JP2009500366A5 - - Google Patents
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- Publication number
- JP2009500366A5 JP2009500366A5 JP2008519862A JP2008519862A JP2009500366A5 JP 2009500366 A5 JP2009500366 A5 JP 2009500366A5 JP 2008519862 A JP2008519862 A JP 2008519862A JP 2008519862 A JP2008519862 A JP 2008519862A JP 2009500366 A5 JP2009500366 A5 JP 2009500366A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- tetrahydropyrazolo
- azepin
- compound
- phenyl
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims 38
- 150000001875 compounds Chemical class 0.000 claims 28
- 150000003839 salts Chemical class 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- -1 hydroxy, cyano, amino Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 208000012902 Nervous system disease Diseases 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- KMROEJOHJJYSOS-UHFFFAOYSA-N n-methyl-4-[6-(2-methylpropyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl]benzamide Chemical compound C1=CC(C(=O)NC)=CC=C1N1N=C2CCN(CC(C)C)CCC2=C1 KMROEJOHJJYSOS-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- DTFNQANOSNEOCD-UHFFFAOYSA-N 1-[4-(6-cyclobutyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)phenyl]-3-methylimidazolidin-2-one Chemical compound O=C1N(C)CCN1C1=CC=C(N2N=C3CCN(CCC3=C2)C2CCC2)C=C1 DTFNQANOSNEOCD-UHFFFAOYSA-N 0.000 claims 1
- SWGKYHKUYIKLDC-UHFFFAOYSA-N 1-[4-(6-cyclobutyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)phenyl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1=CC=C(N2N=C3CCN(CCC3=C2)C2CCC2)C=C1 SWGKYHKUYIKLDC-UHFFFAOYSA-N 0.000 claims 1
- XUXLXFNWTHSVDU-UHFFFAOYSA-N 1-[4-(6-cyclohexyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)phenyl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1=CC=C(N2N=C3CCN(CCC3=C2)C2CCCCC2)C=C1 XUXLXFNWTHSVDU-UHFFFAOYSA-N 0.000 claims 1
- NUCUHFOXKYAJSO-UHFFFAOYSA-N 1-[4-(6-cyclopentyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)phenyl]-3-methylimidazolidin-2-one Chemical compound O=C1N(C)CCN1C1=CC=C(N2N=C3CCN(CCC3=C2)C2CCCC2)C=C1 NUCUHFOXKYAJSO-UHFFFAOYSA-N 0.000 claims 1
- PFKVVKZVZKQJIY-UHFFFAOYSA-N 1-[4-(6-cyclopentyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)phenyl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1=CC=C(N2N=C3CCN(CCC3=C2)C2CCCC2)C=C1 PFKVVKZVZKQJIY-UHFFFAOYSA-N 0.000 claims 1
- UNFFLKKHVRORSL-UHFFFAOYSA-N 1-[4-(6-ethyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)phenyl]pyrrolidin-2-one Chemical compound N1=C2CCN(CC)CCC2=CN1C(C=C1)=CC=C1N1CCCC1=O UNFFLKKHVRORSL-UHFFFAOYSA-N 0.000 claims 1
- NHLUUDFTIYLGCR-UHFFFAOYSA-N 1-[4-(6-propan-2-yl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)phenyl]pyrrolidin-2-one Chemical compound N1=C2CCN(C(C)C)CCC2=CN1C(C=C1)=CC=C1N1CCCC1=O NHLUUDFTIYLGCR-UHFFFAOYSA-N 0.000 claims 1
- QZEZLNQKBWZPDJ-UHFFFAOYSA-N 1-[4-[6-(2-methylpropyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl]phenyl]pyrrolidin-2-one Chemical compound N1=C2CCN(CC(C)C)CCC2=CN1C(C=C1)=CC=C1N1CCCC1=O QZEZLNQKBWZPDJ-UHFFFAOYSA-N 0.000 claims 1
- FBLPODTYWKUWKU-UHFFFAOYSA-N 1-[4-[6-(cyclopropylmethyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl]phenyl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1=CC=C(N2N=C3CCN(CC4CC4)CCC3=C2)C=C1 FBLPODTYWKUWKU-UHFFFAOYSA-N 0.000 claims 1
- PCCHYOUYRRGEJP-UHFFFAOYSA-N 1-[5-(6-cyclobutyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)pyridin-2-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1=CC=C(N2N=C3CCN(CCC3=C2)C2CCC2)C=N1 PCCHYOUYRRGEJP-UHFFFAOYSA-N 0.000 claims 1
- UTZALURJTZPLMS-UHFFFAOYSA-N 1-[5-(6-propan-2-yl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)pyridin-2-yl]pyrrolidin-2-one Chemical compound N1=C2CCN(C(C)C)CCC2=CN1C(C=N1)=CC=C1N1CCCC1=O UTZALURJTZPLMS-UHFFFAOYSA-N 0.000 claims 1
- BKADWIISZKEYEA-UHFFFAOYSA-N 1-methyl-3-[4-(6-propan-2-yl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)phenyl]imidazolidin-2-one Chemical compound N1=C2CCN(C(C)C)CCC2=CN1C(C=C1)=CC=C1N1CCN(C)C1=O BKADWIISZKEYEA-UHFFFAOYSA-N 0.000 claims 1
- DGBYHHMLWZHXBJ-UHFFFAOYSA-N 1-methyl-3-[4-[6-(2-methylpropyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl]phenyl]imidazolidin-2-one Chemical compound N1=C2CCN(CC(C)C)CCC2=CN1C(C=C1)=CC=C1N1CCN(C)C1=O DGBYHHMLWZHXBJ-UHFFFAOYSA-N 0.000 claims 1
- SOAXOIPIFFFTDI-UHFFFAOYSA-N 2-(4-bromophenyl)-6-cyclobutyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine Chemical compound C1=CC(Br)=CC=C1N1N=C2CCN(C3CCC3)CCC2=C1 SOAXOIPIFFFTDI-UHFFFAOYSA-N 0.000 claims 1
- QYXNJPQHJBBEBP-UHFFFAOYSA-N 3-[4-(6-cyclobutyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1C1=CC=C(N2N=C3CCN(CCC3=C2)C2CCC2)C=C1 QYXNJPQHJBBEBP-UHFFFAOYSA-N 0.000 claims 1
- MGKKZYOFKNDJGD-UHFFFAOYSA-N 3-[4-(6-cyclobutyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)phenyl]-1-methylimidazolidine-2,4-dione Chemical compound O=C1N(C)CC(=O)N1C1=CC=C(N2N=C3CCN(CCC3=C2)C2CCC2)C=C1 MGKKZYOFKNDJGD-UHFFFAOYSA-N 0.000 claims 1
- XEZCPAVXKBUPRY-UHFFFAOYSA-N 3-[4-(6-cyclopentyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1C1=CC=C(N2N=C3CCN(CCC3=C2)C2CCCC2)C=C1 XEZCPAVXKBUPRY-UHFFFAOYSA-N 0.000 claims 1
- KQGXBEQKKDNBEF-UHFFFAOYSA-N 3-[4-(6-propan-2-yl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound N1=C2CCN(C(C)C)CCC2=CN1C(C=C1)=CC=C1N1CCOC1=O KQGXBEQKKDNBEF-UHFFFAOYSA-N 0.000 claims 1
- ULDBTTCHMFJGSK-UHFFFAOYSA-N 3-[4-[6-(2-methylpropyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl]phenyl]-1,3-oxazolidin-2-one Chemical compound N1=C2CCN(CC(C)C)CCC2=CN1C(C=C1)=CC=C1N1CCOC1=O ULDBTTCHMFJGSK-UHFFFAOYSA-N 0.000 claims 1
- FBCIOSJGCBSUPO-UHFFFAOYSA-N 3-methyl-5-[4-(6-propan-2-yl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)phenyl]-1,2,4-oxadiazole Chemical compound N1=C2CCN(C(C)C)CCC2=CN1C(C=C1)=CC=C1C1=NC(C)=NO1 FBCIOSJGCBSUPO-UHFFFAOYSA-N 0.000 claims 1
- OSKJMVLSHZZCLF-UHFFFAOYSA-N 3-methyl-5-[4-[6-(2-methylpropyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl]phenyl]-1,2,4-oxadiazole Chemical compound N1=C2CCN(CC(C)C)CCC2=CN1C(C=C1)=CC=C1C1=NC(C)=NO1 OSKJMVLSHZZCLF-UHFFFAOYSA-N 0.000 claims 1
- JSPMYAZGTGJOAI-UHFFFAOYSA-N 4-(6-cyclobutyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1N1N=C2CCN(C3CCC3)CCC2=C1 JSPMYAZGTGJOAI-UHFFFAOYSA-N 0.000 claims 1
- YLZHGJSNBVVMHA-UHFFFAOYSA-N 4-(6-cyclobutyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1N1N=C2CCN(C3CCC3)CCC2=C1 YLZHGJSNBVVMHA-UHFFFAOYSA-N 0.000 claims 1
- NXNUSIGCWNWZFT-UHFFFAOYSA-N 4-(6-cyclopentyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1N1N=C2CCN(C3CCCC3)CCC2=C1 NXNUSIGCWNWZFT-UHFFFAOYSA-N 0.000 claims 1
- ULJXVGFBRBQVFN-UHFFFAOYSA-N 4-(6-propan-2-yl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)benzamide Chemical compound N1=C2CCN(C(C)C)CCC2=CN1C1=CC=C(C(N)=O)C=C1 ULJXVGFBRBQVFN-UHFFFAOYSA-N 0.000 claims 1
- NZGTZGNHBYHCHG-UHFFFAOYSA-N 4-[(6-cyclobutyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)methyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1CN1N=C2CCN(C3CCC3)CCC2=C1 NZGTZGNHBYHCHG-UHFFFAOYSA-N 0.000 claims 1
- XSZLCHNKJCBKCB-UHFFFAOYSA-N 4-[4-(6-cyclobutyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)phenyl]morpholine Chemical compound C1CCC1N1CCC2=NN(C=3C=CC(=CC=3)N3CCOCC3)C=C2CC1 XSZLCHNKJCBKCB-UHFFFAOYSA-N 0.000 claims 1
- WRTSWARSQLNKPU-UHFFFAOYSA-N 4-[6-(2-methylpropyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl]benzamide Chemical compound N1=C2CCN(CC(C)C)CCC2=CN1C1=CC=C(C(N)=O)C=C1 WRTSWARSQLNKPU-UHFFFAOYSA-N 0.000 claims 1
- BYXQPVYYCODYFR-UHFFFAOYSA-N 6-cyclobutyl-2-(4-methylsulfonylphenyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1N=C2CCN(C3CCC3)CCC2=C1 BYXQPVYYCODYFR-UHFFFAOYSA-N 0.000 claims 1
- IRXCERGGZYNFJI-UHFFFAOYSA-N 6-cyclobutyl-2-(4-piperidin-1-ylphenyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine Chemical compound C1CCC1N1CCC2=NN(C=3C=CC(=CC=3)N3CCCCC3)C=C2CC1 IRXCERGGZYNFJI-UHFFFAOYSA-N 0.000 claims 1
- RUGQPDGXAJMLNQ-UHFFFAOYSA-N 6-cyclobutyl-2-(4-pyrrolidin-1-ylphenyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine Chemical compound C1CCC1N1CCC2=NN(C=3C=CC(=CC=3)N3CCCC3)C=C2CC1 RUGQPDGXAJMLNQ-UHFFFAOYSA-N 0.000 claims 1
- IUMZUJYPSCQKNK-UHFFFAOYSA-N 6-cyclobutyl-2-[1-(6-methylpyridin-3-yl)piperidin-4-yl]-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine Chemical compound C1=NC(C)=CC=C1N1CCC(N2N=C3CCN(CCC3=C2)C2CCC2)CC1 IUMZUJYPSCQKNK-UHFFFAOYSA-N 0.000 claims 1
- SCYQCPUBNNKNFU-UHFFFAOYSA-N 6-cyclobutyl-2-phenyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine Chemical compound C1CCC1N1CCC2=NN(C=3C=CC=CC=3)C=C2CC1 SCYQCPUBNNKNFU-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 125000005418 aryl aryl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- KMPBTRDNKULAIB-UHFFFAOYSA-N n,n-dimethyl-4-[6-(2-methylpropyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl]benzamide Chemical compound N1=C2CCN(CC(C)C)CCC2=CN1C1=CC=C(C(=O)N(C)C)C=C1 KMPBTRDNKULAIB-UHFFFAOYSA-N 0.000 claims 1
- LNUZKOYKRTWVLK-UHFFFAOYSA-N n-[4-(6-cyclobutyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-2-yl)phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1N1N=C2CCN(C3CCC3)CCC2=C1 LNUZKOYKRTWVLK-UHFFFAOYSA-N 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0513886.2 | 2005-07-06 | ||
| GBGB0513886.2A GB0513886D0 (en) | 2005-07-06 | 2005-07-06 | Novel compounds |
| PCT/EP2006/006613 WO2007025596A1 (en) | 2005-07-06 | 2006-07-04 | Pyrazolo [3 , 4-d] azepine derivatives as histamine h3 antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009500366A JP2009500366A (ja) | 2009-01-08 |
| JP2009500366A5 true JP2009500366A5 (enExample) | 2009-08-20 |
| JP5145218B2 JP5145218B2 (ja) | 2013-02-13 |
Family
ID=34856781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008519862A Expired - Fee Related JP5145218B2 (ja) | 2005-07-06 | 2006-07-04 | ヒスタミンｈ３アンタゴニストとしてのピラゾロ［３，４−ｄ］アゼピン誘導体 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7888347B2 (enExample) |
| EP (1) | EP1899350B1 (enExample) |
| JP (1) | JP5145218B2 (enExample) |
| KR (1) | KR20080037651A (enExample) |
| CN (1) | CN101258154B (enExample) |
| AT (1) | ATE467636T1 (enExample) |
| AU (1) | AU2006286897A1 (enExample) |
| BR (1) | BRPI0612719A2 (enExample) |
| CA (1) | CA2614232A1 (enExample) |
| CR (1) | CR9622A (enExample) |
| CY (1) | CY1110711T1 (enExample) |
| DE (1) | DE602006014273D1 (enExample) |
| DK (1) | DK1899350T3 (enExample) |
| EA (1) | EA013600B1 (enExample) |
| ES (1) | ES2345841T3 (enExample) |
| GB (1) | GB0513886D0 (enExample) |
| HR (1) | HRP20100401T1 (enExample) |
| IL (1) | IL188184A0 (enExample) |
| MA (1) | MA29623B1 (enExample) |
| MX (1) | MX2008000383A (enExample) |
| NO (1) | NO20080563L (enExample) |
| PL (1) | PL1899350T3 (enExample) |
| PT (1) | PT1899350E (enExample) |
| SI (1) | SI1899350T1 (enExample) |
| UA (1) | UA93047C2 (enExample) |
| WO (1) | WO2007025596A1 (enExample) |
| ZA (1) | ZA200710798B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0712823A2 (pt) | 2006-06-23 | 2012-07-24 | Abbott Lab | derivados de ciclopropil amina como moduladores de receptor de histamina h3 |
| US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| MX2010002938A (es) | 2007-09-24 | 2010-04-01 | Comentis Inc | Derivados de (3-hidroxi-4-amino-butan-2-il)-3-(2-tiazol-2-il-pirro lidin-1-carbonil)benzamida y compuestos relacionados como inhibidores de beta-secretasa para tratar enfermedad de alzheimer. |
| US9186353B2 (en) * | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
| US8853390B2 (en) | 2010-09-16 | 2014-10-07 | Abbvie Inc. | Processes for preparing 1,2-substituted cyclopropyl derivatives |
| CN102952139B (zh) * | 2011-08-30 | 2016-08-10 | 上海药明康德新药开发有限公司 | 反式-3a-氟吡咯烷[3,4-C]并环化合物及其制备方法 |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| EP2647377A1 (en) | 2012-04-06 | 2013-10-09 | Sanofi | Use of an h3 receptor antagonist for the treatment of alzheimer's disease |
| JO3407B1 (ar) | 2012-05-31 | 2019-10-20 | Eisai R&D Man Co Ltd | مركبات رباعي هيدرو بيرازولو بيريميدين |
| US9910887B2 (en) * | 2013-04-25 | 2018-03-06 | Facebook, Inc. | Variable search query vertical access |
| SG11201810292YA (en) * | 2016-05-25 | 2018-12-28 | Akarna Therapeutics Ltd | Fused bicyclic compounds for the treatment of disease |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6573218B1 (en) * | 1998-09-09 | 2003-06-03 | Ishihara Sangyo Kaisha, Ltd. | Fused-benzene derivatives useful as herbicides |
| EP1173438A1 (en) * | 1999-04-16 | 2002-01-23 | Novo Nordisk A/S | Substituted imidazoles, their preparation and use |
| JP2001220390A (ja) | 2000-02-09 | 2001-08-14 | Yamanouchi Pharmaceut Co Ltd | 縮合ピラゾール誘導体 |
| WO2003104235A1 (en) * | 2002-06-06 | 2003-12-18 | Novo Nordisk A/S | Substituted hexahydropyrrolo[1,2-a]pyrazines, octahydropyrido[1,2-a]pyrazines and decahydropyrazino[1,2-a]azepines |
| US6770597B2 (en) | 2002-07-17 | 2004-08-03 | Ishihara Sangyo Kaisha, Ltd. | Benzohydrazide derivatives as herbicides and desiccant compositions containing them |
| JP2005537290A (ja) | 2002-07-25 | 2005-12-08 | ファルマシア・イタリア・エス・ピー・エー | キナーゼ阻害剤として活性なビシクロピラゾール類、その製造方法、およびそれを含有する薬学的組成物 |
| JP2006500376A (ja) * | 2002-08-20 | 2006-01-05 | イーライ・リリー・アンド・カンパニー | ヒスタミンｈ３受容体アンタゴニストとしての置換アゼピン、製造および治療上の使用 |
| GB0224083D0 (en) | 2002-10-16 | 2002-11-27 | Glaxo Group Ltd | Novel compounds |
| GB0224557D0 (en) | 2002-10-22 | 2002-11-27 | Glaxo Group Ltd | Novel compounds |
| ES2333008T3 (es) | 2002-12-20 | 2010-02-16 | Glaxo Group Limited | Derivados de benzo(d)azepina para el tratamiento de trastornos neurologicos. |
| US7402680B2 (en) * | 2003-09-17 | 2008-07-22 | Janssen Pharmaceutica, N.V. | Fused heterocyclic compounds |
| GB0329214D0 (en) | 2003-12-17 | 2004-01-21 | Glaxo Group Ltd | Novel compounds |
| GB0405628D0 (en) | 2004-03-12 | 2004-04-21 | Glaxo Group Ltd | Novel compounds |
| GB0408083D0 (en) | 2004-04-08 | 2004-05-12 | Glaxo Group Ltd | Novel compounds |
| JP2008502644A (ja) | 2004-06-18 | 2008-01-31 | グラクソ グループ リミテッド | ヒスタミンｈ３アンタゴニストとしての３−シクロアルキルベンズアゼピン |
| GB0418267D0 (en) | 2004-08-16 | 2004-09-15 | Glaxo Group Ltd | Novel compounds |
| RU2007125648A (ru) | 2004-12-07 | 2009-01-20 | Глэксо Груп Лимитед (GB) | Инденильные производные и их применение для лечения неврологических расстройств |
| ATE420091T1 (de) | 2005-03-14 | 2009-01-15 | Glaxo Group Ltd | Kondensierte thiazolderivate mit affinität für den histamin-h3-rezeptor |
-
2005
- 2005-07-06 GB GBGB0513886.2A patent/GB0513886D0/en not_active Ceased
-
2006
- 2006-07-04 DE DE602006014273T patent/DE602006014273D1/de active Active
- 2006-07-04 BR BRPI0612719-3A patent/BRPI0612719A2/pt not_active IP Right Cessation
- 2006-07-04 JP JP2008519862A patent/JP5145218B2/ja not_active Expired - Fee Related
- 2006-07-04 ES ES06818218T patent/ES2345841T3/es active Active
- 2006-07-04 PT PT06818218T patent/PT1899350E/pt unknown
- 2006-07-04 AT AT06818218T patent/ATE467636T1/de active
- 2006-07-04 UA UAA200800190A patent/UA93047C2/ru unknown
- 2006-07-04 CA CA002614232A patent/CA2614232A1/en not_active Abandoned
- 2006-07-04 HR HR20100401T patent/HRP20100401T1/hr unknown
- 2006-07-04 SI SI200630733T patent/SI1899350T1/sl unknown
- 2006-07-04 EA EA200800264A patent/EA013600B1/ru not_active IP Right Cessation
- 2006-07-04 KR KR1020087000265A patent/KR20080037651A/ko not_active Ceased
- 2006-07-04 AU AU2006286897A patent/AU2006286897A1/en not_active Abandoned
- 2006-07-04 DK DK06818218.7T patent/DK1899350T3/da active
- 2006-07-04 CN CN2006800322776A patent/CN101258154B/zh not_active Expired - Fee Related
- 2006-07-04 PL PL06818218T patent/PL1899350T3/pl unknown
- 2006-07-04 MX MX2008000383A patent/MX2008000383A/es active IP Right Grant
- 2006-07-04 WO PCT/EP2006/006613 patent/WO2007025596A1/en not_active Ceased
- 2006-07-04 EP EP06818218A patent/EP1899350B1/en active Active
- 2006-07-04 US US11/994,689 patent/US7888347B2/en not_active Expired - Fee Related
-
2007
- 2007-12-12 ZA ZA200710798A patent/ZA200710798B/xx unknown
- 2007-12-17 IL IL188184A patent/IL188184A0/en unknown
- 2007-12-20 CR CR9622A patent/CR9622A/es not_active Application Discontinuation
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2008
- 2008-01-09 MA MA30562A patent/MA29623B1/fr unknown
- 2008-01-30 NO NO20080563A patent/NO20080563L/no not_active Application Discontinuation
-
2010
- 2010-07-29 CY CY20101100713T patent/CY1110711T1/el unknown
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