JP2005536507A5 - - Google Patents
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- JP2005536507A5 JP2005536507A5 JP2004521592A JP2004521592A JP2005536507A5 JP 2005536507 A5 JP2005536507 A5 JP 2005536507A5 JP 2004521592 A JP2004521592 A JP 2004521592A JP 2004521592 A JP2004521592 A JP 2004521592A JP 2005536507 A5 JP2005536507 A5 JP 2005536507A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pyrrolo
- compound
- pyridazine
- pharmaceutically acceptable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 39
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 150000003839 salts Chemical class 0.000 claims 19
- 239000003814 drug Substances 0.000 claims 16
- 238000004519 manufacturing process Methods 0.000 claims 15
- 230000002265 prevention Effects 0.000 claims 14
- -1 -C 3-7 cycloalkyl Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 208000019901 Anxiety disease Diseases 0.000 claims 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 208000002193 Pain Diseases 0.000 claims 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000005557 antagonist Substances 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 208000004296 neuralgia Diseases 0.000 claims 3
- 208000021722 neuropathic pain Diseases 0.000 claims 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 2
- DSBRUNYUDHQXDZ-UHFFFAOYSA-N 1,4-dimethyl-9-phenylpyridazino[4,5-a]indolizine-5-carbonitrile Chemical compound C1=CN2C(C#N)=C3C(C)=NN=C(C)C3=C2C=C1C1=CC=CC=C1 DSBRUNYUDHQXDZ-UHFFFAOYSA-N 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims 2
- 206010065390 Inflammatory pain Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 229960002069 diamorphine Drugs 0.000 claims 2
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 230000007659 motor function Effects 0.000 claims 2
- 229960002715 nicotine Drugs 0.000 claims 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 2
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims 2
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims 1
- HZYJAXYIINXNRI-UHFFFAOYSA-N 1,4,5,6,7-pentakis-phenylpyrrolo[3,4-d]pyridazine Chemical compound C1=CC=CC=C1C1=C2C(C=3C=CC=CC=3)=NN=C(C=3C=CC=CC=3)C2=C(C=2C=CC=CC=2)N1C1=CC=CC=C1 HZYJAXYIINXNRI-UHFFFAOYSA-N 0.000 claims 1
- RHLJIDRQGFKRDC-UHFFFAOYSA-N 1,4,5,7-tetramethyl-6-phenylpyrrolo[3,4-d]pyridazine Chemical compound CC1=C2C(C)=NN=C(C)C2=C(C)N1C1=CC=CC=C1 RHLJIDRQGFKRDC-UHFFFAOYSA-N 0.000 claims 1
- NXUVOVYSWCEJGN-UHFFFAOYSA-N 1,4,5,7-tetramethyl-6h-pyrrolo[3,4-d]pyridazine Chemical compound CC1=NN=C(C)C2=C(C)NC(C)=C21 NXUVOVYSWCEJGN-UHFFFAOYSA-N 0.000 claims 1
- OOGFRVWKQVWDAP-UHFFFAOYSA-N 1,4,5,7-tetramethylpyrrolo[3,4-d]pyridazin-6-amine Chemical compound CC1=NN=C(C)C2=C(C)N(N)C(C)=C21 OOGFRVWKQVWDAP-UHFFFAOYSA-N 0.000 claims 1
- QJVMPCHRZIZFBI-UHFFFAOYSA-N 1,4,5,7-tetramethylpyrrolo[3,4-d]pyridazin-6-amine;2,4,6-trinitrophenol Chemical compound CC1=NN=C(C)C2=C(C)N(N)C(C)=C21.OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O QJVMPCHRZIZFBI-UHFFFAOYSA-N 0.000 claims 1
- GYYCQHQUWUJRJP-UHFFFAOYSA-N 1,4,7-trimethyl-5,6-diphenylpyrrolo[3,4-d]pyridazine Chemical compound C=12C(C)=NN=C(C)C2=C(C)N(C=2C=CC=CC=2)C=1C1=CC=CC=C1 GYYCQHQUWUJRJP-UHFFFAOYSA-N 0.000 claims 1
- QJIZOOGYDLLXRU-UHFFFAOYSA-N 1,4,9-trimethylpyridazino[4,5-a]indolizine-5-carbonitrile Chemical compound N#CC1=C2C(C)=NN=C(C)C2=C2N1C=CC(C)=C2 QJIZOOGYDLLXRU-UHFFFAOYSA-N 0.000 claims 1
- JXABELVNDMTLMM-UHFFFAOYSA-N 1,4,9-triphenylpyridazino[4,5-a]indolizine-5-carbonitrile Chemical compound C12=C3C=C(C=4C=CC=CC=4)C=CN3C(C#N)=C2C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 JXABELVNDMTLMM-UHFFFAOYSA-N 0.000 claims 1
- VYHUIROTSMWTNT-UHFFFAOYSA-N 1,4-bis(4-methoxyphenyl)-5,7-dimethyl-6-phenylpyrrolo[3,4-d]pyridazine Chemical compound C1=CC(OC)=CC=C1C(C1=C(C)N(C(C)=C11)C=2C=CC=CC=2)=NN=C1C1=CC=C(OC)C=C1 VYHUIROTSMWTNT-UHFFFAOYSA-N 0.000 claims 1
- ZVUPRWNRSFBPBT-UHFFFAOYSA-N 1,4-bis(4-methoxyphenyl)-7-methyl-5,6-diphenylpyrrolo[3,4-d]pyridazine Chemical compound C1=CC(OC)=CC=C1C(C1=C(C)N(C(C=2C=CC=CC=2)=C11)C=2C=CC=CC=2)=NN=C1C1=CC=C(OC)C=C1 ZVUPRWNRSFBPBT-UHFFFAOYSA-N 0.000 claims 1
- VPPONMLCEFJPSC-UHFFFAOYSA-N 1,4-dichloro-5,6,7-trimethylpyrrolo[3,4-d]pyridazine Chemical compound ClC1=NN=C(Cl)C2=C(C)N(C)C(C)=C21 VPPONMLCEFJPSC-UHFFFAOYSA-N 0.000 claims 1
- IJGSFOGHCQQCIS-UHFFFAOYSA-N 1,4-diethyl-5,7-dimethyl-6-phenylpyrrolo[3,4-d]pyridazine Chemical compound CC1=C2C(CC)=NN=C(CC)C2=C(C)N1C1=CC=CC=C1 IJGSFOGHCQQCIS-UHFFFAOYSA-N 0.000 claims 1
- SFFSKDNUPGGKEL-UHFFFAOYSA-N 1,4-dimethylpyridazino[4,5-a]indolizine-5-carbonitrile Chemical compound C1=CC=CN2C(C#N)=C3C(C)=NN=C(C)C3=C21 SFFSKDNUPGGKEL-UHFFFAOYSA-N 0.000 claims 1
- RVUSDEPFBTTZKK-UHFFFAOYSA-N 1,4-diphenyl-7,8,9,10-tetrahydropyridazino[4,5-a]indolizine Chemical compound C12=C3CCCCN3C=C2C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 RVUSDEPFBTTZKK-UHFFFAOYSA-N 0.000 claims 1
- KLBXJUWWVCYQDO-UHFFFAOYSA-N 1,4-diphenylpyridazino[4,5-a]indolizine-5-carbonitrile Chemical compound C12=C3C=CC=CN3C(C#N)=C2C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 KLBXJUWWVCYQDO-UHFFFAOYSA-N 0.000 claims 1
- MFXZOERSYWSCGJ-UHFFFAOYSA-N 12,15-diphenyl-1,13,14-triazatetracyclo[8.7.0.02,7.011,16]heptadeca-2,4,6,8,10,12,14,16-octaene Chemical compound C12=C3C=CC4=CC=CC=C4N3C=C2C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 MFXZOERSYWSCGJ-UHFFFAOYSA-N 0.000 claims 1
- KPCXIYJXVWQULP-UHFFFAOYSA-N 13,16-diphenyl-10,14,15-triazatetracyclo[8.7.0.02,7.012,17]heptadeca-1(17),2,4,6,8,11,13,15-octaene Chemical compound C12=C3C4=CC=CC=C4C=CN3C=C2C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 KPCXIYJXVWQULP-UHFFFAOYSA-N 0.000 claims 1
- UWEJVEPLZODXGI-UHFFFAOYSA-N 13,16-diphenyl-10,14,15-triazatetracyclo[8.7.0.02,7.012,17]heptadeca-1(17),2,4,6,8,11,13,15-octaene-11-carbonitrile Chemical compound C12=C3C4=CC=CC=C4C=CN3C(C#N)=C2C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 UWEJVEPLZODXGI-UHFFFAOYSA-N 0.000 claims 1
- DDXFYSMONIVWLR-UHFFFAOYSA-N 16,19-diphenyl-1,17,18-triazapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-2,4,6,8,10,12,14,16,18,20-decaene Chemical compound C12=C3C4=CC=CC=C4C4=CC=CC=C4N3C=C2C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 DDXFYSMONIVWLR-UHFFFAOYSA-N 0.000 claims 1
- WAGQVIFHXLTSQQ-UHFFFAOYSA-N 17-(4-nitrophenyl)-9,12,15-triphenyl-1,8,13,14-tetrazatetracyclo[8.7.0.02,7.011,16]heptadeca-2,4,6,8,10,12,14,16-octaene Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=C(C(=NN=C2C=3C=CC=CC=3)C=3C=CC=CC=3)C2=C2N1C1=CC=CC=C1N=C2C1=CC=CC=C1 WAGQVIFHXLTSQQ-UHFFFAOYSA-N 0.000 claims 1
- PWLLQSFWSYAQRU-UHFFFAOYSA-N 2-(5,7-dimethyl-6h-pyrrolo[3,4-d]pyridazin-3-ium-3-yl)-1-phenylethanone;bromide Chemical compound [Br-].N1=CC2=C(C)NC(C)=C2C=[N+]1CC(=O)C1=CC=CC=C1 PWLLQSFWSYAQRU-UHFFFAOYSA-N 0.000 claims 1
- LIGQPYQBLXBNKW-UHFFFAOYSA-N 3-methyl-6,9-diphenyl-[1,3]thiazolo[5,6]pyrrolo[1,2-c]pyridine Chemical compound C12=CN3C(C)=CSC3=C2C(C=2C=CC=CC=2)=CN=C1C1=CC=CC=C1 LIGQPYQBLXBNKW-UHFFFAOYSA-N 0.000 claims 1
- XUVUTYSNCUIFON-UHFFFAOYSA-N 4,5-dimethoxy-10,14,15-triazatetracyclo[8.7.0.02,7.012,17]heptadeca-1(17),2,4,6,11,15-hexaen-13-one Chemical compound C1CN2C=C(C(NN=C3)=O)C3=C2C2=C1C=C(OC)C(OC)=C2 XUVUTYSNCUIFON-UHFFFAOYSA-N 0.000 claims 1
- PWYPWKFCPLMHSF-UHFFFAOYSA-N 4,5-dimethoxy-10,14,15-triazatetracyclo[8.7.0.02,7.012,17]heptadeca-1(17),2,4,6,11,15-hexaen-13-one hydrochloride Chemical compound Cl.C1CN2C=C(C(NN=C3)=O)C3=C2C2=C1C=C(OC)C(OC)=C2 PWYPWKFCPLMHSF-UHFFFAOYSA-N 0.000 claims 1
- CTUFSEHSWHZYPB-UHFFFAOYSA-N 4-chloro-1-ethoxy-5,6,7-trimethylpyrrolo[3,4-d]pyridazine Chemical compound CCOC1=NN=C(Cl)C2=C(C)N(C)C(C)=C12 CTUFSEHSWHZYPB-UHFFFAOYSA-N 0.000 claims 1
- SSJAZRJBDZCETI-UHFFFAOYSA-N 4-chloro-5,6,7-trimethylpyrrolo[3,4-d]pyridazin-2-ium;chloride Chemical compound Cl.ClC1=NN=CC2=C(C)N(C)C(C)=C21 SSJAZRJBDZCETI-UHFFFAOYSA-N 0.000 claims 1
- XCTCUWXXHPDXNJ-UHFFFAOYSA-N 4-ethoxy-5,6,7-trimethylpyrrolo[3,4-d]pyridazine Chemical compound CCOC1=NN=CC2=C(C)N(C)C(C)=C12 XCTCUWXXHPDXNJ-UHFFFAOYSA-N 0.000 claims 1
- 229940127239 5 Hydroxytryptamine receptor antagonist Drugs 0.000 claims 1
- JNDWOQAFZBBTFT-UHFFFAOYSA-N 5,6,7-trimethylpyrrolo[3,4-d]pyridazine Chemical compound C1=NN=CC2=C(C)N(C)C(C)=C21 JNDWOQAFZBBTFT-UHFFFAOYSA-N 0.000 claims 1
- VMZROHYTDQGKAU-UHFFFAOYSA-N 5,7-dimethyl-1,4,6-triphenylpyrrolo[3,4-d]pyridazine Chemical compound C12=C(C)N(C=3C=CC=CC=3)C(C)=C2C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 VMZROHYTDQGKAU-UHFFFAOYSA-N 0.000 claims 1
- IYCSRWWJOZMSRS-UHFFFAOYSA-N 5,7-dimethyl-6-phenylpyrrolo[3,4-d]pyridazine Chemical compound CC1=C2C=NN=CC2=C(C)N1C1=CC=CC=C1 IYCSRWWJOZMSRS-UHFFFAOYSA-N 0.000 claims 1
- ZTPGXWSYJZFYJI-UHFFFAOYSA-N 5,7-diphenyl-6h-pyrrolo[3,4-d]pyridazine Chemical compound C1=CC=CC=C1C1=C2C=NN=CC2=C(C=2C=CC=CC=2)N1 ZTPGXWSYJZFYJI-UHFFFAOYSA-N 0.000 claims 1
- ZOEXGMWGZZDHIS-UHFFFAOYSA-N 5-methyl-1,4-diphenyl-7,8,9,10-tetrahydropyridazino[4,5-a]indolizine Chemical compound C12=C(C)N3CCCCC3=C2C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 ZOEXGMWGZZDHIS-UHFFFAOYSA-N 0.000 claims 1
- RAWWPZXOUKHUGY-UHFFFAOYSA-N 5-methylsulfanyl-1,4,6,7-tetraphenylpyrrolo[3,4-d]pyridazine Chemical compound C=12C(C=3C=CC=CC=3)=NN=C(C=3C=CC=CC=3)C2=C(SC)N(C=2C=CC=CC=2)C=1C1=CC=CC=C1 RAWWPZXOUKHUGY-UHFFFAOYSA-N 0.000 claims 1
- USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 claims 1
- CYPUWZASYHLAAP-UHFFFAOYSA-N 6-benzyl-1,4,5-triphenylpyrrolo[3,4-d]pyridazine Chemical compound C1=C2C(C=3C=CC=CC=3)=NN=C(C=3C=CC=CC=3)C2=C(C=2C=CC=CC=2)N1CC1=CC=CC=C1 CYPUWZASYHLAAP-UHFFFAOYSA-N 0.000 claims 1
- VDQQXVCIVKOPOU-UHFFFAOYSA-N 6-benzyl-5-(2-chlorophenyl)-1,4-diphenylpyrrolo[3,4-d]pyridazine Chemical compound ClC1=CC=CC=C1C1=C2C(C=3C=CC=CC=3)=NN=C(C=3C=CC=CC=3)C2=CN1CC1=CC=CC=C1 VDQQXVCIVKOPOU-UHFFFAOYSA-N 0.000 claims 1
- ZQWQZLSASKWBNO-UHFFFAOYSA-N 6-benzyl-5-(4-methylphenyl)-1,4-diphenylpyrrolo[3,4-d]pyridazine Chemical compound C1=CC(C)=CC=C1C1=C2C(C=3C=CC=CC=3)=NN=C(C=3C=CC=CC=3)C2=CN1CC1=CC=CC=C1 ZQWQZLSASKWBNO-UHFFFAOYSA-N 0.000 claims 1
- PIKXCZJVTUIPLE-UHFFFAOYSA-N 6-methylpyrrolo[3,4-d]pyridazine Chemical compound C1=NN=CC2=CN(C)C=C21 PIKXCZJVTUIPLE-UHFFFAOYSA-N 0.000 claims 1
- JPZWCICTVRAKTM-UHFFFAOYSA-N 7-methyl-1,4,5,6-tetraphenylpyrrolo[3,4-d]pyridazine Chemical compound C=12C(C=3C=CC=CC=3)=NN=C(C=3C=CC=CC=3)C2=C(C)N(C=2C=CC=CC=2)C=1C1=CC=CC=C1 JPZWCICTVRAKTM-UHFFFAOYSA-N 0.000 claims 1
- SGIDWFXFBNUHFA-UHFFFAOYSA-N 8,10-dimethyl-1,4-diphenylpyridazino[4,5-a]indolizine-5-carbonitrile Chemical compound C12=C(C#N)N3C=C(C)C=C(C)C3=C2C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 SGIDWFXFBNUHFA-UHFFFAOYSA-N 0.000 claims 1
- DTINROBEQLRWPH-UHFFFAOYSA-N 9,12,15,17-tetraphenyl-1,8,13,14-tetrazatetracyclo[8.7.0.02,7.011,16]heptadeca-2,4,6,8,10,12,14,16-octaene Chemical compound C1=CC=CC=C1C1=C(C(=NN=C2C=3C=CC=CC=3)C=3C=CC=CC=3)C2=C2N1C1=CC=CC=C1N=C2C1=CC=CC=C1 DTINROBEQLRWPH-UHFFFAOYSA-N 0.000 claims 1
- LJPFEZJTAYLDLN-UHFFFAOYSA-N 9-benzoyl-1,4-diphenylpyridazino[4,5-a]indolizine-5-carbonitrile Chemical compound C1=CN2C(C#N)=C3C(C=4C=CC=CC=4)=NN=C(C=4C=CC=CC=4)C3=C2C=C1C(=O)C1=CC=CC=C1 LJPFEZJTAYLDLN-UHFFFAOYSA-N 0.000 claims 1
- ISYJHHAZIHCWKH-UHFFFAOYSA-N 9-benzyl-1,4-diphenylpyridazino[4,5-a]indolizine-5-carbonitrile Chemical compound C12=C3C=C(CC=4C=CC=CC=4)C=CN3C(C#N)=C2C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 ISYJHHAZIHCWKH-UHFFFAOYSA-N 0.000 claims 1
- MEXHSBKWVPCCGT-UHFFFAOYSA-N 9-methyl-1,4-diphenylpyridazino[4,5-a]indolizine-5-carbonitrile Chemical compound C12=C3C=C(C)C=CN3C(C#N)=C2C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 MEXHSBKWVPCCGT-UHFFFAOYSA-N 0.000 claims 1
- 208000008811 Agoraphobia Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000000044 Amnesia Diseases 0.000 claims 1
- 108090000312 Calcium Channels Proteins 0.000 claims 1
- 102000003922 Calcium Channels Human genes 0.000 claims 1
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- 206010012289 Dementia Diseases 0.000 claims 1
- 206010013654 Drug abuse Diseases 0.000 claims 1
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- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 102000004300 GABA-A Receptors Human genes 0.000 claims 1
- 108090000839 GABA-A Receptors Proteins 0.000 claims 1
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims 1
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims 1
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims 1
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims 1
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims 1
- 229940127523 NMDA Receptor Antagonists Drugs 0.000 claims 1
- 241000208125 Nicotiana Species 0.000 claims 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- 206010033664 Panic attack Diseases 0.000 claims 1
- 206010033799 Paralysis Diseases 0.000 claims 1
- 206010034912 Phobia Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 229940089973 Sodium channel antagonist Drugs 0.000 claims 1
- 208000027520 Somatoform disease Diseases 0.000 claims 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 1
- 208000000323 Tourette Syndrome Diseases 0.000 claims 1
- 208000016620 Tourette disease Diseases 0.000 claims 1
- 208000031674 Traumatic Acute Stress disease Diseases 0.000 claims 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 claims 1
- 229960004047 acamprosate Drugs 0.000 claims 1
- AFCGFAGUEYAMAO-UHFFFAOYSA-N acamprosate Chemical compound CC(=O)NCCCS(O)(=O)=O AFCGFAGUEYAMAO-UHFFFAOYSA-N 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 208000026345 acute stress disease Diseases 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 239000003420 antiserotonin agent Substances 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 claims 1
- 229960001736 buprenorphine Drugs 0.000 claims 1
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- XBMIVRRWGCYBTQ-AVRDEDQJSA-N levacetylmethadol Chemical compound C=1C=CC=CC=1C(C[C@H](C)N(C)C)([C@@H](OC(C)=O)CC)C1=CC=CC=C1 XBMIVRRWGCYBTQ-AVRDEDQJSA-N 0.000 claims 1
- 229910003002 lithium salt Inorganic materials 0.000 claims 1
- 159000000002 lithium salts Chemical class 0.000 claims 1
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- NTXVDJNAFCQLRT-UHFFFAOYSA-N n-(1,4,5,7-tetramethylpyrrolo[3,4-d]pyridazin-6-yl)benzamide Chemical compound CC1=C2C(C)=NN=C(C)C2=C(C)N1NC(=O)C1=CC=CC=C1 NTXVDJNAFCQLRT-UHFFFAOYSA-N 0.000 claims 1
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| US39473402P | 2002-07-11 | 2002-07-11 | |
| PCT/US2003/021493 WO2004006836A2 (en) | 2002-07-11 | 2003-07-08 | Treatment of neuropathic pain with 6h-pyrrolo[3,4-d]pyridazine compounds |
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| JP2005536507A JP2005536507A (ja) | 2005-12-02 |
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| EP (1) | EP1539168A2 (enExample) |
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| UY28538A1 (es) | 2003-09-26 | 2005-04-29 | Vertex Pharma | Derivados de fenil-piperazina como moduladores de receptores muscarínicos |
| GB0405200D0 (en) * | 2004-03-08 | 2004-04-21 | Pfizer Ltd | Combinations comprising alpha-2-delta ligands |
| WO2007038684A2 (en) | 2005-09-27 | 2007-04-05 | Myriad Genetics, Inc. | Pyrrole derivatives as therapeutic compounds |
| CN101003537A (zh) * | 2006-01-17 | 2007-07-25 | 上海恒瑞医药有限公司 | 吡咯并哒嗪类衍生物及其制备方法和用途 |
| TW200914457A (en) * | 2007-05-31 | 2009-04-01 | Kyowa Hakko Kogyo Kk | Pyrimidodiazepinone derivative |
| CN103483169A (zh) | 2007-09-28 | 2014-01-01 | 第一三共株式会社 | 用于制备双环γ-氨基酸衍生物的中间体 |
| EP2252608A4 (en) | 2008-02-29 | 2012-10-03 | Vm Discovery Inc | METHOD FOR TREATING PAIN SYNDROME AND OTHER SUFFERING |
| EP2313102A2 (en) | 2008-07-03 | 2011-04-27 | Biota Scientific Management | Bycyclic nucleosides and nucleotides as therapeutic agents |
| GB0813144D0 (en) | 2008-07-17 | 2008-08-27 | Glaxo Group Ltd | Novel compounds |
| JP5557292B2 (ja) | 2009-03-26 | 2014-07-23 | 第一三共株式会社 | 二環性γ−アミノ酸誘導体の製造方法 |
| EP2719677B1 (en) | 2011-06-08 | 2017-09-06 | Daiichi Sankyo Company, Limited | Method for producing bicyclic compound via claisen rearrangement |
| WO2012169474A1 (ja) | 2011-06-08 | 2012-12-13 | 第一三共株式会社 | イミニウム塩を経由する二環性化合物の製造方法 |
| BR112014014432B1 (pt) | 2011-12-15 | 2022-03-29 | Daiichi Sankyo Company, Limited | Método para produzir um composto |
| JP6023794B2 (ja) | 2012-04-10 | 2016-11-09 | 第一三共株式会社 | 酵素を用いる二環性化合物の光学分割方法 |
| WO2014069626A1 (ja) * | 2012-11-01 | 2014-05-08 | 協和発酵キリン株式会社 | ピリミドジアゼピノン化合物の製造方法 |
| CA2892677A1 (en) * | 2012-12-04 | 2014-06-12 | Rigel Pharmaceuticals, Inc. | Protein kinase c inhibitors and uses thereof |
| TWI635071B (zh) | 2013-07-08 | 2018-09-11 | 第一三共股份有限公司 | 光學活性二環γ－胺基酸衍生物及其製造方法 |
| WO2018100045A1 (en) * | 2016-11-30 | 2018-06-07 | Laboratorios Del Dr. Esteve, S.A. | Ortho substituted phenylpyrazolo- and phenylpyrrolo-pyridazine derivatives having multimodal activity against pain |
| US20200190081A1 (en) * | 2016-11-30 | 2020-06-18 | Esteve Pharmaceuticals, S.A. | Meta substituted phenylpyrazolo- and phenylpyrrolo- pyridazine derivatives having multimodal activity against pain |
| EP3630765A1 (en) * | 2017-05-30 | 2020-04-08 | Esteve Pharmaceuticals, S.A. | Substituted pyrrolidinyl and piperidinyl pyrazolopyridazine derivatives having multimodal activity against pain |
| GB202106872D0 (en) * | 2021-05-13 | 2021-06-30 | Addex Pharmaceuticals Sa | Novel compounds |
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| US5622948A (en) * | 1994-12-01 | 1997-04-22 | Syntex (U.S.A.) Inc. | Pyrrole pyridazine and pyridazinone anti-inflammatory agents |
| GB9726701D0 (en) * | 1997-12-18 | 1998-02-18 | Merck Sharp & Dohme | Therapeutic use |
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2003
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- 2003-07-08 WO PCT/US2003/021493 patent/WO2004006836A2/en not_active Ceased
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- 2003-07-08 AU AU2003248907A patent/AU2003248907B2/en not_active Ceased
- 2003-07-08 CA CA002492022A patent/CA2492022A1/en not_active Abandoned
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