ZA200302521B - Piperidine compounds as anti-allergic. - Google Patents
Piperidine compounds as anti-allergic. Download PDFInfo
- Publication number
- ZA200302521B ZA200302521B ZA200302521A ZA200302521A ZA200302521B ZA 200302521 B ZA200302521 B ZA 200302521B ZA 200302521 A ZA200302521 A ZA 200302521A ZA 200302521 A ZA200302521 A ZA 200302521A ZA 200302521 B ZA200302521 B ZA 200302521B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- alkyl
- allergy
- composition
- substituted
- Prior art date
Links
- 150000003053 piperidines Chemical class 0.000 title description 2
- 230000003266 anti-allergic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 239000002464 receptor antagonist Substances 0.000 claims description 41
- 229940044551 receptor antagonist Drugs 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 37
- 206010020751 Hypersensitivity Diseases 0.000 claims description 30
- 208000026935 allergic disease Diseases 0.000 claims description 30
- 230000007815 allergy Effects 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- -1 for example Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 229960001271 desloratadine Drugs 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 208000027744 congestion Diseases 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 229960003088 loratadine Drugs 0.000 claims description 13
- 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 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 230000008369 airway response Effects 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 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 10
- 229960001803 cetirizine Drugs 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229960003592 fexofenadine Drugs 0.000 claims description 10
- 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 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 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 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 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 6
- 206010028735 Nasal congestion Diseases 0.000 claims description 6
- 229960000383 azatadine Drugs 0.000 claims description 6
- SEBMTIQKRHYNIT-UHFFFAOYSA-N azatadine Chemical compound C1CN(C)CCC1=C1C2=NC=CC=C2CCC2=CC=CC=C21 SEBMTIQKRHYNIT-UHFFFAOYSA-N 0.000 claims description 6
- 229960000725 brompheniramine Drugs 0.000 claims description 6
- 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 6
- 229950010123 carebastine Drugs 0.000 claims description 6
- 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 6
- 229960003291 chlorphenamine Drugs 0.000 claims description 6
- 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 6
- 229960000520 diphenhydramine Drugs 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 229960001971 ebastine Drugs 0.000 claims description 6
- 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 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 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 5
- 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 5
- 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 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 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 5
- 229960004574 azelastine Drugs 0.000 claims description 5
- 210000003169 central nervous system Anatomy 0.000 claims description 5
- 229960002881 clemastine Drugs 0.000 claims description 5
- 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 5
- 229960005178 doxylamine Drugs 0.000 claims description 5
- 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 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 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 5
- 229960001120 levocabastine Drugs 0.000 claims description 5
- 229960001144 mizolastine Drugs 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229960000351 terfenadine Drugs 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 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 4
- 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 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 description 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
- 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 4
- ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- HOKDBMAJZXIPGC-UHFFFAOYSA-N Mequitazine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1CC1C(CC2)CCN2C1 HOKDBMAJZXIPGC-UHFFFAOYSA-N 0.000 claims description 4
- UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 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 4
- 229960003792 acrivastine Drugs 0.000 claims description 4
- 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 4
- 229960003790 alimemazine Drugs 0.000 claims description 4
- 229960000428 carbinoxamine Drugs 0.000 claims description 4
- 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 4
- 229960003564 cyclizine Drugs 0.000 claims description 4
- 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 4
- 229960001140 cyproheptadine Drugs 0.000 claims description 4
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 claims description 4
- 229960001992 dimetindene Drugs 0.000 claims description 4
- 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 4
- 229950003420 efletirizine Drugs 0.000 claims description 4
- 229960003449 epinastine Drugs 0.000 claims description 4
- WHWZLSFABNNENI-UHFFFAOYSA-N epinastine Chemical compound C1C2=CC=CC=C2C2CN=C(N)N2C2=CC=CC=C21 WHWZLSFABNNENI-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229960000930 hydroxyzine Drugs 0.000 claims description 4
- 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 4
- 229960004958 ketotifen Drugs 0.000 claims description 4
- 229960001474 meclozine Drugs 0.000 claims description 4
- 229960000582 mepyramine Drugs 0.000 claims description 4
- 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 4
- 229960005042 mequitazine Drugs 0.000 claims description 4
- 229960003955 mianserin Drugs 0.000 claims description 4
- 229950009470 noberastine Drugs 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 229950010674 picumast Drugs 0.000 claims description 4
- 229960003910 promethazine Drugs 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 229950005829 temelastine Drugs 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 229960003223 tripelennamine Drugs 0.000 claims description 4
- 229960001128 triprolidine Drugs 0.000 claims description 4
- 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 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 206010011953 Decreased activity Diseases 0.000 claims description 3
- 208000019695 Migraine disease Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
- 208000013403 hyperactivity Diseases 0.000 claims description 3
- 206010027599 migraine Diseases 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 230000004899 motility Effects 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 230000028327 secretion Effects 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 208000024827 Alzheimer 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 claims 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 claims 1
- 229940125833 compound 23 Drugs 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 239000005557 antagonist Substances 0.000 description 12
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 10
- 241000124008 Mammalia Species 0.000 description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
- 125000002837 carbocyclic group Chemical group 0.000 description 5
- 229960001340 histamine Drugs 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 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 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 102000004384 Histamine H3 receptors Human genes 0.000 description 4
- 108090000981 Histamine H3 receptors Proteins 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VLSDXINSOMDCBK-BQYQJAHWSA-N (E)-1,1'-azobis(N,N-dimethylformamide) Chemical compound CN(C)C(=O)\N=N\C(=O)N(C)C VLSDXINSOMDCBK-BQYQJAHWSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 description 1
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
- ILWJAOPQHOZXAN-UHFFFAOYSA-N 1,3-dithianyl Chemical group [CH]1SCCCS1 ILWJAOPQHOZXAN-UHFFFAOYSA-N 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical group C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical compound CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 description 1
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 1
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 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
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 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
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 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
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000764238 Isis Species 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 229910020889 NaBH3 Inorganic materials 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
- 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
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WGNZRLMOMHJUSP-UHFFFAOYSA-N benzotriazol-1-yloxy(tripyrrolidin-1-yl)phosphanium Chemical compound C1CCCN1[P+](N1CCCC1)(N1CCCC1)ON1C2=CC=CC=C2N=N1 WGNZRLMOMHJUSP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 229910052801 chlorine Inorganic materials 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
- 239000003937 drug carrier Substances 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
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 206010020765 hypersomnia Diseases 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 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
- 150000007524 organic acids Chemical class 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 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
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 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
- 125000002098 pyridazinyl 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 125000001984 thiazolidinyl 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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/04—Drugs for disorders of the respiratory system for throat disorders
-
- 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
- A61P25/18—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
-
- 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
- A61P5/00—Drugs for disorders of the endocrine 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D401/02—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 two hetero rings
- C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Otolaryngology (AREA)
- Immunology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Endocrinology (AREA)
- Ophthalmology & Optometry (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24090100P | 2000-10-17 | 2000-10-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200302521B true ZA200302521B (en) | 2004-06-30 |
Family
ID=22908389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200302521A ZA200302521B (en) | 2000-10-17 | 2003-03-31 | Piperidine compounds as anti-allergic. |
Country Status (30)
| Country | Link |
|---|---|
| US (3) | US6720328B2 (fr) |
| EP (2) | EP1326858B1 (fr) |
| JP (2) | JP4093859B2 (fr) |
| KR (1) | KR100567266B1 (fr) |
| CN (2) | CN1243751C (fr) |
| AR (1) | AR035497A1 (fr) |
| AT (2) | ATE420863T1 (fr) |
| AU (2) | AU1535502A (fr) |
| BR (1) | BR0114754A (fr) |
| CA (1) | CA2424664C (fr) |
| CY (2) | CY1105227T1 (fr) |
| DE (2) | DE60115937T2 (fr) |
| DK (2) | DK1326858T3 (fr) |
| EC (1) | ECSP034559A (fr) |
| ES (2) | ES2320008T3 (fr) |
| HK (2) | HK1052935B (fr) |
| HU (1) | HUP0303835A3 (fr) |
| IL (1) | IL155031A0 (fr) |
| MX (1) | MXPA03003529A (fr) |
| NO (1) | NO325997B1 (fr) |
| NZ (1) | NZ524857A (fr) |
| PE (1) | PE20020507A1 (fr) |
| PL (1) | PL361978A1 (fr) |
| PT (1) | PT1571145E (fr) |
| RU (2) | RU2301231C2 (fr) |
| SI (1) | SI1326858T1 (fr) |
| SK (1) | SK4672003A3 (fr) |
| TW (2) | TWI258474B (fr) |
| WO (1) | WO2002032893A2 (fr) |
| ZA (1) | ZA200302521B (fr) |
Families Citing this family (52)
| 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 |
| GB2373186A (en) * | 2001-02-23 | 2002-09-18 | Astrazeneca Ab | Pharmaceutical combinations of a CCR3 antagonist and a compound which is usefulreatment of asthma, allergic disease or inflammation |
| AU2002244271A1 (en) * | 2001-03-13 | 2002-09-24 | Pharmacopeia, Inc. | Non-imidazole compounds as histamine h3 antagonists |
| AR036881A1 (es) * | 2001-10-15 | 2004-10-13 | Schering Corp | Un proceso para la preparacion de 4-(piperidil)(2-piridil)metanona-(e)-o-metiloxima y sales |
| US7105505B2 (en) | 2002-04-18 | 2006-09-12 | Schering Corporation | Benzimidazole derivatives useful as histamine H3 antagonists |
| AR040406A1 (es) | 2002-04-18 | 2005-04-06 | Schering Corp | Antagonistas de histamina h3 de benzimidazolona |
| EP1539742B1 (fr) * | 2002-06-24 | 2006-11-08 | Schering Corporation | Derives d'indole utilises en tant qu'antagonistes h3 d'histamine |
| EP2194058B1 (fr) | 2002-09-04 | 2013-11-27 | Merck Sharp & Dohme Corp. | Pyrazolopyrimidines utiisables pour le traitement de maladies cancéreuses |
| US8580782B2 (en) | 2002-09-04 | 2013-11-12 | Merck Sharp & Dohme Corp. | Substituted pyrazolo[1,5-a]pyrimidines as cyclin dependent kinase inhibitors |
| US8673924B2 (en) | 2002-09-04 | 2014-03-18 | Merck Sharp & Dohme Corp. | Substituted pyrazolo[1,5-a]pyrimidines as cyclin dependent kinase inhibitors |
| CA2512899A1 (fr) | 2003-01-14 | 2004-08-05 | Arena Pharmaceuticals Inc. | Derives aryles et heteroaryles tri-substitues en position 1,2,3 en tant que modulateurs de metabolisme et prophylaxie et traitement de troubles lies au metabolisme |
| US20050090527A1 (en) * | 2003-01-28 | 2005-04-28 | Schering Corporation | Combination of H1, H3 and H4 receptor antagonists for treatment of allergic and non-allergic pulmonary inflammation, congestion and allergic rhinitis |
| PL1615909T3 (pl) | 2003-04-23 | 2009-01-30 | Glaxo Group Ltd | Pochodne piperazyny i ich zastosowanie w leczeniu chorób neurologicznych i psychicznych |
| EP1646620B1 (fr) * | 2003-07-18 | 2007-08-15 | Glaxo Group Limited | Piperidines substituees utilisees en tant que ligands du recepteur h3 de l'histamine |
| MX2007001561A (es) * | 2004-08-04 | 2007-04-16 | Schering Corp | Formulacion farmaceutica que comprende pleconaril para tratamiento de enfermedades de vias aereas. |
| GB0420831D0 (en) | 2004-09-17 | 2004-10-20 | Glaxo Group Ltd | Novel compounds |
| DE602006010864D1 (de) * | 2005-06-20 | 2010-01-14 | Schering Corp | Kohlenstoffgebundene substituierte piperidine und derivate daraus als histamin-h3-antagonisten |
| KR20080021082A (ko) | 2005-06-20 | 2008-03-06 | 쉐링 코포레이션 | 히스타민 ｈ3 길항제로서 유용한 피페리딘 유도체 |
| EP1931665A1 (fr) * | 2005-09-20 | 2008-06-18 | Schering Corporation | La 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, utile en tant qu'antagoniste de l'histamine h3 |
| AU2006331770A1 (en) * | 2005-12-21 | 2007-07-05 | Schering Corporation | Treatment of nonalcoholic fatty liver disease using cholesterol lowering agents and H3 receptor antagonist/inverse agonist |
| WO2007075688A2 (fr) * | 2005-12-21 | 2007-07-05 | Schering Corporation | Derives substitues de l'aniline utilisables en tant qu'antagonistes de l'histamine h3 |
| JP2009521448A (ja) * | 2005-12-21 | 2009-06-04 | 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フェノキシピペリジンおよびそのアナログ |
| EP1965862A2 (fr) * | 2005-12-21 | 2008-09-10 | Schering Corporation | Combinaison d'un antagoniste/agoniste inverse de h3 et d'un moderateur de l'appetit |
| PE20071320A1 (es) | 2006-01-18 | 2007-12-29 | Schering Corp | Moduladores de receptores cannabinoides |
| JP2010520199A (ja) * | 2007-03-02 | 2010-06-10 | シェーリング コーポレイション | ピペリジン誘導体およびその使用方法 |
| KR20100051625A (ko) * | 2007-06-28 | 2010-05-17 | 인터벳 인터내셔널 비.브이. | Ｃｂ1 길항제로서의 치환된 피페라진 |
| WO2009052068A1 (fr) * | 2007-10-17 | 2009-04-23 | Sanofi-Aventis | Urées de n-phényl-bipyrrolidine substituées et leur utilisation thérapeutique |
| RU2477719C2 (ru) * | 2007-10-17 | 2013-03-20 | Санофи-Авентис | Замещенные n-фенилбипирролидинкарбоксамиды и их терапевтическое применение |
| KR20100072077A (ko) * | 2007-10-17 | 2010-06-29 | 사노피-아벤티스 | 치환된 ｎ페닐비피롤리딘 카복스아미드 및 이의 치료적 용도 |
| EP2205558B1 (fr) * | 2007-10-17 | 2012-07-25 | Sanofi | Amides de n-phényl-pyrrolidinylméthylpyrrolidine substitués et leur utilisation thérapeutique comme modulateurs du récepteur h3 de l'histamine |
| US8383657B2 (en) * | 2007-12-21 | 2013-02-26 | Abbott Laboratories | Thiazolylidine urea and amide derivatives and methods of use thereof |
| US20090221648A1 (en) * | 2007-12-21 | 2009-09-03 | Abbott Laboratories | Compositions for treatment of cognitive disorders |
| ES2590604T3 (es) | 2008-01-04 | 2016-11-22 | Schabar Research Associates Llc | Composición que comprende un analgésico y un antihistamínico |
| EP2318388A2 (fr) | 2008-07-23 | 2011-05-11 | Schering Corporation | Dérivés spirocycliques tricycliques et leurs procédés d utilisation |
| CA2739491A1 (fr) | 2008-10-16 | 2010-04-22 | Schering Corporation | Derives d'azine et leurs methodes d'utilisation |
| EP2379564A1 (fr) | 2008-12-19 | 2011-10-26 | Schering Corporation | Dérivés hétérocycliques bicycliques et leurs procédés d'utilisation |
| WO2010071822A1 (fr) | 2008-12-19 | 2010-06-24 | Schering Corporation | Dérivés de pipéridine et de pipérazine et leurs méthodes d'utilisation |
| DK2421852T3 (da) * | 2009-04-22 | 2014-08-18 | Janssen Pharmaceutica Nv | Heteroaromatiske og aromatiske piperazinylazetidinylamider som monoacylglycerollipaseinhibitor |
| US20120171126A1 (en) | 2009-06-16 | 2012-07-05 | Purakkattle Biju J | NOVEL [3,2-c] HETEROARYL STEROIDS AS GLUCOCORTICOID RECEPTOR AGONISTS COMPOSITIONS AND USES THEREOF |
| US8785440B2 (en) | 2009-09-04 | 2014-07-22 | Biogen Idec Ma, Inc. | Bruton's tyrosine kinase inhibitors |
| CN102712626B (zh) * | 2010-01-22 | 2014-09-17 | 大鹏药品工业株式会社 | 具有pgds抑制作用的哌嗪化合物 |
| EP2619198A1 (fr) | 2010-09-22 | 2013-07-31 | Arena Pharmaceuticals, Inc. | Modulateurs du récepteur gpr119 et traitement des troubles qui lui sont liés |
| 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 |
| AR091273A1 (es) | 2012-06-08 | 2015-01-21 | Biogen Idec Inc | Inhibidores de pirimidinil tirosina quinasa |
| CN105315267B (zh) * | 2014-07-30 | 2019-06-04 | 江苏恩华药业股份有限公司 | 一种酰胺类衍生物及其应用 |
| MX2021011472A (es) | 2015-01-06 | 2022-08-17 | Arena Pharm Inc | Metodos de condiciones de tratamiento relacionadas con el receptor s1p1. |
| SI3310760T1 (sl) | 2015-06-22 | 2023-02-28 | Arena Pharmaceuticals, Inc. | Kristalinična L-argininska sol (R)-2-(7-(4-ciklopentil-3-(trifluorometil)benziloksi)-1,2,3,4- tetrahidrociklo-penta(b)indol-3-il)ocetne kisline za uporabo pri motnjah, povezanih z receptorjem S1P1 |
| CN110049976A (zh) | 2016-07-21 | 2019-07-23 | 比奥根Ma公司 | 布鲁顿氏酪氨酸激酶抑制剂的琥珀酸盐形式和组合物 |
| KR20190116416A (ko) | 2017-02-16 | 2019-10-14 | 아레나 파마슈티칼스, 인크. | 원발 담즙성 담관염을 치료하기 위한 화합물 및 방법 |
| CN110105263A (zh) * | 2019-05-13 | 2019-08-09 | 常州大学 | 一种阿米卡星中间体的合成方法 |
| WO2022015784A1 (fr) | 2020-07-15 | 2022-01-20 | Schabar Research Associates Llc | Compositions de dose orale unitaire composées d'ibuprofène et de famotidine pour le traitement de la douleur aiguë et la réduction de la gravité et/ou du risque de brûlures d'estomac |
| 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 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR920701167A (ko) | 1989-07-07 | 1992-08-11 | 에릭 에스. 딕커 | 약제학적 활성 화합물 |
| US5633250A (en) | 1991-12-18 | 1997-05-27 | Schering Corporation | Imidazoylalkyl substituted with a six or seven membered heterocyclic ring containing two nitrogen atoms |
| US5807872A (en) | 1992-12-16 | 1998-09-15 | Schering Corporation | Imidazoylalkyl substituted with a six membered nitrogen containing heterocyclic ring |
| JPH07121939B2 (ja) | 1991-12-18 | 1995-12-25 | シェリング・コーポレーション | 窒素含有４または５員複素環で置換されたイミダゾリルまたはイミダゾイルアルキル化合物 |
| HUT74386A (en) | 1993-11-15 | 1996-12-30 | Schering Corp | Phenyl-alkyl imidazoles as h3-receptor antagonists and pharmaceutical compositions containing them |
| NZ323543A (en) * | 1995-11-17 | 1999-06-29 | Hoechst Marion Roussel Inc | Substituted 4-(1h-benzimidazol-2-yl-amino)piperidine derivatives useful for the treatment of allergic diseases |
| CN1152682C (zh) | 1996-08-16 | 2004-06-09 | 先灵公司 | 用组胺受体拮抗剂组合物制备治疗上呼吸道变态反应的药物的用途 |
| US5869479A (en) | 1997-08-14 | 1999-02-09 | Schering Corporation | Treatment of upper airway allergic responses |
| US5990147A (en) | 1997-11-07 | 1999-11-23 | Schering Corporation | H3 receptor ligands of the phenyl-alkyl-imidazoles type |
| US6034251A (en) | 1997-11-07 | 2000-03-07 | Schering Corporation | Phenyl-alkyl-imidazoles |
| IL135729A0 (en) * | 1997-11-07 | 2001-05-20 | Schering Corp | H3 receptor ligands of the phenyl-alkyl-imidazoles type |
| CN1329490A (zh) * | 1998-10-09 | 2002-01-02 | 先灵公司 | 用于治疗变应性疾病的组合物和方法 |
| US6100279A (en) | 1998-11-05 | 2000-08-08 | Schering Corporation | Imidazoylalkyl substituted with a five, six or seven membered heterocyclic ring containing one nitrogen atom |
| PE20020507A1 (es) * | 2000-10-17 | 2002-06-25 | Schering Corp | Compuestos no-imidazoles como antagonistas del receptor histamina h3 |
| AU2002244271A1 (en) | 2001-03-13 | 2002-09-24 | Pharmacopeia, Inc. | Non-imidazole compounds as histamine h3 antagonists |
| AR040406A1 (es) * | 2002-04-18 | 2005-04-06 | Schering Corp | Antagonistas de histamina h3 de benzimidazolona |
| US7105505B2 (en) * | 2002-04-18 | 2006-09-12 | Schering Corporation | Benzimidazole derivatives useful as histamine H3 antagonists |
| EP1539742B1 (fr) * | 2002-06-24 | 2006-11-08 | Schering Corporation | Derives d'indole utilises en tant qu'antagonistes h3 d'histamine |
| WO2004069338A1 (fr) * | 2003-01-31 | 2004-08-19 | Schering Corporation | Utilisation de combinaisons d'antagonistes du recepteur h1 et h3 de l'histamine pour la preparation d'un medicament destine au traitement d'etats cutanes et oculaires d'origine allergique |
-
2001
- 2001-10-12 PE PE2001001016A patent/PE20020507A1/es not_active Application Discontinuation
- 2001-10-15 DE DE60115937T patent/DE60115937T2/de not_active Expired - Lifetime
- 2001-10-15 EP EP01983968A patent/EP1326858B1/fr not_active Expired - Lifetime
- 2001-10-15 TW TW090125385A patent/TWI258474B/zh not_active IP Right Cessation
- 2001-10-15 CA CA002424664A patent/CA2424664C/fr not_active Expired - Fee Related
- 2001-10-15 EP EP05009405A patent/EP1571145B1/fr not_active Expired - Lifetime
- 2001-10-15 IL IL15503101A patent/IL155031A0/xx unknown
- 2001-10-15 PT PT05009405T patent/PT1571145E/pt unknown
- 2001-10-15 RU RU2003114748/04A patent/RU2301231C2/ru not_active IP Right Cessation
- 2001-10-15 CN CNB018175120A patent/CN1243751C/zh not_active Expired - Fee Related
- 2001-10-15 PL PL01361978A patent/PL361978A1/xx not_active Application Discontinuation
- 2001-10-15 SI SI200130466T patent/SI1326858T1/sl unknown
- 2001-10-15 KR KR1020037005283A patent/KR100567266B1/ko not_active IP Right Cessation
- 2001-10-15 AR ARP010104831A patent/AR035497A1/es not_active Application Discontinuation
- 2001-10-15 CN CN2005101310947A patent/CN1803795B/zh not_active Expired - Fee Related
- 2001-10-15 DK DK01983968T patent/DK1326858T3/da active
- 2001-10-15 AU AU1535502A patent/AU1535502A/xx active Pending
- 2001-10-15 US US09/978,267 patent/US6720328B2/en not_active Expired - Fee Related
- 2001-10-15 SK SK467-2003A patent/SK4672003A3/sk unknown
- 2001-10-15 NZ NZ524857A patent/NZ524857A/xx unknown
- 2001-10-15 AT AT05009405T patent/ATE420863T1/de active
- 2001-10-15 MX MXPA03003529A patent/MXPA03003529A/es active IP Right Grant
- 2001-10-15 HU HU0303835A patent/HUP0303835A3/hu unknown
- 2001-10-15 DE DE60137461T patent/DE60137461D1/de not_active Expired - Lifetime
- 2001-10-15 AT AT01983968T patent/ATE312833T1/de active
- 2001-10-15 ES ES05009405T patent/ES2320008T3/es not_active Expired - Lifetime
- 2001-10-15 AU AU2002215355A patent/AU2002215355B2/en not_active Ceased
- 2001-10-15 TW TW093131752A patent/TWI292399B/zh active
- 2001-10-15 BR BR0114754-4A patent/BR0114754A/pt not_active IP Right Cessation
- 2001-10-15 ES ES01983968T patent/ES2250500T3/es not_active Expired - Lifetime
- 2001-10-15 WO PCT/US2001/032151 patent/WO2002032893A2/fr active IP Right Grant
- 2001-10-15 DK DK05009405T patent/DK1571145T3/da active
- 2001-10-15 JP JP2002536275A patent/JP4093859B2/ja not_active Expired - Fee Related
-
2003
- 2003-03-31 ZA ZA200302521A patent/ZA200302521B/en unknown
- 2003-04-15 NO NO20031744A patent/NO325997B1/no not_active IP Right Cessation
- 2003-04-16 EC EC2003004559A patent/ECSP034559A/es unknown
- 2003-07-17 HK HK03105161.9A patent/HK1052935B/zh not_active IP Right Cessation
- 2003-10-31 US US10/699,189 patent/US7300941B2/en not_active Expired - Fee Related
-
2006
- 2006-01-23 HK HK06101045.7A patent/HK1081182A1/xx not_active IP Right Cessation
- 2006-03-09 CY CY20061100329T patent/CY1105227T1/el unknown
-
2007
- 2007-02-02 RU RU2007104096/04A patent/RU2007104096A/ru not_active Application Discontinuation
- 2007-03-09 JP JP2007061074A patent/JP2007145866A/ja active Pending
- 2007-11-20 US US11/943,315 patent/US20080119487A1/en not_active Abandoned
-
2009
- 2009-04-10 CY CY20091100417T patent/CY1110262T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200302521B (en) | Piperidine compounds as anti-allergic. | |
| AU2002215355A1 (en) | Piperidine compounds as anti-allergic | |
| JP4522651B2 (ja) | 新規非イミダゾール化合物 | |
| US20040097483A1 (en) | Benzimidazole derivatives useful as histamine H3 antagonists | |
| HRP20210094T1 (hr) | POSTUPAK PRIPRAVE DERIVATIVA OKSAZOLO[4,5-b]PIRIDINA I TIAZOLO[4,5-b]PIRIDINA KAO INHIBITORA IRAK4 NAMIJENJENIH LIJEČENJU RAKA | |
| ZA200410213B (en) | Indole derivatives useful as histamine H3 antagonists. | |
| US20040048843A1 (en) | Benzimidazolone histamine H3 antagonists | |
| EP1499316A1 (fr) | Derives de (1-4-piperidinyl)benzimidazole servant d'antagonistes des recepteurs h3 de l'histamine | |
| RU2003114748A (ru) | Новые соединения, не являющиеся имидазолами | |
| US7482468B2 (en) | Imidazole and benzimidazole derivatives useful as histamine H3 antagonists | |
| KR20040015271A (ko) | 비대칭 환상 디아민 화합물 | |
| KR100878421B1 (ko) | 5원 환식기를 가지는 환상 디아민 화합물 |