Adenine compound and use thereof

• US 7,754,728 B2
• Filed: 09/26/2003
• Issued: 07/13/2010
• Est. Priority Date: 09/27/2002
• Status: Expired due to Fees

• Current Assignee: Dainippon Sumitomo Pharma Company Limited (Sumitomo Chemical Company Limited)
• Original Assignee: Dainippon Sumitomo Pharma Company Limited (Sumitomo Chemical Company Limited)
• Inventors: Ogino, Tetsuhiro, Ogita, Haruhisa, Takaku, Haruo, Tobe, Masanori, Fujita, Hitoshi, Kurimoto, Ayumu, Isobe, Yoshiaki
• Primary Examiner(s): Berch; Mark L
• Application Number:
  US10/528,343
• Publication Number:
  US 20060052403A1
• Time in Patent Office: 2,482 Days
• Field of Search: 544/118, 544/276, 540/600, 514/263.2, 514/263.21, 514/263.22, 514/263.23, 514/263.24, 514/263.37
• US Class Current: 514/263.2
• CPC Class Codes: A61K 31/522 having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
• CPC Class Codes: A61K 31/5377 not condensed and containing further heterocyclic rings, e.g. timolol
• CPC Class Codes: A61K 31/55 having seven-membered rings, e.g. azelastine, pentylenetetrazole
• CPC Class Codes: A61P 11/06 Antiasthmatics
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 37/00 Drugs for immunological or allergic disorders
• CPC Class Codes: A61P 37/02 Immunomodulators
• CPC Class Codes: A61P 37/08 Antiallergic agents antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Abstract

A drug for topically administration which is effective as an antiallergic agent. The drug for topically administration contains as an active ingredient an adenine compound represented by the general formula (1):

[wherein ring A represents a 6 to 10 membered, mono or bicyclic, aromatic hydrocarbon or a 5 to 10 membered, mono or bicyclic, aromatic heterocycle containing one to three heteroatoms selected among 0 to 2 nitrogen atoms, 0 or 1 oxygen atom, and 0 or 1 sulfur atom; n is an integer of 0 to 2; m is an integer of 0 to 2; R represents halogeno, (un)substituted alkyl, etc.; X¹ represents oxygen, sulfur, NR¹ (R¹ represents hydrogen or alkyl), or a single bond; Y¹ represents a single bond, alkylene, etc.; Y² represents a single bond, alkylene, etc.; Z represents alkylene; and at least one of Q¹ and Q² represents —COOR¹⁰ (wherein R¹⁰ represents (un)substituted alkyl, etc.), etc.] or a pharmaceutically acceptable salt of the compound.

Claims

1. An adenine compound represented by a general formula (1):

2. The adenine compound according to claim 1, wherein in the general formula (1), the substituent(s), by which alkyl group, alkenyl group or alkynyl group in R¹⁰ is substituted, are the same or different and at least one substituent selected from the group consisting of halogen atom, hydroxy group, substituted or unsubstituted alkoxy group, substituted or unsubstituted amino group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group.

3. The adenine compound according to claim 1, wherein in the general formula (1), Ring A is pyridine.

4. The adenine compound according to claim 1, wherein in the general formula (1), Y¹ is C_1-5 alkylene, Q¹ is hydrogen atom, hydroxy group or alkoxy group, Y² is a single bond, and Q² is —

COOR¹⁰.

5. The adenine compound according to claim 1, wherein in the general formula (1), R¹⁰ is alkyl group substituted by hydroxy group, amino group, alkylamino group or dialkylamino group, and m is 1.

6. The adenine compound according to claim 1, wherein in the general formula (1), Y¹ is C_1-5 alkylene, Q¹ is hydrogen atom, hydroxy group or alkoxy group, Y² is C_1-3 alkylene, Q² is —

COOR¹⁰, and m is 1.

7. The adenine compound according to claim 1, wherein in the general formula (1), m is 0, Y¹ is C_1-6 alkylene which may be substituted with oxo group, and Q¹ is —

COOR¹⁰.

8. The adenine compound according to claim 1, wherein in the general formula (1), and X¹ is oxygen atom, sulfur atom or NR¹ (wherein R¹ is hydrogen atom or alkyl group).

9. The adenine compound according to claim 1, wherein in the general formula (1), m is 0, X¹ is a single bond, Y¹ is C_1-4 alkylene which may be substituted by oxo group, and Q¹ is —

COOR¹⁰.

10. The adenine compound according to claim 1, wherein in the general formula (1), either 1) or 2) below obtains:

1) n is 0;

2) n is 1 or 2, and R is alkyl group, alkoxy group or halogen atom.

11. A compound selected from the group consisting of:

8-Hydroxy-2-methoxycarbonylmethylamino-9-{(6-methyl-3-pyridyl)methyl}adenine,

2-{2-(Methoxycarbonyloxy)ethoxy}-8-hydroxy-9-{(6-methyl-3-pyridyl)methyl}adenine,

8-Hydroxy-2-methoxycarbonylethyl-9-{(6-methyl-3-pyridyl)methyl}adenine,

2-Butoxy-8-hydroxy-9-(5-methoxycarbonylfurfuryl)adenine,

2-Butoxy-8-hydroxy-9-(5-isopropoxycarbonylfurfuryl)adenine,

2-Butoxy-8-hydroxy-9-{(6-methoxycarbonyl-3-pyridyl)methyl}adenine,

2-Butoxy-8-hydroxy-9-{(6-isopropoxycarbonyl-3-pyridyl)methyl}adenine,

2-Butylamino-8-hydroxy-9-(5-ethoxycarbonylfurfuryl)adenine,

2-Butoxy-8-hydroxy-9-(5-methoxycarbonylmethylfurfuryl)adenine,

2-Butoxy-8-hydroxy-9-{(6-S-methylthiocarbonyl-3-pyridyl)methyl}adenine,

2-Butoxy-8-hydroxy-9-{(6-methoxycarbonylmethyl-3-pyridyl)methyl}adenine,

2-Butoxy-8-hydroxy-9-{(2-methoxycarbonyl-4-pyridyl)methyl}adenine,

2-Butoxy-8-hydroxy-9-{(5-methoxycarbonyl-2-thienyl)methyl}adenine, and

2-Butoxy-8-hydroxy-9-{(5-methoxycarbonylmethyl-3-pyridyl)methyl}adenine.