JP5372751B2 - Ａｚａ−ペプチドプロテアーゼ阻害剤 - Google Patents
Ａｚａ−ペプチドプロテアーゼ阻害剤 Download PDFInfo
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- JP5372751B2 JP5372751B2 JP2009520841A JP2009520841A JP5372751B2 JP 5372751 B2 JP5372751 B2 JP 5372751B2 JP 2009520841 A JP2009520841 A JP 2009520841A JP 2009520841 A JP2009520841 A JP 2009520841A JP 5372751 B2 JP5372751 B2 JP 5372751B2
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- Prior art keywords
- substituted
- aryl
- alkylene
- alkyl
- heterocyclyl
- Prior art date
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- 239000000137 peptide hydrolase inhibitor Substances 0.000 title description 2
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 573
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- 239000012453 solvate Substances 0.000 claims abstract description 41
- 125000003118 aryl group Chemical group 0.000 claims description 290
- 125000002947 alkylene group Chemical group 0.000 claims description 242
- 125000000217 alkyl group Chemical group 0.000 claims description 233
- 125000003107 substituted aryl group Chemical group 0.000 claims description 50
- 125000001188 haloalkyl group Chemical group 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 abstract description 89
- 150000002148 esters Chemical class 0.000 abstract description 38
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract description 30
- 238000002560 therapeutic procedure Methods 0.000 abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 337
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 179
- 239000000651 prodrug Substances 0.000 description 176
- 229940002612 prodrug Drugs 0.000 description 176
- 239000003112 inhibitor Substances 0.000 description 174
- -1 cyano, formyl Chemical group 0.000 description 160
- 125000001424 substituent group Chemical group 0.000 description 127
- 239000011541 reaction mixture Substances 0.000 description 100
- 229910052760 oxygen Inorganic materials 0.000 description 89
- 235000019439 ethyl acetate Nutrition 0.000 description 88
- 125000004432 carbon atom Chemical group C* 0.000 description 87
- 229910052740 iodine Inorganic materials 0.000 description 87
- 125000001072 heteroaryl group Chemical group 0.000 description 84
- 125000000547 substituted alkyl group Chemical group 0.000 description 84
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- 229910052717 sulfur Inorganic materials 0.000 description 58
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- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 51
- 125000006239 protecting group Chemical group 0.000 description 50
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 47
- 238000000034 method Methods 0.000 description 47
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- 150000003833 nucleoside derivatives Chemical class 0.000 description 44
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- 239000007787 solid Substances 0.000 description 43
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 34
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- FVJRBJIENDRNBE-UHFFFAOYSA-N N-(6-aminohexyl)-1-naphthalenesulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)NCCCCCCN)=CC=CC2=C1 FVJRBJIENDRNBE-UHFFFAOYSA-N 0.000 description 31
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 31
- 238000001819 mass spectrum Methods 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 125000003342 alkenyl group Chemical group 0.000 description 30
- 125000000304 alkynyl group Chemical group 0.000 description 30
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- 229940124597 therapeutic agent Drugs 0.000 description 29
- 239000012267 brine Substances 0.000 description 27
- 239000004030 hiv protease inhibitor Substances 0.000 description 27
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 27
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 26
- 238000003818 flash chromatography Methods 0.000 description 26
- 239000008194 pharmaceutical composition Substances 0.000 description 26
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 23
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- 238000006243 chemical reaction Methods 0.000 description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 229940122440 HIV protease inhibitor Drugs 0.000 description 21
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- 229910052739 hydrogen Inorganic materials 0.000 description 21
- 239000002773 nucleotide Substances 0.000 description 21
- 125000003729 nucleotide group Chemical group 0.000 description 21
- 239000011734 sodium Substances 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 108010007843 NADH oxidase Proteins 0.000 description 20
- XQSPYNMVSIKCOC-NTSWFWBYSA-N Emtricitabine Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1 XQSPYNMVSIKCOC-NTSWFWBYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 229940099797 HIV integrase inhibitor Drugs 0.000 description 19
- 238000005481 NMR spectroscopy Methods 0.000 description 19
- 125000000753 cycloalkyl group Chemical group 0.000 description 19
- 239000003084 hiv integrase inhibitor Substances 0.000 description 19
- 239000000843 powder Substances 0.000 description 19
- 125000001544 thienyl group Chemical group 0.000 description 19
- MPNGLQDRSJNLPL-UHFFFAOYSA-N 4-[[2-[[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-1,2,4-triazol-3-yl]sulfanyl]acetyl]amino]-3-chlorobenzoic acid Chemical compound ClC1=CC(C(=O)O)=CC=C1NC(=O)CSC1=NN=C(Br)N1C(C1=CC=CC=C11)=CC=C1C1CC1 MPNGLQDRSJNLPL-UHFFFAOYSA-N 0.000 description 18
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 18
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 18
- 229940124784 gp41 inhibitor Drugs 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 17
- 239000013543 active substance Substances 0.000 description 16
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 125000004076 pyridyl group Chemical group 0.000 description 16
- PRXGMEURJXGKOP-UHFFFAOYSA-N NP(N)=O Chemical class NP(N)=O PRXGMEURJXGKOP-UHFFFAOYSA-N 0.000 description 15
- 125000004404 heteroalkyl group Chemical group 0.000 description 15
- CUFQBQOBLVLKRF-RZDMPUFOSA-N (4r)-3-[(2s,3s)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-phenylbutanoyl]-5,5-dimethyl-n-[(2-methylphenyl)methyl]-1,3-thiazolidine-4-carboxamide Chemical compound CC1=CC=CC=C1CNC(=O)[C@@H]1C(C)(C)SCN1C(=O)[C@@H](O)[C@@H](NC(=O)C=1C(=C(O)C=CC=1)C)CC1=CC=CC=C1 CUFQBQOBLVLKRF-RZDMPUFOSA-N 0.000 description 14
- KYRSNWPSSXSNEP-ZRTHHSRSSA-N (4r,5s,6s,7r)-1,3-bis[(3-aminophenyl)methyl]-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one Chemical compound NC1=CC=CC(CN2C(N(CC=3C=C(N)C=CC=3)[C@H](CC=3C=CC=CC=3)[C@H](O)[C@@H](O)[C@H]2CC=2C=CC=CC=2)=O)=C1 KYRSNWPSSXSNEP-ZRTHHSRSSA-N 0.000 description 14
- KRZBCHWVBQOTNZ-PSEXTPKNSA-N 3,5-di-O-caffeoyl quinic acid Chemical compound O([C@@H]1C[C@](O)(C[C@H]([C@@H]1O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 KRZBCHWVBQOTNZ-PSEXTPKNSA-N 0.000 description 14
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- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 14
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- YIBOMRUWOWDFLG-ONEGZZNKSA-N rilpivirine Chemical compound CC1=CC(\C=C\C#N)=CC(C)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 YIBOMRUWOWDFLG-ONEGZZNKSA-N 0.000 description 14
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- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- 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
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
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- Engineering & Computer Science (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| US83245906P | 2006-07-21 | 2006-07-21 | |
| US60/832,459 | 2006-07-21 | ||
| PCT/US2007/016397 WO2008011116A2 (en) | 2006-07-21 | 2007-07-19 | Aza-peptide protease inhibitors |
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| US20140031250A1 (en) | 2010-10-07 | 2014-01-30 | David Tsai Ting | Biomarkers of Cancer |
| EP2764002B1 (en) | 2012-10-03 | 2018-02-28 | Gilead Sciences, Inc. | Methods for preparing anti-viral nucleotide analogs |
| WO2015157623A1 (en) | 2014-04-11 | 2015-10-15 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Immune gene signatures in urothelial carcinoma (uc) |
| EP3142659B1 (en) * | 2014-05-16 | 2021-03-24 | Purdue Research Foundation | Hiv-1 protease inhibitors and uses thereof |
| EP3760208B1 (en) | 2014-06-25 | 2024-05-29 | The General Hospital Corporation | Targeting human satellite ii (hsatii) |
| CN104356054B (zh) * | 2014-09-30 | 2017-04-19 | 东北制药集团股份有限公司 | 一种制备阿扎那韦单体的方法 |
| US9724395B2 (en) | 2014-10-21 | 2017-08-08 | Sciclone Pharmaceuticals, Inc. | Treatment of cancer with immune stimulators |
| CN118286245A (zh) | 2014-12-26 | 2024-07-05 | 埃莫里大学 | N4-羟基胞苷和衍生物及与其相关的抗病毒用途 |
| US10034901B2 (en) | 2015-01-22 | 2018-07-31 | University Of Massachusetts | Cancer immunotherapy |
| CN108139375A (zh) | 2015-06-26 | 2018-06-08 | 贝斯以色列女执事医疗中心股份有限公司 | 靶向髓样衍生的抑制细胞中的四跨膜蛋白33(tspan33)的癌症疗法 |
| JP7178906B2 (ja) | 2016-05-19 | 2022-11-28 | ザ ジェネラル ホスピタル コーポレイション | ナチュラルキラー細胞および制御性Ｔ細胞の活性を強化するためのプラットフォームである、その受容体ＩＬ－２Ｒβに繋ぎ止められたインターロイキン－２ |
| EP3532638A4 (en) | 2016-10-31 | 2020-07-29 | University of Massachusetts | TARGETING MICROARN-101-3 P IN CARCINOTHERAPY |
| JOP20180009A1 (ar) | 2017-02-06 | 2019-01-30 | Gilead Sciences Inc | مركبات مثبط فيروس hiv |
| US11331331B2 (en) | 2017-12-07 | 2022-05-17 | Emory University | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
| US11766455B2 (en) | 2017-12-14 | 2023-09-26 | Ezy Biotech Llc | Subject-specific tumor inhibiting cells and the use thereof |
| US11814623B2 (en) | 2018-01-30 | 2023-11-14 | University Of Massachusetts | Methods of treating a wound using epigenetic regulation |
| EP4317972A3 (en) | 2018-02-06 | 2024-03-13 | The General Hospital Corporation | Repeat rna as biomarkers of tumor immune response |
| TWI766172B (zh) * | 2018-07-30 | 2022-06-01 | 美商基利科學股份有限公司 | 抗hiv化合物 |
| EP3947640A4 (en) | 2019-04-02 | 2022-12-14 | The Brigham & Women's Hospital, Inc. | PROCEDURE FOR DETERMINING THE PROGRESSION OF PRIMARY MELANOMA |
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| US4816570A (en) * | 1982-11-30 | 1989-03-28 | The Board Of Regents Of The University Of Texas System | Biologically reversible phosphate and phosphonate protective groups |
| US4968788A (en) * | 1986-04-04 | 1990-11-06 | Board Of Regents, The University Of Texas System | Biologically reversible phosphate and phosphonate protective gruops |
| ES2118069T3 (es) * | 1990-09-14 | 1998-09-16 | Acad Of Science Czech Republic | Profarmacos de fosfonatos. |
| DK0521827T3 (da) * | 1991-07-03 | 1996-11-11 | Ciba Geigy Ag | Farmakologisk virksomme hydrazinderivater og fremgangsmåde til deres fremstilling |
| ES2093394T3 (es) * | 1992-12-23 | 1996-12-16 | Ciba Geigy Ag | Derivados de hidrazina antiretrovirales. |
| US5461067A (en) * | 1993-02-25 | 1995-10-24 | Abbott Laboratories | Retroviral protease inhibiting compounds |
| WO1997046514A1 (en) * | 1996-05-31 | 1997-12-11 | Novartis Ag | Process for the preparation of hydrazine derivatives useful as intermediates for the preparation of peptide analogues |
| US20050239054A1 (en) | 2002-04-26 | 2005-10-27 | Arimilli Murty N | Method and compositions for identifying anti-HIV therapeutic compounds |
| US7339930B2 (en) | 2002-11-22 | 2008-03-04 | Sun Microsystems, Inc. | Method and apparatus for performing an address lookup using a multi-bit trie with backtracking |
| WO2005061487A1 (en) * | 2003-12-11 | 2005-07-07 | Abbott Laboratories | Hiv protease inhibiting compounds |
| EP1713470A1 (en) * | 2004-01-30 | 2006-10-25 | Pfizer, Inc. | Therapeutic combinations |
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- 2007-07-19 NZ NZ573888A patent/NZ573888A/en unknown
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2012
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| WO2008011116A3 (en) | 2008-04-24 |
| CA2657821A1 (en) | 2008-01-24 |
| EP2049547A2 (en) | 2009-04-22 |
| JP2009544612A (ja) | 2009-12-17 |
| US20090099096A1 (en) | 2009-04-16 |
| WO2008011116A2 (en) | 2008-01-24 |
| JP2013056926A (ja) | 2013-03-28 |
| AU2007275689A1 (en) | 2008-01-24 |
| US7741345B2 (en) | 2010-06-22 |
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