AR046201A1 - Metodos para preparar derivados 7-(beta-d-ribofuranosilo sustituido en 2'-r1)-4(nr2r3)-5-(etin-1-ilo sustituido)- pirrol[2,3- d]pirimidina - Google Patents
Metodos para preparar derivados 7-(beta-d-ribofuranosilo sustituido en 2'-r1)-4(nr2r3)-5-(etin-1-ilo sustituido)- pirrol[2,3- d]pirimidinaInfo
- Publication number
- AR046201A1 AR046201A1 ARP040103896A ARP040103896A AR046201A1 AR 046201 A1 AR046201 A1 AR 046201A1 AR P040103896 A ARP040103896 A AR P040103896A AR P040103896 A ARP040103896 A AR P040103896A AR 046201 A1 AR046201 A1 AR 046201A1
- Authority
- AR
- Argentina
- Prior art keywords
- substituted
- amino
- hydrogen
- pyrimidine
- alkyl
- Prior art date
Links
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title abstract 9
- 238000000034 method Methods 0.000 title abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 10
- 125000001072 heteroaryl group Chemical group 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- -1 amino, substituted amino, hydroxy Chemical group 0.000 abstract 6
- HMFHBZSHGGEWLO-TXICZTDVSA-N beta-D-ribose Chemical group OC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-TXICZTDVSA-N 0.000 abstract 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 230000008878 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- 125000005415 substituted alkoxy group Chemical group 0.000 abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 2
- 125000004665 trialkylsilyl group Chemical group 0.000 abstract 2
- 150000000841 D-ribofuranose derivatives Chemical class 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000005017 substituted alkenyl group Chemical group 0.000 abstract 1
- 125000004426 substituted alkynyl group Chemical group 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/14—Pyrrolo-pyrimidine radicals
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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
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Virology (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Reivindicación 1: Un método para preparar 7-(beta-D-ribofuranosilo sustituido en 2´-R1)-4-(NR2R3)-5-(etin-1-il)-pirro[2,3-d]pirimidina de la fórmula (1), donde: R1 se selecciona del grupo formado por alquilo, alquilo sustituido, alquenilo, alquenilo sustituido, alquinilo, alquinilo sustituido; R2 y R3 se seleccionan independientemente entre hidrógeno, alquilo, alquilo sustituido, amino, amino sustituido, hidroxi, alcoxi, alcoxi sustituido, formilo y acilo, y donde R2 y R3, junto con el átomo de nitrógeno unido a los mismos, se unen para formar un anillo heterocíclico o heterocíclico sustituido, con la condición que cuando uno de R2 o R3 es amino, amino sustituido, hidroxi, alcoxi, alcoxi sustituido, entonces el otro es hidrógeno; caracterizado porque dicho método comprende: a) hacer reaccionar al menos un equivalente estequiométrico de 4,5-dihalo-7H-pirro[2,3-d]pirimidina con D-ribofuranosa sustituida en 2-R1 protegida con 1-bromo-3,5-di-O bajo condiciones que permitan el acoplamiento para proveer 7-(beta-D-ribofuranosilo sustituido en 2'-R1 protegido con 3',5'-di-O)-4,5-dihalo-pirrol[2,3-d]pirimidina, donde los grupos halo de 4,5-dihalo son ortogonales entre sí; b) separar los grupos protectores del compuesto preparado previamente en a) para proveer la 7-(beta-D-ribofuranosilo sustituido en 2'-R1)-4,5-dihalo-pirrol[2,3-d]pirimidina; c) aminar selectivamente el grupo 4-halo en dicha 7-(beta-D-ribofuranosilo sustituido en 2'-R1)-4,5-dihalo-pirrol[2,3- d]pirimidina para proveer un sustituyente 4-amino opcionalmente sustituido de la fórmula NR2R3, donde R2 y R3 son como se definieron previamente; d) hacer reaccionar la 7-(beta-ribofuranosilo sustituido en 2'-R1)-4-(NR2R3)-5-halo-pirrol[2,3- d]pirimidina con un compuesto acetileno monoprotegido bajo condiciones de acoplamiento para proveer la 7-(beta-D-ribofuranosilo sustituido en 2'-R1)-4-(NR2R3)-5-(etin-1-ilo protegido)-pirrol[2,3-d]pirimidina; y e) separar dicho grupo protector de dicha 5-(etin-1-ilo protegido) para proveer la 7-(beta-D-ribofuranosilo sustituido en 2'-R1)-4-(NR2R3)-5-(etin-1-il)-pirrol[2,3-d]pirimidina. Reivindicación 52: Un compuesto, caracterizado porque es de la fórmula (2), donde: R7 se selecciona del grupo formado por hidrógeno, trialquilsililo, fenilo, fenilo sustituido, alcoxialquilo, heteroarilo, heteroarilo sustituido, -C(O)OR4, donde R4 es hidrógeno o alquilo, -C(O)NR5R6, donde R5 y R6 se seleccionan independientemente del grupo formado por hidrógeno, alquilo, alquilo sustituido, amino, amino sustituido, arilo, arilo sustituido, heteroarilo, heteroarilo sustituido, heterociclos y heterociclos sustituido, siempre que solamente uno de R5 y R6 sea amino o amino sustituido, y además donde R5 y R6, junto con el átomo de nitrógeno unido a los mismos, forman un heterociclo o heterociclo sustituido; y Pg3 es un grupo protector de amino o hidrógeno. Reivindicación 54: Un compuesto, caracterizado porque es de la fórmula (3), donde: R7 se selecciona del grupo formado por hidrógeno, trialquilsililo, fenilo, fenilo sustituido, alcoxialquilo, heteroarilo, heteroarilo sustituido, -C(O)OR4, donde R4 es hidrógeno o alquilo, -C(O)NR5R6, donde R5 y R6 se seleccionan independientemente del grupo formado por hidrógeno, alquilo, alquilo sustituido, amino, amino sustituido, arilo, arilo sustituido, heteroarilo, heteroarilo sustituido, heterociclos y heterociclos sustituido, siempre que solamente uno de R5 y R6 sea amino o amino sustituido, y además donde R5 y R6, junto con el átomo de nitrógeno unido a los mismos, forman un heterociclo o heterociclo sustituido; y Pg3 es un grupo protector de amino o hidrógeno.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51515303P | 2003-10-27 | 2003-10-27 | |
| US10/861,090 US7202223B2 (en) | 2003-10-27 | 2004-06-04 | Nucleoside compounds for treating viral infections |
| US10/861,311 US7144868B2 (en) | 2003-10-27 | 2004-06-04 | Nucleoside compounds for treating viral infections |
| US60281504P | 2004-08-18 | 2004-08-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR046201A1 true AR046201A1 (es) | 2005-11-30 |
Family
ID=34577847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP040103896A AR046201A1 (es) | 2003-10-27 | 2004-10-26 | Metodos para preparar derivados 7-(beta-d-ribofuranosilo sustituido en 2'-r1)-4(nr2r3)-5-(etin-1-ilo sustituido)- pirrol[2,3- d]pirimidina |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7169918B2 (es) |
| EP (1) | EP1682564A1 (es) |
| AR (1) | AR046201A1 (es) |
| CA (1) | CA2543116A1 (es) |
| SV (1) | SV2005001918A (es) |
| UY (1) | UY28582A1 (es) |
| WO (1) | WO2005044835A1 (es) |
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| WO2003100017A2 (en) | 2002-05-24 | 2003-12-04 | Isis Pharmaceuticals, Inc. | Oligonucleotides having modified nucleoside units |
| WO2003104420A2 (en) * | 2002-06-07 | 2003-12-18 | The Regents Of The University Of California | Electrochemical detection of single nucleotide polymorphisms (snps) |
| CA2490666A1 (en) | 2002-07-16 | 2004-01-22 | Merck & Co., Inc. | Nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase |
| KR20050037559A (ko) | 2002-07-25 | 2005-04-22 | 마이크로로직스 바이오테크, 인코포레이티드 | 항바이러스성 ７-데아자 ｄ-뉴클레오시드 및 그의 용도 |
| EA200500584A1 (ru) | 2002-09-30 | 2006-02-24 | Дженелэбс Текнолоджиз, Инк. | Нуклеозидные производные для лечения инфекционных заболеваний, вызванных вирусом гепатита c |
| US7094768B2 (en) * | 2002-09-30 | 2006-08-22 | Genelabs Technologies, Inc. | Nucleoside derivatives for treating hepatitis C virus infection |
| AU2003291682A1 (en) | 2002-11-05 | 2004-06-03 | Isis Pharmaceuticals, Inc. | 2'-methoxy substituted oligomeric compounds and compositions for use in gene modulations |
-
2004
- 2004-10-20 CA CA002543116A patent/CA2543116A1/en not_active Abandoned
- 2004-10-20 US US10/970,641 patent/US7169918B2/en not_active Expired - Fee Related
- 2004-10-20 WO PCT/US2004/034756 patent/WO2005044835A1/en not_active Ceased
- 2004-10-20 EP EP04795860A patent/EP1682564A1/en not_active Withdrawn
- 2004-10-26 UY UY28582A patent/UY28582A1/es not_active Application Discontinuation
- 2004-10-26 AR ARP040103896A patent/AR046201A1/es unknown
- 2004-10-27 SV SV2004001918A patent/SV2005001918A/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| UY28582A1 (es) | 2005-05-31 |
| SV2005001918A (es) | 2005-04-18 |
| EP1682564A1 (en) | 2006-07-26 |
| US7169918B2 (en) | 2007-01-30 |
| WO2005044835A1 (en) | 2005-05-19 |
| CA2543116A1 (en) | 2005-05-19 |
| US20050215510A1 (en) | 2005-09-29 |
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