Pyrrolo[2,3-D]pyrimidine compounds
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Abstract
Described herein are pyrrolo[2,3-d]pyrimidine compounds, their use as Janus Kinase (JAK) inhibitors, pharmaceutical compositions containing these compounds, and methods for their preparation.
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Citations
28 Claims
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1. A compound of formula I
- View Dependent Claims (2, 3, 25, 26)
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2. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein the A ring is selected from the group consisting of optionally substituted piperidinyl, pyrrolidinyl, azetidinyl, and piperazinyl.
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3. The compound of claim 2 or a pharmaceutically acceptable salt thereof, wherein the A ring is selected from the group consisting of piperidinyl, pyrrolidinyl, azetidinyl, and piperazinyl;
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wherein the A ring is optionally substituted with one or more substituents selected from the group consisting of carboxy, cyano, oxo, fluoro, (C1-C8)alkyl, phenyl, oxadiazolyl, pyridinyl, pyrimidinyl, tetrazolyl, pyrrolidinyl, —
OP(O)(R10)n, —
OR11, —
OC(O)R12, —
C(O)OR12, —
C(O)R13, —
C(O)NR14R15, —
NR16R17, —
N(R18)C(O)R19, —
N(R18)S(O)2R19, —
SO2R20, and —
SO2NR21R22;
wherein the (C1-C8)alkyl is optionally substituted with one or more substituents selected from the group consisting of fluoro, cyano, phenyl, pyridinyl, piperazinyl, pyrazinyl, pyrazolyl, pyridazinyl, isoxazolyl, pyrimidinyl, pyrrolidinyl, —
OR23, —
OC(O)R24, —
NR25R26, —
C(O)NR27R28, —
SR29, —
SO2R30, —
SO2NR31R32, and —
N(R33)C(O)R34;R10 is selected from the group consisting of hydroxy and (C1-C6)alkoxy; n is one or two; R11 is selected from the group consisting of hydrogen, methyl, ethyl, isopropyl, tert-butyl, aminocarbonylmethyl, ethoxyethyl, phenyl, and pyrrolidinylcarbonylmethyl; R12, R13, R14, R15, R16, R17, R18, R21, R22, R24, R25, R26, R27, R28, R31, R32, R33 and R34 are independently selected from the group consisting of hydrogen, methyl, and ethyl; R19 is selected from the group consisting of hydrogen, tert-butoxy, trifluoromethyl, methoxy, and phenylmethoxy; R20 is selected from the group consisting of hydrogen, methyl, phenyl, benzyl, phenylethyl, and cyclopropylmethyl; R23 is selected from the group consisting of hydrogen, methyl, phenyl, pyridinylmethyl, and cyclopropylmethyl; R29 is selected from the group consisting of hydrogen and pyridinyl; and R30 is selected from the group consisting of hydrogen, methyl, propyl, and cyclopropylmethyl; wherein phenyl, wherever it occurs, is optionally substituted with one or more substituents selected from the group consisting of fluoro, cyano, and methoxy; wherein isoxazolyl, oxadiazolyl, pyridinyl, piperazinyl, and pyridazinyl, wherever they occur in the A ring substituents, the R23 substituents and the R29 substituents, are optionally and independently substituted with one or more substituents selected from the group consisting of oxo, cyano, methyl, ethyl, methylsulfonylmethyl, and cyclopropylaminocarbonyl.
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25. The compound of claim 1, wherein the compound is selected from the group consisting of:
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N-(trans-4-{[(3-methoxypiperidin-1-yl)sulfonyl]methyl}cyclohexyl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine; 1-[({trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}methyl)-sulfonyl]piperidin-3-ol; (3R)-1-[({trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}-methyl)sulfonyl]piperidin-3-ol; (3R)-1-[({(1S,3R,4S)-3-methyl-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-cyclohexyl}methyl)sulfonyl]piperidin-3-ol; trans-(R)-1-((4-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)-methylsulfonyl)piperidin-3-yl pivalate; (3S)-1-[({trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}-methyl)sulfonyl]-piperidin-3-ol; Diethyl (3R)-1-[({trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-cyclohexyl}methyl)sulfonyl]piperidin-3-yl phosphate; N-[trans-4-({[3-(2-methoxyethoxy)piperidin-1-yl]sulfonyl}methyl)cyclohexyl]-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine; N-(trans-4-{[(3-isobutoxypiperidin-1-yl)sulfonyl]methyl}cyclohexyl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine; N-(trans-4-{[(3-ethoxypiperidin-1-yl)sulfonyl]methyl}cyclohexyl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine; {1-[({trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}methyl)-sulfonyl]piperidin-3-yl}methanol; N-[trans-4-({[4-(methoxymethyl)piperidin-1-yl]sulfonyl}methyl)cyclohexyl]-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine; (1-((Trans-4-(methyl (7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)-methylsulfonyl)piperidin-4-yl)methanol; (3S)-1-[({(1S,3R,4S)-3-methyl-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-cyclohexyl}methyl)sulfonyl]piperidin-3-ol; (3R,4R)-1-[({trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}-methyl)sulfonyl]piperidine-3,4-diol; 1-[({trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}methyl)-sulfonyl]piperidin-4-ol; (3R,4S)-1-[({trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}-methyl)sulfonyl]piperidine-3,4-diol; 4-(2-methoxyethyl)-1-[({trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-cyclohexyl}methyl)sulfonyl]piperidine-4-carboxamide; N-(trans-4-{[(4-methoxypiperidin-1-yl)sulfonyl]methyl}cyclohexyl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine; (R)-1-(trans-4-(methyl (7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)-methylsulfonyl)-pyrrolidin-3-ol; {(3r,4r)-4-methyl-1-[({trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-cyclohexyl}methyl)-sulfonyl]pyrrolidin-3-yl}methanol; {(3R,4R)-4-methyl-1-[({trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-cyclohexyl}methyl)-sulfonyl]pyrrolidin-3-yl}methanol; 3-methyl-1-[({trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}-methyl)sulfonyl]-pyrrolidin-3-ol; (3R,4S)-1-[({trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}-methyl)sulfonyl]-pyrrolidine-3,4-diol; N-[trans-4-({[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]sulfonyl}methyl)cyclohexyl]-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine; ((3S)-1-((3-methyl-4-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)-methylsulfonyl)-pyrrolidin-3-yl)methanol; (3R,4R)-1-[({trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}-methyl)sulfonyl]-pyrrolidine-3,4-diol; N-[trans-4-({[(3R)-3-(2-ethoxyethoxy)pyrrolidin-1-yl]sulfonyl}methyl)cyclohexyl]-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine; 3-methyl-1-[({trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}-methyl)sulfonyl]-pyrrolidin-3-ol; tert-butyl {(3S)-1-[({trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-cyclohexyl}methyl)-sulfonyl]pyrrolidin-3-yl}carbamate; N-[trans-4-({[(3R,4R)-3,4-difluoropyrrolidin-1-yl]sulfonyl}methyl)cyclohexyl]-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine; N-[trans-4-({[3-(methoxymethyl)pyrrolidin-1-yl]sulfonyl}methyl)cyclohexyl]-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine; and N-[trans-4-({[(3R)-3-methoxypyrrolidin-1-yl]sulfonyl}methyl)cyclohexyl]-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine;
ora pharmaceutically acceptable salt thereof.
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26. A pharmaceutical composition comprising a compound of claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
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2. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein the A ring is selected from the group consisting of optionally substituted piperidinyl, pyrrolidinyl, azetidinyl, and piperazinyl.
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4. A compound of formula Ia
- View Dependent Claims (5, 27)
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5. The compound of claim 4 or a pharmaceutically acceptable salt thereof,
wherein the A ring is optionally substituted with one or more substituents selected from the group consisting of carboxy, cyano, oxo, fluoro, (C1-C8)alkyl, phenyl, oxadiazolyl, pyridinyl, pyrimidinyl, tetrazolyl, pyrrolidinyl, — - OP(O)(R10)n, —
OR11, —
OC(O)R12, —
C(O)OR12, —
C(O)R13, —
C(O)NR14R15, —
NR16R17, —
N(R18)C(O)R19, —
N(R18)S(O)2R19, —
SO2R20, and —
SO2NR21R22;
wherein the (C1-C8)alkyl is optionally substituted with one or more substituents selected from the group consisting of fluoro, cyano, phenyl, pyridinyl, piperazinyl, pyrazinyl, pyrazolyl, pyridazinyl, isoxazolyl, pyrimidinyl, pyrrolidinyl, —
OR23, —
OC(O)R24, —
NR25R26, —
C(O)NR27R28, —
SR29, —
SO2R30, —
SO2NR31R32, and —
N(R33)C(O)R34;R10 is selected from the group consisting of hydroxy and (C1-C6)alkoxy; n is one or two; R11 is selected from the group consisting of hydrogen, methyl, ethyl, isopropyl, tert-butyl, aminocarbonylmethyl, ethoxyethyl, phenyl, and pyrrolidinylcarbonylmethyl; R12, R13, R14, R15, R16, R17, R18, R21, R22, R24, R25, R26, R27, R28, R31, R32, R33, and R34 are independently selected from the group consisting of hydrogen, methyl, and ethyl; R19 is selected from the group consisting of hydrogen, tert-butoxy, trifluoromethyl, methoxy, and phenylmethoxy; R20 is selected from the group consisting of hydrogen, methyl, phenyl, benzyl, phenylethyl, and cyclopropylmethyl; R23 is selected from the group consisting of hydrogen, methyl, phenyl, pyridinylmethyl, and cyclopropylmethyl; R29 is selected from the group consisting of hydrogen and pyridinyl; and R30 is selected from the group consisting of hydrogen, methyl, propyl, and cyclopropylmethyl; wherein phenyl, wherever it occurs, is optionally substituted with one or more substituents selected from the group consisting of fluoro, cyano, and methoxy; wherein isoxazolyl, oxadiazolyl, pyridinyl, piperazinyl, and pyridazinyl, wherever they occur in the A ring substituents, the R23 substituents and the R29 substituents, are optionally and independently substituted with one or more substituents selected from the group consisting of oxo, cyano, methyl, ethyl, methylsulfonylmethyl, and cyclopropylaminocarbonyl.
- OP(O)(R10)n, —
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27. A pharmaceutical composition comprising a compound of claim 4 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
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5. The compound of claim 4 or a pharmaceutically acceptable salt thereof,
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6. A compound of Formula II
- View Dependent Claims (7, 8, 9, 10)
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7. The compound of claim 6 or a pharmaceutically acceptable salt thereof, wherein
R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, R5a, and R5b are independently selected from the group consisting of hydrogen, fluoro, carboxy, cyano, (C1-C8)alkyl, phenyl, oxadiazolyl, — - OP(O)(R10)n, —
OR11, —
OC(O)R12, —
C(O)R13, —
C(O)NR14R15, —
NR16R17 and —
N(R18)C(O)R19;
wherein the (C1-C8)alkyl is optionally substituted with one or more substituents selected from the group consisting of fluoro, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolidinyl, —
OR23, —
C(O)NR27R28, —
SO2R30, and —
SO2NR31R32;R10 is selected from the group consisting of hydroxy and ethoxy; n is one or two; R11 is selected from the group consisting of hydrogen, methyl, ethyl, tert-butyl, isopropyl, and aminocarbonylmethyl; R12, R13, R14, R15, R16, R17R18, R27, R28, R31, and R32 are independently selected from the group consisting of hydrogen, methyl, and ethyl; R19 is selected from the group consisting of hydrogen and phenylmethoxy; R23 is selected from the group consisting of hydrogen, methyl, cyclopropylmethyl, and phenyl; and R30 is selected from the group consisting of hydrogen, methyl, propyl, and cyclopropylmethyl; wherein phenyl, wherever it occurs, is optionally substituted with one or more fluoro; wherein oxadiazolyl or pyridazinyl, wherever they occur, are optionally and independently substituted with one or more substituents selected from the group consisting of methyl and methylsulfonylmethyl.
- OP(O)(R10)n, —
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8. The compound of claim 7 or a pharmaceutically acceptable salt thereof, wherein
R1a, R1b, R5a, and R5b are hydrogen; -
R2a and R2b are independently selected from the group consisting of hydrogen, ethyl, methoxy, and benzyloxycarbonylamino; R3a and R3b are independently selected from the group consisting of hydrogen, cyano, hydroxy, hydroxymethyl, hydroxypropyl, methyl, ethyl, methoxy, methoxymethyl, methoxyethyl, methylaminocarbonyl, diethylaminocarbonyl, amino, aminocarbonyl, aminocarbonylmethyl, phenyl, methylsulfonylmethyloxadiazolyl, pyrimidinylmethyl, cyclopropylmethoxymethyl, and cyclopropylmethylsulfonylmethyl; and R4a and R4b are independently selected from the group consisting of hydrogen, hydroxy, carboxy, fluoro, trifluoromethyl, cyano, methyl, ethoxy, methylcarbonyl, methylsulfonylmethyl, dimethylaminosulfonylmethyl, propylsulfonylmethyl, hydroxymethyl, aminocarbonyl, aminocarbonylmethoxy, aminosulfonylmethyl, methyloxadiazolyl, pyridinylmethyl, pyrrolidinylmethyl, and fluorophenoxymethyl.
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9. The compound of claim 8 or a pharmaceutically acceptable salt thereof, wherein
R1a, R1b, R5a, and R5b are hydrogen; -
R2a and R2b are selected from the group consisting of hydrogen, ethyl, methoxy, and benzyloxycarbonylamino; R3a and R3b are selected from the group consisting of hydrogen, cyano, hydroxy, hydroxymethyl, hydroxypropyl, methyl, ethyl, methoxy, methoxymethyl, methoxyethyl, methylaminocarbonyl, diethylaminocarbonyl, amino, aminocarbonyl, aminocarbonylmethyl, phenyl,
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10. The compound of claim 6 or a pharmaceutically acceptable salt thereof, wherein
R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, R5a, and R5b are independently selected from the group consisting of (C1-C8)alkyl, — - OP(O)(R10)n, —
OR11, —
OC(O)R12, and —
C(O)NR14R15;
wherein the (C1-C8)alkyl is optionally substituted with —
OR23;R10 is selected from the group consisting of hydroxy and (C1-C6)alkoxy; n is one or two; R1 is selected from the group consisting of hydrogen, (C1-C6)alkyl, and (C1-C6)alkoxy(C1-C6)alkyl; R12, R14, and R15 are independently selected from the group consisting of hydrogen and (C1-C6)alkyl; R23 is selected from the group consisting of hydrogen and (C1-C6)alkyl.
- OP(O)(R10)n, —
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7. The compound of claim 6 or a pharmaceutically acceptable salt thereof, wherein
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11. A compound of Formula III
- View Dependent Claims (12, 13, 14, 15)
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12. The compound of claim 11 or a pharmaceutically acceptable salt thereof, wherein
R6a, R6b, R7a, R7b, R8a, R8b, R9a, and R9b are independently selected from the group consisting of hydrogen, cyano, fluoro, (C1-C8)alkyl, phenyl, pyridinyl, pyrimidinyl, — - OR11, —
OC(O)R12, —
NR16R17, —
N(R18)C(O)R19, —
SO2R20, and —
SO2NR21R22;
wherein the (C1-C8)alkyl is optionally substituted with one or more substituents selected from the group consisting of cyano, phenyl, isoxazolyl, piperazinyl, pyrazinyl, pyrazolyl, pyridinyl, pyrrolidinyl, —
OR23, —
NR25R26, and —
SR29;R11 is selected from the group consisting of hydrogen, methyl, tert-butyl, isopropyl, ethoxyethyl, phenyl, and pyrrolidinylcarbonylmethyl; R12, R16, R17, R18, R21, R22, R25, and R26 are independently selected from the group consisting of hydrogen, methyl, and ethyl; R19 is selected from the group consisting of hydrogen, tert-butoxy, and trifluoromethyl; R20 selected from the group consisting of hydrogen, methyl, benzyl, and phenylethyl; R23 is selected from the group consisting of hydrogen, methyl, phenyl, and pyridinylmethyl; and R29 is selected from the group consisting of hydrogen and pyridinyl; wherein phenyl, wherever it occurs, is optionally substituted with one or more substituents independently selected from the group consisting of fluoro and methoxy; wherein isoxazolyl, pyridinyl, or piperazinyl, wherever they occur, are optionally and independently substituted with one or more substituents selected from the group consisting of oxo, methyl, and ethyl.
- OR11, —
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13. The compound of claim 12 or a pharmaceutically acceptable salt thereof, wherein
R6a, R6b, and R9b are hydrogen; R7a and R7b are independently selected from the group consisting of hydrogen, fluoro, hydroxy, cyano, methyl, methoxy, methoxymethyl, hydroxymethyl, phenyl, pyridinyl, and
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14. The compound of claim 13 or a pharmaceutically acceptable salt thereof, wherein
R6a, R6b, and R9b are hydrogen; R7a and R7b are independently selected from the group consisting of hydrogen, fluoro, hydroxy, cyano, methyl, methoxy, methoxymethyl, hydroxymethyl, phenyl,
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15. The compound of claim 11 or a pharmaceutically acceptable salt thereof, wherein
R6a, R6b, R7a, R7b, R8a, R8b, R9a, and R9b are independently selected from the group consisting of halo, (C1-C8)alkyl, — - OR11, and —
N(R18)C(O)R19;
wherein the (C1-C8)alkyl is optionally substituted with —
OR23;R11 is selected from the group consisting of hydrogen and (C1-C6)alkoxy(C1-C6)alkyl; R18 is selected from the group consisting of hydrogen and (C1-C6)alkyl; R19 is selected from the group consisting of hydrogen and (C1-C6)alkoxy; and R23 is selected from the group consisting of hydrogen and (C1-C6)alkyl.
- OR11, and —
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12. The compound of claim 11 or a pharmaceutically acceptable salt thereof, wherein
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16. A compound of Formula IV
- View Dependent Claims (17, 18, 19)
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17. The compound of claim 16 or a pharmaceutically acceptable salt thereof, wherein
R37a, R37b, R38a, R38b, R39a and R39b are independently selected from the group consisting of hydrogen, hydroxy, fluoro, pyrimidinyl, pyridinyl, tetrazolyl, cyclopropylmethylsulfonyl, phenylsulfonyl, and methoxycarbonylamino. -
18. The compound of claim 17 or a pharmaceutically acceptable salt thereof, wherein
R37a, R37b, R38b, R39a, and R39b are hydrogen; - and
R38a is selected from the group consisting of hydrogen, fluoro, hydroxy, methoxycarbonylamino, cyclopropylmethylsulfonyl, phenylsulfonyl, pyrimidinyl, pyridinyl, and tetrazolyl.
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19. The compound of claim 18 or a pharmaceutically acceptable salt thereof, wherein
R37a, R37b, R38b, R39a, and R39b are hydrogen; - and
R38a is selected from the group consisting of hydrogen, fluoro, hydroxy, methoxycarbonylamino,
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17. The compound of claim 16 or a pharmaceutically acceptable salt thereof, wherein
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20. A compound of Formula V
- View Dependent Claims (21, 22, 23)
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21. The compound of claim 20 or a pharmaceutically acceptable salt thereof,
wherein R40, R41, R42, R43, and R44 are independently selected from the group consisting of hydrogen, methyl, pyridinyl, and pyridinylmethyl; - and
wherein pyridinyl, wherever it occurs, is optionally substituted with one or more substituents selected from the group consisting of cyano, methyl, and cyclopropylaminocarbonyl.
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22. The compound of claim 21 or a pharmaceutically acceptable salt thereof, wherein
R40, R41, and R43 are hydrogen; -
R42 is selected from the group consisting of methyl, pyridinyl, pyridinylmethyl, methylpyridinyl, cyanopyridinyl, and cyclopropylaminocarbonylpyridinyl; and R44 is selected from the group consisting of hydrogen and methyl.
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23. The compound of claim 22 or a pharmaceutically acceptable salt thereof, wherein
R40, R41, and R43 are hydrogen; R42 is selected from the group consisting of methyl,
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21. The compound of claim 20 or a pharmaceutically acceptable salt thereof,
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24. A compound or pharmaceutically acceptable salt thereof, having the structure:
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28. A pharmaceutical composition comprising the compound or pharmaceutically acceptable salt thereof, having the structure:
Specification
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Current AssigneePfizer Inc.
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Original AssigneePfizer Inc.
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InventorsPromo, Michele Ann, Xie, Jin, Acker, Brad A., Hartmann, Susan J., Wolfson, Sergey Gregory, Huang, Horng-Chih, Jacobsen, Eric Jon
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Primary Examiner(s)Moore, Susanna
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Application NumberUS12/903,554Publication NumberTime in Patent Office1,196 DaysField of Search544/280, 514/265.1US Class Current514/265.1CPC Class CodesA61P 1/04 for ulcers, gastritis or re...A61P 11/00 Drugs for disorders of the ...A61P 11/06 AntiasthmaticsA61P 15/00 Drugs for genital or sexual...A61P 17/06 AntipsoriaticsA61P 19/02 for joint disorders, e.g. a...A61P 25/00 Drugs for disorders of the ...A61P 25/28 for treating neurodegenerat...A61P 27/02 Ophthalmic agentsA61P 27/04 Artificial tears; Irrigatio...A61P 29/00 Non-central analgesic, anti...A61P 3/10 for hyperglycaemia, e.g. an...A61P 31/04 Antibacterial agentsA61P 31/12 AntiviralsA61P 35/00 Antineoplastic agentsA61P 35/02 specific for leukemiaA61P 37/00 Drugs for immunological or ...A61P 37/02 ImmunomodulatorsA61P 37/06 Immunosuppressants, e.g. dr...A61P 37/08 Antiallergic agents antiast...A61P 43/00 : Drugs for specific purposes...A61P 5/14 : of the thyroid hormones, e....C07D 487/04 : Ortho-condensed systems