AU2935300A - New pharmaceutical combinations for nos inhibitors - Google Patents
New pharmaceutical combinations for nos inhibitors Download PDFInfo
- Publication number
- AU2935300A AU2935300A AU29353/00A AU2935300A AU2935300A AU 2935300 A AU2935300 A AU 2935300A AU 29353/00 A AU29353/00 A AU 29353/00A AU 2935300 A AU2935300 A AU 2935300A AU 2935300 A AU2935300 A AU 2935300A
- Authority
- AU
- Australia
- Prior art keywords
- pyridin
- phenyl
- ylamine
- amino
- ethoxy
- 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.)
- Abandoned
Links
- 239000003112 inhibitor Substances 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims description 356
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 125
- -1 oct-3-yloxy Chemical group 0.000 claims description 117
- 238000000034 method Methods 0.000 claims description 97
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 90
- 208000035475 disorder Diseases 0.000 claims description 86
- 150000003839 salts Chemical class 0.000 claims description 68
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 41
- 239000008194 pharmaceutical composition Substances 0.000 claims description 37
- 208000019116 sleep disease Diseases 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 241000124008 Mammalia Species 0.000 claims description 34
- 230000002401 inhibitory effect Effects 0.000 claims description 31
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 24
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims description 21
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims description 21
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 claims description 20
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 claims description 20
- 239000002464 receptor antagonist Substances 0.000 claims description 20
- 229940044551 receptor antagonist Drugs 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 230000027288 circadian rhythm Effects 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 15
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims description 15
- 208000006199 Parasomnias Diseases 0.000 claims description 15
- 208000005793 Restless legs syndrome Diseases 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 15
- 230000001788 irregular Effects 0.000 claims description 15
- 208000020925 Bipolar disease Diseases 0.000 claims description 14
- 201000004569 Blindness Diseases 0.000 claims description 14
- 206010012289 Dementia Diseases 0.000 claims description 14
- 208000008967 Enuresis Diseases 0.000 claims description 14
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 14
- 208000008589 Obesity Diseases 0.000 claims description 14
- 208000010340 Sleep Deprivation Diseases 0.000 claims description 14
- 230000002060 circadian Effects 0.000 claims description 14
- 206010020765 hypersomnia Diseases 0.000 claims description 14
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 14
- 201000003631 narcolepsy Diseases 0.000 claims description 14
- 208000005346 nocturnal enuresis Diseases 0.000 claims description 14
- 235000020824 obesity Nutrition 0.000 claims description 14
- 230000036385 rapid eye movement (rem) sleep Effects 0.000 claims description 14
- 230000033764 rhythmic process Effects 0.000 claims description 14
- 208000012672 seasonal affective disease Diseases 0.000 claims description 14
- 230000007958 sleep Effects 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 201000002859 sleep apnea Diseases 0.000 claims description 10
- 208000020685 sleep-wake disease Diseases 0.000 claims description 9
- ZGBXROBHDHIQGY-UHFFFAOYSA-N 2,4-dimethyl-1,3-thiazole-5-sulfonic acid Chemical compound CC1=NC(C)=C(S(O)(=O)=O)S1 ZGBXROBHDHIQGY-UHFFFAOYSA-N 0.000 claims description 8
- 208000008811 Agoraphobia Diseases 0.000 claims description 8
- 208000019901 Anxiety disease Diseases 0.000 claims description 8
- 208000011688 Generalised anxiety disease Diseases 0.000 claims description 8
- 208000026139 Memory disease Diseases 0.000 claims description 8
- 208000019022 Mood disease Diseases 0.000 claims description 8
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 8
- 206010041250 Social phobia Diseases 0.000 claims description 8
- 208000006011 Stroke Diseases 0.000 claims description 8
- 208000010877 cognitive disease Diseases 0.000 claims description 8
- 208000024732 dysthymic disease Diseases 0.000 claims description 8
- 208000029364 generalized anxiety disease Diseases 0.000 claims description 8
- 206010022437 insomnia Diseases 0.000 claims description 8
- 208000024714 major depressive disease Diseases 0.000 claims description 8
- 208000019906 panic disease Diseases 0.000 claims description 8
- 208000019899 phobic disease Diseases 0.000 claims description 8
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 8
- CWSYOPLMQPFBRW-UHFFFAOYSA-N 6-(2-propan-2-yloxy-4-pyrrolidin-3-yloxyphenyl)pyridin-2-amine Chemical compound C=1C=C(C=2N=C(N)C=CC=2)C(OC(C)C)=CC=1OC1CCNC1 CWSYOPLMQPFBRW-UHFFFAOYSA-N 0.000 claims description 6
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- DLFQYLFMHDOVDP-FPOVZHCZSA-N (2s,3s)-n-[[5-tert-butyl-2-(trifluoromethoxy)phenyl]methyl]-2-phenylpiperidin-3-amine Chemical compound CC(C)(C)C1=CC=C(OC(F)(F)F)C(CN[C@@H]2[C@@H](NCCC2)C=2C=CC=CC=2)=C1 DLFQYLFMHDOVDP-FPOVZHCZSA-N 0.000 claims description 5
- JASMWYNKLTULAN-UHFFFAOYSA-N octan-3-amine Chemical compound CCCCCC(N)CC JASMWYNKLTULAN-UHFFFAOYSA-N 0.000 claims description 5
- 229960002073 sertraline Drugs 0.000 claims description 5
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 claims description 5
- DTQNEFOKTXXQKV-HKUYNNGSSA-N (2s,3s)-n-[(2-methoxyphenyl)methyl]-2-phenylpiperidin-3-amine Chemical compound COC1=CC=CC=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)NCCC1 DTQNEFOKTXXQKV-HKUYNNGSSA-N 0.000 claims description 4
- HOFSYLASMQYAFY-UHFFFAOYSA-N 6-(2-methoxy-4-pyrrolidin-3-yloxyphenyl)pyridin-2-amine Chemical compound C=1C=C(C=2N=C(N)C=CC=2)C(OC)=CC=1OC1CCNC1 HOFSYLASMQYAFY-UHFFFAOYSA-N 0.000 claims description 4
- KMMNYCOYYZWPDM-UHFFFAOYSA-N 6-[3-[[2-(2-phenylethylamino)cyclopentyl]methyl]phenyl]pyridin-2-amine Chemical compound NC1=CC=CC(C=2C=C(CC3C(CCC3)NCCC=3C=CC=CC=3)C=CC=2)=N1 KMMNYCOYYZWPDM-UHFFFAOYSA-N 0.000 claims description 4
- XPNMCDYOYIKVGB-CONSDPRKSA-N (2s,3s)-2-benzhydryl-n-[(2-methoxy-5-propan-2-ylphenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine Chemical compound COC1=CC=C(C(C)C)C=C1CN[C@@H]1[C@H](C(C=2C=CC=CC=2)C=2C=CC=CC=2)N2CCC1CC2 XPNMCDYOYIKVGB-CONSDPRKSA-N 0.000 claims description 3
- ZLWDGHYWWGZMJZ-PKOBYXMFSA-N (2s,3s)-2-phenyl-3-[[2-(2,2,2-trifluoroethoxy)phenyl]methyl]piperidin-1-amine Chemical compound C([C@@H]1CCCN([C@@H]1C=1C=CC=CC=1)N)C1=CC=CC=C1OCC(F)(F)F ZLWDGHYWWGZMJZ-PKOBYXMFSA-N 0.000 claims description 3
- JCWUMZJLLJIIIA-FUHWJXTLSA-N (2s,3s)-2-phenyl-3-[[3-(trifluoromethoxy)phenyl]methyl]piperidin-1-amine Chemical compound C([C@@H]1CCCN([C@@H]1C=1C=CC=CC=1)N)C1=CC=CC(OC(F)(F)F)=C1 JCWUMZJLLJIIIA-FUHWJXTLSA-N 0.000 claims description 3
- UREZEIFIEYLVGN-WMZOPIPTSA-N (2s,3s)-2-phenyl-n-[[2-(trifluoromethoxy)phenyl]methyl]piperidin-3-amine Chemical compound FC(F)(F)OC1=CC=CC=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)NCCC1 UREZEIFIEYLVGN-WMZOPIPTSA-N 0.000 claims description 3
- FUIWZFZNPGWKOX-UNMCSNQZSA-N (2s,3s)-2-phenyl-n-[[5-propan-2-yl-2-(2,2,2-trifluoroethoxy)phenyl]methyl]piperidin-3-amine Chemical compound CC(C)C1=CC=C(OCC(F)(F)F)C(CN[C@@H]2[C@@H](NCCC2)C=2C=CC=CC=2)=C1 FUIWZFZNPGWKOX-UNMCSNQZSA-N 0.000 claims description 3
- NNNAFENHFFKFSL-KBXCAEBGSA-N (2s,3s)-3-[[2-(difluoromethoxy)-5-(trifluoromethoxy)phenyl]methyl]-2-phenylpiperidin-1-amine Chemical compound C([C@@H]1CCCN([C@@H]1C=1C=CC=CC=1)N)C1=CC(OC(F)(F)F)=CC=C1OC(F)F NNNAFENHFFKFSL-KBXCAEBGSA-N 0.000 claims description 3
- SGKKYWRWZXXOKO-UNMCSNQZSA-N (2s,3s)-n-[(5-tert-butyl-2-methoxyphenyl)methyl]-2-[3-(trifluoromethoxy)phenyl]piperidin-3-amine Chemical compound COC1=CC=C(C(C)(C)C)C=C1CN[C@@H]1[C@H](C=2C=C(OC(F)(F)F)C=CC=2)NCCC1 SGKKYWRWZXXOKO-UNMCSNQZSA-N 0.000 claims description 3
- JPQLYXMJKNOOIS-UNMCSNQZSA-N (2s,3s)-n-[(5-tert-butyl-2-methoxyphenyl)methyl]-2-phenylpiperidin-3-amine Chemical compound COC1=CC=C(C(C)(C)C)C=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)NCCC1 JPQLYXMJKNOOIS-UNMCSNQZSA-N 0.000 claims description 3
- PXNNZXYLKCTKJG-ICSRJNTNSA-N (2s,3s)-n-[[2-(difluoromethoxy)-5-ethylphenyl]methyl]-2-phenylpiperidin-3-amine Chemical compound CCC1=CC=C(OC(F)F)C(CN[C@@H]2[C@@H](NCCC2)C=2C=CC=CC=2)=C1 PXNNZXYLKCTKJG-ICSRJNTNSA-N 0.000 claims description 3
- WMKQOBGEBPVZQI-HKUYNNGSSA-N (2s,3s)-n-[[2-(difluoromethoxy)-5-methylphenyl]methyl]-2-phenylpiperidin-3-amine Chemical compound CC1=CC=C(OC(F)F)C(CN[C@@H]2[C@@H](NCCC2)C=2C=CC=CC=2)=C1 WMKQOBGEBPVZQI-HKUYNNGSSA-N 0.000 claims description 3
- CMZPQJUSQAQSPK-WMZOPIPTSA-N (2s,3s)-n-[[2-(difluoromethoxy)-5-nitrophenyl]methyl]-2-phenylpiperidin-3-amine Chemical compound [O-][N+](=O)C1=CC=C(OC(F)F)C(CN[C@@H]2[C@@H](NCCC2)C=2C=CC=CC=2)=C1 CMZPQJUSQAQSPK-WMZOPIPTSA-N 0.000 claims description 3
- USBRZPMXLUXIOM-FPOVZHCZSA-N (2s,3s)-n-[[2-(difluoromethoxy)-5-propan-2-ylphenyl]methyl]-2-phenylpiperidin-3-amine Chemical compound CC(C)C1=CC=C(OC(F)F)C(CN[C@@H]2[C@@H](NCCC2)C=2C=CC=CC=2)=C1 USBRZPMXLUXIOM-FPOVZHCZSA-N 0.000 claims description 3
- ZPQUTMAPZMKLCT-ICSRJNTNSA-N (2s,3s)-n-[[2-ethoxy-5-(trifluoromethoxy)phenyl]methyl]-2-phenylpiperidin-3-amine Chemical compound CCOC1=CC=C(OC(F)(F)F)C=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)NCCC1 ZPQUTMAPZMKLCT-ICSRJNTNSA-N 0.000 claims description 3
- ZIWFCOIGUNPHPM-HKUYNNGSSA-N (2s,3s)-n-[[2-methoxy-5-(trifluoromethoxy)phenyl]methyl]-2-phenylpiperidin-3-amine Chemical compound COC1=CC=C(OC(F)(F)F)C=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)NCCC1 ZIWFCOIGUNPHPM-HKUYNNGSSA-N 0.000 claims description 3
- WSGDMCZUYDGFBX-HKUYNNGSSA-N (2s,3s)-n-[[5-chloro-2-(2,2,2-trifluoroethoxy)phenyl]methyl]-2-phenylpiperidin-3-amine Chemical compound FC(F)(F)COC1=CC=C(Cl)C=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)NCCC1 WSGDMCZUYDGFBX-HKUYNNGSSA-N 0.000 claims description 3
- OWFLLZWJAFLEIE-FPOVZHCZSA-N (2s,3s)-n-[[5-tert-butyl-2-(difluoromethoxy)phenyl]methyl]-2-phenylpiperidin-3-amine Chemical compound CC(C)(C)C1=CC=C(OC(F)F)C(CN[C@@H]2[C@@H](NCCC2)C=2C=CC=CC=2)=C1 OWFLLZWJAFLEIE-FPOVZHCZSA-N 0.000 claims description 3
- NPKIOBYABGRQLF-YTMVLYRLSA-N 2,4-dimethyl-n-(2-methylpropyl)-n-[3-[[[(2s,3s)-2-phenylpiperidin-3-yl]amino]methyl]-4-propan-2-yloxyphenyl]-1,3-thiazole-5-sulfonamide Chemical compound C1([C@@H]2NCCC[C@@H]2NCC=2C(OC(C)C)=CC=C(C=2)N(CC(C)C)S(=O)(=O)C2=C(N=C(C)S2)C)=CC=CC=C1 NPKIOBYABGRQLF-YTMVLYRLSA-N 0.000 claims description 3
- QPZCQYBSSCOAOM-XCZPVHLTSA-N 2,4-dimethyl-n-[3-[[[(2s,3s)-2-phenylpiperidin-3-yl]amino]methyl]-4-propan-2-yloxyphenyl]-n-propan-2-yl-1,3-thiazole-5-sulfonamide Chemical compound C1([C@@H]2NCCC[C@@H]2NCC2=CC(=CC=C2OC(C)C)N(C(C)C)S(=O)(=O)C2=C(N=C(C)S2)C)=CC=CC=C1 QPZCQYBSSCOAOM-XCZPVHLTSA-N 0.000 claims description 3
- IZRHKURJIQCXMT-WMZOPIPTSA-N 2-[[[(2s,3s)-2-phenylpiperidin-3-yl]amino]methyl]-4-(trifluoromethoxy)phenol Chemical compound OC1=CC=C(OC(F)(F)F)C=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)NCCC1 IZRHKURJIQCXMT-WMZOPIPTSA-N 0.000 claims description 3
- BHNXFFADSMHMAM-UHFFFAOYSA-N 2-benzhydryl-1-azabicyclo[2.2.2]octane-2-carboxylic acid Chemical compound C1C(CC2)CCN2C1(C(=O)O)C(C=1C=CC=CC=1)C1=CC=CC=C1 BHNXFFADSMHMAM-UHFFFAOYSA-N 0.000 claims description 3
- AJWHPFMEKZXCCP-UHFFFAOYSA-N 2-benzhydryl-1-azabicyclo[2.2.2]octane-3-carboxylic acid Chemical compound OC(=O)C1C(CC2)CCN2C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AJWHPFMEKZXCCP-UHFFFAOYSA-N 0.000 claims description 3
- VCXPJIZDOYOACQ-UHFFFAOYSA-N 6-[3-[[2-(cyclohexylamino)cyclopentyl]methyl]phenyl]pyridin-2-amine Chemical compound NC1=CC=CC(C=2C=C(CC3C(CCC3)NC3CCCCC3)C=CC=2)=N1 VCXPJIZDOYOACQ-UHFFFAOYSA-N 0.000 claims description 3
- DTYUPHYOUWWLNO-UHFFFAOYSA-N 6-[4-[2-(dimethylamino)ethoxy]-2-methoxyphenyl]pyridin-2-amine Chemical compound COC1=CC(OCCN(C)C)=CC=C1C1=CC=CC(N)=N1 DTYUPHYOUWWLNO-UHFFFAOYSA-N 0.000 claims description 3
- WVUIJEOINWQJMC-UHFFFAOYSA-N 6-[4-[2-(dimethylamino)ethoxy]-2-propan-2-ylphenyl]pyridin-2-amine Chemical compound CC(C)C1=CC(OCCN(C)C)=CC=C1C1=CC=CC(N)=N1 WVUIJEOINWQJMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- XXXAPFHGQOEKLI-UHFFFAOYSA-N n-[(2-methoxyphenyl)methyl]-2,4-diphenylpiperidin-3-amine Chemical compound COC1=CC=CC=C1CNC1C(C=2C=CC=CC=2)NCCC1C1=CC=CC=C1 XXXAPFHGQOEKLI-UHFFFAOYSA-N 0.000 claims description 3
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims description 2
- WOLRCLJAHCZADK-XICMLOBYSA-N (2s,3s)-1-(5,6-dimethoxyhexyl)-n-[[2-methoxy-5-(trifluoromethoxy)phenyl]methyl]-2-phenylpiperidin-3-amine Chemical compound N([C@H]1CCCN([C@H]1C=1C=CC=CC=1)CCCCC(COC)OC)CC1=CC(OC(F)(F)F)=CC=C1OC WOLRCLJAHCZADK-XICMLOBYSA-N 0.000 claims description 2
- JMPFLCLLMDQYKW-FPOVZHCZSA-N (2s,3s)-2-phenyl-n-[[2-propan-2-yloxy-5-(trifluoromethoxy)phenyl]methyl]piperidin-3-amine Chemical compound CC(C)OC1=CC=C(OC(F)(F)F)C=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)NCCC1 JMPFLCLLMDQYKW-FPOVZHCZSA-N 0.000 claims description 2
- JWFRVJYQGQVKBH-ICSRJNTNSA-N (2s,3s)-n-[(2,5-dimethoxyphenyl)methyl]-2-phenylpiperidin-3-amine Chemical compound COC1=CC=C(OC)C(CN[C@@H]2[C@@H](NCCC2)C=2C=CC=CC=2)=C1 JWFRVJYQGQVKBH-ICSRJNTNSA-N 0.000 claims description 2
- CVJILTLPVIPLLN-ZCYQVOJMSA-N (2s,3s)-n-[(2-methoxy-5-phenylphenyl)methyl]-2-phenylpiperidin-3-amine Chemical compound C1([C@@H]2NCCC[C@@H]2NCC2=CC(=CC=C2OC)C=2C=CC=CC=2)=CC=CC=C1 CVJILTLPVIPLLN-ZCYQVOJMSA-N 0.000 claims description 2
- NVAJOEWMHMGWCN-UNMCSNQZSA-N (2s,3s)-n-[(2-methoxy-5-propylphenyl)methyl]-2-phenylpiperidin-3-amine Chemical compound CCCC1=CC=C(OC)C(CN[C@@H]2[C@@H](NCCC2)C=2C=CC=CC=2)=C1 NVAJOEWMHMGWCN-UNMCSNQZSA-N 0.000 claims description 2
- HVWRVAHBKREIOR-HKUYNNGSSA-N (2s,3s)-n-[(5-chloro-2-methoxyphenyl)methyl]-2-phenylpiperidin-3-amine Chemical compound COC1=CC=C(Cl)C=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)NCCC1 HVWRVAHBKREIOR-HKUYNNGSSA-N 0.000 claims description 2
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 claims description 2
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims description 2
- GRBSRKIQJCLYFU-WNJJXGMVSA-N 1-(4-fluorophenyl)-4-[(2s,3s)-3-[(2-methoxyphenyl)methylamino]-2-phenylpiperidin-1-yl]butan-1-one Chemical compound COC1=CC=CC=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)N(CCCC(=O)C=2C=CC(F)=CC=2)CCC1 GRBSRKIQJCLYFU-WNJJXGMVSA-N 0.000 claims description 2
- LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical compound C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000972 4,5-dimethylthiazol-2-yl group Chemical group [H]C([H])([H])C1=C(N=C(*)S1)C([H])([H])[H] 0.000 claims description 2
- HQZONHWUUKPDRH-QGWOSTIUSA-N 4-[(2s,3s)-3-[(2-methoxyphenyl)methylamino]-2-phenylpiperidin-1-yl]-1-phenylbutan-1-ol Chemical compound COC1=CC=CC=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)N(CCCC(O)C=2C=CC=CC=2)CCC1 HQZONHWUUKPDRH-QGWOSTIUSA-N 0.000 claims description 2
- HJGPOTAUGCEFKX-UHFFFAOYSA-N 6-(2-ethoxy-4-pyrrolidin-3-yloxyphenyl)pyridin-2-amine Chemical compound C=1C=C(C=2N=C(N)C=CC=2)C(OCC)=CC=1OC1CCNC1 HJGPOTAUGCEFKX-UHFFFAOYSA-N 0.000 claims description 2
- WGOAHGIIQAMZFD-UHFFFAOYSA-N 6-(2-methoxy-4-piperidin-4-yloxyphenyl)pyridin-2-amine Chemical compound C=1C=C(C=2N=C(N)C=CC=2)C(OC)=CC=1OC1CCNCC1 WGOAHGIIQAMZFD-UHFFFAOYSA-N 0.000 claims description 2
- AFMGEKOPFBWJAK-UHFFFAOYSA-N 6-[2,3-dimethyl-4-(2-pyrrolidin-1-ylethoxy)phenyl]pyridin-2-amine Chemical compound CC1=C(C)C(C=2N=C(N)C=CC=2)=CC=C1OCCN1CCCC1 AFMGEKOPFBWJAK-UHFFFAOYSA-N 0.000 claims description 2
- LMKXDKOQJADKQY-UHFFFAOYSA-N 6-[2-cyclobutyl-4-(1-methylpyrrolidin-3-yl)oxyphenyl]pyridin-2-amine Chemical compound C1N(C)CCC1OC(C=C1C2CCC2)=CC=C1C1=CC=CC(N)=N1 LMKXDKOQJADKQY-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229960001790 sodium citrate Drugs 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
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- 239000003890 substance P antagonist Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- KWQRKOSMSFLBTJ-UHFFFAOYSA-N tert-butyl 3-methylsulfonyloxypyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(OS(C)(=O)=O)C1 KWQRKOSMSFLBTJ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-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
Classifications
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- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Child & Adolescent Psychology (AREA)
- Hematology (AREA)
- Ophthalmology & Optometry (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13552099P | 1999-05-21 | 1999-05-21 | |
| US60135520 | 1999-05-21 | ||
| PCT/IB2000/000295 WO2000071107A2 (fr) | 1999-05-21 | 2000-03-16 | Nouvelles combinaisons pharmaceutiques pour les inhibiteurs de nos |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2935300A true AU2935300A (en) | 2000-12-12 |
Family
ID=22468464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU29353/00A Abandoned AU2935300A (en) | 1999-05-21 | 2000-03-16 | New pharmaceutical combinations for nos inhibitors |
Country Status (33)
| Country | Link |
|---|---|
| EP (1) | EP1178784A1 (fr) |
| JP (1) | JP2003523941A (fr) |
| KR (1) | KR20020010916A (fr) |
| CN (1) | CN1617743A (fr) |
| AP (1) | AP2001002326A0 (fr) |
| AR (1) | AR022640A1 (fr) |
| AU (1) | AU2935300A (fr) |
| BG (1) | BG106208A (fr) |
| BR (1) | BR0010820A (fr) |
| CA (1) | CA2374668A1 (fr) |
| CO (1) | CO5160295A1 (fr) |
| DZ (1) | DZ3041A1 (fr) |
| EA (1) | EA200101110A1 (fr) |
| EE (1) | EE200100611A (fr) |
| GT (1) | GT200000071A (fr) |
| HN (1) | HN2000000045A (fr) |
| HR (1) | HRP20010862A2 (fr) |
| HU (1) | HUP0301287A3 (fr) |
| IL (1) | IL145955A0 (fr) |
| IS (1) | IS6126A (fr) |
| MA (1) | MA26732A1 (fr) |
| MX (1) | MXPA01011978A (fr) |
| NO (1) | NO20015651L (fr) |
| OA (1) | OA11943A (fr) |
| PA (1) | PA8494601A1 (fr) |
| PE (1) | PE20010157A1 (fr) |
| PL (1) | PL358538A1 (fr) |
| SK (1) | SK16602001A3 (fr) |
| TN (1) | TNSN00106A1 (fr) |
| TR (1) | TR200103351T2 (fr) |
| UY (1) | UY26148A1 (fr) |
| WO (1) | WO2000071107A2 (fr) |
| ZA (1) | ZA200109555B (fr) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10001785A1 (de) * | 2000-01-18 | 2001-07-19 | Boehringer Ingelheim Pharma | NK¶1¶-Rezeptor-Antagonisten zur Behandlung des Restless Legs Syndroms |
| GB0019006D0 (en) * | 2000-08-04 | 2000-09-20 | Astrazeneca Ab | Novel compounds |
| US20030045449A1 (en) * | 2001-08-15 | 2003-03-06 | Pfizer, Inc. | Pharmaceutical combinations for the treatment of neurodegenerative diseases |
| US6803470B2 (en) * | 2001-10-10 | 2004-10-12 | Pfizer Inc | 2-amino-6-(2,4,5-substituted-phenyl)-pyridines |
| DOP2002000467A (es) * | 2001-10-10 | 2003-04-15 | Pfizer Prod Inc | 2-amino-6 (fenilo sustituido en las posiciones 2,4,5)-piridinas |
| BRPI0411608A (pt) * | 2003-06-24 | 2006-08-08 | Neurosearch As | derivado de 8-aza-biciclo [3.2.1] octano, composição farmacêutica, uso do composto, e, método de tratamento, prevenção ou alìvio de uma doença, um distúrbio ou uma condição de um organismo animal vivo |
| EP1634598A1 (fr) * | 2004-09-07 | 2006-03-15 | Laboratorios Del Dr. Esteve, S.A. | Utilisation de dérivés de piperazine et ses analogues pour prevenir et traiter des désordres liés à l'ingestion de nourriture |
| JO2972B1 (en) | 2007-06-08 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Piperidine / piperazine derivatives |
| EP2152271B1 (fr) | 2007-06-08 | 2015-10-21 | Janssen Pharmaceutica, N.V. | Dérivés de piperidine/piperazine |
| ES2536406T3 (es) | 2007-06-08 | 2015-05-25 | Janssen Pharmaceutica, N.V. | Derivados de piperidina/piperazina |
| JP5464709B2 (ja) | 2007-06-08 | 2014-04-09 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ピペリジン/ピペラジン誘導体 |
| PE20100083A1 (es) | 2008-06-05 | 2010-02-17 | Janssen Pharmaceutica Nv | Combinaciones de drogas que comprenden un inhibidor de dgat y un agonista de ppar |
| JP5642661B2 (ja) * | 2009-03-05 | 2014-12-17 | 塩野義製薬株式会社 | Npyy5受容体拮抗作用を有するピペリジンおよびピロリジン誘導体 |
| US20140206667A1 (en) | 2012-11-14 | 2014-07-24 | Michela Gallagher | Methods and compositions for treating schizophrenia |
| AU2020291468A1 (en) * | 2019-06-14 | 2022-01-06 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
| US12115154B2 (en) | 2020-12-16 | 2024-10-15 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
-
2000
- 2000-03-16 TR TR2001/03351T patent/TR200103351T2/xx unknown
- 2000-03-16 JP JP2000619414A patent/JP2003523941A/ja not_active Withdrawn
- 2000-03-16 HU HU0301287A patent/HUP0301287A3/hu unknown
- 2000-03-16 AP APAP/P/2001/002326A patent/AP2001002326A0/en unknown
- 2000-03-16 MX MXPA01011978A patent/MXPA01011978A/es unknown
- 2000-03-16 HR HR20010862A patent/HRP20010862A2/hr not_active Application Discontinuation
- 2000-03-16 WO PCT/IB2000/000295 patent/WO2000071107A2/fr not_active Ceased
- 2000-03-16 PL PL00358538A patent/PL358538A1/xx not_active Application Discontinuation
- 2000-03-16 EP EP00907891A patent/EP1178784A1/fr not_active Ceased
- 2000-03-16 EA EA200101110A patent/EA200101110A1/ru unknown
- 2000-03-16 AU AU29353/00A patent/AU2935300A/en not_active Abandoned
- 2000-03-16 CN CNA008078785A patent/CN1617743A/zh active Pending
- 2000-03-16 BR BR0010820-0A patent/BR0010820A/pt not_active IP Right Cessation
- 2000-03-16 CA CA002374668A patent/CA2374668A1/fr not_active Abandoned
- 2000-03-16 OA OA1200100301A patent/OA11943A/en unknown
- 2000-03-16 IL IL14595500A patent/IL145955A0/xx unknown
- 2000-03-16 KR KR1020017014884A patent/KR20020010916A/ko not_active Withdrawn
- 2000-03-16 EE EEP200100611A patent/EE200100611A/xx unknown
- 2000-03-16 SK SK1660-2001A patent/SK16602001A3/sk unknown
- 2000-04-04 CO CO00024427A patent/CO5160295A1/es unknown
- 2000-04-04 HN HN2000000045A patent/HN2000000045A/es unknown
- 2000-04-25 PA PA20008494601A patent/PA8494601A1/es unknown
- 2000-05-17 TN TNTNSN00106A patent/TNSN00106A1/fr unknown
- 2000-05-17 MA MA25976A patent/MA26732A1/fr unknown
- 2000-05-17 DZ DZ000084A patent/DZ3041A1/fr active
- 2000-05-17 GT GT200000071A patent/GT200000071A/es unknown
- 2000-05-18 UY UY26148A patent/UY26148A1/es not_active Application Discontinuation
- 2000-05-19 PE PE2000000473A patent/PE20010157A1/es not_active Application Discontinuation
- 2000-05-19 AR ARP000102387A patent/AR022640A1/es not_active Application Discontinuation
-
2001
- 2001-10-26 IS IS6126A patent/IS6126A/is unknown
- 2001-11-20 NO NO20015651A patent/NO20015651L/no not_active Application Discontinuation
- 2001-11-20 ZA ZA200109555A patent/ZA200109555B/en unknown
- 2001-12-11 BG BG06208A patent/BG106208A/xx unknown
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