JP2016500068A5 - - Google Patents
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- Publication number
- JP2016500068A5 JP2016500068A5 JP2015542860A JP2015542860A JP2016500068A5 JP 2016500068 A5 JP2016500068 A5 JP 2016500068A5 JP 2015542860 A JP2015542860 A JP 2015542860A JP 2015542860 A JP2015542860 A JP 2015542860A JP 2016500068 A5 JP2016500068 A5 JP 2016500068A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolo
- pyrimidin
- amine
- butyl
- pentyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
- 208000035473 Communicable disease Diseases 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 208000026935 allergic disease Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 230000004968 inflammatory condition Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229960005486 vaccine Drugs 0.000 claims description 5
- TZLSTRPCSHSSJJ-UHFFFAOYSA-N 2-butyl-6-methyl-7-(6-pyrrolidin-1-ylhexyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC(C)=C1CCCCCCN1CCCC1 TZLSTRPCSHSSJJ-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 201000010105 allergic rhinitis Diseases 0.000 claims description 4
- 239000000427 antigen Substances 0.000 claims description 4
- 102000036639 antigens Human genes 0.000 claims description 4
- 108091007433 antigens Proteins 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- JNSVNACCUJRHFR-UHFFFAOYSA-N 2-butyl-7-(5-pyrrolidin-1-ylpentyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCN1CCCC1 JNSVNACCUJRHFR-UHFFFAOYSA-N 0.000 claims description 3
- ONLBRQXZJKHCHO-HNNXBMFYSA-N (3s)-1-[5-(4-amino-2-butyl-5h-pyrrolo[3,2-d]pyrimidin-7-yl)pentyl]pyrrolidin-3-ol Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCN1CC[C@H](O)C1 ONLBRQXZJKHCHO-HNNXBMFYSA-N 0.000 claims description 2
- UJKLLMLXDMSHGM-UHFFFAOYSA-N 1-[5-(4-amino-2-butyl-5h-pyrrolo[3,2-d]pyrimidin-7-yl)pentyl]azetidin-3-ol Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCN1CC(O)C1 UJKLLMLXDMSHGM-UHFFFAOYSA-N 0.000 claims description 2
- NUIFYBSFJSWRDC-UHFFFAOYSA-N 1-[5-(4-amino-2-butyl-5h-pyrrolo[3,2-d]pyrimidin-7-yl)pentyl]piperidin-4-ol Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCN1CCC(O)CC1 NUIFYBSFJSWRDC-UHFFFAOYSA-N 0.000 claims description 2
- QOVXBXDUTWRRLZ-UHFFFAOYSA-N 2-(2-methoxyethyl)-7-(5-pyrrolidin-1-ylpentyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCOC)=NC(N)=C2NC=C1CCCCCN1CCCC1 QOVXBXDUTWRRLZ-UHFFFAOYSA-N 0.000 claims description 2
- CJPDSDQTCRHROJ-UHFFFAOYSA-N 2-(2-methoxyethyl)-7-(6-piperidin-1-ylhexyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCOC)=NC(N)=C2NC=C1CCCCCCN1CCCCC1 CJPDSDQTCRHROJ-UHFFFAOYSA-N 0.000 claims description 2
- NRKGRVDVTLKHEK-UHFFFAOYSA-N 2-(ethoxymethyl)-7-(6-piperidin-1-ylhexyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(COCC)=NC(N)=C2NC=C1CCCCCCN1CCCCC1 NRKGRVDVTLKHEK-UHFFFAOYSA-N 0.000 claims description 2
- YDSBKNJZTMGORA-UHFFFAOYSA-N 2-butyl-6-methyl-7-(4-piperidin-1-ylbutyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC(C)=C1CCCCN1CCCCC1 YDSBKNJZTMGORA-UHFFFAOYSA-N 0.000 claims description 2
- JFRRKMLRRBYRII-UHFFFAOYSA-N 2-butyl-6-methyl-7-(4-pyrrolidin-1-ylbutyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC(C)=C1CCCCN1CCCC1 JFRRKMLRRBYRII-UHFFFAOYSA-N 0.000 claims description 2
- BBYYXIYMTHQBAN-UHFFFAOYSA-N 2-butyl-6-methyl-7-(5-piperidin-1-ylpentyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC(C)=C1CCCCCN1CCCCC1 BBYYXIYMTHQBAN-UHFFFAOYSA-N 0.000 claims description 2
- XJXYEBAKTVNASV-UHFFFAOYSA-N 2-butyl-6-methyl-7-(5-pyrrolidin-1-ylpentyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC(C)=C1CCCCCN1CCCC1 XJXYEBAKTVNASV-UHFFFAOYSA-N 0.000 claims description 2
- HVPPYXLDUJABGI-UHFFFAOYSA-N 2-butyl-6-methyl-7-(6-piperidin-1-ylhexyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC(C)=C1CCCCCCN1CCCCC1 HVPPYXLDUJABGI-UHFFFAOYSA-N 0.000 claims description 2
- KOIZLYAOQNLWEG-UHFFFAOYSA-N 2-butyl-7-(4-piperidin-1-ylbutyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCN1CCCCC1 KOIZLYAOQNLWEG-UHFFFAOYSA-N 0.000 claims description 2
- XUSRJGRTPVPVMS-UHFFFAOYSA-N 2-butyl-7-(5-piperidin-1-ylpentyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCN1CCCCC1 XUSRJGRTPVPVMS-UHFFFAOYSA-N 0.000 claims description 2
- BXNDDJRFAGNGMK-UHFFFAOYSA-N 2-butyl-7-(6-piperidin-1-ylhexyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCCN1CCCCC1 BXNDDJRFAGNGMK-UHFFFAOYSA-N 0.000 claims description 2
- HGKIESKSVLFTCX-UHFFFAOYSA-N 2-butyl-7-(6-pyrrolidin-1-ylhexyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCCN1CCCC1 HGKIESKSVLFTCX-UHFFFAOYSA-N 0.000 claims description 2
- GIZMIPUBWIVEMY-UHFFFAOYSA-N 2-butyl-7-[5-(3-fluoroazetidin-1-yl)pentyl]-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCN1CC(F)C1 GIZMIPUBWIVEMY-UHFFFAOYSA-N 0.000 claims description 2
- PLCQDPIZUBFPME-UHFFFAOYSA-N 2-butyl-7-[5-(3-fluoroazetidin-1-yl)pentyl]-6-methyl-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC(C)=C1CCCCCN1CC(F)C1 PLCQDPIZUBFPME-UHFFFAOYSA-N 0.000 claims description 2
- LOJMQSDMWAEWIU-UHFFFAOYSA-N 2-butyl-7-[5-(3-methylazetidin-1-yl)pentyl]-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCN1CC(C)C1 LOJMQSDMWAEWIU-UHFFFAOYSA-N 0.000 claims description 2
- GKPSHVSZVUHZAE-UHFFFAOYSA-N 2-butyl-7-[5-(4,4-difluoropiperidin-1-yl)pentyl]-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCN1CCC(F)(F)CC1 GKPSHVSZVUHZAE-UHFFFAOYSA-N 0.000 claims description 2
- UXXCZVQDTUOKDS-UHFFFAOYSA-N 2-butyl-7-[5-(4-fluoropiperidin-1-yl)pentyl]-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCN1CCC(F)CC1 UXXCZVQDTUOKDS-UHFFFAOYSA-N 0.000 claims description 2
- PDYLKPZLDUGILJ-OAHLLOKOSA-N 2-butyl-7-[5-[(2r)-2-methylpyrrolidin-1-yl]pentyl]-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCN1CCC[C@H]1C PDYLKPZLDUGILJ-OAHLLOKOSA-N 0.000 claims description 2
- PDYLKPZLDUGILJ-HNNXBMFYSA-N 2-butyl-7-[5-[(2s)-2-methylpyrrolidin-1-yl]pentyl]-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCN1CCC[C@@H]1C PDYLKPZLDUGILJ-HNNXBMFYSA-N 0.000 claims description 2
- DFCDHUHEVOQGMB-OAHLLOKOSA-N 2-butyl-7-[5-[(3r)-3-fluoropyrrolidin-1-yl]pentyl]-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCN1CC[C@@H](F)C1 DFCDHUHEVOQGMB-OAHLLOKOSA-N 0.000 claims description 2
- KRSBEXDSLZJPCB-OAHLLOKOSA-N 2-butyl-7-[5-[(3r)-3-fluoropyrrolidin-1-yl]pentyl]-6-methyl-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC(C)=C1CCCCCN1CC[C@@H](F)C1 KRSBEXDSLZJPCB-OAHLLOKOSA-N 0.000 claims description 2
- DFCDHUHEVOQGMB-HNNXBMFYSA-N 2-butyl-7-[5-[(3s)-3-fluoropyrrolidin-1-yl]pentyl]-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCN1CC[C@H](F)C1 DFCDHUHEVOQGMB-HNNXBMFYSA-N 0.000 claims description 2
- KRSBEXDSLZJPCB-HNNXBMFYSA-N 2-butyl-7-[5-[(3s)-3-fluoropyrrolidin-1-yl]pentyl]-6-methyl-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC(C)=C1CCCCCN1CC[C@H](F)C1 KRSBEXDSLZJPCB-HNNXBMFYSA-N 0.000 claims description 2
- DVZMVHKJRALNNZ-UHFFFAOYSA-N 2-butyl-7-[6-(4-fluoropiperidin-1-yl)hexyl]-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCCN1CCC(F)CC1 DVZMVHKJRALNNZ-UHFFFAOYSA-N 0.000 claims description 2
- ZYYVJTHLNWJMGI-MRXNPFEDSA-N 2-butyl-7-[6-[(3r)-3-fluoropyrrolidin-1-yl]hexyl]-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCCN1CC[C@@H](F)C1 ZYYVJTHLNWJMGI-MRXNPFEDSA-N 0.000 claims description 2
- ZYYVJTHLNWJMGI-INIZCTEOSA-N 2-butyl-7-[6-[(3s)-3-fluoropyrrolidin-1-yl]hexyl]-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCCN1CC[C@H](F)C1 ZYYVJTHLNWJMGI-INIZCTEOSA-N 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- HQAGHNHNCDXPNX-UHFFFAOYSA-N 2-pentyl-7-(6-piperidin-1-ylhexyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCCC)=NC(N)=C2NC=C1CCCCCCN1CCCCC1 HQAGHNHNCDXPNX-UHFFFAOYSA-N 0.000 claims description 2
- -1 5- (4-fluoropiperidin-1-yl) pentyl Chemical group 0.000 claims description 2
- BMCHFRSACPPETD-UHFFFAOYSA-N 7-[4-(azepan-1-yl)butyl]-2-butyl-6-methyl-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC(C)=C1CCCCN1CCCCCC1 BMCHFRSACPPETD-UHFFFAOYSA-N 0.000 claims description 2
- YLVPWHVYQCDVEH-UHFFFAOYSA-N 7-[5-(4-fluoropiperidin-1-yl)pentyl]-2-(2-methoxyethyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCOC)=NC(N)=C2NC=C1CCCCCN1CCC(F)CC1 YLVPWHVYQCDVEH-UHFFFAOYSA-N 0.000 claims description 2
- RDJYOQQEFXXBOS-UHFFFAOYSA-N 7-[5-(azepan-1-yl)pentyl]-2-butyl-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCN1CCCCCC1 RDJYOQQEFXXBOS-UHFFFAOYSA-N 0.000 claims description 2
- SSONSLOIXPFRKK-UHFFFAOYSA-N 7-[5-(azetidin-1-yl)pentyl]-2-butyl-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC=C1CCCCCN1CCC1 SSONSLOIXPFRKK-UHFFFAOYSA-N 0.000 claims description 2
- DBRAROMRCAHKED-UHFFFAOYSA-N 7-[5-(azetidin-1-yl)pentyl]-2-butyl-6-methyl-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC(C)=C1CCCCCN1CCC1 DBRAROMRCAHKED-UHFFFAOYSA-N 0.000 claims description 2
- HQQDWWKPOBOUTN-CQSZACIVSA-N 7-[5-[(3r)-3-fluoropyrrolidin-1-yl]pentyl]-2-(2-methoxyethyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCOC)=NC(N)=C2NC=C1CCCCCN1CC[C@@H](F)C1 HQQDWWKPOBOUTN-CQSZACIVSA-N 0.000 claims description 2
- HQQDWWKPOBOUTN-AWEZNQCLSA-N 7-[5-[(3s)-3-fluoropyrrolidin-1-yl]pentyl]-2-(2-methoxyethyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCOC)=NC(N)=C2NC=C1CCCCCN1CC[C@H](F)C1 HQQDWWKPOBOUTN-AWEZNQCLSA-N 0.000 claims description 2
- KMOKGGFYQWSCBS-UHFFFAOYSA-N 7-[6-(azepan-1-yl)hexyl]-2-(2-methoxyethyl)-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCOC)=NC(N)=C2NC=C1CCCCCCN1CCCCCC1 KMOKGGFYQWSCBS-UHFFFAOYSA-N 0.000 claims description 2
- QWPFKANQWPPUBP-UHFFFAOYSA-N 7-[6-(azetidin-1-yl)hexyl]-2-butyl-6-methyl-5h-pyrrolo[3,2-d]pyrimidin-4-amine Chemical compound C12=NC(CCCC)=NC(N)=C2NC(C)=C1CCCCCCN1CCC1 QWPFKANQWPPUBP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 102000006992 Interferon-alpha Human genes 0.000 description 1
- 108010047761 Interferon-alpha Proteins 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- OHDXDNUPVVYWOV-UHFFFAOYSA-N n-methyl-1-(2-naphthalen-1-ylsulfanylphenyl)methanamine Chemical compound CNCC1=CC=CC=C1SC1=CC=CC2=CC=CC=C12 OHDXDNUPVVYWOV-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261728390P | 2012-11-20 | 2012-11-20 | |
| US61/728,390 | 2012-11-20 | ||
| US201361774087P | 2013-03-07 | 2013-03-07 | |
| US61/774,087 | 2013-03-07 | ||
| PCT/US2013/070472 WO2014081645A1 (en) | 2012-11-20 | 2013-11-18 | Novel compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016500068A JP2016500068A (ja) | 2016-01-07 |
| JP2016500068A5 true JP2016500068A5 (OSRAM) | 2016-12-15 |
| JP6228223B2 JP6228223B2 (ja) | 2017-11-08 |
Family
ID=50776485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015542860A Expired - Fee Related JP6228223B2 (ja) | 2012-11-20 | 2013-11-18 | 新規化合物 |
Country Status (32)
| Country | Link |
|---|---|
| US (3) | US9540383B2 (OSRAM) |
| EP (1) | EP2922549B1 (OSRAM) |
| JP (1) | JP6228223B2 (OSRAM) |
| KR (1) | KR20150085055A (OSRAM) |
| CN (1) | CN104780922B (OSRAM) |
| AU (1) | AU2013348218B2 (OSRAM) |
| BR (1) | BR112015011400A8 (OSRAM) |
| CA (1) | CA2892218A1 (OSRAM) |
| CL (1) | CL2015001342A1 (OSRAM) |
| CR (1) | CR20150268A (OSRAM) |
| CY (1) | CY1119557T1 (OSRAM) |
| DK (1) | DK2922549T3 (OSRAM) |
| DO (1) | DOP2015000121A (OSRAM) |
| EA (1) | EA028480B1 (OSRAM) |
| ES (1) | ES2639789T3 (OSRAM) |
| HR (1) | HRP20171150T1 (OSRAM) |
| HU (1) | HUE13857477T2 (OSRAM) |
| IL (1) | IL238800B (OSRAM) |
| LT (1) | LT2922549T (OSRAM) |
| ME (1) | ME02867B (OSRAM) |
| MX (1) | MX358025B (OSRAM) |
| NZ (1) | NZ707319A (OSRAM) |
| PE (1) | PE20151086A1 (OSRAM) |
| PH (1) | PH12015501100B1 (OSRAM) |
| PL (1) | PL2922549T3 (OSRAM) |
| PT (1) | PT2922549T (OSRAM) |
| RS (1) | RS56233B1 (OSRAM) |
| SG (1) | SG11201503282RA (OSRAM) |
| SI (1) | SI2922549T1 (OSRAM) |
| SM (1) | SMT201700378T1 (OSRAM) |
| UA (1) | UA114645C2 (OSRAM) |
| WO (1) | WO2014081645A1 (OSRAM) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA103195C2 (uk) | 2008-08-11 | 2013-09-25 | Глаксосмитклайн Ллк | Похідні пурину для застосування у лікуванні алергій, запальних та інфекційних захворювань |
| EP2734186B1 (en) | 2011-07-22 | 2018-09-12 | GlaxoSmithKline LLC | Composition |
| CA2880576A1 (en) | 2012-08-24 | 2014-02-27 | Glaxosmithkline Llc | Pyrazolopyrimidine compounds |
| CA2890198A1 (en) | 2012-11-20 | 2014-05-30 | Diane Mary Coe | Novel compounds |
| RU2643371C2 (ru) | 2012-11-20 | 2018-02-01 | ГЛАКСОСМИТКЛАЙН ЭлЭлСи | Новые соединения |
| NZ707319A (en) | 2012-11-20 | 2019-09-27 | Glaxosmithkline Llc | 5h-pyrrolo[3,2-d]pyrimidin-4-amine compounds and their use in the treatment of allergic diseases and other inflammatory conditions |
| CN106029668B (zh) * | 2014-02-20 | 2018-02-23 | 葛兰素史克知识产权第二有限公司 | 吡咯并[3,2]嘧啶衍生物作为人类干扰素诱导剂 |
| SI3190113T1 (sl) * | 2014-08-15 | 2021-09-30 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Pirolopirimidinske spojine, ki se uporabljajo kot agonist TLR7 |
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