JP2007531753A5 - - Google Patents
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- JP2007531753A5 JP2007531753A5 JP2007506483A JP2007506483A JP2007531753A5 JP 2007531753 A5 JP2007531753 A5 JP 2007531753A5 JP 2007506483 A JP2007506483 A JP 2007506483A JP 2007506483 A JP2007506483 A JP 2007506483A JP 2007531753 A5 JP2007531753 A5 JP 2007531753A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- piperidin
- isopropyl
- ylmethyl
- group
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 80
- 150000001875 compounds Chemical class 0.000 claims 50
- -1 —C 3-7 cycloalkyl Chemical group 0.000 claims 47
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 44
- 229910052757 nitrogen Inorganic materials 0.000 claims 25
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 24
- 229910052799 carbon Inorganic materials 0.000 claims 20
- 125000005842 heteroatom Chemical group 0.000 claims 20
- 229910052760 oxygen Inorganic materials 0.000 claims 20
- 229910052717 sulfur Inorganic materials 0.000 claims 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 16
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 16
- 125000004076 pyridyl group Chemical group 0.000 claims 16
- 125000000168 pyrrolyl group Chemical group 0.000 claims 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 13
- 125000002541 furyl group Chemical group 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000000623 heterocyclic group Chemical class 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 12
- 125000001544 thienyl group Chemical group 0.000 claims 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 10
- 125000003386 piperidinyl group Chemical group 0.000 claims 10
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 8
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 8
- 125000002950 monocyclic group Chemical group 0.000 claims 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 206010016256 fatigue Diseases 0.000 claims 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 6
- 206010041349 Somnolence Diseases 0.000 claims 5
- 239000004480 active ingredient Substances 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 208000032140 Sleepiness Diseases 0.000 claims 4
- 125000003725 azepanyl group Chemical group 0.000 claims 4
- 125000005605 benzo group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 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 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 229960001340 histamine Drugs 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 4
- OIAJPFFTFXBSJX-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[6-(4-propan-2-ylpiperazin-1-yl)pyridin-3-yl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CC=C(N2CCN(CC2)C(C)C)N=C1 OIAJPFFTFXBSJX-UHFFFAOYSA-N 0.000 claims 3
- YPSYERLUIKJCIR-UHFFFAOYSA-N 2-(4-piperidin-1-ylbut-1-ynyl)-5-(piperidin-1-ylmethyl)pyridine Chemical compound C=1C=C(CN2CCCCC2)C=NC=1C#CCCN1CCCCC1 YPSYERLUIKJCIR-UHFFFAOYSA-N 0.000 claims 3
- CHOVROLMBZWCJS-UHFFFAOYSA-N 2-(4-piperidin-1-ylbut-1-ynyl)-6-(piperidin-1-ylmethyl)pyridine Chemical compound C=1C=CC(CN2CCCCC2)=NC=1C#CCCN1CCCCC1 CHOVROLMBZWCJS-UHFFFAOYSA-N 0.000 claims 3
- WKWXSSAQMKWZEO-UHFFFAOYSA-N 2-(piperidin-1-ylmethyl)-5-(3-piperidin-1-ylpropoxy)pyridine Chemical compound C1CCCCN1CCCOC(C=N1)=CC=C1CN1CCCCC1 WKWXSSAQMKWZEO-UHFFFAOYSA-N 0.000 claims 3
- WMCAAXRHPIJBKV-UHFFFAOYSA-N 3-(4-piperidin-1-ylbut-1-ynyl)-5-(piperidin-1-ylmethyl)pyridine Chemical compound C=1N=CC(CN2CCCCC2)=CC=1C#CCCN1CCCCC1 WMCAAXRHPIJBKV-UHFFFAOYSA-N 0.000 claims 3
- HBRMMMIKWGTGEY-UHFFFAOYSA-N 5-(piperidin-4-ylmethyl)-3-(3-piperidin-1-ylpropoxy)-1,2-oxazole Chemical compound C1CCCCN1CCCOC(=NO1)C=C1CC1CCNCC1 HBRMMMIKWGTGEY-UHFFFAOYSA-N 0.000 claims 3
- GYHPIGHVWUMTDM-UHFFFAOYSA-N [2-(2-piperidin-1-ylethylamino)pyridin-4-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CC=NC(NCCN2CCCCC2)=C1 GYHPIGHVWUMTDM-UHFFFAOYSA-N 0.000 claims 3
- USOUXPUSQBUUOL-UHFFFAOYSA-N [5-(piperidin-1-ylmethyl)pyrazin-2-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(N=C1)=CN=C1CN1CCCCC1 USOUXPUSQBUUOL-UHFFFAOYSA-N 0.000 claims 3
- QARLWQQWNLVURD-UHFFFAOYSA-N [5-(piperidin-1-ylmethyl)pyridin-2-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(N=C1)=CC=C1CN1CCCCC1 QARLWQQWNLVURD-UHFFFAOYSA-N 0.000 claims 3
- AOHGNUVYWCFCAB-UHFFFAOYSA-N [6-(2-piperidin-1-ylethylamino)pyridin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=N1)=CC=C1NCCN1CCCCC1 AOHGNUVYWCFCAB-UHFFFAOYSA-N 0.000 claims 3
- UPLGWHHVDUGCBV-UHFFFAOYSA-N [6-(4-methylpiperazin-1-yl)pyridin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CC=C(N2CCN(C)CC2)N=C1 UPLGWHHVDUGCBV-UHFFFAOYSA-N 0.000 claims 3
- HGMKONUWLRPGDN-UHFFFAOYSA-N [6-(piperidin-1-ylmethyl)pyridin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=N1)=CC=C1CN1CCCCC1 HGMKONUWLRPGDN-UHFFFAOYSA-N 0.000 claims 3
- QKZQWVNCJGIHKR-UHFFFAOYSA-N [6-[2-(diethylamino)ethyl-methylamino]pyridin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1=NC(N(C)CCN(CC)CC)=CC=C1C(=O)N1CCN(C(C)C)CC1 QKZQWVNCJGIHKR-UHFFFAOYSA-N 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 3
- CKXAANQKPSPHLE-UHFFFAOYSA-N 2-methoxy-n-[[6-(4-piperidin-1-ylbut-1-ynyl)pyridin-2-yl]methyl]ethanamine Chemical compound COCCNCC1=CC=CC(C#CCCN2CCCCC2)=N1 CKXAANQKPSPHLE-UHFFFAOYSA-N 0.000 claims 2
- AKESFWSNMOFOQC-UHFFFAOYSA-N 4-[[5-(3-piperidin-1-ylpropoxy)pyridin-2-yl]methyl]morpholine Chemical compound C1CCCCN1CCCOC(C=N1)=CC=C1CN1CCOCC1 AKESFWSNMOFOQC-UHFFFAOYSA-N 0.000 claims 2
- FWRQHCPMFYKQDK-UHFFFAOYSA-N 4-[[5-(4-piperidin-1-ylbut-1-ynyl)pyridin-3-yl]methyl]morpholine Chemical compound C=1N=CC(CN2CCOCC2)=CC=1C#CCCN1CCCCC1 FWRQHCPMFYKQDK-UHFFFAOYSA-N 0.000 claims 2
- WYTHXDDMVDKEGH-UHFFFAOYSA-N 4-[[6-(4-piperidin-1-ylbut-1-ynyl)pyridin-2-yl]methyl]morpholine Chemical compound C=1C=CC(CN2CCOCC2)=NC=1C#CCCN1CCCCC1 WYTHXDDMVDKEGH-UHFFFAOYSA-N 0.000 claims 2
- QBLLOOKBLTTXHB-UHFFFAOYSA-N 4-fluoropiperidine Chemical compound FC1CCNCC1 QBLLOOKBLTTXHB-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 208000024827 Alzheimer 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
- 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
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-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
- IHVNECQDFNGHMR-UHFFFAOYSA-N [5-(morpholin-4-ylmethyl)pyrazin-2-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(N=C1)=CN=C1CN1CCOCC1 IHVNECQDFNGHMR-UHFFFAOYSA-N 0.000 claims 2
- SMTAOJXZSKNKPY-UHFFFAOYSA-N [6-(2-morpholin-4-ylethylamino)pyridin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=N1)=CC=C1NCCN1CCOCC1 SMTAOJXZSKNKPY-UHFFFAOYSA-N 0.000 claims 2
- FXPLHFGBSQNNAN-UHFFFAOYSA-N [6-(morpholin-4-ylmethyl)pyridin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=N1)=CC=C1CN1CCOCC1 FXPLHFGBSQNNAN-UHFFFAOYSA-N 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 230000006735 deficit Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 208000013403 hyperactivity Diseases 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
- 201000003631 narcolepsy Diseases 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 230000037321 sleepiness Effects 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- HURMQHJALYVPRY-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[6-(2-pyridin-2-ylethylamino)pyridin-3-yl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=N1)=CC=C1NCCC1=CC=CC=N1 HURMQHJALYVPRY-UHFFFAOYSA-N 0.000 claims 1
- 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
- UUUVBWRORGAQIW-UHFFFAOYSA-N 2-methoxy-n-[[3-(3-piperidin-1-ylpropoxy)-1,2-oxazol-5-yl]methyl]ethanamine Chemical compound O1C(CNCCOC)=CC(OCCCN2CCCCC2)=N1 UUUVBWRORGAQIW-UHFFFAOYSA-N 0.000 claims 1
- ADLWZDMYNOGVRT-UHFFFAOYSA-N 4-[[3-(3-piperidin-1-ylpropoxy)-1,2-oxazol-5-yl]methyl]morpholine Chemical compound C1CCCCN1CCCOC(=NO1)C=C1CN1CCOCC1 ADLWZDMYNOGVRT-UHFFFAOYSA-N 0.000 claims 1
- MJFRUZWZLAZUGG-UHFFFAOYSA-N 5-(piperidin-1-ylmethyl)-2-(3-piperidin-1-ylpropoxy)pyridine Chemical compound C1CCCCN1CCCOC(N=C1)=CC=C1CN1CCCCC1 MJFRUZWZLAZUGG-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 208000000044 Amnesia Diseases 0.000 claims 1
- 206010002091 Anaesthesia Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease 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
- 206010013654 Drug abuse Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 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
- 208000026139 Memory disease 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
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
- OZNWGBRNCLPCEK-UHFFFAOYSA-N [2-(2-piperidin-1-ylethylamino)pyridin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CC=CN=C1NCCN1CCCCC1 OZNWGBRNCLPCEK-UHFFFAOYSA-N 0.000 claims 1
- CYKIJOQYHLZFST-UHFFFAOYSA-N [6-(piperidin-1-ylmethyl)pyridin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanethione Chemical compound C1CN(C(C)C)CCN1C(=S)C(C=N1)=CC=C1CN1CCCCC1 CYKIJOQYHLZFST-UHFFFAOYSA-N 0.000 claims 1
- 229940022663 acetate Drugs 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 230000037005 anaesthesia Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000010668 atopic eczema 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
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 206010008129 cerebral palsy Diseases 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
- 208000027744 congestion Diseases 0.000 claims 1
- 238000001514 detection method Methods 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 208000002173 dizziness Diseases 0.000 claims 1
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| JP2009542706A (ja) * | 2006-06-29 | 2009-12-03 | 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 | ヒスタミンｈ３受容体の置換ベンズアミドモジュレーター |
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-
2005
- 2005-03-31 AU AU2005230902A patent/AU2005230902A1/en not_active Abandoned
- 2005-03-31 MX MXPA06011414A patent/MXPA06011414A/es active IP Right Grant
- 2005-03-31 CA CA002561791A patent/CA2561791A1/en not_active Abandoned
- 2005-03-31 JP JP2007506483A patent/JP2007531753A/ja not_active Withdrawn
- 2005-03-31 US US11/095,398 patent/US7423147B2/en not_active Expired - Lifetime
- 2005-03-31 CN CNA2005800176690A patent/CN1972914A/zh active Pending
- 2005-03-31 EP EP05735453A patent/EP1761496A2/en not_active Withdrawn
- 2005-03-31 WO PCT/US2005/010570 patent/WO2005097751A2/en not_active Ceased
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2008
- 2008-08-06 US US12/186,927 patent/US20080306066A1/en not_active Abandoned
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2009
- 2009-09-15 US US12/559,823 patent/US7947718B2/en not_active Expired - Fee Related
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