JP2011510991A5 - - Google Patents
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- Publication number
- JP2011510991A5 JP2011510991A5 JP2010545097A JP2010545097A JP2011510991A5 JP 2011510991 A5 JP2011510991 A5 JP 2011510991A5 JP 2010545097 A JP2010545097 A JP 2010545097A JP 2010545097 A JP2010545097 A JP 2010545097A JP 2011510991 A5 JP2011510991 A5 JP 2011510991A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- propoxy
- methyl
- pyridazine
- pyrrolidin
- 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 32
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 11
- 208000035475 disorder Diseases 0.000 claims 9
- 201000010099 disease Diseases 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 5
- 125000006546 (C4-C10) cycloalkyl group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 4
- -1 Methyl- (6- {4- [3-((R) -2-methyl-pyrrolidin-1-yl) -propoxy] phenyl} pyridazin-3-yl) amine Chemical class 0.000 claims 4
- 206010062519 Poor quality sleep Diseases 0.000 claims 4
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 201000003631 narcolepsy Diseases 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 3
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 206010000117 Abnormal behaviour Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 208000020401 Depressive disease Diseases 0.000 claims 2
- 208000030814 Eating disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000026139 Memory disease Diseases 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 230000037007 arousal Effects 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 230000020595 eating behavior Effects 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 230000036651 mood Effects 0.000 claims 2
- 201000003152 motion sickness Diseases 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- LJKASJQJHADFNZ-MRXNPFEDSA-N 1-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-4-methylsulfanyl-6,7-dihydro-5h-cyclopenta[d]pyridazine Chemical compound C1=2CCCC=2C(SC)=NN=C1C(C=C1)=CC=C1OCCCN1CCC[C@H]1C LJKASJQJHADFNZ-MRXNPFEDSA-N 0.000 claims 1
- IRCSUSACGMABQS-GOSISDBHSA-N 1-[6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazin-3-yl]piperidin-4-ol Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC(=CC=2)N2CCC(O)CC2)C=C1 IRCSUSACGMABQS-GOSISDBHSA-N 0.000 claims 1
- ANPINRFBSAUQDU-LJQANCHMSA-N 3-(1-benzofuran-2-yl)-6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC(=CC=2)C=2OC3=CC=CC=C3C=2)C=C1 ANPINRFBSAUQDU-LJQANCHMSA-N 0.000 claims 1
- DLBQMYQJBCWNHW-LJQANCHMSA-N 3-[(4-fluorophenyl)methoxy]-6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC(OCC=3C=CC(F)=CC=3)=CC=2)C=C1 DLBQMYQJBCWNHW-LJQANCHMSA-N 0.000 claims 1
- RVLALNWAZGWDCV-LJQANCHMSA-N 3-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-6-[[4-(trifluoromethyl)phenyl]methoxy]pyridazine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC(OCC=3C=CC(=CC=3)C(F)(F)F)=CC=2)C=C1 RVLALNWAZGWDCV-LJQANCHMSA-N 0.000 claims 1
- XARCMYZPBBBSAG-HXUWFJFHSA-N 3-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-6-phenylmethoxypyridazine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC(OCC=3C=CC=CC=3)=CC=2)C=C1 XARCMYZPBBBSAG-HXUWFJFHSA-N 0.000 claims 1
- VSFQQSITUVDHTA-LJQANCHMSA-N 3-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-6-phenylpyridazine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC(=CC=2)C=2C=CC=CC=2)C=C1 VSFQQSITUVDHTA-LJQANCHMSA-N 0.000 claims 1
- VLPKPZKIZYOELA-GOSISDBHSA-N 3-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-6-pyrrolidin-1-ylpyridazine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC(=CC=2)N2CCCC2)C=C1 VLPKPZKIZYOELA-GOSISDBHSA-N 0.000 claims 1
- AWWYLUCTZLYBTG-QGZVFWFLSA-N 3-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-6-thiophen-2-ylpyridazine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC(=CC=2)C=2SC=CC=2)C=C1 AWWYLUCTZLYBTG-QGZVFWFLSA-N 0.000 claims 1
- GVXRVCBWRAMGSI-OAHLLOKOSA-N 3-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC=CC=2)C=C1 GVXRVCBWRAMGSI-OAHLLOKOSA-N 0.000 claims 1
- USECFGWRJBOAEK-UHFFFAOYSA-N 3-benzylsulfanyl-6-[4-(3-piperidin-1-ylpropoxy)phenyl]pyridazine Chemical compound C1CCCCN1CCCOC(C=C1)=CC=C1C(N=N1)=CC=C1SCC1=CC=CC=C1 USECFGWRJBOAEK-UHFFFAOYSA-N 0.000 claims 1
- MNZUASQQMDHYCQ-HXUWFJFHSA-N 3-benzylsulfanyl-6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC(SCC=3C=CC=CC=3)=CC=2)C=C1 MNZUASQQMDHYCQ-HXUWFJFHSA-N 0.000 claims 1
- POGQXQOEERNJFB-UHFFFAOYSA-N 3-benzylsulfinyl-6-[4-(3-piperidin-1-ylpropoxy)phenyl]pyridazine Chemical compound C=1C=C(C=2C=CC(OCCCN3CCCCC3)=CC=2)N=NC=1S(=O)CC1=CC=CC=C1 POGQXQOEERNJFB-UHFFFAOYSA-N 0.000 claims 1
- VEUONXQPMCACHO-DXHYANOHSA-N 3-benzylsulfinyl-6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC(=CC=2)S(=O)CC=2C=CC=CC=2)C=C1 VEUONXQPMCACHO-DXHYANOHSA-N 0.000 claims 1
- AJNZISMWSGKOCY-UHFFFAOYSA-N 3-benzylsulfonyl-6-[4-(3-piperidin-1-ylpropoxy)phenyl]pyridazine Chemical compound C=1C=C(C=2C=CC(OCCCN3CCCCC3)=CC=2)N=NC=1S(=O)(=O)CC1=CC=CC=C1 AJNZISMWSGKOCY-UHFFFAOYSA-N 0.000 claims 1
- MCIKUTXFDWKRDG-HXUWFJFHSA-N 3-benzylsulfonyl-6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC(=CC=2)S(=O)(=O)CC=2C=CC=CC=2)C=C1 MCIKUTXFDWKRDG-HXUWFJFHSA-N 0.000 claims 1
- BFOKNONCWSKSNR-UHFFFAOYSA-N 3-chloro-6-[2-methyl-4-(3-piperidin-1-ylpropoxy)phenyl]pyridazine Chemical compound C=1C=C(C=2N=NC(Cl)=CC=2)C(C)=CC=1OCCCN1CCCCC1 BFOKNONCWSKSNR-UHFFFAOYSA-N 0.000 claims 1
- VNNBSXMZBLFYON-UHFFFAOYSA-N 3-chloro-6-[3-methoxy-4-(3-piperidin-1-ylpropoxy)phenyl]pyridazine Chemical compound COC1=CC(C=2N=NC(Cl)=CC=2)=CC=C1OCCCN1CCCCC1 VNNBSXMZBLFYON-UHFFFAOYSA-N 0.000 claims 1
- HXSABWRMROMERN-UHFFFAOYSA-N 3-chloro-6-[4-(3-piperidin-1-ylpropoxy)phenyl]pyridazine Chemical compound N1=NC(Cl)=CC=C1C(C=C1)=CC=C1OCCCN1CCCCC1 HXSABWRMROMERN-UHFFFAOYSA-N 0.000 claims 1
- QCWCZSKIYSEBNJ-VYRBHSGPSA-N 3-chloro-6-[4-[(2s)-2-methyl-3-(2-methylpiperidin-1-yl)propoxy]phenyl]pyridazine Chemical compound C([C@@H](C)CN1C(CCCC1)C)OC(C=C1)=CC=C1C1=CC=C(Cl)N=N1 QCWCZSKIYSEBNJ-VYRBHSGPSA-N 0.000 claims 1
- VXSLUXQRULNTNE-LSDHHAIUSA-N 3-chloro-6-[4-[(2s)-2-methyl-3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazine Chemical compound C([C@@H](C)CN1[C@@H](CCC1)C)OC(C=C1)=CC=C1C1=CC=C(Cl)N=N1 VXSLUXQRULNTNE-LSDHHAIUSA-N 0.000 claims 1
- KHKHKQXRQPBTON-CQSZACIVSA-N 3-chloro-6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC(Cl)=CC=2)C=C1 KHKHKQXRQPBTON-CQSZACIVSA-N 0.000 claims 1
- ZCYMPPUULSIWCT-MRXNPFEDSA-N 3-methyl-6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC(C)=CC=2)C=C1 ZCYMPPUULSIWCT-MRXNPFEDSA-N 0.000 claims 1
- GTQROZRIYRHZHV-UHFFFAOYSA-N 3-methylsulfanyl-6-[4-(3-piperidin-1-ylpropoxy)phenyl]pyridazine Chemical compound N1=NC(SC)=CC=C1C(C=C1)=CC=C1OCCCN1CCCCC1 GTQROZRIYRHZHV-UHFFFAOYSA-N 0.000 claims 1
- BLHPCLKYVQFWPU-UHFFFAOYSA-N 3-phenoxy-6-[4-(3-piperidin-1-ylpropoxy)phenyl]pyridazine Chemical compound C1CCCCN1CCCOC(C=C1)=CC=C1C(N=N1)=CC=C1OC1=CC=CC=C1 BLHPCLKYVQFWPU-UHFFFAOYSA-N 0.000 claims 1
- IVDIJSIYQKBWDS-UHFFFAOYSA-N 3-phenylmethoxy-6-[4-(3-piperidin-1-ylpropoxy)phenyl]pyridazine Chemical compound C1CCCCN1CCCOC(C=C1)=CC=C1C(N=N1)=CC=C1OCC1=CC=CC=C1 IVDIJSIYQKBWDS-UHFFFAOYSA-N 0.000 claims 1
- ADRYHRMBTICFMB-GOSISDBHSA-N 4-[6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazin-3-yl]morpholine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC(=CC=2)N2CCOCC2)C=C1 ADRYHRMBTICFMB-GOSISDBHSA-N 0.000 claims 1
- AWTAJTYCGQYBHX-OAQYLSRUSA-N 4-benzylsulfanyl-1-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-6,7-dihydro-5h-cyclopenta[d]pyridazine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2C=3CCCC=3C(SCC=3C=CC=CC=3)=NN=2)C=C1 AWTAJTYCGQYBHX-OAQYLSRUSA-N 0.000 claims 1
- QWRAVYBIWLFPQN-UHFFFAOYSA-N 4-chloro-1-[4-(3-piperidin-1-ylpropoxy)phenyl]-6,7-dihydro-5h-cyclopenta[d]pyridazine Chemical compound C1=2CCCC=2C(Cl)=NN=C1C(C=C1)=CC=C1OCCCN1CCCCC1 QWRAVYBIWLFPQN-UHFFFAOYSA-N 0.000 claims 1
- ZKUDFOIOBRFLFD-OAHLLOKOSA-N 4-chloro-1-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-6,7-dihydro-5h-cyclopenta[d]pyridazine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2C=3CCCC=3C(Cl)=NN=2)C=C1 ZKUDFOIOBRFLFD-OAHLLOKOSA-N 0.000 claims 1
- IBOGRSGEINDRLY-MRXNPFEDSA-N 4-methoxy-1-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-6,7-dihydro-5h-cyclopenta[d]pyridazine Chemical compound C1=2CCCC=2C(OC)=NN=C1C(C=C1)=CC=C1OCCCN1CCC[C@H]1C IBOGRSGEINDRLY-MRXNPFEDSA-N 0.000 claims 1
- GAPZGVQUOCWPPW-UHFFFAOYSA-N 5-(6-chloropyridazin-3-yl)-2-(3-piperidin-1-ylpropoxy)benzonitrile Chemical compound N1=NC(Cl)=CC=C1C(C=C1C#N)=CC=C1OCCCN1CCCCC1 GAPZGVQUOCWPPW-UHFFFAOYSA-N 0.000 claims 1
- DKXPWQDBPJOGQW-CQSZACIVSA-N 5-(6-chloropyridazin-3-yl)-2-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]benzonitrile Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC(Cl)=CC=2)C=C1C#N DKXPWQDBPJOGQW-CQSZACIVSA-N 0.000 claims 1
- TYLXTAQPFOKERE-CQSZACIVSA-N 6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazin-3-amine Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2N=NC(N)=CC=2)C=C1 TYLXTAQPFOKERE-CQSZACIVSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 1
- 230000019771 cognition Effects 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6290808P | 2008-01-30 | 2008-01-30 | |
| US61/062,908 | 2008-01-30 | ||
| PCT/US2009/032187 WO2009097306A1 (en) | 2008-01-30 | 2009-01-28 | Substituted pyridazine derivatives which have histamine h3 antagonist activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011510991A JP2011510991A (ja) | 2011-04-07 |
| JP2011510991A5 true JP2011510991A5 (enExample) | 2013-04-04 |
| JP5539230B2 JP5539230B2 (ja) | 2014-07-02 |
Family
ID=40435072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010545097A Expired - Fee Related JP5539230B2 (ja) | 2008-01-30 | 2009-01-28 | ヒスタミンｈ３アンタゴニスト活性を有する置換ピリダジン誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US8076331B2 (enExample) |
| EP (2) | EP2252593B1 (enExample) |
| JP (1) | JP5539230B2 (enExample) |
| CA (1) | CA2712885A1 (enExample) |
| ES (1) | ES2479440T3 (enExample) |
| HR (1) | HRP20140568T1 (enExample) |
| MX (1) | MX2010008384A (enExample) |
| WO (1) | WO2009097306A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5335675B2 (ja) * | 2006-07-25 | 2013-11-06 | セファロン、インク． | ピリジジノン誘導体 |
| WO2009097306A1 (en) | 2008-01-30 | 2009-08-06 | Cephalon, Inc. | Substituted pyridazine derivatives which have histamine h3 antagonist activity |
| EP2328586A2 (en) * | 2008-05-20 | 2011-06-08 | Cephalon, Inc. | Substituted pyridazinone derivatives as histamine-3 (h3) receptor ligands |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| TWI568942B (zh) * | 2013-09-26 | 2017-02-01 | 崔文德 | 球座標轉向平行機構 |
| CN109111400B (zh) * | 2017-06-23 | 2020-10-16 | 杭州百诚医药科技股份有限公司 | 苯基喹啉酮类和黄酮类衍生物的制备和应用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3239523A (en) * | 1965-05-06 | 1966-03-08 | Harman S Lowrie | 3-(4-dialkylaminoalkoxyphenyl) cinnolines |
| US5241062A (en) | 1993-01-19 | 1993-08-31 | Sun Company, Inc. (R&M) | Synthetic route to meso-tetra hydrocarbyl or substituted hydrocarbyl porphyrins and derivatives |
| MXPA06011167A (es) * | 2004-04-01 | 2007-01-25 | Eli Lilli And Company | Agentes del receptor h3 de histamina, preparacion y usos terapeuticos. |
| EP1717235A3 (en) * | 2005-04-29 | 2007-02-28 | Bioprojet | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands |
| BRPI0613564A2 (pt) * | 2005-07-04 | 2011-01-18 | Novo Nordisk As | compostos, seus usos na preparação de composições farmacêuticas e composições farmacêuticas compreendendo os mesmos |
| JP5335675B2 (ja) | 2006-07-25 | 2013-11-06 | セファロン、インク． | ピリジジノン誘導体 |
| AU2008248168B2 (en) * | 2007-05-03 | 2013-03-21 | Cephalon, Inc. | Processes for preparing (R)-2-methylpyrrolidine and (S)-2-methylpyrrolidine and tartrate salts thereof |
| WO2009097306A1 (en) | 2008-01-30 | 2009-08-06 | Cephalon, Inc. | Substituted pyridazine derivatives which have histamine h3 antagonist activity |
| ES2390004T3 (es) | 2008-01-30 | 2012-11-05 | Cephalon, Inc. | Derivados sustituidos de piperidina espirocíclica como ligandos del receptor de la histamina 3(H3) |
| JP5524082B2 (ja) | 2008-01-30 | 2014-06-18 | セファロン、インク． | ヒスタミン−３（ｈ３）受容体リガンドとしての置換スピロ環状ピペリジン誘導体 |
| AU2009237650B2 (en) * | 2008-04-17 | 2012-05-31 | Proximagen Limited | Indoles as modulators of nicoticic acetylcholine receptor subtype alpha-7 |
| EP2328586A2 (en) | 2008-05-20 | 2011-06-08 | Cephalon, Inc. | Substituted pyridazinone derivatives as histamine-3 (h3) receptor ligands |
| WO2011002984A1 (en) | 2009-07-02 | 2011-01-06 | Cephalon, Inc. | Substituted phenoxypropylcycloamine derivatives as histamine-3 (h3) receptor ligands |
-
2009
- 2009-01-28 WO PCT/US2009/032187 patent/WO2009097306A1/en not_active Ceased
- 2009-01-28 MX MX2010008384A patent/MX2010008384A/es active IP Right Grant
- 2009-01-28 EP EP09706750.8A patent/EP2252593B1/en not_active Not-in-force
- 2009-01-28 ES ES09706750.8T patent/ES2479440T3/es active Active
- 2009-01-28 CA CA2712885A patent/CA2712885A1/en not_active Abandoned
- 2009-01-28 JP JP2010545097A patent/JP5539230B2/ja not_active Expired - Fee Related
- 2009-01-28 EP EP14162835.4A patent/EP2752406A1/en not_active Withdrawn
- 2009-01-28 HR HRP20140568AT patent/HRP20140568T1/hr unknown
-
2010
- 2010-07-29 US US12/846,112 patent/US8076331B2/en not_active Expired - Fee Related
-
2011
- 2011-09-13 US US13/231,293 patent/US8912183B2/en not_active Expired - Fee Related
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