JP2005529116A5 - - Google Patents
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- Publication number
- JP2005529116A5 JP2005529116A5 JP2003585719A JP2003585719A JP2005529116A5 JP 2005529116 A5 JP2005529116 A5 JP 2005529116A5 JP 2003585719 A JP2003585719 A JP 2003585719A JP 2003585719 A JP2003585719 A JP 2003585719A JP 2005529116 A5 JP2005529116 A5 JP 2005529116A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- alkoxy
- group
- independently selected
- 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
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 229910052799 carbon Inorganic materials 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 12
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims 10
- 206010020751 Hypersensitivity Diseases 0.000 claims 10
- 230000007815 allergy Effects 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 239000002464 receptor antagonist Substances 0.000 claims 10
- 229940044551 receptor antagonist Drugs 0.000 claims 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 9
- 230000008369 airway response Effects 0.000 claims 8
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 7
- 208000027744 congestion Diseases 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 claims 6
- ZZHLYYDVIOPZBE-UHFFFAOYSA-N Trimeprazine Chemical compound C1=CC=C2N(CC(CN(C)C)C)C3=CC=CC=C3SC2=C1 ZZHLYYDVIOPZBE-UHFFFAOYSA-N 0.000 claims 6
- 229960001271 desloratadine Drugs 0.000 claims 6
- 229960003088 loratadine Drugs 0.000 claims 6
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims 4
- 208000001953 Hypotension Diseases 0.000 claims 4
- 208000019695 Migraine disease Diseases 0.000 claims 4
- 208000008589 Obesity Diseases 0.000 claims 4
- 230000009858 acid secretion Effects 0.000 claims 4
- 239000013566 allergen Substances 0.000 claims 4
- 208000026935 allergic disease Diseases 0.000 claims 4
- 210000003169 central nervous system Anatomy 0.000 claims 4
- 208000015114 central nervous system disease Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 230000036543 hypotension Effects 0.000 claims 4
- 206010027599 migraine Diseases 0.000 claims 4
- 230000004899 motility Effects 0.000 claims 4
- 235000020824 obesity Nutrition 0.000 claims 4
- 201000000980 schizophrenia Diseases 0.000 claims 4
- 208000019116 sleep disease Diseases 0.000 claims 4
- USCSJAIWXWYTEH-UHFFFAOYSA-N 7-[3-[4-[(4-chlorophenyl)methyl]piperazin-1-yl]propoxy]-3,4-dimethylchromen-2-one Chemical compound C1=CC=2C(C)=C(C)C(=O)OC=2C=C1OCCCN(CC1)CCN1CC1=CC=C(Cl)C=C1 USCSJAIWXWYTEH-UHFFFAOYSA-N 0.000 claims 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 3
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 3
- MBUVEWMHONZEQD-UHFFFAOYSA-N Azeptin Chemical compound C1CN(C)CCCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 MBUVEWMHONZEQD-UHFFFAOYSA-N 0.000 claims 3
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 claims 3
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 claims 3
- ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 claims 3
- OCJYIGYOJCODJL-UHFFFAOYSA-N Meclizine Chemical compound CC1=CC=CC(CN2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=C1 OCJYIGYOJCODJL-UHFFFAOYSA-N 0.000 claims 3
- HOKDBMAJZXIPGC-UHFFFAOYSA-N Mequitazine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1CC1C(CC2)CCN2C1 HOKDBMAJZXIPGC-UHFFFAOYSA-N 0.000 claims 3
- UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 claims 3
- PVLJETXTTWAYEW-UHFFFAOYSA-N Mizolastine Chemical compound N=1C=CC(=O)NC=1N(C)C(CC1)CCN1C1=NC2=CC=CC=C2N1CC1=CC=C(F)C=C1 PVLJETXTTWAYEW-UHFFFAOYSA-N 0.000 claims 3
- OGEAASSLWZDQBM-UHFFFAOYSA-N Temelastine Chemical compound C1=NC(C)=CC=C1CC(C(N1)=O)=CN=C1NCCCCC1=NC=C(Br)C=C1C OGEAASSLWZDQBM-UHFFFAOYSA-N 0.000 claims 3
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims 3
- UFLGIAIHIAPJJC-UHFFFAOYSA-N Tripelennamine Chemical compound C=1C=CC=NC=1N(CCN(C)C)CC1=CC=CC=C1 UFLGIAIHIAPJJC-UHFFFAOYSA-N 0.000 claims 3
- 229960003790 alimemazine Drugs 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- GXDALQBWZGODGZ-UHFFFAOYSA-N astemizole Chemical compound C1=CC(OC)=CC=C1CCN1CCC(NC=2N(C3=CC=CC=C3N=2)CC=2C=CC(F)=CC=2)CC1 GXDALQBWZGODGZ-UHFFFAOYSA-N 0.000 claims 3
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 3
- 229960004574 azelastine Drugs 0.000 claims 3
- 229960000725 brompheniramine Drugs 0.000 claims 3
- ZDIGNSYAACHWNL-UHFFFAOYSA-N brompheniramine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Br)C=C1 ZDIGNSYAACHWNL-UHFFFAOYSA-N 0.000 claims 3
- 229960000428 carbinoxamine Drugs 0.000 claims 3
- OJFSXZCBGQGRNV-UHFFFAOYSA-N carbinoxamine Chemical compound C=1C=CC=NC=1C(OCCN(C)C)C1=CC=C(Cl)C=C1 OJFSXZCBGQGRNV-UHFFFAOYSA-N 0.000 claims 3
- 229960001803 cetirizine Drugs 0.000 claims 3
- 229960003291 chlorphenamine Drugs 0.000 claims 3
- SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 claims 3
- 229960002881 clemastine Drugs 0.000 claims 3
- YNNUSGIPVFPVBX-NHCUHLMSSA-N clemastine Chemical compound CN1CCC[C@@H]1CCO[C@@](C)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 YNNUSGIPVFPVBX-NHCUHLMSSA-N 0.000 claims 3
- 229960001140 cyproheptadine Drugs 0.000 claims 3
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 claims 3
- 229960000520 diphenhydramine Drugs 0.000 claims 3
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 3
- 229960005178 doxylamine Drugs 0.000 claims 3
- HCFDWZZGGLSKEP-UHFFFAOYSA-N doxylamine Chemical compound C=1C=CC=NC=1C(C)(OCCN(C)C)C1=CC=CC=C1 HCFDWZZGGLSKEP-UHFFFAOYSA-N 0.000 claims 3
- 229960001971 ebastine Drugs 0.000 claims 3
- MJJALKDDGIKVBE-UHFFFAOYSA-N ebastine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)CCCN1CCC(OC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 MJJALKDDGIKVBE-UHFFFAOYSA-N 0.000 claims 3
- 229960003592 fexofenadine Drugs 0.000 claims 3
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 3
- 229960000930 hydroxyzine Drugs 0.000 claims 3
- ZQDWXGKKHFNSQK-UHFFFAOYSA-N hydroxyzine Chemical compound C1CN(CCOCCO)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZQDWXGKKHFNSQK-UHFFFAOYSA-N 0.000 claims 3
- 229960004958 ketotifen Drugs 0.000 claims 3
- 229960001120 levocabastine Drugs 0.000 claims 3
- ZCGOMHNNNFPNMX-KYTRFIICSA-N levocabastine Chemical compound C1([C@@]2(C(O)=O)CCN(C[C@H]2C)[C@@H]2CC[C@@](CC2)(C#N)C=2C=CC(F)=CC=2)=CC=CC=C1 ZCGOMHNNNFPNMX-KYTRFIICSA-N 0.000 claims 3
- 229960001474 meclozine Drugs 0.000 claims 3
- 229960005042 mequitazine Drugs 0.000 claims 3
- 229960003955 mianserin Drugs 0.000 claims 3
- 229960001144 mizolastine Drugs 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229950010674 picumast Drugs 0.000 claims 3
- 229960003910 promethazine Drugs 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 229950005829 temelastine Drugs 0.000 claims 3
- 229960000351 terfenadine Drugs 0.000 claims 3
- 229960003223 tripelennamine Drugs 0.000 claims 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 239000000938 histamine H1 antagonist Substances 0.000 claims 2
- 208000013403 hyperactivity Diseases 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 230000002009 allergenic effect Effects 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000010276 construction Methods 0.000 claims 1
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000005306 thianaphthenyl group Chemical group 0.000 claims 1
- 229960001128 triprolidine Drugs 0.000 claims 1
- CBEQULMOCCWAQT-WOJGMQOQSA-N triprolidine Chemical compound C1=CC(C)=CC=C1C(\C=1N=CC=CC=1)=C/CN1CCCC1 CBEQULMOCCWAQT-WOJGMQOQSA-N 0.000 claims 1
- 0 *c1nc(cc(cc2)F)c2[n]1C(CC1)CCN1C(C1(CCN(Cc2cnc(N)nc2)CC1)F)=O Chemical compound *c1nc(cc(cc2)F)c2[n]1C(CC1)CCN1C(C1(CCN(Cc2cnc(N)nc2)CC1)F)=O 0.000 description 4
- ORBVZPNZPGRGKS-UHFFFAOYSA-N C(CNCC1)C1[n]1c(nccc2)c2nc1-c1cc2ccccc2[nH]1 Chemical compound C(CNCC1)C1[n]1c(nccc2)c2nc1-c1cc2ccccc2[nH]1 ORBVZPNZPGRGKS-UHFFFAOYSA-N 0.000 description 1
- KMQWSMHYXYXNRT-UHFFFAOYSA-N COc1nc2cccnc2[n]1C(CC1)CCN1C(C1(CCN(Cc2cnc(N)nc2)CC1)F)=O Chemical compound COc1nc2cccnc2[n]1C(CC1)CCN1C(C1(CCN(Cc2cnc(N)nc2)CC1)F)=O KMQWSMHYXYXNRT-UHFFFAOYSA-N 0.000 description 1
- VKDJZOXMKLOALY-UHFFFAOYSA-N CSc([n]1C(CC2)CCN2C(C2(CCN(Cc3cnc(N)nc3)CC2)F)=O)nc2c1nccc2 Chemical compound CSc([n]1C(CC2)CCN2C(C2(CCN(Cc3cnc(N)nc3)CC2)F)=O)nc2c1nccc2 VKDJZOXMKLOALY-UHFFFAOYSA-N 0.000 description 1
- FNIQXFAXPBTTBF-UHFFFAOYSA-N CSc1nc(C=C(CC2)F)c2[n]1C(CC1)CCN1C(C1CCN(Cc2cnc(N)nc2)CC1)=O Chemical compound CSc1nc(C=C(CC2)F)c2[n]1C(CC1)CCN1C(C1CCN(Cc2cnc(N)nc2)CC1)=O FNIQXFAXPBTTBF-UHFFFAOYSA-N 0.000 description 1
- MSWZRRQDGCYMNN-UHFFFAOYSA-N CSc1nc(cc(cc2)F)c2[n]1C(CC1)CCN1C(C1(CCN(Cc2cnc(N)nc2)CC1)F)=O Chemical compound CSc1nc(cc(cc2)F)c2[n]1C(CC1)CCN1C(C1(CCN(Cc2cnc(N)nc2)CC1)F)=O MSWZRRQDGCYMNN-UHFFFAOYSA-N 0.000 description 1
- GORJZHAQJFRYCJ-UHFFFAOYSA-N CSc1nc(cc(cc2)F)c2[n]1C(CC1)CCN1C(C1CCN(Cc2ccnc(N)c2)CC1)=O Chemical compound CSc1nc(cc(cc2)F)c2[n]1C(CC1)CCN1C(C1CCN(Cc2ccnc(N)c2)CC1)=O GORJZHAQJFRYCJ-UHFFFAOYSA-N 0.000 description 1
- XFEOMNAEJJMTOX-UHFFFAOYSA-N Nc1ncc(CN(CC2)CCC2(C=O)F)cn1 Chemical compound Nc1ncc(CN(CC2)CCC2(C=O)F)cn1 XFEOMNAEJJMTOX-UHFFFAOYSA-N 0.000 description 1
- WMMXGSMJCAWWSF-UHFFFAOYSA-N Nc1ncc(CN(CC2)CCC2C=O)cn1 Chemical compound Nc1ncc(CN(CC2)CCC2C=O)cn1 WMMXGSMJCAWWSF-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37373102P | 2002-04-18 | 2002-04-18 | |
| PCT/US2003/011672 WO2003088967A1 (en) | 2002-04-18 | 2003-04-16 | (1-4-piperidinyl) benzimidazole derivatives useful as histamine h3 antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005529116A JP2005529116A (ja) | 2005-09-29 |
| JP2005529116A5 true JP2005529116A5 (https=) | 2006-12-21 |
| JP4384918B2 JP4384918B2 (ja) | 2009-12-16 |
Family
ID=29251069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003585719A Expired - Lifetime JP4384918B2 (ja) | 2002-04-18 | 2003-04-16 | ヒスタミンｈ３アンタゴニストとして有用な（１−４−ピペリジニル）ベンズイミダゾール誘導体 |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP1499316B1 (https=) |
| JP (1) | JP4384918B2 (https=) |
| KR (1) | KR100827470B1 (https=) |
| CN (1) | CN100522166C (https=) |
| AR (1) | AR040405A1 (https=) |
| AT (1) | ATE389406T1 (https=) |
| AU (1) | AU2003223627B2 (https=) |
| BR (1) | BR0309348A (https=) |
| CA (1) | CA2481940A1 (https=) |
| CY (1) | CY1110363T1 (https=) |
| DE (1) | DE60319813T2 (https=) |
| DK (1) | DK1499316T3 (https=) |
| EC (1) | ECSP045367A (https=) |
| ES (1) | ES2301791T3 (https=) |
| IL (1) | IL164584A (https=) |
| MX (1) | MXPA04010173A (https=) |
| NO (1) | NO20045002L (https=) |
| NZ (1) | NZ535763A (https=) |
| PE (1) | PE20040684A1 (https=) |
| PL (1) | PL373889A1 (https=) |
| PT (1) | PT1499316E (https=) |
| RU (1) | RU2323935C2 (https=) |
| SI (1) | SI1499316T1 (https=) |
| TW (1) | TW200306183A (https=) |
| WO (1) | WO2003088967A1 (https=) |
| ZA (1) | ZA200407984B (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE552236T1 (de) | 2003-01-14 | 2012-04-15 | Cytokinetics Inc | Verbindungen, zusammensetzungen und verfahren zur behandlung von herzinsuffizienz |
| CA2523431A1 (en) | 2003-04-23 | 2004-11-25 | Glaxo Group Limited | Piperazine derivatives and their use for the treatment of neurological and psychiatric diseases |
| ES2522579T3 (es) | 2004-06-17 | 2014-11-17 | Cytokinetics, Inc. | Compuestos, composiciones y métodos |
| US7176222B2 (en) | 2004-07-27 | 2007-02-13 | Cytokinetics, Inc. | Syntheses of ureas |
| US20080021069A1 (en) * | 2004-10-08 | 2008-01-24 | Takeda Pharmaceutical Company Limited | Receptor Function Regulating Agent |
| EP1848696A1 (en) * | 2005-01-21 | 2007-10-31 | Schering Corporation | Imidazole and benzimidazole derivates useful as histamine h3 antagonists |
| TW200738676A (en) * | 2005-06-20 | 2007-10-16 | Schering Corp | Heteroatom-linked substituted piperidines and derivatives thereof useful as histamine H3 antagonists |
| ATE450525T1 (de) * | 2005-06-20 | 2009-12-15 | Schering Corp | Kohlenstoffgebundene substituierte piperidine und derivate daraus als histamin-h3-antagonisten |
| US7538223B2 (en) | 2005-08-04 | 2009-05-26 | Cytokinetics, Inc. | Compounds, compositions and methods |
| WO2007035703A1 (en) * | 2005-09-20 | 2007-03-29 | Schering Corporation | 1- [ [1- [ (2-amin0-6-methyl-4-pyridinyl) methyl] -4-flu0r0-4-piperidinyl,] carbonyl] -4- [2- (2-pyridinyl) -3h-imidaz0 [4 , 5-b] pyridin-3-yl] piperidine useful as histamine h3 antagonist |
| ATE429428T1 (de) | 2005-09-30 | 2009-05-15 | Hoffmann La Roche | Indanderivate als antagonisten des mch-rezeptors |
| ES2419007T3 (es) | 2005-12-15 | 2013-08-19 | Cytokinetics, Inc. | Ciertas entidades químicas, composiciones y procedimientos |
| US7825120B2 (en) | 2005-12-15 | 2010-11-02 | Cytokinetics, Inc. | Certain substituted ((piperazin-1-ylmethyl)benzyl)ureas |
| WO2007078815A2 (en) | 2005-12-16 | 2007-07-12 | Cytokinetics, Inc. | Certain chemical entities, compositions, and methods |
| WO2007078839A2 (en) | 2005-12-19 | 2007-07-12 | Cytokinetics, Inc. | Compounds, compositions and methods |
| US7638531B2 (en) | 2005-12-21 | 2009-12-29 | Schering Corporation | Phenoxypiperidines and analogs thereof useful as histamine H3 antagonists |
| EP1965862A2 (en) * | 2005-12-21 | 2008-09-10 | Schering Corporation | Combination of an h3 antagonist/inverse agonist and an appetite suppressant |
| RU2008132966A (ru) * | 2006-01-13 | 2010-02-20 | Ф.Хоффманн-Ля Рош Аг (Ch) | Производные циклогексилпиперазинилметанона и их применение в качестве модуляторов гистамин н3 рецептора |
| TW200813018A (en) | 2006-06-09 | 2008-03-16 | Astrazeneca Ab | Novel compounds |
| US8119661B2 (en) | 2007-09-11 | 2012-02-21 | Astrazeneca Ab | Piperidine derivatives and their use as muscarinic receptor modulators |
| CN101809021B (zh) * | 2007-09-11 | 2013-04-24 | 雅培制药有限公司 | 八氢-吡咯并[3,4-b]吡咯n-氧化物 |
| GB0813144D0 (en) | 2008-07-17 | 2008-08-27 | Glaxo Group Ltd | Novel compounds |
| GB0813142D0 (en) | 2008-07-17 | 2008-08-27 | Glaxo Group Ltd | Novel compounds |
| CA2785536C (en) | 2009-12-30 | 2018-02-27 | Arqule, Inc. | Substituted imidazopyridinyl-aminopyridine compounds |
| WO2012177852A1 (en) | 2011-06-24 | 2012-12-27 | Arqule, Inc | Substituted imidazopyridinyl compounds |
| US8609688B2 (en) | 2011-06-24 | 2013-12-17 | Arqule, Inc. | Substituted imidazopyridinyl-aminopyridine compounds |
| KR101127756B1 (ko) | 2011-09-02 | 2012-03-23 | 한국과학기술원 | Ｇｉｔ１ 유전자 결손 마우스 및 이를 이용한 약물 스크리닝 방법 |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| JP6046646B2 (ja) * | 2014-01-10 | 2016-12-21 | 信越化学工業株式会社 | オニウム塩、化学増幅型ポジ型レジスト組成物、及びパターン形成方法 |
| US10595550B2 (en) * | 2014-01-22 | 2020-03-24 | Vision Pharma, Llc | Therapeutic composition including carbonated solution |
| WO2017035114A1 (en) * | 2015-08-25 | 2017-03-02 | Janssen Pharmaceutica Nv | Benzimidazole derivatives useful as cb-1 inverse agonists |
| MA55556A (fr) | 2019-04-02 | 2022-02-09 | Aligos Therapeutics Inc | Composés ciblant prmt5 |
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| DD290192A5 (de) * | 1986-11-13 | 1991-05-23 | Eisai Co. Ltd,Jp | Pyridinderivat mit antiulzeroeser wirkung |
| ES2048109B1 (es) * | 1992-07-20 | 1994-12-16 | Espanola Prod Quimicos | Procedimiento de preparacion de nuevos derivados piperidicos del bencimidazol. |
| DE69415391T2 (de) * | 1993-05-26 | 1999-08-26 | Sumitomo Pharmaceuticals Co. | Chinazolinonderivate |
| US6211199B1 (en) * | 1995-11-17 | 2001-04-03 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl-amino)piperidines useful for the treatment of allergic diseases |
| CA2247105C (en) * | 1996-02-21 | 2002-05-14 | Hoechst Marion Roussel, Inc. | Novel substituted n-methyl-n-(4-(4-(1h-benzimidazol-2-yl-amino)piperidin-1-yl)-2-(aryl)butyl)benzamides useful for the treatment of allergic di seases |
| EP0980359B1 (en) * | 1997-05-01 | 2004-06-23 | Nissan Chemical Industries, Ltd. | Benzimidazole derivative |
| US6133291A (en) * | 1998-10-16 | 2000-10-17 | Schering Corporation | N-(imidazolylalkyl)substituted cyclic amines as histamine-H3 agonists or antagonists |
| AU2001292730A1 (en) * | 2000-09-20 | 2002-04-02 | Schering Corporation | Substituted imidazoles as dual histamine h1 and h3 agonists or antgonists |
| PE20020507A1 (es) * | 2000-10-17 | 2002-06-25 | Schering Corp | Compuestos no-imidazoles como antagonistas del receptor histamina h3 |
| US7220735B2 (en) * | 2002-04-18 | 2007-05-22 | Schering Corporation | Benzimidazolone histamine H3 antagonists |
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2003
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- 2003-04-16 BR BR0309348-4A patent/BR0309348A/pt not_active IP Right Cessation
- 2003-04-16 AT AT03719766T patent/ATE389406T1/de not_active IP Right Cessation
- 2003-04-16 PE PE2003000390A patent/PE20040684A1/es not_active Application Discontinuation
- 2003-04-16 ES ES03719766T patent/ES2301791T3/es not_active Expired - Lifetime
- 2003-04-16 AR AR20030101340A patent/AR040405A1/es active IP Right Grant
- 2003-04-16 MX MXPA04010173A patent/MXPA04010173A/es active IP Right Grant
- 2003-04-16 CN CNB038137798A patent/CN100522166C/zh not_active Expired - Fee Related
- 2003-04-16 PL PL03373889A patent/PL373889A1/xx not_active Application Discontinuation
- 2003-04-16 SI SI200331201T patent/SI1499316T1/sl unknown
- 2003-04-16 EP EP03719766A patent/EP1499316B1/en not_active Expired - Lifetime
- 2003-04-16 DE DE60319813T patent/DE60319813T2/de not_active Expired - Lifetime
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- 2003-04-16 JP JP2003585719A patent/JP4384918B2/ja not_active Expired - Lifetime
- 2003-04-16 CA CA002481940A patent/CA2481940A1/en not_active Abandoned
- 2003-04-16 DK DK03719766T patent/DK1499316T3/da active
- 2003-04-16 WO PCT/US2003/011672 patent/WO2003088967A1/en not_active Ceased
- 2003-04-16 AU AU2003223627A patent/AU2003223627B2/en not_active Ceased
- 2003-04-16 KR KR1020047016508A patent/KR100827470B1/ko not_active Expired - Fee Related
- 2003-04-16 RU RU2004133764/04A patent/RU2323935C2/ru not_active IP Right Cessation
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