ZA200410213B - Indole derivatives useful as histamine H3 antagonists. - Google Patents
Indole derivatives useful as histamine H3 antagonists. Download PDFInfo
- Publication number
- ZA200410213B ZA200410213B ZA200410213A ZA200410213A ZA200410213B ZA 200410213 B ZA200410213 B ZA 200410213B ZA 200410213 A ZA200410213 A ZA 200410213A ZA 200410213 A ZA200410213 A ZA 200410213A ZA 200410213 B ZA200410213 B ZA 200410213B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- aryl
- compound
- alkoxy
- independently selected
- Prior art date
Links
- 150000002475 indoles Chemical class 0.000 title description 3
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
- 239000003395 histamine H3 receptor antagonist Substances 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 98
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 206010020751 Hypersensitivity Diseases 0.000 claims description 18
- 208000026935 allergic disease Diseases 0.000 claims description 18
- 229940044551 receptor antagonist Drugs 0.000 claims description 18
- 239000002464 receptor antagonist Substances 0.000 claims description 18
- 230000007815 allergy Effects 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- -1 piperidinoethyl Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 230000008369 airway response Effects 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 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 description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 210000003169 central nervous system Anatomy 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 208000027744 congestion Diseases 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- SFOVDSLXFUGAIV-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-n-piperidin-4-ylbenzimidazol-2-amine Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2N=C1NC1CCNCC1 SFOVDSLXFUGAIV-UHFFFAOYSA-N 0.000 claims description 3
- BAWMMJAUVBLLEE-UHFFFAOYSA-N 2-[2-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]ethoxy]acetic acid Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 BAWMMJAUVBLLEE-UHFFFAOYSA-N 0.000 claims description 3
- VNIOQSAWKLOGLY-UHFFFAOYSA-N 3-[(5-methylfuran-2-yl)methyl]-n-piperidin-4-ylimidazo[4,5-b]pyridin-2-amine Chemical compound O1C(C)=CC=C1CN1C2=NC=CC=C2N=C1NC1CCNCC1 VNIOQSAWKLOGLY-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 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 description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 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 description 3
- 206010011953 Decreased activity Diseases 0.000 claims description 3
- 208000001953 Hypotension Diseases 0.000 claims description 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 description 3
- ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 claims description 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 description 3
- HOKDBMAJZXIPGC-UHFFFAOYSA-N Mequitazine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1CC1C(CC2)CCN2C1 HOKDBMAJZXIPGC-UHFFFAOYSA-N 0.000 claims description 3
- UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 claims description 3
- 208000019695 Migraine disease Diseases 0.000 claims description 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 description 3
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 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 description 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 description 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 description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229960003792 acrivastine Drugs 0.000 claims description 3
- PWACSDKDOHSSQD-IUTFFREVSA-N acrivastine Chemical compound C1=CC(C)=CC=C1C(\C=1N=C(\C=C\C(O)=O)C=CC=1)=C/CN1CCCC1 PWACSDKDOHSSQD-IUTFFREVSA-N 0.000 claims description 3
- 229960003790 alimemazine Drugs 0.000 claims description 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 description 3
- 229960000383 azatadine Drugs 0.000 claims description 3
- SEBMTIQKRHYNIT-UHFFFAOYSA-N azatadine Chemical compound C1CN(C)CCC1=C1C2=NC=CC=C2CCC2=CC=CC=C21 SEBMTIQKRHYNIT-UHFFFAOYSA-N 0.000 claims description 3
- 229960004574 azelastine Drugs 0.000 claims description 3
- 229960000725 brompheniramine Drugs 0.000 claims description 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 description 3
- 229960000428 carbinoxamine Drugs 0.000 claims description 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 description 3
- 229950010123 carebastine Drugs 0.000 claims description 3
- XGHOVGYJHWQGCC-UHFFFAOYSA-N carebastine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(=O)CCCN1CCC(OC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 XGHOVGYJHWQGCC-UHFFFAOYSA-N 0.000 claims description 3
- 229960001803 cetirizine Drugs 0.000 claims description 3
- 229960003291 chlorphenamine Drugs 0.000 claims description 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 description 3
- 229960002881 clemastine Drugs 0.000 claims description 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 description 3
- 229960003564 cyclizine Drugs 0.000 claims description 3
- UVKZSORBKUEBAZ-UHFFFAOYSA-N cyclizine Chemical compound C1CN(C)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 UVKZSORBKUEBAZ-UHFFFAOYSA-N 0.000 claims description 3
- 229960001140 cyproheptadine Drugs 0.000 claims description 3
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 claims description 3
- 229960001271 desloratadine Drugs 0.000 claims description 3
- 229960001992 dimetindene Drugs 0.000 claims description 3
- MVMQESMQSYOVGV-UHFFFAOYSA-N dimetindene Chemical compound CN(C)CCC=1CC2=CC=CC=C2C=1C(C)C1=CC=CC=N1 MVMQESMQSYOVGV-UHFFFAOYSA-N 0.000 claims description 3
- 229960000520 diphenhydramine Drugs 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 229960005178 doxylamine Drugs 0.000 claims description 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 description 3
- 229960001971 ebastine Drugs 0.000 claims description 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 description 3
- 229950003420 efletirizine Drugs 0.000 claims description 3
- 229960003449 epinastine Drugs 0.000 claims description 3
- WHWZLSFABNNENI-UHFFFAOYSA-N epinastine Chemical compound C1C2=CC=CC=C2C2CN=C(N)N2C2=CC=CC=C21 WHWZLSFABNNENI-UHFFFAOYSA-N 0.000 claims description 3
- 229960003592 fexofenadine Drugs 0.000 claims description 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 description 3
- 229960000930 hydroxyzine Drugs 0.000 claims description 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 description 3
- 208000013403 hyperactivity Diseases 0.000 claims description 3
- 230000036543 hypotension Effects 0.000 claims description 3
- 229960004958 ketotifen Drugs 0.000 claims description 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 description 3
- 229960001120 levocabastine Drugs 0.000 claims description 3
- 229960003088 loratadine Drugs 0.000 claims description 3
- 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 description 3
- 229960001474 meclozine Drugs 0.000 claims description 3
- 229960000582 mepyramine Drugs 0.000 claims description 3
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 claims description 3
- 229960005042 mequitazine Drugs 0.000 claims description 3
- 229960003955 mianserin Drugs 0.000 claims description 3
- 206010027599 migraine Diseases 0.000 claims description 3
- 229960001144 mizolastine Drugs 0.000 claims description 3
- 230000004899 motility Effects 0.000 claims description 3
- 229950009470 noberastine Drugs 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 229950010674 picumast Drugs 0.000 claims description 3
- 229960003910 promethazine Drugs 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 230000028327 secretion Effects 0.000 claims description 3
- 229950005829 temelastine Drugs 0.000 claims description 3
- 229960000351 terfenadine Drugs 0.000 claims description 3
- 229960003223 tripelennamine Drugs 0.000 claims description 3
- 229960001128 triprolidine Drugs 0.000 claims description 3
- CBEQULMOCCWAQT-WOJGMQOQSA-N triprolidine Chemical compound C1=CC(C)=CC=C1C(\C=1N=CC=CC=1)=C/CN1CCCC1 CBEQULMOCCWAQT-WOJGMQOQSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 229910014585 C2-Ce Inorganic materials 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 20
- 229960001340 histamine Drugs 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 7
- 108020003175 receptors Proteins 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000002837 carbocyclic group Chemical group 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 206010027654 Allergic conditions Diseases 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010028735 Nasal congestion Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 208000015114 central nervous system disease Diseases 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000003396 histamine H4 receptor antagonist Substances 0.000 description 2
- 210000003405 ileum Anatomy 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 230000002889 sympathetic effect Effects 0.000 description 2
- ILWJAOPQHOZXAN-UHFFFAOYSA-N 1,3-dithianyl Chemical group [CH]1SCCCS1 ILWJAOPQHOZXAN-UHFFFAOYSA-N 0.000 description 1
- SPCKHVPPRJWQRZ-UHFFFAOYSA-N 2-benzhydryloxy-n,n-dimethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 SPCKHVPPRJWQRZ-UHFFFAOYSA-N 0.000 description 1
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 1
- 125000006164 6-membered heteroaryl group Chemical group 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229940124056 Histamine H1 receptor antagonist Drugs 0.000 description 1
- 229940115480 Histamine H3 receptor antagonist Drugs 0.000 description 1
- 102000004384 Histamine H3 receptors Human genes 0.000 description 1
- 108090000981 Histamine H3 receptors Proteins 0.000 description 1
- 229940119240 Histamine H4 receptor antagonist Drugs 0.000 description 1
- 102000000543 Histamine Receptors Human genes 0.000 description 1
- 108010002059 Histamine Receptors Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 208000032140 Sleepiness Diseases 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000002057 chronotropic effect Effects 0.000 description 1
- 230000009989 contractile response Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 150000002171 ethylene diamines Chemical class 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 239000000938 histamine H1 antagonist Substances 0.000 description 1
- 206010020765 hypersomnia Diseases 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 201000003631 narcolepsy Diseases 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Ophthalmology & Optometry (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39098702P | 2002-06-24 | 2002-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200410213B true ZA200410213B (en) | 2005-10-20 |
Family
ID=30000654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200410213A ZA200410213B (en) | 2002-06-24 | 2004-12-17 | Indole derivatives useful as histamine H3 antagonists. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6951871B2 (fr) |
| EP (2) | EP1777223A1 (fr) |
| JP (1) | JP4326468B2 (fr) |
| KR (1) | KR20050009757A (fr) |
| CN (1) | CN100497334C (fr) |
| AR (1) | AR039718A1 (fr) |
| AT (1) | ATE344798T1 (fr) |
| AU (1) | AU2003243709B2 (fr) |
| CA (1) | CA2489337C (fr) |
| CY (1) | CY1105986T1 (fr) |
| DE (1) | DE60309598T2 (fr) |
| DK (1) | DK1539742T3 (fr) |
| ES (1) | ES2271644T3 (fr) |
| HK (1) | HK1072259A1 (fr) |
| IL (1) | IL165863A0 (fr) |
| MX (1) | MXPA05000193A (fr) |
| MY (1) | MY135686A (fr) |
| NZ (1) | NZ537200A (fr) |
| PT (1) | PT1539742E (fr) |
| TW (1) | TW200400031A (fr) |
| WO (1) | WO2004000831A1 (fr) |
| ZA (1) | ZA200410213B (fr) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20020507A1 (es) * | 2000-10-17 | 2002-06-25 | Schering Corp | Compuestos no-imidazoles como antagonistas del receptor histamina h3 |
| US7279493B2 (en) * | 2002-06-28 | 2007-10-09 | Euro-Celtique S.A. | Therapeutic agents useful for treating pain |
| KR20050100615A (ko) | 2003-01-14 | 2005-10-19 | 싸이토키네틱스, 인코포레이티드 | 화합물, 조성물 및 방법 |
| MXPA06014495A (es) * | 2004-06-17 | 2007-03-01 | Cytokinetics Inc | Compuestos, composiciones y metodos. |
| AU2005254658B2 (en) | 2004-06-21 | 2011-06-16 | F. Hoffmann-La Roche Ag | Indole derivatives as histamine receptor antagonists |
| US7176222B2 (en) | 2004-07-27 | 2007-02-13 | Cytokinetics, Inc. | Syntheses of ureas |
| FR2878849B1 (fr) * | 2004-12-06 | 2008-09-12 | Aventis Pharma Sa | Indoles substitues, compositions les contenant, procede de fabrication et utilisation |
| BRPI0515811A (pt) * | 2004-12-06 | 2008-08-05 | Aventis Pharma Sa | indóis substituìdos, processo para preparação, bem como utilização dos mesmos, medicamento e composição farmacêutica |
| MX2007008676A (es) | 2005-01-19 | 2007-07-25 | Hoffmann La Roche | Derivados de 5-aminoindol. |
| ES2337727T3 (es) * | 2005-06-20 | 2010-04-28 | Schering Corporation | Derivados de piperidina utiles como antagonistas de histamina h3. |
| US7408066B2 (en) | 2005-06-20 | 2008-08-05 | Schering Corproation | Carbon-linked substituted piperidines and derivatives thereof useful as histamine H3 antagonists |
| AU2006275568A1 (en) * | 2005-08-02 | 2007-02-08 | Neurogen Corporation | Dipiperazinyl ketones and related analogues |
| US7538223B2 (en) | 2005-08-04 | 2009-05-26 | Cytokinetics, Inc. | Compounds, compositions and methods |
| JP4860700B2 (ja) | 2005-09-20 | 2012-01-25 | シェーリング コーポレイション | ヒスタミンＨ３アンタゴニストとして有用な、１−［［１−［（２−アミノ−６−メチル−４−ピリジニル）メチル］−４−フルオロ−４−ピペリジニル］カルボニル］−４−［２−（２−ピリジニル）−３Ｈ−イミダゾ［４，５−ｂ］ピリジン−３−イル］ピペリジン |
| GB2431927B (en) * | 2005-11-04 | 2010-03-17 | Amira Pharmaceuticals Inc | 5-Lipoxygenase-activating protein (FLAP) inhibitors |
| US7977359B2 (en) | 2005-11-04 | 2011-07-12 | Amira Pharmaceuticals, Inc. | 5-lipdxygenase-activating protein (FLAP) inhibitors |
| WO2007057329A1 (fr) * | 2005-11-18 | 2007-05-24 | F. Hoffmann-La Roche Ag | Derives d’azaindole-2-carboxamide |
| ES2342979T3 (es) * | 2005-11-30 | 2010-07-20 | F. Hoffmann-La Roche Ag | Derivados de indol-2-carboxamida sustituidos en 5. |
| US7825120B2 (en) * | 2005-12-15 | 2010-11-02 | Cytokinetics, Inc. | Certain substituted ((piperazin-1-ylmethyl)benzyl)ureas |
| US20070161617A1 (en) | 2005-12-15 | 2007-07-12 | Morgan Bradley P | Certain chemical entities, compositions and methods |
| WO2007078815A2 (fr) | 2005-12-16 | 2007-07-12 | Cytokinetics, Inc. | Entites chimiques, compositions et methodes |
| WO2007078839A2 (fr) | 2005-12-19 | 2007-07-12 | Cytokinetics, Inc. | Composes, compositions et methodes |
| JP2009521445A (ja) * | 2005-12-21 | 2009-06-04 | シェーリング コーポレイション | Ｈ３アンタゴニスト／逆アゴニストと食欲抑制剤との組み合わせ |
| CA2634250A1 (fr) * | 2005-12-21 | 2007-07-05 | Schering Corporation | Phenoxypiperidines et leurs analogues utilisables en tant qu'antagonistes de l'histamine h3 |
| AR058558A1 (es) * | 2005-12-21 | 2008-02-13 | Schering Corp | Derivados de anilina sustituida utiles como antagonistas de la histamina h3 |
| CA2637531A1 (fr) * | 2006-02-17 | 2007-08-30 | Memory Pharmaceuticals Corporation | Composes ayant une affinite pour le recepteur 5-ht6 |
| US7514433B2 (en) | 2006-08-03 | 2009-04-07 | Hoffmann-La Roche Inc. | 1H-indole-6-yl-piperazin-1-yl-methanone derivatives |
| ATE524461T1 (de) | 2006-10-27 | 2011-09-15 | Boehringer Ingelheim Int | Neue substituierte piperidylpropanthiole |
| WO2008049874A1 (fr) * | 2006-10-27 | 2008-05-02 | Boehringer Ingelheim International Gmbh | Modulateurs ccr3 de pipéridyl-propane-thiol |
| KR20100053626A (ko) * | 2007-08-15 | 2010-05-20 | 메모리 파마슈티칼스 코포레이션 | 5-ｈｔ6 수용체 친화성을 나타내는 3'-치환된 화합물 |
| WO2009089134A1 (fr) * | 2008-01-04 | 2009-07-16 | Src, Inc. | Méthodes de mesure de la réponse d'un patient à l'administration d'un médicament ou de ses compositions |
| US20110160249A1 (en) | 2008-05-23 | 2011-06-30 | Schaab Kevin Murray | 5-lipoxygenase-activating protein inhibitor |
| US20100016297A1 (en) * | 2008-06-24 | 2010-01-21 | Memory Pharmaceuticals Corporation | Alkyl-substituted 3' compounds having 5-ht6 receptor affinity |
| US20100035862A1 (en) * | 2008-06-25 | 2010-02-11 | Abbott Laboratories | Novel aza-cyclic indole-2-carboxamides and methods of use thereof |
| AR072297A1 (es) | 2008-06-27 | 2010-08-18 | Novartis Ag | Derivados de indol-2-il-piridin-3-ilo, composicion farmaceutica que los comprende y su uso en medicamentos para el tratamiento de enfermedades mediadas por la sintasa aldosterona. |
| WO2010011657A1 (fr) * | 2008-07-23 | 2010-01-28 | Schering Corporation | Dérivés d'hétérocycles bicycliques utilisés en tant qu'antagonistes de récepteur d'histamine h3 |
| US20100029629A1 (en) * | 2008-07-25 | 2010-02-04 | Memory Pharmaceuticals Corporation | Acyclic compounds having 5-ht6 receptor affinity |
| US20100056531A1 (en) * | 2008-08-22 | 2010-03-04 | Memory Pharmaceuticals Corporation | Alkyl-substituted 3' compounds having 5-ht6 receptor affinity |
| WO2011124930A1 (fr) | 2010-04-08 | 2011-10-13 | Respivert Limited | Inhibiteurs de la map kinase p38 |
| AU2011261375B2 (en) | 2010-06-04 | 2016-09-22 | Albany Molecular Research, Inc. | Glycine transporter-1 inhibitors, methods of making them, and uses thereof |
| WO2013151982A1 (fr) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Méthodes et composés utiles pour traiter le prurit, et procédés d'identification desdits composés |
| TWI748194B (zh) | 2018-06-28 | 2021-12-01 | 德商菲尼克斯 Ｆｘｒ有限責任公司 | 含有雙環核心部分之新穎lxr調節劑 |
| EP3797769A1 (fr) | 2019-09-25 | 2021-03-31 | Fontès, M. Michel | Composition a usage therapeutique |
| US11324727B2 (en) | 2020-07-15 | 2022-05-10 | Schabar Research Associates, Llc | Unit oral dose compositions composed of naproxen sodium and famotidine for the treatment of acute pain and the reduction of the severity of heartburn and/or the risk of heartburn |
| CN116194102A (zh) | 2020-07-15 | 2023-05-30 | 沙巴研究联合有限责任公司 | 用于治疗急性疼痛和降低胃灼热的严重程度和/或风险的包含布洛芬和法莫替丁的单位口服剂量组合物 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0730037B2 (ja) | 1987-03-13 | 1995-04-05 | 第一製薬株式会社 | ピリミジニルプロピオン酸誘導体 |
| DK181190D0 (da) | 1990-07-30 | 1990-07-30 | Lundbeck & Co As H | 3-aryl-indol- eller 3-aryl-indazolderivater |
| US5217986A (en) * | 1992-03-26 | 1993-06-08 | Harbor Branch Oceanographic Institution, Inc. | Anti-allergy agent |
| US5352707A (en) * | 1992-03-26 | 1994-10-04 | Harbor Branch Oceanographic Institution, Inc. | Method for treating airway congestion |
| US5846982A (en) * | 1996-06-14 | 1998-12-08 | Eli Lilly And Company | Inhibition of serotonin reuptake |
| AU722040B2 (en) | 1996-08-16 | 2000-07-20 | Schering Corporation | Treatment of upper airway allergic responses with a combination of histamine receptor antagonists |
| CA2271841C (fr) * | 1996-11-25 | 2003-07-08 | The Procter & Gamble Company | Composes de 2-imidazolinylaminoindole servant de recepteurs adrenergiques alpha-2 |
| US5869479A (en) * | 1997-08-14 | 1999-02-09 | Schering Corporation | Treatment of upper airway allergic responses |
| DE60026581T2 (de) | 1999-12-20 | 2006-12-28 | Eli Lilly And Co., Indianapolis | Indolderivate zur behandlung von depression und angstzuständen |
| PE20020507A1 (es) * | 2000-10-17 | 2002-06-25 | Schering Corp | Compuestos no-imidazoles como antagonistas del receptor histamina h3 |
| ES2172436B1 (es) * | 2000-10-31 | 2004-01-16 | Almirall Prodesfarma Sa | Derivados de indolilpiperidina como agentes antihistaminicos y antialergicos. |
| AU2002253929A1 (en) | 2001-02-08 | 2002-09-24 | Schering Corporation | Use of dual h3/m2 antagonists with a bipiperidinic structure in the treatment of cognition deficit disorders |
| MY131890A (en) | 2001-03-13 | 2007-09-28 | Schering Corp | Piperidine compounds |
-
2003
- 2003-06-20 AU AU2003243709A patent/AU2003243709B2/en not_active Ceased
- 2003-06-20 TW TW092116874A patent/TW200400031A/zh unknown
- 2003-06-20 EP EP06020215A patent/EP1777223A1/fr not_active Withdrawn
- 2003-06-20 DK DK03761216T patent/DK1539742T3/da active
- 2003-06-20 ES ES03761216T patent/ES2271644T3/es not_active Expired - Lifetime
- 2003-06-20 CA CA2489337A patent/CA2489337C/fr not_active Expired - Fee Related
- 2003-06-20 DE DE60309598T patent/DE60309598T2/de not_active Expired - Lifetime
- 2003-06-20 WO PCT/US2003/019619 patent/WO2004000831A1/fr active IP Right Grant
- 2003-06-20 AR ARP030102203A patent/AR039718A1/es unknown
- 2003-06-20 JP JP2004516072A patent/JP4326468B2/ja not_active Expired - Fee Related
- 2003-06-20 MX MXPA05000193A patent/MXPA05000193A/es active IP Right Grant
- 2003-06-20 NZ NZ537200A patent/NZ537200A/en unknown
- 2003-06-20 IL IL16586303A patent/IL165863A0/xx unknown
- 2003-06-20 KR KR10-2004-7020914A patent/KR20050009757A/ko not_active Application Discontinuation
- 2003-06-20 EP EP03761216A patent/EP1539742B1/fr not_active Expired - Lifetime
- 2003-06-20 US US10/600,674 patent/US6951871B2/en not_active Expired - Fee Related
- 2003-06-20 CN CNB038147173A patent/CN100497334C/zh not_active Expired - Fee Related
- 2003-06-20 PT PT03761216T patent/PT1539742E/pt unknown
- 2003-06-20 AT AT03761216T patent/ATE344798T1/de not_active IP Right Cessation
- 2003-06-20 MY MYPI20032323A patent/MY135686A/en unknown
-
2004
- 2004-12-17 ZA ZA200410213A patent/ZA200410213B/en unknown
-
2005
- 2005-06-18 HK HK05105092A patent/HK1072259A1/xx not_active IP Right Cessation
-
2007
- 2007-02-05 CY CY20071100153T patent/CY1105986T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1539742A1 (fr) | 2005-06-15 |
| ES2271644T3 (es) | 2007-04-16 |
| US20040019099A1 (en) | 2004-01-29 |
| JP4326468B2 (ja) | 2009-09-09 |
| MY135686A (en) | 2008-06-30 |
| AU2003243709B2 (en) | 2007-01-18 |
| DE60309598T2 (de) | 2007-09-13 |
| US6951871B2 (en) | 2005-10-04 |
| DK1539742T3 (da) | 2006-12-27 |
| MXPA05000193A (es) | 2005-04-08 |
| CN100497334C (zh) | 2009-06-10 |
| ATE344798T1 (de) | 2006-11-15 |
| CA2489337A1 (fr) | 2003-12-31 |
| AR039718A1 (es) | 2005-03-09 |
| HK1072259A1 (en) | 2005-08-19 |
| IL165863A0 (en) | 2006-01-15 |
| CA2489337C (fr) | 2010-05-25 |
| AU2003243709A1 (en) | 2004-01-06 |
| DE60309598D1 (de) | 2006-12-21 |
| NZ537200A (en) | 2007-09-28 |
| PT1539742E (pt) | 2007-01-31 |
| WO2004000831A1 (fr) | 2003-12-31 |
| CY1105986T1 (el) | 2011-04-06 |
| EP1777223A1 (fr) | 2007-04-25 |
| EP1539742B1 (fr) | 2006-11-08 |
| KR20050009757A (ko) | 2005-01-25 |
| CN1662524A (zh) | 2005-08-31 |
| TW200400031A (en) | 2004-01-01 |
| JP2005531615A (ja) | 2005-10-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200410213B (en) | Indole derivatives useful as histamine H3 antagonists. | |
| US11931350B2 (en) | Opioid receptor ligands and methods of using and making same | |
| ZA200302521B (en) | Piperidine compounds as anti-allergic. | |
| TWI567068B (zh) | Ｔｒｋ抑制化合物 | |
| EP1499316B1 (fr) | Derives de (1-4-piperidinyl)benzimidazole servant d'antagonistes des recepteurs h3 de l'histamine | |
| AU2016372028B2 (en) | Methods of treating hyperalgesia | |
| AU2006323700A1 (en) | Diarylether derivatives as antitumor agents | |
| JP2014505037A5 (fr) | ||
| NO20083520L (no) | Tricykliske N-heteroaryl-karboksamidderivater inneholdende en benzimidazolenhet, fremgangsmate for fremstilling av samme og deres terapeutiske anvendelser | |
| WO2017106547A1 (fr) | Combinaisons de ligands de récepteurs opioïdes et d'inhibiteurs du cytochrome p450 | |
| JP2008526895A (ja) | ヒスタミンｈ３アンタゴニストとして有用なイミダゾールおよびベンゾイミダゾール誘導体 | |
| TWI254706B (en) | Cyclic amine compounds and pharmaceutical composition containing the same | |
| AR046114A1 (es) | Compuesto de 8- azoniabiciclo (3.2.1) octano, composicion farmaceutica para el tratamiento de enfermedades mediadas por receptores de acetilcolina muscarinicos y uso del compuesto para preparar dicha composicion | |
| JP2006199656A (ja) | アミド基を有する環状アミン化合物 | |
| ES2759650T3 (es) | Compuestos quinoxalina y sus usos | |
| TH134920A (th) | Cgrp รีเซปเตอร์แอนตาโกนิสต์ |