MXPA04011472A - Derivados de amino-piridina, piridina y piridazina para usarse como ligandos del receptor vaniloide para el tratamiento del dolor. - Google Patents
Derivados de amino-piridina, piridina y piridazina para usarse como ligandos del receptor vaniloide para el tratamiento del dolor.Info
- Publication number
- MXPA04011472A MXPA04011472A MXPA04011472A MXPA04011472A MXPA04011472A MX PA04011472 A MXPA04011472 A MX PA04011472A MX PA04011472 A MXPA04011472 A MX PA04011472A MX PA04011472 A MXPA04011472 A MX PA04011472A MX PA04011472 A MXPA04011472 A MX PA04011472A
- Authority
- MX
- Mexico
- Prior art keywords
- 8alkyl
- nrara
- dihydro
- atoms
- nrarf
- Prior art date
Links
- 208000002193 Pain Diseases 0.000 title claims abstract description 32
- 238000011282 treatment Methods 0.000 title claims abstract description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 14
- 108010062740 TRPV Cation Channels Proteins 0.000 title description 14
- 102000011040 TRPV Cation Channels Human genes 0.000 title description 9
- 239000003446 ligand Substances 0.000 title description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 title 1
- 150000004892 pyridazines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 163
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 32
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
- 208000004296 neuralgia Diseases 0.000 claims abstract description 25
- 208000021722 neuropathic pain Diseases 0.000 claims abstract description 24
- 208000004454 Hyperalgesia Diseases 0.000 claims abstract description 22
- 230000002496 gastric effect Effects 0.000 claims abstract description 22
- 230000002792 vascular Effects 0.000 claims abstract description 19
- 206010065390 Inflammatory pain Diseases 0.000 claims abstract description 17
- 206010019233 Headaches Diseases 0.000 claims abstract description 16
- 208000035475 disorder Diseases 0.000 claims abstract description 15
- 231100000869 headache Toxicity 0.000 claims abstract description 15
- 208000011580 syndromic disease Diseases 0.000 claims abstract description 15
- 206010053552 allodynia Diseases 0.000 claims abstract description 12
- 208000035154 Hyperesthesia Diseases 0.000 claims abstract description 10
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 10
- 230000001154 acute effect Effects 0.000 claims abstract description 10
- 206010027599 migraine Diseases 0.000 claims abstract description 10
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 9
- 208000006673 asthma Diseases 0.000 claims abstract description 9
- 201000008482 osteoarthritis Diseases 0.000 claims abstract description 9
- 206010061218 Inflammation Diseases 0.000 claims abstract description 8
- 206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 8
- 208000025865 Ulcer Diseases 0.000 claims abstract description 8
- 201000010105 allergic rhinitis Diseases 0.000 claims abstract description 8
- 230000004054 inflammatory process Effects 0.000 claims abstract description 8
- 230000003902 lesion Effects 0.000 claims abstract description 8
- 208000001319 vasomotor rhinitis Diseases 0.000 claims abstract description 8
- 230000009278 visceral effect Effects 0.000 claims abstract description 8
- 208000014181 Bronchial disease Diseases 0.000 claims abstract description 7
- 208000001387 Causalgia Diseases 0.000 claims abstract description 7
- 208000023890 Complex Regional Pain Syndromes Diseases 0.000 claims abstract description 7
- 206010012434 Dermatitis allergic Diseases 0.000 claims abstract description 7
- 208000003251 Pruritus Diseases 0.000 claims abstract description 7
- 208000025747 Rheumatic disease Diseases 0.000 claims abstract description 7
- 206010047642 Vitiligo Diseases 0.000 claims abstract description 7
- 206010052428 Wound Diseases 0.000 claims abstract description 7
- 208000027418 Wounds and injury Diseases 0.000 claims abstract description 7
- 206010003246 arthritis Diseases 0.000 claims abstract description 7
- 208000029162 bladder disease Diseases 0.000 claims abstract description 7
- 208000014439 complex regional pain syndrome type 2 Diseases 0.000 claims abstract description 7
- 210000000981 epithelium Anatomy 0.000 claims abstract description 7
- 230000000241 respiratory effect Effects 0.000 claims abstract description 7
- 230000036269 ulceration Effects 0.000 claims abstract description 7
- 206010012735 Diarrhoea Diseases 0.000 claims abstract description 6
- 208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 6
- 208000009889 Herpes Simplex Diseases 0.000 claims abstract description 6
- 206010043269 Tension headache Diseases 0.000 claims abstract description 6
- 208000008548 Tension-Type Headache Diseases 0.000 claims abstract description 6
- 208000000718 duodenal ulcer Diseases 0.000 claims abstract description 6
- 208000030533 eye disease Diseases 0.000 claims abstract description 6
- 230000000451 tissue damage Effects 0.000 claims abstract description 6
- 231100000827 tissue damage Toxicity 0.000 claims abstract description 6
- 230000009092 tissue dysfunction Effects 0.000 claims abstract description 6
- 230000003779 hair growth Effects 0.000 claims abstract description 5
- 206010020853 Hypertonic bladder Diseases 0.000 claims abstract description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 266
- 125000004429 atom Chemical group 0.000 claims description 226
- 125000005843 halogen group Chemical group 0.000 claims description 189
- -1 3,5-ditrifluoromethylphenyl Chemical group 0.000 claims description 187
- 229920006395 saturated elastomer Polymers 0.000 claims description 172
- 125000001424 substituent group Chemical group 0.000 claims description 139
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 136
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 136
- 125000000623 heterocyclic group Chemical group 0.000 claims description 122
- 229910052717 sulfur Inorganic materials 0.000 claims description 113
- 229910052757 nitrogen Inorganic materials 0.000 claims description 92
- 229910052760 oxygen Inorganic materials 0.000 claims description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims description 66
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 61
- 229910052799 carbon Inorganic materials 0.000 claims description 60
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
- 150000001412 amines Chemical class 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 51
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 47
- 125000004043 oxo group Chemical group O=* 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 claims description 38
- 125000005605 benzo group Chemical group 0.000 claims description 29
- 125000004434 sulfur atom Chemical group 0.000 claims description 29
- 125000002950 monocyclic group Chemical group 0.000 claims description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 26
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 26
- 125000002619 bicyclic group Chemical group 0.000 claims description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 24
- 229910052702 rhenium Inorganic materials 0.000 claims description 23
- 125000001624 naphthyl group Chemical group 0.000 claims description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 20
- JWPMHRXIIOEZRU-UHFFFAOYSA-N 2,5-dihydro-1,2,4-thiadiazole Chemical compound C1NC=NS1 JWPMHRXIIOEZRU-UHFFFAOYSA-N 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- HBJUQLMVCIEESP-UHFFFAOYSA-N 2,5-dihydro-1,2,4-oxadiazole Chemical compound C1NC=NO1 HBJUQLMVCIEESP-UHFFFAOYSA-N 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 8
- QYMGRIFMUQCAJW-UHFFFAOYSA-N 1,2-dihydropyrazine Chemical compound C1NC=CN=C1 QYMGRIFMUQCAJW-UHFFFAOYSA-N 0.000 claims description 8
- LOZWAPSEEHRYPG-UHFFFAOYSA-N 1,4-dithiane Chemical compound C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 claims description 8
- CQHHFSBXAPCQFG-UHFFFAOYSA-N 2,3-dihydro-1,2,4-oxadiazole Chemical compound C1NOC=N1 CQHHFSBXAPCQFG-UHFFFAOYSA-N 0.000 claims description 8
- KWIVRAVCZJXOQC-UHFFFAOYSA-N 3h-oxathiazole Chemical compound N1SOC=C1 KWIVRAVCZJXOQC-UHFFFAOYSA-N 0.000 claims description 8
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 8
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 7
- FAYAYUOZWYJNBD-UHFFFAOYSA-N 1,3-benzothiazol-6-amine Chemical compound NC1=CC=C2N=CSC2=C1 FAYAYUOZWYJNBD-UHFFFAOYSA-N 0.000 claims description 7
- JBYHSSAVUBIJMK-UHFFFAOYSA-N 1,4-oxathiane Chemical compound C1CSCCO1 JBYHSSAVUBIJMK-UHFFFAOYSA-N 0.000 claims description 7
- PFXWIDHJNPULAS-UHFFFAOYSA-N 2-chloro-n-[6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl]quinolin-7-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC(NC=2C=C3N=C(Cl)C=CC3=CC=2)=NC=N1 PFXWIDHJNPULAS-UHFFFAOYSA-N 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 7
- 230000002981 neuropathic effect Effects 0.000 claims description 7
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 7
- 208000017520 skin disease Diseases 0.000 claims description 7
- 230000002889 sympathetic effect Effects 0.000 claims description 7
- PNJBXRVMRQIFKK-UHFFFAOYSA-N 1,4-dihydrotriazine Chemical compound C1C=CNN=N1 PNJBXRVMRQIFKK-UHFFFAOYSA-N 0.000 claims description 6
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 6
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 6
- RLDJTWKQIMTLEN-UHFFFAOYSA-N 5,6-dihydro-1,4,2-dioxazine Chemical compound C1CON=CO1 RLDJTWKQIMTLEN-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 230000004075 alteration Effects 0.000 claims description 6
- 230000004069 differentiation Effects 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- IIATVLXXAYLQIZ-UHFFFAOYSA-N 2,5-dihydro-1,2,4-triazine Chemical compound C1C=NNC=N1 IIATVLXXAYLQIZ-UHFFFAOYSA-N 0.000 claims description 5
- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 claims description 5
- NTYABNDBNKVWOO-UHFFFAOYSA-N 2h-1,3-thiazine Chemical compound C1SC=CC=N1 NTYABNDBNKVWOO-UHFFFAOYSA-N 0.000 claims description 5
- ZAISDHPZTZIFQF-UHFFFAOYSA-N 2h-1,4-thiazine Chemical compound C1SC=CN=C1 ZAISDHPZTZIFQF-UHFFFAOYSA-N 0.000 claims description 5
- 230000000172 allergic effect Effects 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- FUIQANIDAMJELP-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,3,5-triazine Chemical compound C1NCN=CN1 FUIQANIDAMJELP-UHFFFAOYSA-N 0.000 claims description 4
- OQJVXNHMUWQQEW-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrazine Chemical compound C1CNC=CN1 OQJVXNHMUWQQEW-UHFFFAOYSA-N 0.000 claims description 4
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims description 4
- XLEDBLKSWOYHES-UHFFFAOYSA-N 1,2,3,5-thiatriazole Chemical compound C=1N=NSN=1 XLEDBLKSWOYHES-UHFFFAOYSA-N 0.000 claims description 4
- LVEKWSMAGKNFCF-UHFFFAOYSA-N 1,2,3,6-tetrahydro-1,2,4-triazine Chemical compound C1NNCN=C1 LVEKWSMAGKNFCF-UHFFFAOYSA-N 0.000 claims description 4
- IOLQWFQLCNMKAZ-UHFFFAOYSA-N 1,2,3,6-tetrahydropyrazine Chemical compound C1CN=CCN1 IOLQWFQLCNMKAZ-UHFFFAOYSA-N 0.000 claims description 4
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims description 4
- GBLQGXFTPLQBTA-UHFFFAOYSA-N 1,2,3-triazoline Chemical compound C1CN=NN1 GBLQGXFTPLQBTA-UHFFFAOYSA-N 0.000 claims description 4
- BLWJJPNXUDWVCG-UHFFFAOYSA-N 1,2,4-oxadiazolidine Chemical compound C1NCON1 BLWJJPNXUDWVCG-UHFFFAOYSA-N 0.000 claims description 4
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims description 4
- YFCCVJQVYQHMOG-UHFFFAOYSA-N 1,2,4-thiadiazolidine Chemical compound C1NCSN1 YFCCVJQVYQHMOG-UHFFFAOYSA-N 0.000 claims description 4
- JRLFRFTXXMZSND-UHFFFAOYSA-N 1,2,4-triazoline Chemical compound C1NNC=N1 JRLFRFTXXMZSND-UHFFFAOYSA-N 0.000 claims description 4
- BKWQKVJYXODDAC-UHFFFAOYSA-N 1,2-dihydropyridazine Chemical compound N1NC=CC=C1 BKWQKVJYXODDAC-UHFFFAOYSA-N 0.000 claims description 4
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 claims description 4
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 claims description 4
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims description 4
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 4
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 4
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 4
- UKOMUVPFRFPHDS-UHFFFAOYSA-N 1,4,2-dioxazine Chemical compound O1C=CON=C1 UKOMUVPFRFPHDS-UHFFFAOYSA-N 0.000 claims description 4
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 4
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 claims description 4
- RMQOXNXLVICLNK-UHFFFAOYSA-N 1,4-dihydro-1,3,5-triazine Chemical compound C1NC=NC=N1 RMQOXNXLVICLNK-UHFFFAOYSA-N 0.000 claims description 4
- XYNBEQAWBCGIMD-UHFFFAOYSA-N 1,4-dihydropyrazine Chemical compound N1C=CNC=C1 XYNBEQAWBCGIMD-UHFFFAOYSA-N 0.000 claims description 4
- HZVGMPJZVYBYEK-UHFFFAOYSA-N 1,4-dihydropyridazine Chemical compound C1C=CNN=C1 HZVGMPJZVYBYEK-UHFFFAOYSA-N 0.000 claims description 4
- OKGNMRKOGWTADH-UHFFFAOYSA-N 1,4-dihydropyrimidine Chemical compound C1C=CNC=N1 OKGNMRKOGWTADH-UHFFFAOYSA-N 0.000 claims description 4
- ZEFGUWRQFNTGGX-UHFFFAOYSA-N 1,6-dihydropyridazine Chemical compound C1NN=CC=C1 ZEFGUWRQFNTGGX-UHFFFAOYSA-N 0.000 claims description 4
- DWKUKQRKVCMOLP-UHFFFAOYSA-N 1-piperideine Chemical compound C1CCN=CC1 DWKUKQRKVCMOLP-UHFFFAOYSA-N 0.000 claims description 4
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 4
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims description 4
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 claims description 4
- RZQQXRVPPOOCQR-UHFFFAOYSA-N 2,3-dihydro-1,3,4-oxadiazole Chemical compound C1NN=CO1 RZQQXRVPPOOCQR-UHFFFAOYSA-N 0.000 claims description 4
- UETXZUQLCCCICD-UHFFFAOYSA-N 2,3-dihydro-1,4,2-oxathiazine Chemical compound C1NOC=CS1 UETXZUQLCCCICD-UHFFFAOYSA-N 0.000 claims description 4
- RTQGSDHQFAONPG-UHFFFAOYSA-N 2,3-dihydro-1,4,3-oxathiazine Chemical compound C1NSC=CO1 RTQGSDHQFAONPG-UHFFFAOYSA-N 0.000 claims description 4
- WUCWFMVYIKMAPG-UHFFFAOYSA-N 2,3-dihydropyrazine Chemical compound C1CN=CC=N1 WUCWFMVYIKMAPG-UHFFFAOYSA-N 0.000 claims description 4
- NHZLLKNRTDIFAD-UHFFFAOYSA-N 2,5-dihydro-1,3-oxazole Chemical compound C1OCN=C1 NHZLLKNRTDIFAD-UHFFFAOYSA-N 0.000 claims description 4
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 claims description 4
- BNDCYQXUFIHUHS-UHFFFAOYSA-N 2,5-dihydropyrazine Chemical compound C1C=NCC=N1 BNDCYQXUFIHUHS-UHFFFAOYSA-N 0.000 claims description 4
- WRLAXLNSBDVNRL-UHFFFAOYSA-N 2,5-dihydropyrimidine Chemical compound C1C=NCN=C1 WRLAXLNSBDVNRL-UHFFFAOYSA-N 0.000 claims description 4
- CJUYNKWJWWMLJW-UHFFFAOYSA-N 2,5-dihydrotriazine Chemical compound C1C=NNN=C1 CJUYNKWJWWMLJW-UHFFFAOYSA-N 0.000 claims description 4
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 4
- HCNVXDPRTRLNFX-UHFFFAOYSA-N 2h-1,3,4-oxadiazine Chemical compound C1OC=CN=N1 HCNVXDPRTRLNFX-UHFFFAOYSA-N 0.000 claims description 4
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims description 4
- GNNHQRGDLMQALS-UHFFFAOYSA-N 3,4-dihydro-2h-1,3,5-thiadiazine Chemical compound C1NCN=CS1 GNNHQRGDLMQALS-UHFFFAOYSA-N 0.000 claims description 4
- NARLFVSETWHKRP-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-thiazine Chemical compound C1CSC=CN1 NARLFVSETWHKRP-UHFFFAOYSA-N 0.000 claims description 4
- RDOAUPPSCNSYPM-UHFFFAOYSA-N 3,4-dihydropyridine Chemical compound C1CC=NC=C1 RDOAUPPSCNSYPM-UHFFFAOYSA-N 0.000 claims description 4
- LPHWCAUEPAUFHZ-UHFFFAOYSA-N 3,6-Dihydropyridine Chemical compound C1C=CCN=C1 LPHWCAUEPAUFHZ-UHFFFAOYSA-N 0.000 claims description 4
- AMKVFOFJZLHHDC-UHFFFAOYSA-N 3,6-dihydro-2h-1,3,4-thiadiazine Chemical compound C1NN=CCS1 AMKVFOFJZLHHDC-UHFFFAOYSA-N 0.000 claims description 4
- RUPLWPYHVWSFEF-UHFFFAOYSA-N 3,6-dihydro-2h-1,3-oxazine Chemical compound C1NC=CCO1 RUPLWPYHVWSFEF-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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| US38333102P | 2002-05-22 | 2002-05-22 | |
| PCT/US2003/016655 WO2003099284A1 (en) | 2002-05-22 | 2003-05-20 | Amino-pyridine, -pyridine and pyridazine derivatives for use as vanilloid receptor ligands for the treatment of pain |
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| MXPA04011472A true MXPA04011472A (es) | 2005-02-14 |
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| CA2509233A1 (en) * | 2002-12-13 | 2004-07-01 | Neurogen Corporation | 2-substituted quinazolin-4-ylamine analogues as capsaicin receptor modulators |
| GB0310726D0 (en) | 2003-05-09 | 2003-06-11 | Merck Sharp & Dohme | Therapeutic agents |
| JP2007523875A (ja) * | 2003-07-15 | 2007-08-23 | ニューロジェン・コーポレーション | バニロイド受容体リガンドとしての置換ピリミジン−4−イルアミン類縁体 |
| AU2004278382B2 (en) | 2003-09-30 | 2008-09-18 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| EP1685124A1 (en) | 2003-11-10 | 2006-08-02 | MERCK SHARP & DOHME LTD. | Substituted nitrogen-containing six-membered amino-heterocycles as vanilloid-1 receptor antagonists for treating pain |
| WO2005073193A1 (en) * | 2004-01-23 | 2005-08-11 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| JP2007522233A (ja) * | 2004-02-11 | 2007-08-09 | アムジエン・インコーポレーテツド | バニロイド受容体リガンド及び治療におけるそれらの使用 |
| MY139645A (en) * | 2004-02-11 | 2009-10-30 | Amgen Inc | Vanilloid receptor ligands and their use in treatments |
| MY149038A (en) * | 2004-05-26 | 2013-07-15 | Eisai R&D Man Co Ltd | Cinnamide compound |
| US7762951B2 (en) * | 2004-06-25 | 2010-07-27 | Medtronic, Inc. | Vein harvesting system including dilator shaft and removable retractor housing |
| EP1775283A4 (en) * | 2004-07-14 | 2008-12-10 | Japan Tobacco Inc | 3-AMINOBENZAMIDE COMPOUND AND INHIBITORS OF THE ACTIVITY OF VANILLOID RECEPTOR 1 (VR1) |
| KR101042490B1 (ko) | 2004-07-15 | 2011-06-16 | 니뽄 다바코 산교 가부시키가이샤 | 축합 벤즈아미드 화합물 및 바닐로이드 수용체 1형(vr1)활성 저해제 |
| FR2874015B1 (fr) * | 2004-08-05 | 2006-09-15 | Sanofi Synthelabo | Derives de n-(1h-indolyl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique |
| US20070259856A1 (en) * | 2004-09-07 | 2007-11-08 | Sanjay Kumar | Method for Activating Trpv4 Channel Receptors by Agonists |
| EP1789413A1 (en) | 2004-09-13 | 2007-05-30 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| WO2006038041A1 (en) * | 2004-10-08 | 2006-04-13 | Merck Sharp & Dohme Limited | Besylate salts of six-membered amino-heterocycles as vanilloid-1 receptor antagonists for treating pain |
| WO2006047492A2 (en) * | 2004-10-22 | 2006-05-04 | Amgen Inc. | Substituted nitrogen-containing heterocycles as vanilloid receptor ligands and their uses as medicament |
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| WO2006071940A2 (en) | 2004-12-23 | 2006-07-06 | Deciphera Pharmaceuticals, Llc | Enzyme modulators and treatments |
| KR20060087386A (ko) | 2005-01-28 | 2006-08-02 | 주식회사 대웅제약 | 신규 벤조이미다졸 유도체 및 이를 함유하는 약제학적조성물 |
| US20060235036A1 (en) * | 2005-04-15 | 2006-10-19 | Doherty Elizabeth M | Vanilloid receptor ligands and their use in treatments |
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| DE102005044813A1 (de) * | 2005-05-19 | 2007-10-04 | Grünenthal GmbH | Substituierte Spiro-Verbindungen und deren Verwendung zur Herstellung von Arzneimitteln |
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- 2003-05-20 WO PCT/US2003/016655 patent/WO2003099284A1/en not_active Ceased
- 2003-05-20 AU AU2003247425A patent/AU2003247425B2/en not_active Ceased
- 2003-05-20 US US10/445,170 patent/US7053088B2/en not_active Expired - Fee Related
- 2003-05-20 DE DE60335635T patent/DE60335635D1/de not_active Expired - Lifetime
- 2003-05-20 AT AT03755509T patent/ATE493987T1/de not_active IP Right Cessation
- 2003-05-20 MX MXPA04011472A patent/MXPA04011472A/es active IP Right Grant
- 2003-05-20 ES ES03755509T patent/ES2355472T3/es not_active Expired - Lifetime
- 2003-05-20 EP EP03755509A patent/EP1542692B1/en not_active Expired - Lifetime
- 2003-05-20 CA CA002486376A patent/CA2486376A1/en not_active Abandoned
- 2003-05-20 JP JP2004506808A patent/JP2005531574A/ja not_active Withdrawn
- 2003-05-20 PL PL03375552A patent/PL375552A1/xx not_active Application Discontinuation
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2005
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- 2005-08-01 US US11/195,302 patent/US7524874B2/en not_active Expired - Fee Related
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| DE60335635D1 (de) | 2011-02-17 |
| AU2003247425A1 (en) | 2003-12-12 |
| US20050267163A1 (en) | 2005-12-01 |
| US20040038969A1 (en) | 2004-02-26 |
| ATE493987T1 (de) | 2011-01-15 |
| EP1542692B1 (en) | 2011-01-05 |
| WO2003099284A1 (en) | 2003-12-04 |
| CA2486376A1 (en) | 2003-12-04 |
| JP2005531574A (ja) | 2005-10-20 |
| EP1542692A1 (en) | 2005-06-22 |
| US20050277646A1 (en) | 2005-12-15 |
| US7396831B2 (en) | 2008-07-08 |
| AU2003247425B2 (en) | 2007-03-08 |
| US7524874B2 (en) | 2009-04-28 |
| PL375552A1 (en) | 2005-11-28 |
| US7053088B2 (en) | 2006-05-30 |
| WO2003099284B1 (en) | 2004-04-01 |
| ES2355472T3 (es) | 2011-03-28 |
| AU2003247425B8 (en) | 2003-12-12 |
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