# US 7,608,601 B2 · 4′-Substituted nucleoside derivatives as inhibitors of HCV RNA replication

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- Number: US 7,608,601 B2
- Document ID: US7608601B2
- Status: Granted
- Kind: B2
- Application number: 10/891,967
- Filed: 2004-07-15
- Published: 2004-12-30
- Granted: 2009-10-27
- Earliest claimed: 2001-06-12
- Assignees: Roche Palo Alto LLC
- Inventors: Rene Robert Devos; Christopher John Hobbs; Wen Rong Jiang; Joseph Armstrong Martin; John Herbert Merrett; Isabel Najera; Nobuo Shimma; Takuo Tsukuda
- Web page: https://patentgrep.com/patent/US7608601B2

## CPC

- A61K 31/7076: containing purines, e.g. adenosine, adenylic acid
- A61K 31/52: Purines, e.g. adenine
- A61K 31/7068: having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
- A61K 31/7072: having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
- A61K 31/708: having oxo groups directly attached to the purine ring system, e.g. guanosine, guanylic acid
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 31/12: Antivirals
- A61P 31/14: for RNA viruses
- A61P 37/02: Immunomodulators
- C07H 19/04: Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- Y02P 20/582: Recycling of unreacted starting or intermediate materials
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The present invention relates to the use of nucleoside derivatives of formula I wherein B signifies a 9-purinyl residue B1 of formula or a 1-pyrimidyl residue B2 of formula wherein the symbols are as defined in the specification, and of pharmaceutically acceptable salts thereof; for the treatment of diseases mediated by the Hepatitis C Virus (HCV), for the preparation of a medicament for such treatment and to pharmaceutical compositions containing such compounds.

## Claims

### Claim 1

A method of treating a hepatitis C virus (HCV) infection comprising administering to a patient in need thereof an effective amount of a compound of formula I
wherein the compound of formula I is in the D configuration, and;
R is hydrogen;
R1 is alkyl, alkenyl, alkynyl, haloalkyl, alkylcarbonyl, hydroxyalkyl, alkoxyalkyl, alkoxy, cyano, azido, hydroxyiminomethyl, alkoxyiminomethyl, halogen, alkylcarbonylamino, alkylaminocarbonyl, or aminomethyl, alkylaminomethyl, dialkylaminomethyl or heterocyclyl;
R2 is hydrogen, hydroxy, alkyl, hydroxyalkyl, alkoxy, halogen or cyano;
R3 and R4 (i) independently are hydrogen, hydroxy, alkoxy, halogen or hydroxyalkyl, provided that at least one of R3 and R4 is hydrogen; or
(ii) together represent ═CH2 or ═N—OH, or
(iii) both represent fluorine;
R5 is hydrogen, hydroxy, alkyl, alkoxy, alkylthio, NHR8, halogen or SH;
R6 is hydroxy, NHR8, NHOR9, NHNR8, —NHC(O)OR9′ or SH;
R7 is hydrogen, hydroxy, alkyl, alkoxy, alkylthio, NHR8, halogen, SH or cyano;
R8 is hydrogen, alkyl, hydroxyalkyl, arylcarbonyl or alkylcarbonyl;
R9 is hydrogen or alkyl;
R9′ is alkyl;
and pharmaceutically acceptable salts thereof.

### Claim 2 (depends on 1)

The method of claim 1 wherein
R1 is alkyl, alkenyl, alkynyl, haloalkyl, alkylcarbonyl, alkoxy, hydroxymethyl, cyano, azidoalkoxyiminomethyl, alkylcarbonylamino, alkylaminomethyl or dialkylaminomethyl;
R2 is hydrogen, hydroxy, alkoxy, or halogen;
R3 and R4 (i) are independently hydrogen, hydroxy, alkoxy, halogen or hydroxyalkyl, provided that at least one of R3 and R4 is hydrogen; or
(ii) together are ═CH2; or,
(ii) both represent fluorine.

### Claim 3 (depends on 2)

The method of claim 2 wherein:
R1 is C2-6 alkynyl, azido or hydroxymethyl;
R2 is hydrogen, hydroxyl, alkoxy or halogen;
R3 and R4 (i) independently are hydrogen, hydroxyl, alkoxy or halogen, or
(ii) both are fluorine;
R5 is hydrogen or amino;
R6 is hydrogen amino or hydroxyl;
R7 is hydrogen.

### Claim 4 (depends on 1)

The method of claim 1, wherein the compound is delivered in a dose of between 1 and 100 mg/kg/body weight of the patient/day.