン[(2,4-ジメチル-フェニル)-ホスフィン酸]-5-フェニル-チオフェン-2-カルボキシラート)
(3-メチレン[(2,4-ジメチル-フェニル)-ホスフィン酸メチルエステル]-5-フェニル-チオフェン-2-カルボン酸)
(3-メチレン[(2,4-ジメチル-フェニル)-ホスフィン酸メチルエステル]-5-フェニル-チオフェン-2-カルボン酸)
(メチル 3-(ビス[ターブトキシカルボニル]アミノ)-5-(4-ピラゾロ[1,5-a]ピリミジン-2-イル-フェニル)-2-チオフェンカルボキシラート)
(メチル 3-アミノ-5-(4-ピラゾロ[1,5-a]ピリミジン-2-イル-フェニル)-2-チオフェンカルボキシラート)
(メチル 3-(ビス[ターブトキシカルボニル]アミノ)-5-(4-フェニル-エチニル-1,3-チアゾール)-2-チオフェンカルボキシラート)
(メチル 3-アミノ-5-(4-フェニル-エチニル-1,3-チアゾール)-2-チオフェンカルボキシラート)
(メチル 3-(ビス[ターブトキシカルボニル]アミノ)-5-(4-フロ[3,2-b]ピリジン-2-イルフェニル)-2-チオフェンカルボキシラート)
(メチル 3-アミノ-5-(4-フロ[3,2-b]ピリジン-2-イルフェニル)-2-チオフェンカルボキシラート)
(5-チアゾールカルボキシリックメチルエステル, 4-クロロ-2-[フェニル-ピラゾロ[1,5-a]ピリミジン])
((2,4-ジメチル-フェニル)-O-メトキシ-ホスホンアミデート)
(5-チアゾールカルボキシリックメチルエステル, 4-クロロ-2-[4-メトキシ-フェニル])
(5-チアゾールカルボキシリックメチルエステル, 4-クロロ-2-[4-クロロ-フェニル])
(5-チアゾールカルボキシリックメチルエステル, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル](化合物191))
(5-チアゾールカルボキシリックメチルエステル, 2-ヨード-4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル](化合物192))
(5-チアゾールカルボキシリックメチルエステル, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[フェニル-8aH-イミダゾ[1,2-a]ピリジン](化合物193))
(5-チアゾールカルボン酸, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[フェニル-8aH-イミダゾ[1,2-a]ピリジン](化合物183))
(5-チアゾールカルボキシリックメチルエステル, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[フェニル-5-メチル-ピラゾロ[1,5-a]ピリミジン-7-イルアミン](化合物194))
(5-チアゾールカルボン酸, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[フェニル-5-メチル-ピラゾロ[1,5-a]ピリミジン-7-イルアミン](化合物181))
(5-チアゾールカルボキシリックメチルエステル, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[フェニル-ピラゾロ[1,5-a]ピリミジン-イル-アミン](化合物195))
(5-チアゾールカルボン酸, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[フェニル-ピラゾロ[1,5-a]ピリミジン-イル-アミン](化合物180))
(5-チアゾールカルボキシリックメチルエステル, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[フェニル-5-メチル-ピラゾロ[1,5-a]ピリミジン](化合物196))
(5-チアゾールカルボン酸, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[フェニル-5-メチル-ピラゾロ[1,5-a]ピリミジン](化合物182))
(5-チアゾールカルボキシリックメチルエステル, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[フェニル-ピラゾロ[1,5-a]ピリミジン](化合物197))
(5-チアゾールカルボン酸, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[フェニル-ピラゾロ[1,5-a]ピリミジン](化合物186))
(5-チアゾールカルボキシリックメチルエステル, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[4-メトキシ-フェニル](化合物198))
(5-チアゾールカルボン酸, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[4-メトキシ-フェニル](化合物187))
(5-チアゾールカルボキシリックメチルエステル, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[4-クロロ-フェニル](化合物188))
(5-チアゾールカルボキシリックメチルエステル, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[2-フェニル-ベンゾ[b]チオフェン](化合物199))
(5-チアゾールカルボン酸, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[2-フェニル-ベンゾ[b]チオフェン](化合物184))
(5-チアゾールカルボキシリックメチルエステル, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[2-フェニル-ベンゾフラン](化合物200))
(5-チアゾールカルボン酸, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-[2-フェニル-ベンゾフラン](化合物185))
(5-チアゾールカルボキシリックメチルエステル, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-フェニル(化合物201))
(5-チアゾールカルボン酸, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル]-2-フェニル(化合物190))
(5-(4-ブロモ-フェニル)-チオフェン-3-イルアミン)
(4-N-[(2,4-ジメチルフェニル)-ホスホンアミデートメチルエステル]-2-(4-ブロモ-フェニル)-チオフェン)
(4-N-[(2,4-ジメチルフェニル)-ホスホンアミデートメチルエステル]-2-[(ベンゾフラン-2-イル)-フェニル]-チオフェン)
(3-N-[(2,4-ジメチルフェニル)-ホスホンアミデートメチルエステル]-5-[(ベンゾフラン-2-イル)-フェニル]-2-ヨード-チオフェン)
(3-N-[(2,4-ジメチルフェニル)-ホスホンアミデートメチルエステル]-5-[(ベンゾフラン-2-イル)-フェニル]-2-チオフェン-2-O-ベンジルホスホン酸)
(3-N-[(2,4-ジメチルフェニル)-ホスホンアミデートメチルエステル]-5-[(ベンゾフラン-2-イル)-フェニル]-2-チオフェン-2-ホスホン酸)
(5-チアゾールカルボキシリックメチルエステル, 4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル])
(5-チアゾールカルボキシリックメチルエステル, 2-ヨード-4-N-[(2,4-ジメチル-フェニル)-ホスホンアミデートメチルエステル])
(4-N-[(2,4-ジメチルフェニル)-ホスホンアミデートメチルエステル]-2-(5-ヒドロキシ-ピリジン-3-イルエチニル)-チアゾール-5-カルボン酸メチルエステル)
(4-N-[(2,4-ジメチルフェニル)-ホスホンアミデートメチルエステル]-2-(5-ヒドロキシ-ピリジン-3-イルエチニル)-チアゾール-5-カルボン酸)
一般的手法:10%ウシ胎仔血清(FBS)、2mM GlutaMAX(L-グルタミン)、1% MEM非必須アミノ酸、100IU/mLペニシリン、100μg/mLストレプトマイシン、及び0.5mg/mL Geneticin(登録商標)(G418)を補充したダルベッコ変法イーグル培地(DMEM)において、遺伝子型1bのHCV Con1サブゲノムレプリコンを含むHuh-7細胞(GS4.1細胞)を増殖させた。用量反応試験のために、50μLの容積で7.5×103個細胞/ウェルで96ウェルプレートに細胞を播種し、37℃/5%CO2でインキュベートした。播種の3時間後、10回連続2倍希釈した50μLの化合物(最高濃度75μM)を添加し、0.5%DMSOの存在下で細胞培養物を37℃/5%CO2でインキュベートした。或いは、15μMの単一濃度で化合物を試験した。全ての場合において、HCVレプリコンを欠失するHuh-7細胞は、陰性対照として機能した。化合物の存在下で細胞を72時間インキュベートした後、酵素結合免疫吸着検定法(ELISA)によってNS4Aタンパク質の発現をモニターした。このために、次にプレートをアセトン/メタノール(1:1(v/v))で1分間固定し、リン酸緩衝塩類溶液(PBS)、0.1%トゥイーン20で2回洗浄し、10%FBSを含有するTNE緩衝液を使用して室温で1時間ブロックした後、同一の緩衝液に希釈した抗-NS4Aマウスモノクローナル抗体A-236(ViroGen社)と共に37℃で2時間インキュベートした。PBS、0.1%トゥイーン20で3回洗浄した後、TNE、10%FBS中の抗-マウス免疫グロブリンG-ペルオキシダーゼ複合体と共に、細胞を37℃で1時間インキュベートした。上述のとおり洗浄した後、反応物をO-フェニレンジアミン(Zymed社)で発色させた。2N H2SO4を使用して反応を30分後に停止し、SUNRISE TECAN分光光度計を使用して492nmで吸光度を読み取った。EC50値は、その最大作用の50%が認められた化合物の濃度を表す。TECAN MAGELLANソフトウェアを使用した4つのパラメータに基づいたS字形の非線形回帰分析を使用して、%阻害対濃度のデータからIC50値を決定した。単一濃度でスクリーニングする場合、結果は15μMでの%阻害で表した。CC50値とは、そのような反応を測定するアッセイにおける最大反応の50%を阻害するのに必要とされる化合物の濃度をいう。
一般的手法:10%ウシ胎仔血清(FBS)、2mM GlutaMAX、1% MEM非必須アミノ酸、100IU/mLペニシリン、100g/mLストレプトマイシン、及び0.5mg/mL GENETICIN(登録商標)(G418)を補充したダルベッコ変法イーグル培地(DMEM)において、HCV遺伝子型1bレプリコン及びルシフェラーゼレポーター遺伝子を収容するHuh-7-由来細胞株(Zluc)を増殖させた。用量反応試験のために、50Lの容積で7.5×103個細胞/ウェルで96ウェルプレートに細胞を播種し、37℃/5%CO2でインキュベートした。薬物溶液は、2×ストックとしてHuh-7培地中に新たに作製した。これらのストックから、G418を含まないDMEM中に、10回の追加の5-倍希釈物を調製した。Zluc細胞の播種の少なくとも3時間後、薬物希釈物50Lのプレートへの2つ組みでの添加により、薬物処理を開始した。薬物の最終濃度は、100nM〜0.0000512nMの範囲であった。次に細胞を、37℃/5%CO2でインキュベートした。或いは、化合物を、2種の濃度で試験した(10nMと100nM)。全ての場合において、Huh-7(HCVレプリコンを収容しない)は、陰性対照として機能した。72時間インキュベーションした後、HCV複製の阻害を、ホタルルシフェラーゼによる5'-フルオロルシフェリンのオキシフルオロルシフェリンへの一酸素添加後に放出された光子の定量により測定した。これのために、穏やかにたたき、培地をプレートから除去した。ONE-gloルシフェラーゼアッセイ試薬50μLを、各ウェルに添加した。プレートを、室温で3分間穏やかに振盪し、Victor3 V 1420マルチラベルカウンター(Perkin Elmer社)上で、700nmカットオフフィルターを用い、1秒間の測定時間で、ルミネセンスを測定した。EC50値は、MICROSOFT EXCEL及びXLfit 4.1ソフトウェアにより決定された得られたベストフィット式由来の用量反応曲線から算出した。スクリーニングを2つの固定濃度で行った場合、結果は10nM及び100nMでの%阻害で表した。
一般的手法:完全増殖培地(ダルベッコ変法イーグル培地、10%ウシ胎仔血清、2mM GlutaMAX、1% MEM非必須アミノ酸、100IU/mLペニシリン、100g/mLストレプトマイシン、及び0.5mg/mL GENETICIN(登録商標))において、HCV遺伝子型1bレプリコン及びルシフェラーゼレポーター遺伝子を収容するHuh-7-由来細胞株(Zluc)を増殖させた。用量反応試験のために、40〜45%ヒト血清又は10%ウシ胎仔血清(参照として)のいずれかを補充した50Lアッセイ培地(ダルベッコ変法イーグル培地、2mM GlutaMAX、1%MEM非必須アミノ酸、100IU/mLペニシリン、100g/mLストレプトマイシン)の容積で7.5×103個細胞/ウェルで、不透明な96ウェル組織培養プレートのカラム2-12に細胞を播種した。新鮮なHuh-7細胞を、ルミネセンスバックグラウンド対照のためにカラム1に同様に播種した。プレートを37℃/5%CO2で4時間インキュベートした。薬物溶液は、2×ストック液としてアッセイ培地中に新たに作製した。8回の連続3倍希釈で、40〜45%ヒト血清又は10%ウシ胎仔血清を含有するアッセイ培地を調製した。希釈した薬物(50μL)を、1ウェルにつき100μLの総容積で、96-ウェルプレートに添加した。薬物の最終濃度は、典型的には10μM〜1nMの範囲であった。蒸発を減少するために、PBSを、外側ウェルに、200μLアリコートで添加した。プレートを、37℃、5%CO2で3日間インキュベートした。次にHCV複製の阻害を、ホタルルシフェラーゼによる5'-フルオロルシフェリンのオキシフルオロルシフェリンへの一酸素添加後に放出された光子の定量により測定した。これのために、穏やかにたたいて、培地をプレートから除去した。ONE-gloルシフェラーゼアッセイ試薬50μLを、各ウェルに添加した。プレートを、室温で3分間穏やかに振盪し、Victor3 V 1420マルチラベルカウンター(PERKIN ELMER社)上で、700nmカットオフフィルターを用い、1秒間の測定時間で、ルミネセンスを測定した。EC50値は、MICROSOFT EXCEL及びXLfit 4.1ソフトウェアにより決定された得られたベストフィット式由来の用量反応曲線から算出した。
Claims (55)
- 式Iの化合物、又はそれらの単一の鏡像異性体、鏡像異性体対の混合物、個別のジアステレオマー、ジアステレオマーの混合物、若しくは互変異性体;又は、それらの医薬として許容し得る塩、溶媒和物、若しくはプロドラッグ:
R1及びR2の各々は独立して、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R3は、H、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-P(O)(OR6)2、又は-C(O)NHSO2R21であり;
Xは、N又はCR4であり;
R4及びR5の各々は独立して、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であるか、又はR4及びR5はそれらが結合した2個の炭素原子と一緒に、環を形成し;
Lは、結合、又はO、S、NR16、若しくはCR19R20などの任意の二価の基であり;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20及びR21の各々は、独立して水素、アルキル、アルケニル、アルキニル、シクロアルキル、アリール、ヘテロアリール、ヘテロシクリル、アルキル-シクロアルキレン又はシクロアルキル-アルキレンであり、
ここでアルキル、アリール、アリールアルキル、アルカリル、ヘテロアリール、アルケニル、アルキニル、シクロアルキル、ヘテロシクリル又はアルキル-シクロアルキルの各々は、任意に置換されている。)。 - 式IA又はIBによる請求項1記載の化合物、又はそれらの単一の鏡像異性体、鏡像異性体対の混合物、個別のジアステレオマー、ジアステレオマーの混合物、若しくは互変異性体;又は、それらの医薬として許容し得る塩、溶媒和物、若しくはプロドラッグ:
R1及びR2の各々は独立して、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R3は、H、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-P(O)(OR6)2、又は-C(O)NHSO2R21であり;
R4及びR5の各々は独立して、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であるか、又はR4及びR5はそれらが結合した2個の炭素原子と一緒に、環を形成し;
Lは、結合、又はO、S、NR16、若しくはCR19R20などの任意の二価の基であり;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20及びR21の各々は、独立して水素、アルキル、アルケニル、アルキニル、シクロアルキル、アリール、ヘテロアリール、ヘテロシクリル、アルキル-シクロアルキレン又はシクロアルキル-アルキレンであり、
ここでアルキル、アリール、アリールアルキル、アルカリル、ヘテロアリール、アルケニル、アルキニル、シクロアルキル、ヘテロシクリル又はアルキル-シクロアルキルの各々は、任意に置換されている。)。 - 式IIA、IIIA、IVA、VA、VIA又はVIIAによる請求項1記載の化合物、又はそれらの単一の鏡像異性体、鏡像異性体対の混合物、個別のジアステレオマー、ジアステレオマーの混合物、若しくは互変異性体;又は、それらの医薬として許容し得る塩、溶媒和物、若しくはプロドラッグ:
R1及びR2の各々は独立して、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R3の各々は、H、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-P(O)(OR6)2、又は-C(O)NHSO2R21であり;
R4及びR5の各々は独立して、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であるか、又はR4及びR5はそれらが結合した2個の炭素原子と一緒に、環を形成し;
各Lは、結合、又はO、S、NR16、若しくはCR19R20などの任意の二価の基であり;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20及びR21の各々は、独立して水素、アルキル、アルケニル、アルキニル、シクロアルキル、アリール、ヘテロアリール、ヘテロシクリル、アルキル-シクロアルキレン又はシクロアルキル-アルキレンであり、
ここでアルキル、アリール、アリールアルキル、アルカリル、ヘテロアリール、アルケニル、アルキニル、シクロアルキル、ヘテロシクリル又はアルキル-シクロアルキルの各々は、任意に置換されている。)。 - 式IIAを有する、請求項3記載の化合物。
- 式IIIAを有する、請求項3記載の化合物。
- 式IVAを有する、請求項3記載の化合物。
- 式VAを有する、請求項3記載の化合物。
- 式VIAを有する、請求項3記載の化合物。
- 式VIIAを有する、請求項3記載の化合物。
- 式IIB、IIIB、IVB、VB、VIB又はVIIBによる請求項1記載の化合物、又はそれらの単一の鏡像異性体、鏡像異性体対の混合物、個別のジアステレオマー、ジアステレオマーの混合物、若しくは互変異性体;又は、それらの医薬として許容し得る塩、溶媒和物、若しくはプロドラッグ:
R1及びR2の各々は独立して、-OR6、-NR14R15、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル又はヘテロアリールであり;
R3の各々は、H、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-P(O)(OR6)2、又は-C(O)NHSO2R21であり;
R5の各々は、H、ハロゲン、シアノ、アジド、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルカリル、シクロアルキル、ヘテロシクリル、ヘテロアリール、-OR6、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-NHSO2R13、-NR14R15、-SO3R17、若しくは-SO2R18であり;
各Lは、結合、又はO、S、NR16、若しくはCR19R20などの任意の二価の基であり;かつ
R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20及びR21の各々は、独立して水素、アルキル、アルケニル、アルキニル、シクロアルキル、アリール、ヘテロアリール、ヘテロシクリル、アルキル-シクロアルキレン又はシクロアルキル-アルキレンであり、
ここでアルキル、アリール、アリールアルキル、アルカリル、ヘテロアリール、アルケニル、アルキニル、シクロアルキル、ヘテロシクリル又はアルキル-シクロアルキルの各々は、任意に置換されている。)。 - 式IIBを有する、請求項10記載の化合物。
- 式IIIBを有する、請求項10記載の化合物。
- 式IVBを有する、請求項10記載の化合物。
- 式VBを有する、請求項10記載の化合物。
- 式VIBを有する、請求項10記載の化合物。
- 式VIIBを有する、請求項10記載の化合物。
- アルキル、アリール、アリールアルキル、アルカリル、ヘテロアリール、アルケニル、アルキニル、シクロアルキル、ヘテロシクリル、又はアルキル-シクロアルキルの各々が、置換されていない、請求項1〜16のいずれか一項記載の化合物。
- R1の各々が独立して、アルキル、アルコキシ、ヒドロキシ又はアリールである、請求項1〜3、5〜7、10及び12〜14のいずれか一項記載の化合物。
- R1の各々が独立して、メチル、エチル、メトキシ、エトキシ又はヒドロキシである、請求項1〜3、5〜7、10及び12〜14のいずれか一項記載の化合物。
- R2の各々が独立して、シクロアルキル、アリール又はヘテロアリールであり、かつここでシクロアルキル、アリール又はヘテロアリールの各々が、任意に置換されている、請求項1〜16のいずれか一項記載の化合物。
- R3の各々が独立して、H、-C(O)R7、-C(O)OR8、-C(O)NR9R10、-C(=NR11)R12、-P(O)(OR6)2、又は-C(O)NHSO2R21である、請求項1〜6及び10〜13のいずれか一項記載の化合物。
- R3の各々が独立して、-C(O)OH、又は-C(O)OCH3である、請求項21記載の化合物。
- R4の各々が独立して、H、アルケニル、アルキニル、ハロゲン、アリール、ヘテロアリール又はそれらの組み合わせである、請求項1〜9のいずれか一項記載の化合物。
- R5の各々が独立して、アルキル、アルケニル、アルキニル(alknyl)、アリール、ヘテロアリール又はそれらの組み合わせである、請求項1〜16のいずれか一項記載の化合物。
- R6の各々が独立して、H、メチル、エチル、n-プロピル、iso-プロピル、n-ブチル、iso-ブチル又はtert-ブチルである、請求項1〜4、8〜11及び15〜16のいずれか一項記載の化合物。
- R8の各々が独立して、H、メチル、エチル、n-プロピル、iso-プロピル、n-ブチル、iso-ブチル又はtert-ブチルである、請求項1〜3、7〜10及び14〜16のいずれか一項記載の化合物。
- R16 の各々が独立して、H、メチル、エチル、n-プロピル、iso-プロピル、n-ブチル、iso-ブチル、tert-ブチル、シクロアルキル又はヘテロシクリルである、請求項1〜3、5、7、10、12及び15のいずれか一項記載の化合物。
- 前記化合物が、同位体濃縮されている、請求項1〜31のいずれか一項記載の化合物。
- 請求項1〜32のいずれか一項記載の化合物、及び1種以上の医薬として許容し得る希釈剤、賦形剤、又は担体を含有する、医薬組成物。
- 第二の抗ウイルス薬を更に含有する、請求項33記載の医薬組成物。
- 前記第二の抗ウイルス薬が、インターフェロン、リバビリン、インターロイキン、NS3プロテアーゼ阻害剤、システインプロテアーゼ阻害剤、フェナトレンキノン、チアゾリジン、ベンズアニリド、ヘリカーゼ阻害剤、ポリメラーゼ阻害剤、ヌクレオチド類似体、リオトキシン、アセルレニン、アンチセンスホスホロチオエートオリゴデオキシヌクレオチド、IRES依存性翻訳阻害剤、リボザイム、及びそれらの組み合わせからなる群から選択される、請求項34記載の医薬組成物。
- 前記第二の抗ウイルス薬がインターフェロンである、請求項34記載の医薬組成物。
- 前記インターフェロンが、ペグ化インターフェロンα2a、インターフェロンアルファコン-1、天然インターフェロン、アルブフェロン、インターフェロンβ‐1a、ωインターフェロン、インターフェロンα、インターフェロンγ、インターフェロンτ、インターフェロンδ、インターフェロンγ‐1b、及びそれらの組み合わせからなる群から選択される、請求項36記載の医薬組成物。
- 前記組成物が、単回用量の投与のために製剤される、請求項33〜37のいずれか一項記載の医薬組成物。
- 前記組成物が、経口剤形、非経口剤形、又は静脈内剤形として製剤される、請求項33〜37のいずれか一項記載の医薬組成物。
- 前記経口剤形が、錠剤又はカプセル剤である、請求項39記載の医薬組成物。
- 前記化合物が、約0.5mg〜約1,000mgの用量で毎日投与される、請求項33〜40のいずれか一項記載の医薬組成物。
- 請求項1〜32のいずれか一項記載の化合物又は請求項33〜41のいずれか一項記載の医薬組成物を、HCVに感染した対象に投与することを含む、HCV感染を治療又は予防する方法。
- 請求項1〜32のいずれか一項記載の化合物又は請求項33〜41のいずれか一項記載の医薬組成物を、HCV感染と関連した肝疾患又は肝障害を有する対象に投与することを含む、HCV感染と関連した肝疾患又は肝障害の1つ以上の症状を治療し、予防し、又は寛解する方法。
- 第二の抗ウイルス薬を組み合わせで又は交互に投与することを含む、請求項42又は43のいずれか一項記載の方法。
- 前記第二の抗ウイルス薬が、インターフェロン、リバビリン、アマンタジン、インターロイキン、NS3プロテアーゼ阻害剤、システインプロテアーゼ阻害剤、フェナトレンキノン、チアゾリジン、ベンズアニリド、ヘリカーゼ阻害剤、ポリメラーゼ阻害剤、ヌクレオチド類似体、リオトキシン、アセルレニン、アンチセンスホスホロチオエートオリゴ(ologo)デオキシヌクレオチド、IRES依存性翻訳阻害剤、リボザイム、及びそれらの組み合わせからなる群から選択される、請求項44記載の使用。
- 前記第二の抗ウイルス薬がインターフェロンである、請求項44記載の方法。
- 前記インターフェロンが、ペグ化インターフェロンα2a、インターフェロンアルファコン-1、天然インターフェロン、アルブフェロン、インターフェロンβ‐1a、ωインターフェロン、インターフェロンα、インターフェロンγ、インターフェロンτ、インターフェロンδ、インターフェロンγ‐1b、及びそれらの組み合わせからなる群から選択される、請求項46記載の方法。
- 宿主を、請求項1〜32のいずれか一項記載の化合物又は請求項33〜41のいずれか一項記載の医薬組成物と接触させることを含む、HCVウイルスに感染した宿主におけるHCVウイルスの複製を阻害する方法。
- 前記宿主がヒトである、請求項48記載の方法。
- HCVポリメラーゼを、請求項1〜32のいずれか一項記載の化合物又は請求項33〜41のいずれか一項記載の医薬組成物と接触させることを含む、HCVポリメラーゼの活性を阻害する方法。
- 前記ポリメラーゼが、HCV NS5Bポリメラーゼである、請求項50記載の方法。
- 療法において使用するための、請求項1〜32のいずれか一項記載の化合物又は請求項33〜41のいずれか一項記載の医薬組成物。
- HCV感染の治療又は予防において使用するための、請求項1〜32のいずれか一項記載の化合物又は請求項33〜41のいずれか一項記載の医薬組成物。
- HCV感染の治療又は予防のための医薬品の製造における、請求項1〜32のいずれか一項記載の化合物又は請求項33〜41のいずれか一項記載の医薬組成物の使用。
- HCV感染と関連した肝疾患又は肝障害の1つ以上の症状の治療、予防、又は寛解のための医薬品の製造における、請求項1〜32のいずれか一項記載の化合物又は請求項33〜41のいずれか一項記載の医薬組成物の使用。
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Also Published As
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EP2403860B1 (en) | 2015-11-04 |
JP5690286B2 (ja) | 2015-03-25 |
EP2403860A2 (en) | 2012-01-11 |
TW201036988A (en) | 2010-10-16 |
WO2010101967A2 (en) | 2010-09-10 |
US20100233123A1 (en) | 2010-09-16 |
WO2010101967A3 (en) | 2010-11-11 |
US8193372B2 (en) | 2012-06-05 |
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