OA11943A - New pharmacetical combinations for nos inhibitors - Google Patents
New pharmacetical combinations for nos inhibitors Download PDFInfo
- Publication number
- OA11943A OA11943A OA1200100301A OA1200100301A OA11943A OA 11943 A OA11943 A OA 11943A OA 1200100301 A OA1200100301 A OA 1200100301A OA 1200100301 A OA1200100301 A OA 1200100301A OA 11943 A OA11943 A OA 11943A
- Authority
- OA
- OAPI
- Prior art keywords
- pyridin
- ylamine
- phenyl
- amino
- ethoxy
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 325
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 98
- 208000035475 disorder Diseases 0.000 claims abstract description 94
- 208000019116 sleep disease Diseases 0.000 claims abstract description 33
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims abstract description 31
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 claims abstract description 18
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 claims abstract description 18
- 230000007958 sleep Effects 0.000 claims abstract description 17
- 208000006199 Parasomnias Diseases 0.000 claims abstract description 16
- 230000027288 circadian rhythm Effects 0.000 claims abstract description 16
- 206010020765 hypersomnia Diseases 0.000 claims abstract description 16
- 239000002464 receptor antagonist Substances 0.000 claims abstract description 16
- 229940044551 receptor antagonist Drugs 0.000 claims abstract description 16
- 208000020925 Bipolar disease Diseases 0.000 claims abstract description 15
- 208000008967 Enuresis Diseases 0.000 claims abstract description 15
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims abstract description 15
- 208000008589 Obesity Diseases 0.000 claims abstract description 15
- 208000005793 Restless legs syndrome Diseases 0.000 claims abstract description 15
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims abstract description 15
- 201000003631 narcolepsy Diseases 0.000 claims abstract description 15
- 235000020824 obesity Nutrition 0.000 claims abstract description 15
- 208000012672 seasonal affective disease Diseases 0.000 claims abstract description 15
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims abstract description 14
- 208000010340 Sleep Deprivation Diseases 0.000 claims abstract description 14
- 230000002060 circadian Effects 0.000 claims abstract description 14
- 230000036385 rapid eye movement (rem) sleep Effects 0.000 claims abstract description 14
- 201000004569 Blindness Diseases 0.000 claims abstract description 13
- 230000001788 irregular Effects 0.000 claims abstract description 13
- 230000033764 rhythmic process Effects 0.000 claims abstract description 11
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims abstract 3
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims abstract 3
- -1 Cyclohexyl-methyl-amino Chemical group 0.000 claims description 99
- 238000000034 method Methods 0.000 claims description 87
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 38
- 230000002401 inhibitory effect Effects 0.000 claims description 30
- 239000008194 pharmaceutical composition Substances 0.000 claims description 27
- 241000124008 Mammalia Species 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- ICSNLGPSRYBMBD-UHFFFAOYSA-N alpha-aminopyridine Natural products NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 206010012289 Dementia Diseases 0.000 claims description 12
- 201000002859 sleep apnea Diseases 0.000 claims description 10
- DYWSVUBJGFTOQC-UHFFFAOYSA-N xi-2-Ethylheptanoic acid Chemical compound CCCCCC(CC)C(O)=O DYWSVUBJGFTOQC-UHFFFAOYSA-N 0.000 claims description 10
- 208000019901 Anxiety disease Diseases 0.000 claims description 9
- 208000020685 sleep-wake disease Diseases 0.000 claims description 9
- 208000008811 Agoraphobia Diseases 0.000 claims description 8
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- 206010041250 Social phobia Diseases 0.000 claims description 8
- 208000010877 cognitive disease Diseases 0.000 claims description 8
- 206010022437 insomnia Diseases 0.000 claims description 8
- 208000019906 panic disease Diseases 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 208000011688 Generalised anxiety disease Diseases 0.000 claims description 7
- 208000026139 Memory disease Diseases 0.000 claims description 7
- 208000006011 Stroke Diseases 0.000 claims description 7
- 208000024732 dysthymic disease Diseases 0.000 claims description 7
- 208000029364 generalized anxiety disease Diseases 0.000 claims description 7
- JASMWYNKLTULAN-UHFFFAOYSA-N octan-3-amine Chemical compound CCCCCC(N)CC JASMWYNKLTULAN-UHFFFAOYSA-N 0.000 claims description 7
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 7
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 208000019022 Mood disease Diseases 0.000 claims description 5
- 208000019899 phobic disease Diseases 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
- 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 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 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 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 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
- 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 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
- AUHFOPNHPZPZEI-UHFFFAOYSA-N 2-benzhydryl-n-[[2-methoxy-5-(trifluoromethoxy)phenyl]methyl]-1-azabicyclo[2.2.2]octan-3-amine Chemical compound COC1=CC=C(OC(F)(F)F)C=C1CNC1C(C(C=2C=CC=CC=2)C=2C=CC=CC=2)N2CCC1CC2 AUHFOPNHPZPZEI-UHFFFAOYSA-N 0.000 claims description 2
- WGIAUTGOUJDVEI-UHFFFAOYSA-N 2-phenylpiperidine Chemical compound N1CCCCC1C1=CC=CC=C1 WGIAUTGOUJDVEI-UHFFFAOYSA-N 0.000 claims description 2
- MWNICFXVCUVIBR-UHFFFAOYSA-N 3-[(6-aminopyridin-2-yl)-phenylmethyl]-1-[2-(dimethylamino)ethyl]-3h-indol-2-one Chemical compound C12=CC=CC=C2N(CCN(C)C)C(=O)C1C(C=1N=C(N)C=CC=1)C1=CC=CC=C1 MWNICFXVCUVIBR-UHFFFAOYSA-N 0.000 claims description 2
- ZOMWHUFJIVHYTM-UHFFFAOYSA-N 3-[(6-aminopyridin-2-yl)-phenylmethyl]-1-methyl-3h-indol-2-one Chemical compound C12=CC=CC=C2N(C)C(=O)C1C(C=1N=C(N)C=CC=1)C1=CC=CC=C1 ZOMWHUFJIVHYTM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- KMPIDOMSSJIINY-UHFFFAOYSA-N 4-(6-aminopyridin-2-yl)-3-cyclobutylphenol Chemical compound NC1=CC=CC(C=2C(=CC(O)=CC=2)C2CCC2)=N1 KMPIDOMSSJIINY-UHFFFAOYSA-N 0.000 claims description 2
- DGARGBGOUHCGFH-UHFFFAOYSA-N 4-(6-aminopyridin-2-yl)-5-methoxy-2-prop-2-enylphenol Chemical compound COC1=CC(O)=C(CC=C)C=C1C1=CC=CC(N)=N1 DGARGBGOUHCGFH-UHFFFAOYSA-N 0.000 claims description 2
- RHVZNUMCGSLHME-UHFFFAOYSA-N 4-(6-aminopyridin-2-yl)-5-methoxy-2-propylphenol Chemical compound C1=C(O)C(CCC)=CC(C=2N=C(N)C=CC=2)=C1OC RHVZNUMCGSLHME-UHFFFAOYSA-N 0.000 claims description 2
- QCVNQLHDZDTJCW-UHFFFAOYSA-N 6-(2-methoxy-4-prop-2-enoxyphenyl)pyridin-2-amine Chemical compound COC1=CC(OCC=C)=CC=C1C1=CC=CC(N)=N1 QCVNQLHDZDTJCW-UHFFFAOYSA-N 0.000 claims description 2
- RAALGBGFKBCULV-UHFFFAOYSA-N 6-[2,6-dimethyl-4-(2-morpholin-4-ylethoxy)phenyl]pyridin-2-amine Chemical compound C=1C(C)=C(C=2N=C(N)C=CC=2)C(C)=CC=1OCCN1CCOCC1 RAALGBGFKBCULV-UHFFFAOYSA-N 0.000 claims description 2
- IDYJPRNTQPSUOV-UHFFFAOYSA-N 6-[2-cyclopentyl-4-[2-(dimethylamino)ethoxy]phenyl]pyridin-2-amine Chemical compound C1CCCC1C1=CC(OCCN(C)C)=CC=C1C1=CC=CC(N)=N1 IDYJPRNTQPSUOV-UHFFFAOYSA-N 0.000 claims description 2
- QPCPIBGPAYBODR-UHFFFAOYSA-N 6-[2-methoxy-4-(1-methylazetidin-3-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=C(C=2N=C(N)C=CC=2)C(OC)=CC=1OC1CN(C)C1 QPCPIBGPAYBODR-UHFFFAOYSA-N 0.000 claims description 2
- NUEJSFSSKQWBEB-UHFFFAOYSA-N 6-[2-methoxy-4-[(2-phenylethylamino)methyl]phenyl]pyridin-2-amine Chemical compound C=1C=C(C=2N=C(N)C=CC=2)C(OC)=CC=1CNCCC1=CC=CC=C1 NUEJSFSSKQWBEB-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- ZMWHHNZCXGTSLB-UHFFFAOYSA-N 6-[4-(2-pyrrolidin-1-ylethoxy)-5,6,7,8-tetrahydronaphthalen-1-yl]pyridin-2-amine Chemical compound NC1=CC=CC(C=2C=3CCCCC=3C(OCCN3CCCC3)=CC=2)=N1 ZMWHHNZCXGTSLB-UHFFFAOYSA-N 0.000 claims description 2
- RYHSJNSMHCMNDG-UHFFFAOYSA-N 6-[4-[2-(dimethylamino)ethoxy]-2-methoxy-5-propylphenyl]pyridin-2-amine Chemical compound C1=C(OCCN(C)C)C(CCC)=CC(C=2N=C(N)C=CC=2)=C1OC RYHSJNSMHCMNDG-UHFFFAOYSA-N 0.000 claims description 2
- FKWYUVJVLJKLQO-UHFFFAOYSA-N 6-[4-[[2-(4-benzylpiperazin-1-yl)cyclohexyl]methyl]phenyl]pyridin-2-amine Chemical compound NC1=CC=CC(C=2C=CC(CC3C(CCCC3)N3CCN(CC=4C=CC=CC=4)CC3)=CC=2)=N1 FKWYUVJVLJKLQO-UHFFFAOYSA-N 0.000 claims description 2
- BYQRRDHFZKRLQI-UHFFFAOYSA-N 6-[7-(2-morpholin-4-ylethoxy)-2,3-dihydro-1h-inden-4-yl]pyridin-2-amine Chemical compound NC1=CC=CC(C=2C=3CCCC=3C(OCCN3CCOCC3)=CC=2)=N1 BYQRRDHFZKRLQI-UHFFFAOYSA-N 0.000 claims description 2
- LKMDSVRPEYBFHA-UHFFFAOYSA-N 6-[7-(2-pyrrolidin-1-ylethoxy)-2,3-dihydro-1h-inden-4-yl]pyridin-2-amine Chemical compound NC1=CC=CC(C=2C=3CCCC=3C(OCCN3CCCC3)=CC=2)=N1 LKMDSVRPEYBFHA-UHFFFAOYSA-N 0.000 claims description 2
- ASCIWHQKWHDNRB-UHFFFAOYSA-N 6-[7-[2-(dimethylamino)ethoxy]-2,3-dihydro-1h-inden-4-yl]pyridin-2-amine Chemical compound C1=2CCCC=2C(OCCN(C)C)=CC=C1C1=CC=CC(N)=N1 ASCIWHQKWHDNRB-UHFFFAOYSA-N 0.000 claims description 2
- MXNCJGDSGDBEBK-UHFFFAOYSA-N 8-[4-(6-aminopyridin-2-yl)phenyl]-3-benzyl-3-azabicyclo[3.2.1]octan-8-ol Chemical compound NC1=CC=CC(C=2C=CC(=CC=2)C2(O)C3CCC2CN(CC=2C=CC=CC=2)C3)=N1 MXNCJGDSGDBEBK-UHFFFAOYSA-N 0.000 claims description 2
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims description 2
- SDZOYRPMRJVFNK-UHFFFAOYSA-N [4-[2-[4-(6-aminopyridin-2-yl)phenyl]ethyl]piperazin-1-yl]-cyclopentylmethanone Chemical compound NC1=CC=CC(C=2C=CC(CCN3CCN(CC3)C(=O)C3CCCC3)=CC=2)=N1 SDZOYRPMRJVFNK-UHFFFAOYSA-N 0.000 claims description 2
- 239000005557 antagonist Substances 0.000 claims description 2
- 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 2
- TXHKKANZSDSWIS-UHFFFAOYSA-N chembl39005 Chemical compound C1=2C(C3)CCC3C=2C(OCCN(C)C)=CC=C1C1=CC=CC(N)=N1 TXHKKANZSDSWIS-UHFFFAOYSA-N 0.000 claims description 2
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- CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 claims description 2
- DBKJGIXLYZJDMI-UHFFFAOYSA-N n-[(2-methoxyphenyl)methyl]-6-methyl-2-phenylpiperidin-3-amine Chemical compound COC1=CC=CC=C1CNC1C(C=2C=CC=CC=2)NC(C)CC1 DBKJGIXLYZJDMI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229960002296 paroxetine Drugs 0.000 claims description 2
- 229940080818 propionamide Drugs 0.000 claims description 2
- ZMXMKTCXEPIEDX-UHFFFAOYSA-N tert-butyl 3-[4-(6-aminopyridin-2-yl)-3-methoxyphenoxy]azetidine-1-carboxylate Chemical compound C=1C=C(C=2N=C(N)C=CC=2)C(OC)=CC=1OC1CN(C(=O)OC(C)(C)C)C1 ZMXMKTCXEPIEDX-UHFFFAOYSA-N 0.000 claims description 2
- QOHGGWJARDFFLF-UHFFFAOYSA-N tert-butyl 4-[4-(6-aminopyridin-2-yl)-3-methoxyphenoxy]piperidine-1-carboxylate Chemical compound C=1C=C(C=2N=C(N)C=CC=2)C(OC)=CC=1OC1CCN(C(=O)OC(C)(C)C)CC1 QOHGGWJARDFFLF-UHFFFAOYSA-N 0.000 claims description 2
- 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 1
- LVCKDBYHCLGPDR-LSGCGUROSA-N (2s,3s,4s,5r)-2-benzhydryl-3-[[2-methoxy-5-(trifluoromethoxy)phenyl]methylamino]-1-azabicyclo[2.2.2]octane-5-carboxylic acid Chemical compound C=1C=CC=CC=1C([C@@H]1N2CC[C@@]([C@H](C2)C(O)=O)([C@@H]1NCC=1C(=CC=C(OC(F)(F)F)C=1)OC)[H])C1=CC=CC=C1 LVCKDBYHCLGPDR-LSGCGUROSA-N 0.000 claims 1
- LBYSHULELVFOGE-ATACATFBSA-N (2s,3s,4s,5r)-2-benzhydryl-3-[[5-(dimethylamino)-2-methoxyphenyl]methylamino]-1-azabicyclo[2.2.2]octane-5-carboxylic acid Chemical compound C=1C=CC=CC=1C([C@@H]1N2CC[C@@]([C@H](C2)C(O)=O)([C@@H]1NCC=1C(=CC=C(C=1)N(C)C)OC)[H])C1=CC=CC=C1 LBYSHULELVFOGE-ATACATFBSA-N 0.000 claims 1
- MISWEYWXWVUHES-UHFFFAOYSA-N 1-[4-(6-aminopyridin-2-yl)-3-propan-2-yloxyphenyl]-2-(dimethylamino)ethanol Chemical compound CC(C)OC1=CC(C(O)CN(C)C)=CC=C1C1=CC=CC(N)=N1 MISWEYWXWVUHES-UHFFFAOYSA-N 0.000 claims 1
- AUDFEYHTXCWBLV-UHFFFAOYSA-N 1-[4-[2-[4-(6-aminopyridin-2-yl)-2-methoxyphenyl]ethyl]piperazin-1-yl]-2-phenylethanone Chemical compound COC1=CC(C=2N=C(N)C=CC=2)=CC=C1CCN(CC1)CCN1C(=O)CC1=CC=CC=C1 AUDFEYHTXCWBLV-UHFFFAOYSA-N 0.000 claims 1
- HLRIGBAUGKHTST-UHFFFAOYSA-N 1-[4-[2-[4-(6-aminopyridin-2-yl)-2-methylphenyl]ethyl]piperazin-1-yl]-2-phenylethanone Chemical compound CC1=CC(C=2N=C(N)C=CC=2)=CC=C1CCN(CC1)CCN1C(=O)CC1=CC=CC=C1 HLRIGBAUGKHTST-UHFFFAOYSA-N 0.000 claims 1
- LBKLIVOXVRLCCR-UHFFFAOYSA-N 1-[4-[2-[4-(6-aminopyridin-2-yl)phenyl]ethyl]piperazin-1-yl]-2-methoxyethanone Chemical compound C1CN(C(=O)COC)CCN1CCC1=CC=C(C=2N=C(N)C=CC=2)C=C1 LBKLIVOXVRLCCR-UHFFFAOYSA-N 0.000 claims 1
- UZHZLZHBXWXQRC-UHFFFAOYSA-N 2-[4-(6-aminopyridin-2-yl)-3-methoxyphenoxy]ethanol Chemical compound COC1=CC(OCCO)=CC=C1C1=CC=CC(N)=N1 UZHZLZHBXWXQRC-UHFFFAOYSA-N 0.000 claims 1
- OYWFCMPLRUKUQI-UHFFFAOYSA-N 2-[4-[2-[4-(6-aminopyridin-2-yl)-2-fluorophenyl]ethyl]piperazin-1-yl]-n-propan-2-ylacetamide Chemical compound C1CN(CC(=O)NC(C)C)CCN1CCC1=CC=C(C=2N=C(N)C=CC=2)C=C1F OYWFCMPLRUKUQI-UHFFFAOYSA-N 0.000 claims 1
- SGFRPINTMFASGZ-UHFFFAOYSA-N 2-[4-[2-[4-(6-aminopyridin-2-yl)-2-methoxyphenyl]ethyl]piperazin-1-yl]-1-phenylethanone Chemical compound COC1=CC(C=2N=C(N)C=CC=2)=CC=C1CCN(CC1)CCN1CC(=O)C1=CC=CC=C1 SGFRPINTMFASGZ-UHFFFAOYSA-N 0.000 claims 1
- JXOSMKVSYFUKFR-UHFFFAOYSA-N 2-[4-[2-[4-(6-aminopyridin-2-yl)-2-methylphenyl]ethyl]piperazin-1-yl]-1-phenylethanone Chemical compound CC1=CC(C=2N=C(N)C=CC=2)=CC=C1CCN(CC1)CCN1CC(=O)C1=CC=CC=C1 JXOSMKVSYFUKFR-UHFFFAOYSA-N 0.000 claims 1
- MZLWIQJYMYEJFP-UHFFFAOYSA-N 2-[4-[2-[4-(6-aminopyridin-2-yl)phenyl]ethyl]piperazin-1-yl]-1-(4-chlorophenyl)ethanone Chemical compound NC1=CC=CC(C=2C=CC(CCN3CCN(CC(=O)C=4C=CC(Cl)=CC=4)CC3)=CC=2)=N1 MZLWIQJYMYEJFP-UHFFFAOYSA-N 0.000 claims 1
- GJKKUWOOEFFGOH-UHFFFAOYSA-N 2-[4-[2-[4-(6-aminopyridin-2-yl)phenyl]ethyl]piperazin-1-yl]-n-propan-2-ylacetamide Chemical compound C1CN(CC(=O)NC(C)C)CCN1CCC1=CC=C(C=2N=C(N)C=CC=2)C=C1 GJKKUWOOEFFGOH-UHFFFAOYSA-N 0.000 claims 1
- NWBNXZXGFIIUIP-UHFFFAOYSA-N 4-(6-aminopyridin-2-yl)-3-cyclopentylphenol Chemical compound NC1=CC=CC(C=2C(=CC(O)=CC=2)C2CCCC2)=N1 NWBNXZXGFIIUIP-UHFFFAOYSA-N 0.000 claims 1
- GVUCVRXLDWFFPO-UHFFFAOYSA-N 4-(6-aminopyridin-2-yl)-3-cyclopropylphenol Chemical compound NC1=CC=CC(C=2C(=CC(O)=CC=2)C2CC2)=N1 GVUCVRXLDWFFPO-UHFFFAOYSA-N 0.000 claims 1
- FWXKPCHUSMDKJD-UHFFFAOYSA-N 4-(6-aminopyridin-2-yl)-3-methoxyphenol Chemical compound COC1=CC(O)=CC=C1C1=CC=CC(N)=N1 FWXKPCHUSMDKJD-UHFFFAOYSA-N 0.000 claims 1
- SIBAFGQHMOPOOS-UHFFFAOYSA-N 4-[2-[4-(6-aminopyridin-2-yl)phenyl]ethyl]piperazine-1-carboxylic acid Chemical compound NC1=CC=CC(C=2C=CC(CCN3CCN(CC3)C(O)=O)=CC=2)=N1 SIBAFGQHMOPOOS-UHFFFAOYSA-N 0.000 claims 1
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- SFLXUZPXEWWQNH-UHFFFAOYSA-K tetrabutylazanium;tribromide Chemical compound [Br-].[Br-].[Br-].CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC SFLXUZPXEWWQNH-UHFFFAOYSA-K 0.000 description 1
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- 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
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Classifications
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- 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
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- 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)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Anesthesiology (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Ophthalmology & Optometry (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)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13552099P | 1999-05-21 | 1999-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA11943A true OA11943A (en) | 2006-04-12 |
Family
ID=22468464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200100301A OA11943A (en) | 1999-05-21 | 2000-03-16 | New pharmacetical 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 |
| DOP2002000467A (es) * | 2001-10-10 | 2003-04-15 | Pfizer Prod Inc | 2-amino-6 (fenilo sustituido en las posiciones 2,4,5)-piridinas |
| US6803470B2 (en) * | 2001-10-10 | 2004-10-12 | Pfizer Inc | 2-amino-6-(2,4,5-substituted-phenyl)-pyridines |
| AU2004249441B2 (en) * | 2003-06-24 | 2009-11-12 | Neurosearch A/S | Novel 8-aza-bicyclo(3.2.1)octane derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
| 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 |
| EP2152271B1 (fr) | 2007-06-08 | 2015-10-21 | Janssen Pharmaceutica, N.V. | Dérivés de piperidine/piperazine |
| JO2972B1 (en) | 2007-06-08 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Piperidine / piperazine derivatives |
| CA2687918C (fr) | 2007-06-08 | 2016-11-08 | Janssen Pharmaceutica N.V. | Derives de piperidine/piperazine |
| AU2008258487B2 (en) | 2007-06-08 | 2012-11-15 | Janssen Pharmaceutica N.V. | Piperidine/piperazine derivatives |
| JP5579170B2 (ja) | 2008-06-05 | 2014-08-27 | 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 | Dgat阻害剤とppar作動薬を含有する薬剤組み合わせ物 |
| US8889674B2 (en) | 2009-03-05 | 2014-11-18 | Shionogi & Co., Ltd. | Piperidine and pyrrolidine derivatives having NPY Y5 receptor antagonism |
| JP6440625B2 (ja) | 2012-11-14 | 2018-12-19 | ザ・ジョンズ・ホプキンス・ユニバーシティー | 精神分裂病を処置するための方法および組成物 |
| US20220267269A1 (en) * | 2019-06-14 | 2022-08-25 | 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 BR BR0010820-0A patent/BR0010820A/pt not_active IP Right Cessation
- 2000-03-16 AP APAP/P/2001/002326A patent/AP2001002326A0/en unknown
- 2000-03-16 AU AU29353/00A patent/AU2935300A/en not_active Abandoned
- 2000-03-16 EP EP00907891A patent/EP1178784A1/fr not_active Ceased
- 2000-03-16 KR KR1020017014884A patent/KR20020010916A/ko not_active Withdrawn
- 2000-03-16 EA EA200101110A patent/EA200101110A1/ru unknown
- 2000-03-16 CA CA002374668A patent/CA2374668A1/fr not_active Abandoned
- 2000-03-16 WO PCT/IB2000/000295 patent/WO2000071107A2/fr not_active Ceased
- 2000-03-16 EE EEP200100611A patent/EE200100611A/xx unknown
- 2000-03-16 OA OA1200100301A patent/OA11943A/en unknown
- 2000-03-16 CN CNA008078785A patent/CN1617743A/zh active Pending
- 2000-03-16 TR TR2001/03351T patent/TR200103351T2/xx unknown
- 2000-03-16 PL PL00358538A patent/PL358538A1/xx not_active Application Discontinuation
- 2000-03-16 HR HR20010862A patent/HRP20010862A2/hr not_active Application Discontinuation
- 2000-03-16 JP JP2000619414A patent/JP2003523941A/ja not_active Withdrawn
- 2000-03-16 SK SK1660-2001A patent/SK16602001A3/sk unknown
- 2000-03-16 MX MXPA01011978A patent/MXPA01011978A/es unknown
- 2000-03-16 HU HU0301287A patent/HUP0301287A3/hu unknown
- 2000-03-16 IL IL14595500A patent/IL145955A0/xx 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 MA MA25976A patent/MA26732A1/fr unknown
- 2000-05-17 DZ DZ000084A patent/DZ3041A1/fr active
- 2000-05-17 GT GT200000071A patent/GT200000071A/es unknown
- 2000-05-17 TN TNTNSN00106A patent/TNSN00106A1/fr 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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