JP2007531755A5 - - Google Patents
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- JP2007531755A5 JP2007531755A5 JP2007506498A JP2007506498A JP2007531755A5 JP 2007531755 A5 JP2007531755 A5 JP 2007531755A5 JP 2007506498 A JP2007506498 A JP 2007506498A JP 2007506498 A JP2007506498 A JP 2007506498A JP 2007531755 A5 JP2007531755 A5 JP 2007531755A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- isopropyl
- group
- benzyl
- piperazin
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 68
- 150000001875 compounds Chemical class 0.000 claims 35
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 26
- -1 -C 3-7 cycloalkyl Chemical group 0.000 claims 21
- 229910052760 oxygen Inorganic materials 0.000 claims 17
- 229910052717 sulfur Inorganic materials 0.000 claims 17
- 229910052799 carbon Inorganic materials 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 125000004076 pyridyl group Chemical group 0.000 claims 14
- 125000000168 pyrrolyl group Chemical group 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 12
- 125000002541 furyl group Chemical group 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 10
- 125000001544 thienyl group Chemical group 0.000 claims 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 8
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 206010016256 fatigue Diseases 0.000 claims 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 206010041349 Somnolence Diseases 0.000 claims 5
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims 5
- 239000004480 active ingredient Substances 0.000 claims 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 5
- 125000003386 piperidinyl group Chemical group 0.000 claims 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- 208000032140 Sleepiness Diseases 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229960001340 histamine Drugs 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 3
- 102000005962 receptors Human genes 0.000 claims 3
- 108020003175 receptors Proteins 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 206010028735 Nasal congestion Diseases 0.000 claims 2
- 206010062519 Poor quality sleep Diseases 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims 2
- RNCRXOFZYADCCD-UHFFFAOYSA-N [1-methyl-4-(piperidin-1-ylmethyl)pyrrol-2-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CC(CN2CCCCC2)=CN1C RNCRXOFZYADCCD-UHFFFAOYSA-N 0.000 claims 2
- UDYSZLPFJUYDDW-UHFFFAOYSA-N [5-(morpholin-4-ylmethyl)thiophen-2-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(S1)=CC=C1CN1CCOCC1 UDYSZLPFJUYDDW-UHFFFAOYSA-N 0.000 claims 2
- PUEMTESDRSZFHW-UHFFFAOYSA-N [5-(morpholin-4-ylmethyl)thiophen-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CSC(CN2CCOCC2)=C1 PUEMTESDRSZFHW-UHFFFAOYSA-N 0.000 claims 2
- ZRTGKKHEPIANGY-UHFFFAOYSA-N [5-(piperidin-1-ylmethyl)furan-2-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(O1)=CC=C1CN1CCCCC1 ZRTGKKHEPIANGY-UHFFFAOYSA-N 0.000 claims 2
- HOQXKGNMCZNUCV-UHFFFAOYSA-N [5-(piperidin-1-ylmethyl)thiophen-2-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(S1)=CC=C1CN1CCCCC1 HOQXKGNMCZNUCV-UHFFFAOYSA-N 0.000 claims 2
- LGPIFXWDEIPTNC-UHFFFAOYSA-N [5-(piperidin-1-ylmethyl)thiophen-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CSC(CN2CCCCC2)=C1 LGPIFXWDEIPTNC-UHFFFAOYSA-N 0.000 claims 2
- DTSYZOPDJZRHPG-UHFFFAOYSA-N [5-[(2-methoxyethylamino)methyl]thiophen-2-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound S1C(CNCCOC)=CC=C1C(=O)N1CCN(C(C)C)CC1 DTSYZOPDJZRHPG-UHFFFAOYSA-N 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000003725 azepanyl group Chemical group 0.000 claims 2
- 125000005605 benzo group Chemical group 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 201000003631 narcolepsy Diseases 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 230000037321 sleepiness Effects 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 claims 1
- YFGHCGITMMYXAQ-UHFFFAOYSA-N 2-[(diphenylmethyl)sulfinyl]acetamide Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)N)C1=CC=CC=C1 YFGHCGITMMYXAQ-UHFFFAOYSA-N 0.000 claims 1
- QBLLOOKBLTTXHB-UHFFFAOYSA-N 4-fluoropiperidine Chemical compound FC1CCNCC1 QBLLOOKBLTTXHB-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 206010002091 Anaesthesia Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 1
- 208000017164 Chronobiology disease Diseases 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- 208000008238 Muscle Spasticity Diseases 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- 208000007920 Neurogenic Inflammation Diseases 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 claims 1
- UJZZHEZDYMLTEX-UHFFFAOYSA-N [1-methyl-4-(morpholin-4-ylmethyl)pyrrol-2-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CC(CN2CCOCC2)=CN1C UJZZHEZDYMLTEX-UHFFFAOYSA-N 0.000 claims 1
- XOTIWBWHFMJYFD-UHFFFAOYSA-N [2-(morpholin-4-ylmethyl)-1,3-oxazol-4-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=COC(CN2CCOCC2)=N1 XOTIWBWHFMJYFD-UHFFFAOYSA-N 0.000 claims 1
- DCKHEDSJHZMPDO-UHFFFAOYSA-N [2-(morpholin-4-ylmethyl)-1,3-thiazol-4-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CSC(CN2CCOCC2)=N1 DCKHEDSJHZMPDO-UHFFFAOYSA-N 0.000 claims 1
- OZDKAPJZEZRMED-UHFFFAOYSA-N [2-(piperidin-1-ylmethyl)-1,3-oxazol-4-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=COC(CN2CCCCC2)=N1 OZDKAPJZEZRMED-UHFFFAOYSA-N 0.000 claims 1
- YKFKRDDXFWULSZ-UHFFFAOYSA-N [2-(piperidin-1-ylmethyl)-1,3-thiazol-4-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CSC(CN2CCCCC2)=N1 YKFKRDDXFWULSZ-UHFFFAOYSA-N 0.000 claims 1
- VAJDOQWGIUGYOT-UHFFFAOYSA-N [2-[(2-methoxyethylamino)methyl]-1,3-oxazol-4-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound O1C(CNCCOC)=NC(C(=O)N2CCN(CC2)C(C)C)=C1 VAJDOQWGIUGYOT-UHFFFAOYSA-N 0.000 claims 1
- UDTKKXJBAUFIGP-UHFFFAOYSA-N [2-[(2-methoxyethylamino)methyl]-1,3-thiazol-4-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound S1C(CNCCOC)=NC(C(=O)N2CCN(CC2)C(C)C)=C1 UDTKKXJBAUFIGP-UHFFFAOYSA-N 0.000 claims 1
- RXUVGNWAJYJGDA-UHFFFAOYSA-N [5-(morpholin-4-ylmethyl)furan-2-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(O1)=CC=C1CN1CCOCC1 RXUVGNWAJYJGDA-UHFFFAOYSA-N 0.000 claims 1
- AVVXROQVPORWAJ-UHFFFAOYSA-N [5-(piperidin-1-ylmethyl)furan-2-yl]-(4-propan-2-ylpiperazin-1-yl)methanethione Chemical compound C1CN(C(C)C)CCN1C(=S)C(O1)=CC=C1CN1CCCCC1 AVVXROQVPORWAJ-UHFFFAOYSA-N 0.000 claims 1
- XVVLYXOLLHFURN-UHFFFAOYSA-N [5-[(2-methoxyethylamino)methyl]furan-2-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound O1C(CNCCOC)=CC=C1C(=O)N1CCN(C(C)C)CC1 XVVLYXOLLHFURN-UHFFFAOYSA-N 0.000 claims 1
- JUYJAGHFPJPQIM-UHFFFAOYSA-N [5-[(4-fluoropiperidin-1-yl)methyl]furan-2-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(O1)=CC=C1CN1CCC(F)CC1 JUYJAGHFPJPQIM-UHFFFAOYSA-N 0.000 claims 1
- 229940022663 acetate Drugs 0.000 claims 1
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- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 claims 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 238000001514 detection method Methods 0.000 claims 1
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- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims 1
- 239000000938 histamine H1 antagonist Substances 0.000 claims 1
- 230000013632 homeostatic process Effects 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 229940088597 hormone Drugs 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
- 208000013403 hyperactivity Diseases 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 206010022437 insomnia Diseases 0.000 claims 1
- VMPHSYLJUKZBJJ-UHFFFAOYSA-N lauric acid triglyceride Natural products CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 230000008897 memory decline Effects 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 208000027061 mild cognitive impairment Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229960001165 modafinil Drugs 0.000 claims 1
- 239000003068 molecular probe Substances 0.000 claims 1
- 201000003152 motion sickness Diseases 0.000 claims 1
- 125000005487 naphthalate group Chemical group 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- 229940049964 oleate Drugs 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 229940039748 oxalate Drugs 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 238000002600 positron emission tomography Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000002285 radioactive effect Effects 0.000 claims 1
- 238000002603 single-photon emission computed tomography Methods 0.000 claims 1
- 201000002859 sleep apnea Diseases 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 208000018198 spasticity Diseases 0.000 claims 1
- 201000009032 substance abuse Diseases 0.000 claims 1
- 231100000736 substance abuse Toxicity 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 229940070710 valerate Drugs 0.000 claims 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 1
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| US55793604P | 2004-03-31 | 2004-03-31 | |
| PCT/US2005/010632 WO2005096734A2 (en) | 2004-03-31 | 2005-03-31 | Non-imidazole heterocyclic compounds as histamine h3 receptor modulators |
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| JP2007531755A JP2007531755A (ja) | 2007-11-08 |
| JP2007531755A5 true JP2007531755A5 (https=) | 2008-02-07 |
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| EP (1) | EP1771432B1 (https=) |
| JP (1) | JP2007531755A (https=) |
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| AT (1) | ATE490959T1 (https=) |
| AU (1) | AU2005231375A1 (https=) |
| CA (1) | CA2561945A1 (https=) |
| DE (1) | DE602005025222D1 (https=) |
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| WO (1) | WO2005096734A2 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2008089485A2 (en) * | 2007-01-19 | 2008-07-24 | The Cleveland Clinic Foundation | Carboxyethylpyrrole compounds and methods of their production |
| WO2008089487A2 (en) * | 2007-01-19 | 2008-07-24 | The Cleveland Clinic Foundation | Carboxyethylpyrrole compounds and methods of their production |
| EA018582B1 (ru) | 2007-11-20 | 2013-09-30 | Янссен Фармацевтика Н.В. | Соединения циклоалкилокси- и гетероциклоалкилоксипиридина как модуляторы гистаминового рецептора н |
| AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| US9133123B2 (en) | 2010-04-23 | 2015-09-15 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| GB2497476B (en) * | 2010-09-06 | 2018-01-10 | Guangzhou Inst Biomed & Health | Amide Compounds |
| CA2905457A1 (en) | 2013-03-13 | 2014-10-09 | Aerial Biopharma, Llc | Treatment of cataplexy |
| WO2018089493A1 (en) * | 2016-11-08 | 2018-05-17 | Navitor Pharmaceuticals, Inc. | PYRROLE mTORC INHIBITORS AND USES THEREOF |
| WO2025085347A1 (en) * | 2023-10-19 | 2025-04-24 | Merck Sharp & Dohme Llc | Il4i1 inhibitors and uses thereof |
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| US5352707A (en) | 1992-03-26 | 1994-10-04 | Harbor Branch Oceanographic Institution, Inc. | Method for treating airway congestion |
| US5217986A (en) | 1992-03-26 | 1993-06-08 | Harbor Branch Oceanographic Institution, Inc. | Anti-allergy agent |
| KR100300566B1 (ko) * | 1994-09-17 | 2001-11-22 | 조생현 | 피리미디논유도체와그의제조방법및용도 |
| JPH1017564A (ja) | 1996-07-02 | 1998-01-20 | Yamanouchi Pharmaceut Co Ltd | 新規チオフェン誘導体 |
| US5869479A (en) | 1997-08-14 | 1999-02-09 | Schering Corporation | Treatment of upper airway allergic responses |
| PE107899A1 (es) | 1997-09-09 | 1999-11-17 | Glaxo Group Ltd | Derivados de pirrolopirrolona como inhibidores de elastasa leucocitaria |
| GB9905418D0 (en) | 1999-03-09 | 1999-05-05 | Glaxo Group Ltd | Process |
| JP2004501191A (ja) * | 2000-06-28 | 2004-01-15 | テバ ファーマシューティカル インダストリーズ リミティド | カルベジロール |
| BR0210391A (pt) * | 2001-06-12 | 2004-06-15 | Elan Pharm Inc | Composto, métodos de tratar um paciente que tenha ou de prevenir um paciente de contrair uma doença ou condição e de preparar um composto, e, uso de um composto |
| SI1558595T1 (sl) | 2002-10-23 | 2010-03-31 | Janssen Pharmaceutica Nv | Piperazinilni in diazapanilni benzamidi in benztioamidi |
| US7332508B2 (en) | 2002-12-18 | 2008-02-19 | Novo Nordisk A/S | Substituted homopiperidine, piperidine or pyrrolidine derivatives |
| CL2004002050A1 (es) * | 2003-08-13 | 2005-06-03 | Pharmacia Corp Sa Organizada B | Compuestos derivados de piridinonas sustituidas; su uso en el tratamiento de afecciones causadas o exacerbadas por actividad p38 map kinasa y/o tnf no regulada, tales como inflamaciones, tumores, sida y otros. |
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- 2005-03-31 EP EP05731129A patent/EP1771432B1/en not_active Expired - Lifetime
- 2005-03-31 WO PCT/US2005/010632 patent/WO2005096734A2/en not_active Ceased
- 2005-03-31 CN CNA2005800176578A patent/CN1960981A/zh active Pending
- 2005-03-31 JP JP2007506498A patent/JP2007531755A/ja active Pending
- 2005-03-31 AT AT05731129T patent/ATE490959T1/de not_active IP Right Cessation
- 2005-03-31 MX MXPA06011410A patent/MXPA06011410A/es active IP Right Grant
- 2005-03-31 AU AU2005231375A patent/AU2005231375A1/en not_active Abandoned
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2008
- 2008-08-20 US US12/194,695 patent/US20080317671A1/en not_active Abandoned
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