Claims
- 1. A method of treating asthma in a patient in need of such treatment, said method comprising the step of administering to said patient a therapeutically effective amount of a compound of formula (I) wherein—W represents —CH2— or a bond; Q represents an aryl group Ar1 or Ar2; in the case where W represents —CH2—, Q represents Ar1 wherein Ar1 represents naphthyl, phenyl, quinolyl, isoquinolyl, indolyl, benzofuranyl or benzothienyl; in the case where W represents a bond, Q represents an aryl group Ar2 wherein Ar2 represents acenaphthenyl, fluorenyl or indanyl; wherein the ring systems which Ar1 and Ar2 represent may all be optionally substituted by one or more substituents selected from C1-4 alkyl, C1-4 alkoxy, halogen, or trifluoromethyl; R10 represents X—(A)p—Y; X represents S(O)n, C≡C, (CH2)2, CH═CH or CH2CH═CH; n represents 0, 1 or 2; A represents C1-6 alkylene; p is 0 or 1; Y represents CN, OR11, CO2R12, CONR13R14, NR15R16, NHSO2R17, NHCOR18 or an optionally substituted aryl or heteroaryl group, provided that when X represents S(O)n and Y is other than an optionally substituted aryl or heteroaryl group, then p is 1 and also provided that when X represents S(O)n, p is 1 and Y represents OH, then n is not 0; R13 and R14 independently represent H, C1-5 alkyl or phenyl, which latter group may be substituted by one or more substituents selected from C1-4 alkyl, C1-4 alkoxy, halogen, or CO2R21; and R1, R2, R11, R12, R15, R16, R17, R18 and R21 independently represent H or C1-5 alkyl; or a pharmaceutically acceptable derivative thereof.
- 2. A method according to claim 1, wherein in formula (I), W represents —CH2— and Q represents an aryl group Ar1 wherein Ar1 represents a naphthyl or phenyl group, each of which may be optionally substituted by one or more substituents selected from C1-4 alkyl, C1-4 alkoxy, halogen or trifluoromethyl.
- 3. A method according to claim 1, wherein, in formula (I) W represents a bond and Q represents an aryl group Ar2 wherein Ar2 represents an indanyl group which may be optionally substituted by one or more substituents selected from C1-4 alkyl, C1-4 alkoxy, halogen or trifluoromethyl.
- 4. A method according to claim 1, wherein, in formula (I), X represents S(O)n wherein n is 0, 1 or 2, C≡C, (CH2)2, CH═CH or CH2CH═CH.
- 5. A method according to claim 1, wherein, in formula (I), X represents S(O)n wherein n is 0, 1 or 2.
- 6. A method of according to claim 1, wherein, in formula (I), A represents C1-4 alkylene.
- 7. A method according to claim 1, wherein, in formula (I), each of the groups R1, R2, R11, R12, R15, R16, R17, R18 and R21 represents H or C1-4 alkyl group.
- 8. A method according to claim 1, wherein, in formula (I), each of the groups R13 and R14 represents H, C1-3 alkyl or phenyl, which latter group may be substituted by one or more substituents selected from C1-4 alkyl, C1-4 alkoxy, halogen or CO2R21.
- 9. A method according to claim 1, wherein, in formula (I), W represents —CH2— or a bond; Q represents Ar1 or Ar2; in the case where W represents —CH2—, Q represents Ar1 wherein Ar1 represents naphthyl or phenyl, in the case where W represents a bond, Q represents Ar2 wherein Ar2 represents indanyl; wherein the ring systems which Ar1 and Ar2 represent may all be optionally substituted by one or more substituents selected from C1-4 alkyl, C1-4 alkoxy, halogen, or trifluoromethyl; R10 represents X—(A)p—Y; X represents S(O)n, C≡C, (CH2)2 or CH2CH═CH; n represents 0, 1 or 2; A represents C1-6 alkylene; p is 0 or 1; Y represents CN, OR11, CO2R12, CONR13R14, NR15R16, or an optionally substituted phenyl, pyridyl or tetrazolyl group, provided that when X represents S(O)n and Y is other than an optionally substituted aryl or heteroaryl group, then p is 1 and also provided that when X represents S(O)n, p is 1 and Y represents OH, then n is not 0; R13 and R14 independently represent H, C1-5 alkyl or phenyl, which latter group may be substituted by one or more substituents selected from C1-4 alkyl, C1-4 alkoxy, halogen, or CO2R21; and R1, R2, R11, R12, R15, R16 and R21 independently represent H or C1-5 alkyl.
- 10. A method according to claim 1, wherein, in formula (I), W represents —CH2— or a bond; Q represents Ar1 or Ar2; in the case where W represents —CH2—, Q represents Ar1 wherein Ar1 represents naphthyl; in the case where W represents a bond, Q represents Ar2 wherein Ar2 represents indanyl; R10 represents X—(A)p—Y; X represents S(O)n, C≡C, (CH2)2 or CH2CH═CH; n represents 0, 1 or 2; A represents C1-3 alkylene; p is 0 or 1; Y represents CN, OR11, CO2R12, CONR13R14, NR15R16, or a phenyl, pyridyl or tetrazolyl group optionally substituted by a hydroxy or methoxy group, provided that when X represents S(O)n, and Y is other than an optionally substituted aryl or heteroaryl group, then p is 1 and also provided that when X represents S(O)n, p is 1 and Y represents OH, then n is not 0; R13 and R14 independently represent H; and R1, R2, R11, R12, R15 and R16 independently represent H or C1-4 alkyl.
- 11. A method according to claim 1, wherein the compound of formula I is:5-[(3-hydroxypropyl)sulphinyl]-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; or 5-[(3-hydroxypropyl)sulphonyl]-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; or methyl 4-[(2,3,4,6-tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxo-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thio]butanoate; or 5-[(3-methoxypropyl)thio]-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; or 5-[(2-hydroxyethyl)sulphinyl]-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo-[(3,4-d]pyrimidine-2,4(3H,6H)-dione; or 4-[(2,3,4,6-tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxo-1H-pyrrolo[3,4-d]pyrimidin5-yl)thio]butanoic acid; or 4-[(2,3,4,6,-tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxo-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thio]butanoic acid, sodium salt; or 5[(2-dimethylaminoethyl)thio]-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; or 6-(2,3-dihydro-1-H-inden-2-yl)-5-[(3-hydroxypropyl)sulphinyl]-3-methyl-1-(1-methylethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; or 6-(2,3-dihydro-1H-inden-2-yl)-5-[(3-hydroxypropyl)sulphonyl]-3-methyl-1-(1-methylethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; or 5-[(3-hydroxypropyl)sulphinyl]-3-methyl-1-(1-methylethyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; or 4-[(2,3,4,6-tetrahydro-3-methyl-1-(2-methylpropryl)-6-(1naphthalenylmethyl)-2,4-dioxo-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thio]butanamide; or 5-(2,3,4,6-tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4dioxo-1H-pyrrolo[3,4-d]pyrimidin-5-yl)pent-3-enoic acid; or 5-(5-hydroxypent-1-ynyl)-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; or 5-(5-hydroxypentyl)-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; or 5-(4-hydroxybut-1-ynyl)-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; or 5-(4-hydroxybutyl)-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4-(3H,6H)-dione; 5-(2,3,4,6-tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl-2,4-dioxo-1H-pyrrolo[3,4-d]pyrimidin-5-yl)pentanoic acid; 4-[(2,3,4,6-tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxo-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thio]butanenitrile; 5-[(3-{1-H-tetrazol-5-yl}propyl)thio]-3--methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4-(3H,6H)-dione; 3-methyl-1-(2-methypropyl)-6-(1-naphthalenylmethyl)-5-[(2-pyridinyl)thio]-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; 3-methyl-1-(2methylpropyl)-6-(1-naphthalenylmethyl)-5-[(2-pyridinyl)sulphinyl]-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; 3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-5-[(4-pyridinyl)thio]-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; 5-([3-methoxyphenyl]thio)-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4-(3H,6H)-dione; 5-([3-hydroxyphenyl]thio)-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; 5-([4-methoxyphenyl]thio)-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; 5([4-hydroxyphenyl]thio)-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; 5-([2-methoxyphenyl]thio)-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione; or 5-([2-hydroxyphenyl]thio)-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione.
Priority Claims (2)
Number |
Date |
Country |
Kind |
9626643 |
Dec 1996 |
GB |
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PCT/SE98/02157 |
Dec 1997 |
WO |
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Parent Case Info
This is a continuation of application Ser. No. 09/505,862, filed Feb. 17, 2001, which is a continuation of application Ser. No. 09/011,780 file date Feb. 24, 1998, now U.S. Pat. No. 6,046,204 which is the National Stage Application of PCT/SE97/02157, which claims priority from British Patent Application No. 9626643.2, filed Dec. 21, 1996.
Foreign Referenced Citations (2)
Number |
Date |
Country |
9304047 |
Mar 1993 |
WO |
9617610 |
Jun 1996 |
WO |
Non-Patent Literature Citations (5)
Entry |
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Noguchi et al, “A Facile Preparation of 7-(Substituted amino)-6H-pyrrolo[3,4-d]-pyrimidine Derivatives1,” Bull. Chem. Soc. Jpn., vol. 62, pp. 3043-3045 (1989). |
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Continuations (2)
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Number |
Date |
Country |
Parent |
09/505862 |
Feb 2001 |
US |
Child |
09/707880 |
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US |
Parent |
09/011780 |
Feb 1998 |
US |
Child |
09/505862 |
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US |