JP2003520783A5 - - Google Patents
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- Publication number
- JP2003520783A5 JP2003520783A5 JP2001537327A JP2001537327A JP2003520783A5 JP 2003520783 A5 JP2003520783 A5 JP 2003520783A5 JP 2001537327 A JP2001537327 A JP 2001537327A JP 2001537327 A JP2001537327 A JP 2001537327A JP 2003520783 A5 JP2003520783 A5 JP 2003520783A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- alkyl
- group
- pharmaceutically acceptable
- alkynyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 description 65
- 150000001875 compounds Chemical class 0.000 description 65
- 239000000203 mixture Substances 0.000 description 40
- 210000004027 cell Anatomy 0.000 description 37
- 238000009472 formulation Methods 0.000 description 31
- 229910052717 sulfur Inorganic materials 0.000 description 31
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 30
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 30
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 30
- 125000003342 alkenyl group Chemical group 0.000 description 26
- 125000000304 alkynyl group Chemical group 0.000 description 26
- 150000003839 salts Chemical class 0.000 description 26
- 229910052760 oxygen Inorganic materials 0.000 description 23
- 241000124008 Mammalia Species 0.000 description 21
- 206010028980 Neoplasm Diseases 0.000 description 19
- 239000003814 drug Substances 0.000 description 18
- 229940124597 therapeutic agent Drugs 0.000 description 16
- 229930010555 Inosine Natural products 0.000 description 15
- UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 description 15
- 201000011510 cancer Diseases 0.000 description 15
- 229940104302 cytosine Drugs 0.000 description 15
- 229940124447 delivery agent Drugs 0.000 description 15
- 238000012377 drug delivery Methods 0.000 description 15
- 125000005843 halogen group Chemical group 0.000 description 15
- 229960003786 inosine Drugs 0.000 description 15
- 229940113082 thymine Drugs 0.000 description 15
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 14
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 14
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 14
- 125000002947 alkylene group Chemical group 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000008194 pharmaceutical composition Substances 0.000 description 10
- 239000002246 antineoplastic agent Substances 0.000 description 8
- 210000003169 central nervous system Anatomy 0.000 description 8
- 229930024421 Adenine Natural products 0.000 description 7
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 7
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 229960000643 adenine Drugs 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 210000004698 lymphocyte Anatomy 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- 229940035893 uracil Drugs 0.000 description 7
- 210000004962 mammalian cell Anatomy 0.000 description 6
- 239000000825 pharmaceutical preparation Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- -1 nucleoside monophosphates Chemical class 0.000 description 5
- 230000029812 viral genome replication Effects 0.000 description 5
- 201000009030 Carcinoma Diseases 0.000 description 4
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 4
- 206010025323 Lymphomas Diseases 0.000 description 4
- 206010029260 Neuroblastoma Diseases 0.000 description 4
- 206010039491 Sarcoma Diseases 0.000 description 4
- 241000700605 Viruses Species 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 208000032839 leukemia Diseases 0.000 description 4
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 4
- 239000002777 nucleoside Substances 0.000 description 4
- 241000282414 Homo sapiens Species 0.000 description 3
- 208000036142 Viral infection Diseases 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000009385 viral infection Effects 0.000 description 3
- NMUSYJAQQFHJEW-UHFFFAOYSA-N 5-Azacytidine Natural products O=C1N=C(N)N=CN1C1C(O)C(O)C(CO)O1 NMUSYJAQQFHJEW-UHFFFAOYSA-N 0.000 description 2
- NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 description 2
- PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- 229960002756 azacitidine Drugs 0.000 description 2
- 229960002436 cladribine Drugs 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 description 2
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 2
- 229960005277 gemcitabine Drugs 0.000 description 2
- 208000006454 hepatitis Diseases 0.000 description 2
- 231100000283 hepatitis Toxicity 0.000 description 2
- 229960001428 mercaptopurine Drugs 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000004712 monophosphates Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000003833 nucleoside derivatives Chemical class 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 241001529453 unidentified herpesvirus Species 0.000 description 2
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 1
- 208000014644 Brain disease Diseases 0.000 description 1
- 0 C*(N*)N*I Chemical compound C*(N*)N*I 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000701022 Cytomegalovirus Species 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 241000711557 Hepacivirus Species 0.000 description 1
- 241000700721 Hepatitis B virus Species 0.000 description 1
- 208000005176 Hepatitis C Diseases 0.000 description 1
- 208000005331 Hepatitis D Diseases 0.000 description 1
- 241000724675 Hepatitis E virus Species 0.000 description 1
- 208000037262 Hepatitis delta Diseases 0.000 description 1
- 241000724709 Hepatitis delta virus Species 0.000 description 1
- 241000709721 Hepatovirus A Species 0.000 description 1
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 1
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 1
- 241000701085 Human alphaherpesvirus 3 Species 0.000 description 1
- 241000701041 Human betaherpesvirus 7 Species 0.000 description 1
- 241000701044 Human gammaherpesvirus 4 Species 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- 241000713340 Human immunodeficiency virus 2 Species 0.000 description 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
- 208000018501 Lymphatic disease Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102000015439 Phospholipases Human genes 0.000 description 1
- 108010064785 Phospholipases Proteins 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- 102000014384 Type C Phospholipases Human genes 0.000 description 1
- 108010079194 Type C Phospholipases Proteins 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 210000001130 astrocyte Anatomy 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 208000005252 hepatitis A Diseases 0.000 description 1
- 208000002672 hepatitis B Diseases 0.000 description 1
- 208000029570 hepatitis D virus infection Diseases 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 208000018555 lymphatic system disease Diseases 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- 210000004498 neuroglial cell Anatomy 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 208000017443 reproductive system disease Diseases 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16229099P | 1999-10-28 | 1999-10-28 | |
| US60/162,290 | 1999-10-28 | ||
| PCT/US2000/041352 WO2001034614A2 (en) | 1999-10-28 | 2000-10-20 | Compositions and methods for double-targeting virus infections and targeting cancer cells |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003520783A JP2003520783A (ja) | 2003-07-08 |
| JP2003520783A5 true JP2003520783A5 (https=) | 2007-12-06 |
| JP5031162B2 JP5031162B2 (ja) | 2012-09-19 |
Family
ID=22585012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001537327A Expired - Fee Related JP5031162B2 (ja) | 1999-10-28 | 2000-10-20 | ウイルス感染を二重ターゲティングおよびガン細胞をターゲティングするための組成物および方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6670341B1 (https=) |
| EP (1) | EP1228080A2 (https=) |
| JP (1) | JP5031162B2 (https=) |
| AU (1) | AU784146B2 (https=) |
| CA (1) | CA2389544C (https=) |
| HK (1) | HK1048820A1 (https=) |
| WO (1) | WO2001034614A2 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7135584B2 (en) * | 1995-08-07 | 2006-11-14 | Wake Forest University | Lipid analogs for treating viral infections |
| EP0781138B1 (en) * | 1994-08-29 | 2008-05-21 | Wake Forest University | Lipid analogs for treating viral infections |
| US7026469B2 (en) * | 2000-10-19 | 2006-04-11 | Wake Forest University School Of Medicine | Compositions and methods of double-targeting virus infections and cancer cells |
| US7309696B2 (en) | 2000-10-19 | 2007-12-18 | Wake Forest University | Compositions and methods for targeting cancer cells |
| CN1486289A (zh) * | 2001-05-29 | 2004-03-31 | 皇家菲利浦电子有限公司 | 金属-陶瓷的结合 |
| EP1423976A1 (en) * | 2001-08-31 | 2004-06-02 | Thomson Licensing S.A. | Sequence counter for an audio visual stream |
| EP1460082A1 (en) * | 2003-03-19 | 2004-09-22 | Heidelberg Pharma Holding GmbH | Phospholipid esters of clofarabine derivatives |
| US20050187191A1 (en) * | 2004-02-20 | 2005-08-25 | Kucera Louis S. | Methods and compositions for the treatment of respiratory syncytial virus |
| AU2005228410A1 (en) | 2004-03-29 | 2005-10-13 | University Of South Florida | Effective treatment of tumors and cancer with triciribine and related compounds |
| JP2008538354A (ja) * | 2005-04-08 | 2008-10-23 | キメリクス，インコーポレイテッド | ウイルス感染症およびその他の内科疾患を治療するための化合物、組成物および方法 |
| JP2008535862A (ja) | 2005-04-08 | 2008-09-04 | キメリクス，インコーポレイテッド | ポックスウイルス感染の治療のための化合物、組成物および方法 |
| NO324263B1 (no) * | 2005-12-08 | 2007-09-17 | Clavis Pharma Asa | Kjemiske forbindelser, anvendelse derav ved behandling av kreft, samt farmasoytiske preparater som omfatter slike forbindelser |
| ES2600792T3 (es) | 2006-05-03 | 2017-02-10 | Chimerix, Inc. | Alcoxialquilésteres metabólicamente estables de fosfonatos, fosfonatos nucleosídicos y fosfatos nucleosídicos antivirales o antiproliferativos |
| UA99308C2 (ru) * | 2007-09-26 | 2012-08-10 | Маунт Синай Скул Оф Медсин | Аналог азацитидина и его применение |
| EP2254582B1 (en) | 2008-01-25 | 2016-01-20 | Chimerix, Inc. | Methods of treating viral infections |
| CN102271517B (zh) * | 2008-11-06 | 2015-04-08 | 脉管生物生长有限公司 | 氧化的脂质化合物和其用途 |
| US8614200B2 (en) | 2009-07-21 | 2013-12-24 | Chimerix, Inc. | Compounds, compositions and methods for treating ocular conditions |
| US9006218B2 (en) | 2010-02-12 | 2015-04-14 | Chimerix Inc. | Nucleoside phosphonate salts |
| US9278135B2 (en) | 2010-04-26 | 2016-03-08 | Chimerix Inc. | Methods of treating retroviral infections and related dosage regimes |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4559157A (en) | 1983-04-21 | 1985-12-17 | Creative Products Resource Associates, Ltd. | Cosmetic applicator useful for skin moisturizing |
| LU84979A1 (fr) | 1983-08-30 | 1985-04-24 | Oreal | Composition cosmetique ou pharmaceutique sous forme aqueuse ou anhydre dont la phase grasse contient un polyether oligomere et polyethers oligomeres nouveaux |
| JPS61246196A (ja) * | 1985-04-22 | 1986-11-01 | Fuji Kagaku Kogyo Kk | ５′−０−アシル−５−フルオロウリジン及びその製造方法 |
| US4820508A (en) | 1987-06-23 | 1989-04-11 | Neutrogena Corporation | Skin protective composition |
| US4992478A (en) | 1988-04-04 | 1991-02-12 | Warner-Lambert Company | Antiinflammatory skin moisturizing composition and method of preparing same |
| US4938949A (en) | 1988-09-12 | 1990-07-03 | University Of New York | Treatment of damaged bone marrow and dosage units therefor |
| EP0533825B1 (en) * | 1990-06-15 | 1996-04-24 | Wake Forest University | Ether lipid-nucleoside covalent conjugates |
| IL105244A (en) | 1993-03-31 | 2003-07-31 | Dpharm Ltd | Prodrugs with enhanced penetration into cells |
| US6413949B1 (en) | 1995-06-07 | 2002-07-02 | D-Pharm, Ltd. | Prodrugs with enhanced penetration into cells |
| US5534499A (en) * | 1994-05-19 | 1996-07-09 | The University Of British Columbia | Lipophilic drug derivatives for use in liposomes |
| EP0781138B1 (en) * | 1994-08-29 | 2008-05-21 | Wake Forest University | Lipid analogs for treating viral infections |
| JP3781877B2 (ja) * | 1997-10-03 | 2006-05-31 | 株式会社ムック | アスコルビン酸誘導体またはその塩、および医薬 |
| IL131887A0 (en) | 1999-09-14 | 2001-03-19 | Dpharm Ltd | Phospholipid prodrugs of anti-proliferative drugs |
-
2000
- 2000-10-19 US US09/693,658 patent/US6670341B1/en not_active Expired - Lifetime
- 2000-10-20 CA CA2389544A patent/CA2389544C/en not_active Expired - Fee Related
- 2000-10-20 EP EP00989666A patent/EP1228080A2/en not_active Withdrawn
- 2000-10-20 JP JP2001537327A patent/JP5031162B2/ja not_active Expired - Fee Related
- 2000-10-20 WO PCT/US2000/041352 patent/WO2001034614A2/en not_active Ceased
- 2000-10-20 AU AU26146/01A patent/AU784146B2/en not_active Ceased
- 2000-10-20 HK HK03100904.2A patent/HK1048820A1/zh unknown
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