JP2010506918A5 - - Google Patents
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- JP2010506918A5 JP2010506918A5 JP2009533349A JP2009533349A JP2010506918A5 JP 2010506918 A5 JP2010506918 A5 JP 2010506918A5 JP 2009533349 A JP2009533349 A JP 2009533349A JP 2009533349 A JP2009533349 A JP 2009533349A JP 2010506918 A5 JP2010506918 A5 JP 2010506918A5
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- JP
- Japan
- Prior art keywords
- methyl
- ethyl
- group
- biphenyl
- ring
- 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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- 150000001875 compounds Chemical class 0.000 claims description 125
- 125000000623 heterocyclic group Chemical group 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 39
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 29
- 239000012453 solvate Substances 0.000 claims description 29
- 125000006413 ring segment Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- -1 C 1 -C 8 alkylureyl Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 19
- 150000004677 hydrates Chemical class 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 150000003857 carboxamides Chemical class 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 13
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 12
- 206010020751 Hypersensitivity Diseases 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 208000010877 cognitive disease Diseases 0.000 claims description 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 12
- 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 12
- 229940124530 sulfonamide Drugs 0.000 claims description 12
- 150000003456 sulfonamides Chemical class 0.000 claims description 12
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 claims description 10
- 208000028698 Cognitive impairment Diseases 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 claims description 9
- 201000003631 narcolepsy Diseases 0.000 claims description 9
- 208000019116 sleep disease Diseases 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 7
- 125000005363 dialkylsulfonamide group Chemical group 0.000 claims description 7
- 238000002560 therapeutic procedure Methods 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 6
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 6
- 206010012289 Dementia Diseases 0.000 claims description 6
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 6
- 206010028735 Nasal congestion Diseases 0.000 claims description 6
- 208000008589 Obesity Diseases 0.000 claims description 6
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 6
- 208000032140 Sleepiness Diseases 0.000 claims description 6
- 206010041349 Somnolence Diseases 0.000 claims description 6
- 201000010105 allergic rhinitis Diseases 0.000 claims description 6
- 230000007815 allergy Effects 0.000 claims description 6
- 230000037007 arousal Effects 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 206010015037 epilepsy Diseases 0.000 claims description 6
- 230000001939 inductive effect Effects 0.000 claims description 6
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 6
- 235000020824 obesity Nutrition 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 210000002345 respiratory system Anatomy 0.000 claims description 6
- 201000000980 schizophrenia Diseases 0.000 claims description 6
- 201000002859 sleep apnea Diseases 0.000 claims description 6
- 208000011580 syndromic disease Diseases 0.000 claims description 6
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 5
- 230000006931 brain damage Effects 0.000 claims description 5
- 231100000874 brain damage Toxicity 0.000 claims description 5
- 208000029028 brain injury Diseases 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 208000020685 sleep-wake disease Diseases 0.000 claims description 5
- PTAZTAQXCREXPY-UHFFFAOYSA-N 1-[2-[4-[4-(2-methoxyethylsulfonyl)phenyl]phenyl]ethyl]-2-methylpyrrolidine Chemical compound C1=CC(S(=O)(=O)CCOC)=CC=C1C(C=C1)=CC=C1CCN1C(C)CCC1 PTAZTAQXCREXPY-UHFFFAOYSA-N 0.000 claims description 4
- ADRZQEOBUFIYAZ-UHFFFAOYSA-N 1-[2-[4-[4-(3-methoxypropylsulfonyl)phenyl]phenyl]ethyl]-2-methylpyrrolidine Chemical compound C1=CC(S(=O)(=O)CCCOC)=CC=C1C(C=C1)=CC=C1CCN1C(C)CCC1 ADRZQEOBUFIYAZ-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 206010020765 hypersomnia Diseases 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- VIOOAFIHOMAEBH-UHFFFAOYSA-N 1-[2-[4-(4-benzylsulfonylphenyl)phenyl]ethyl]-2-methylpyrrolidine Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)CC=2C=CC=CC=2)C=C1 VIOOAFIHOMAEBH-UHFFFAOYSA-N 0.000 claims description 2
- DOLUVTOFQXUGGU-UHFFFAOYSA-N 1-[2-[4-(4-cyclopentylsulfonylphenyl)phenyl]ethyl]-2-methylpyrrolidine Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)C2CCCC2)C=C1 DOLUVTOFQXUGGU-UHFFFAOYSA-N 0.000 claims description 2
- IMFFNRUQWLGKGP-UHFFFAOYSA-N 1-[2-[4-(4-ethenylsulfonylphenyl)phenyl]ethyl]-2-methylpyrrolidine Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)C=C)C=C1 IMFFNRUQWLGKGP-UHFFFAOYSA-N 0.000 claims description 2
- ZSEYAGMKVLDVQC-UHFFFAOYSA-N 1-[2-[4-(4-ethylsulfonylphenyl)phenyl]ethyl]-2-methylpyrrolidine Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1C(C=C1)=CC=C1CCN1C(C)CCC1 ZSEYAGMKVLDVQC-UHFFFAOYSA-N 0.000 claims description 2
- FHZNMUUDEYVBOR-UHFFFAOYSA-N 1-[2-[4-[3-(2-methoxyethylsulfonyl)phenyl]phenyl]ethyl]-2-methylpyrrolidine Chemical compound COCCS(=O)(=O)C1=CC=CC(C=2C=CC(CCN3C(CCC3)C)=CC=2)=C1 FHZNMUUDEYVBOR-UHFFFAOYSA-N 0.000 claims description 2
- YMRMKCOJONCFSM-UHFFFAOYSA-N 1-[2-[4-[4-(2-ethoxyethylsulfonyl)phenyl]phenyl]ethyl]-2-methylpyrrolidine Chemical compound C1=CC(S(=O)(=O)CCOCC)=CC=C1C(C=C1)=CC=C1CCN1C(C)CCC1 YMRMKCOJONCFSM-UHFFFAOYSA-N 0.000 claims description 2
- LUOFMHCFCITGCB-UHFFFAOYSA-N 1-[2-[4-[4-(2-methoxypropylsulfonyl)phenyl]phenyl]ethyl]-2-methylpyrrolidine Chemical compound C1=CC(S(=O)(=O)CC(C)OC)=CC=C1C(C=C1)=CC=C1CCN1C(C)CCC1 LUOFMHCFCITGCB-UHFFFAOYSA-N 0.000 claims description 2
- RZDLBFMGIKTVIN-UHFFFAOYSA-N 1-[2-[4-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]phenyl]sulfonylethyl]piperidine-4-carbonitrile Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)CCN2CCC(CC2)C#N)C=C1 RZDLBFMGIKTVIN-UHFFFAOYSA-N 0.000 claims description 2
- SAUYOOBWUJBRCM-UHFFFAOYSA-N 2,2-dimethyl-3-[4-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]phenyl]sulfonylpropan-1-ol Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)CC(C)(C)CO)C=C1 SAUYOOBWUJBRCM-UHFFFAOYSA-N 0.000 claims description 2
- UOBXCSWOZFVLAT-UHFFFAOYSA-N 2-[3-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]phenyl]sulfonylethanol Chemical compound CC1CCCN1CCC1=CC=C(C=2C=C(C=CC=2)S(=O)(=O)CCO)C=C1 UOBXCSWOZFVLAT-UHFFFAOYSA-N 0.000 claims description 2
- AFBOQHQRNKWKST-UHFFFAOYSA-N 2-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]-5-methylsulfonylpyridine Chemical compound CC1CCCN1CCC1=CC=C(C=2N=CC(=CC=2)S(C)(=O)=O)C=C1 AFBOQHQRNKWKST-UHFFFAOYSA-N 0.000 claims description 2
- ODRHOANHOJNYQY-UHFFFAOYSA-N 2-[4-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]phenyl]sulfonylethanamine Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)CCN)C=C1 ODRHOANHOJNYQY-UHFFFAOYSA-N 0.000 claims description 2
- LKSOUSYVEIFFAF-UHFFFAOYSA-N 2-[4-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]phenyl]sulfonylethanol Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)CCO)C=C1 LKSOUSYVEIFFAF-UHFFFAOYSA-N 0.000 claims description 2
- CSCWWVSZGNSSBF-UHFFFAOYSA-N 2-methyl-1-[2-[4-(4-methyl-3-methylsulfonylphenyl)phenyl]ethyl]pyrrolidine Chemical compound CC1CCCN1CCC1=CC=C(C=2C=C(C(C)=CC=2)S(C)(=O)=O)C=C1 CSCWWVSZGNSSBF-UHFFFAOYSA-N 0.000 claims description 2
- WJQMVNBJCNFHHV-UHFFFAOYSA-N 2-methyl-1-[2-[4-(4-methylsulfonylphenyl)phenyl]ethyl]pyrrolidine Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=C1 WJQMVNBJCNFHHV-UHFFFAOYSA-N 0.000 claims description 2
- HZPSRDUVAVYBPP-UHFFFAOYSA-N 2-methyl-1-[2-[4-(4-prop-2-enylsulfonylphenyl)phenyl]ethyl]pyrrolidine Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)CC=C)C=C1 HZPSRDUVAVYBPP-UHFFFAOYSA-N 0.000 claims description 2
- PBEGXDUDGVNPPT-UHFFFAOYSA-N 2-methyl-1-[2-[4-(4-propan-2-ylsulfonylphenyl)phenyl]ethyl]pyrrolidine Chemical compound C1=CC(S(=O)(=O)C(C)C)=CC=C1C(C=C1)=CC=C1CCN1C(C)CCC1 PBEGXDUDGVNPPT-UHFFFAOYSA-N 0.000 claims description 2
- LVYVZXUCWPOALM-UHFFFAOYSA-N 2-methyl-1-[2-[4-(4-propylsulfonylphenyl)phenyl]ethyl]pyrrolidine Chemical compound C1=CC(S(=O)(=O)CCC)=CC=C1C(C=C1)=CC=C1CCN1C(C)CCC1 LVYVZXUCWPOALM-UHFFFAOYSA-N 0.000 claims description 2
- KWKFNOKDAQRAET-UHFFFAOYSA-N 2-methyl-1-[2-[4-[4-(2-methylpropylsulfonyl)phenyl]phenyl]ethyl]pyrrolidine Chemical compound C1=CC(S(=O)(=O)CC(C)C)=CC=C1C(C=C1)=CC=C1CCN1C(C)CCC1 KWKFNOKDAQRAET-UHFFFAOYSA-N 0.000 claims description 2
- AHDCQPKUMADGLJ-UHFFFAOYSA-N 2-methyl-1-[2-[4-[4-(oxan-2-ylmethylsulfonyl)phenyl]phenyl]ethyl]pyrrolidine Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)CC2OCCCC2)C=C1 AHDCQPKUMADGLJ-UHFFFAOYSA-N 0.000 claims description 2
- VXSRVOYXQATZAM-UHFFFAOYSA-N 2-methyl-1-[2-[4-[4-(oxan-4-ylmethylsulfonyl)phenyl]phenyl]ethyl]pyrrolidine Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)CC2CCOCC2)C=C1 VXSRVOYXQATZAM-UHFFFAOYSA-N 0.000 claims description 2
- WCNRAHOGLBRERU-UHFFFAOYSA-N 2-methyl-1-[2-[4-[4-(oxan-4-ylsulfonyl)phenyl]phenyl]ethyl]pyrrolidine Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)C2CCOCC2)C=C1 WCNRAHOGLBRERU-UHFFFAOYSA-N 0.000 claims description 2
- GKQAWJHVDHTEIE-UHFFFAOYSA-N 3-[4-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]phenyl]sulfonyl-1-morpholin-4-ylpropan-1-one Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)CCC(=O)N2CCOCC2)C=C1 GKQAWJHVDHTEIE-UHFFFAOYSA-N 0.000 claims description 2
- LMAMIMLDCZOAJZ-UHFFFAOYSA-N 3-[4-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]phenyl]sulfonylpropan-1-ol Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)CCCO)C=C1 LMAMIMLDCZOAJZ-UHFFFAOYSA-N 0.000 claims description 2
- UVDBIQWHBPAIFV-UHFFFAOYSA-N 3-[4-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]phenyl]sulfonylpropanoic acid Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)CCC(O)=O)C=C1 UVDBIQWHBPAIFV-UHFFFAOYSA-N 0.000 claims description 2
- HUUWCBQVKGSAQM-UHFFFAOYSA-N 4-[2-[4-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]phenyl]sulfonylethyl]morpholine Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)CCN2CCOCC2)C=C1 HUUWCBQVKGSAQM-UHFFFAOYSA-N 0.000 claims description 2
- GTXXUNQBPBJNNY-UHFFFAOYSA-N 4-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]-2-methylsulfonylbenzoic acid Chemical compound CC1CCCN1CCC1=CC=C(C=2C=C(C(C(O)=O)=CC=2)S(C)(=O)=O)C=C1 GTXXUNQBPBJNNY-UHFFFAOYSA-N 0.000 claims description 2
- JHTZDANAIOAKCA-UHFFFAOYSA-N 4-[4-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]phenyl]sulfonylpiperidine Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)C2CCNCC2)C=C1 JHTZDANAIOAKCA-UHFFFAOYSA-N 0.000 claims description 2
- BPBSDRCCDQBUIH-UHFFFAOYSA-N 5-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]-2-methylsulfonylpyridine Chemical compound CC1CCCN1CCC1=CC=C(C=2C=NC(=CC=2)S(C)(=O)=O)C=C1 BPBSDRCCDQBUIH-UHFFFAOYSA-N 0.000 claims description 2
- AJLVABJJAOXSCI-UHFFFAOYSA-N 5-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]-2-methylsulfonylpyrimidine Chemical compound CC1CCCN1CCC1=CC=C(C=2C=NC(=NC=2)S(C)(=O)=O)C=C1 AJLVABJJAOXSCI-UHFFFAOYSA-N 0.000 claims description 2
- WEBDALDZQJGVEV-UHFFFAOYSA-N 5-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]-3-methylsulfonyl-1,2,4-thiadiazole Chemical compound CC1CCCN1CCC1=CC=C(C=2SN=C(N=2)S(C)(=O)=O)C=C1 WEBDALDZQJGVEV-UHFFFAOYSA-N 0.000 claims description 2
- IDFHAHRLLREABU-UHFFFAOYSA-N 6-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]-1,1-dioxo-2,3-dihydrothiochromen-4-one Chemical compound CC1CCCN1CCC1=CC=C(C=2C=C3C(S(CCC3=O)(=O)=O)=CC=2)C=C1 IDFHAHRLLREABU-UHFFFAOYSA-N 0.000 claims description 2
- VHPZQXFBNHOFDK-UHFFFAOYSA-N ethyl 2-[4-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]phenyl]sulfonylacetate Chemical compound C1=CC(S(=O)(=O)CC(=O)OCC)=CC=C1C(C=C1)=CC=C1CCN1C(C)CCC1 VHPZQXFBNHOFDK-UHFFFAOYSA-N 0.000 claims description 2
- VNJSPLOBQZYOQL-UHFFFAOYSA-N methyl 2-[4-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]phenyl]sulfonylacetate Chemical compound C1=CC(S(=O)(=O)CC(=O)OC)=CC=C1C(C=C1)=CC=C1CCN1C(C)CCC1 VNJSPLOBQZYOQL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- AZEZHOPXSWLOJK-UHFFFAOYSA-N n-[2-[4-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]phenyl]sulfonylethyl]cyclohexanamine Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)CCNC2CCCCC2)C=C1 AZEZHOPXSWLOJK-UHFFFAOYSA-N 0.000 claims description 2
- DFKXZDPAGCALTJ-UHFFFAOYSA-N tert-butyl 2-[4-[4-[2-(2-methylpyrrolidin-1-yl)ethyl]phenyl]phenyl]sulfonylacetate Chemical compound CC1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)CC(=O)OC(C)(C)C)C=C1 DFKXZDPAGCALTJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 6
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 6
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 5
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims 5
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 5
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 5
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims 4
- 208000022841 Sleep Arousal disease Diseases 0.000 claims 2
- PTAZTAQXCREXPY-GOSISDBHSA-N (2r)-1-[2-[4-[4-(2-methoxyethylsulfonyl)phenyl]phenyl]ethyl]-2-methylpyrrolidine Chemical compound C1=CC(S(=O)(=O)CCOC)=CC=C1C(C=C1)=CC=C1CCN1[C@H](C)CCC1 PTAZTAQXCREXPY-GOSISDBHSA-N 0.000 claims 1
- ADRZQEOBUFIYAZ-LJQANCHMSA-N (2r)-1-[2-[4-[4-(3-methoxypropylsulfonyl)phenyl]phenyl]ethyl]-2-methylpyrrolidine Chemical compound C1=CC(S(=O)(=O)CCCOC)=CC=C1C(C=C1)=CC=C1CCN1[C@H](C)CCC1 ADRZQEOBUFIYAZ-LJQANCHMSA-N 0.000 claims 1
- VXSRVOYXQATZAM-HXUWFJFHSA-N (2r)-2-methyl-1-[2-[4-[4-(oxan-4-ylmethylsulfonyl)phenyl]phenyl]ethyl]pyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)CC2CCOCC2)C=C1 VXSRVOYXQATZAM-HXUWFJFHSA-N 0.000 claims 1
- WCNRAHOGLBRERU-LJQANCHMSA-N (2r)-2-methyl-1-[2-[4-[4-(oxan-4-ylsulfonyl)phenyl]phenyl]ethyl]pyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)C2CCOCC2)C=C1 WCNRAHOGLBRERU-LJQANCHMSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 208000001573 Cataplexy Diseases 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- VHPZQXFBNHOFDK-GOSISDBHSA-N ethyl 2-[4-[4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]phenyl]phenyl]sulfonylacetate Chemical compound C1=CC(S(=O)(=O)CC(=O)OCC)=CC=C1C(C=C1)=CC=C1CCN1[C@H](C)CCC1 VHPZQXFBNHOFDK-GOSISDBHSA-N 0.000 claims 1
- 230000029058 respiratory gaseous exchange Effects 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 21
- 208000035475 disorder Diseases 0.000 description 21
- 125000003545 alkoxy group Chemical group 0.000 description 18
- 102000004384 Histamine H3 receptors Human genes 0.000 description 12
- 108090000981 Histamine H3 receptors Proteins 0.000 description 12
- 125000001188 haloalkyl group Chemical group 0.000 description 8
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000004423 acyloxy group Chemical group 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 125000004438 haloalkoxy group Chemical group 0.000 description 6
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 6
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 6
- 125000004995 haloalkylthio group Chemical group 0.000 description 6
- 125000004043 oxo group Chemical group O=* 0.000 description 6
- 206010062519 Poor quality sleep Diseases 0.000 description 4
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- 125000002947 alkylene group Chemical group 0.000 description 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- BPPADGBWXFDIBT-UHFFFAOYSA-N 1-[2-[4-[4-(methoxymethylsulfonyl)phenyl]phenyl]ethyl]-2-methylpyrrolidine Chemical compound C1=CC(S(=O)(=O)COC)=CC=C1C(C=C1)=CC=C1CCN1C(C)CCC1 BPPADGBWXFDIBT-UHFFFAOYSA-N 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
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- 230000006735 deficit Effects 0.000 description 1
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| EP1558582B1 (en) | 2003-07-22 | 2005-12-21 | Arena Pharmaceuticals, Inc. | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-ht2a serotonin receptor useful for the prophylaxis and treatment of disorders related thereto |
| TWI415845B (zh) | 2006-10-03 | 2013-11-21 | Arena Pharm Inc | 用於治療與５-ｈｔ2ａ血清素受體相關聯病症之作為５-ｈｔ2ａ血清素受體之調節劑的吡唑衍生物 |
| EP2155668A2 (en) * | 2007-06-08 | 2010-02-24 | Arena Pharmaceuticals, Inc. | Crystalline forms of (r)-1-{2-ý4'- (3-methoxy-propane-1- sulfonyl)-biphenyl-4-yl¨-ethyl}-2-methyl-pyrrolidine, and compositions, and methods related thereto |
| US9567327B2 (en) | 2007-08-15 | 2017-02-14 | Arena Pharmaceuticals, Inc. | Imidazo[1,2-a]pyridine derivatives as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto |
| US20110021538A1 (en) * | 2008-04-02 | 2011-01-27 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
| CA2719373A1 (en) * | 2008-04-16 | 2009-10-22 | Arena Pharmaceuticals, Inc. | Processes useful for the synthesis of (r)-1-{2-[4'-(3-methoxypropane-1-sulfonyl)-biphenyl-4-yl]-ethyl}-2-methyl-pyrrolidine |
| TR201805216T4 (en) | 2008-10-28 | 2018-06-21 | Arena Pharm Inc | COMPOSITIONS OF A USEFUL 5-HT2A SEROTONINE RECEPTOR MODULATOR FOR THE TREATMENT OF RELATED DISORDERS |
| WO2010062321A1 (en) | 2008-10-28 | 2010-06-03 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2h-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)-urea and crystalline forms related thereto |
| GB201005511D0 (en) | 2010-03-31 | 2010-05-19 | Takeda Pharmaceutical | Compounds and their use |
| FR2974729B1 (fr) * | 2011-05-02 | 2013-04-19 | Servier Lab | Nouvelle association entre le 4-{3-[cis-hexahydrocyclopenta[c]pyrrol-2(1h)-yl]propoxy}benzamide et un inhibiteur de l'acetylcholinesterase et les compositions pharmaceutiques qui la contiennent |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| ES2647965T3 (es) * | 2013-01-09 | 2017-12-27 | Arena Pharmaceuticals, Inc. | Derivados de bifenil-etil-pirrolidina como moduladores del receptor de histamina H3 para el tratamiento de trastornos cognitivos |
| HK1245660A1 (zh) | 2015-06-12 | 2018-08-31 | Axovant Sciences Gmbh | 有用於预防和治疗rem睡眠行为障碍的二芳基脲和芳基脲衍生物 |
| WO2017011767A2 (en) | 2015-07-15 | 2017-01-19 | Axovant Sciences Ltd. | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-ht2a serotonin receptor useful for the prophylaxis and treatment of hallucinations associated with a neurodegenerative disease |
| WO2020092604A1 (en) * | 2018-10-30 | 2020-05-07 | Concert Pharmaceuticals, Inc. | Deuterated pitolisant |
| EP4251148A1 (en) | 2020-11-27 | 2023-10-04 | Richter Gedeon Nyrt. | Histamine h3 receptor antagonists/inverse agonists for the treatment of autism spectrum disorder |
| CN115160584B (zh) * | 2022-07-06 | 2024-03-22 | 西北工业大学 | 一种基于阳离子-π与静电作用协同构筑异质孔超分子有机框架及制备方法 |
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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 |
| ATE264323T1 (de) * | 1992-09-14 | 2004-04-15 | Takeda Chemical Industries Ltd | Heterocyclische verbindungen und ihre verwendung als angiotensin ii antagonisten |
| US5541217A (en) * | 1995-05-17 | 1996-07-30 | Ortho Pharmaceutical Corporation | 4-arylcyclopenta[c]pyrrole analgesics |
| US5869479A (en) * | 1997-08-14 | 1999-02-09 | Schering Corporation | Treatment of upper airway allergic responses |
| DE19937537A1 (de) * | 1999-08-09 | 2001-03-08 | Gruenenthal Gmbh | Substituierte 2-Dialkylaminoalkylbiphenyl-Derivate |
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| US7244852B2 (en) * | 2003-02-27 | 2007-07-17 | Abbott Laboratories | Process for preparing 2-methylpyrrolidine and specific enantiomers thereof |
| GB0308333D0 (en) * | 2003-04-10 | 2003-05-14 | Glaxo Group Ltd | Novel compounds |
| CN1960969B (zh) * | 2004-04-01 | 2012-03-28 | 伊莱利利公司 | 组胺h3受体药物、其制备方法及治疗用途 |
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| US7145005B2 (en) * | 2004-05-12 | 2006-12-05 | Abbott Laboratories | 2-(6-{2-[(2R)-2-Methyl-1-pyrrolidin-1-yl]-ethyl}-2-naphthalen-2-yl)-2H-pyridazin-3-one salts and their preparation |
| EP1795527B1 (en) * | 2004-09-07 | 2009-04-22 | Banyu Pharmaceutical Co., Ltd. | Carbamoyl-substituted spiro derivative |
| KR100903248B1 (ko) * | 2004-12-03 | 2009-06-17 | 에프. 호프만-라 로슈 아게 | Ｈ3 길항제로서 3-치환된 피리딘 유도체 |
| BRPI0606502A2 (pt) * | 2005-01-19 | 2009-06-30 | Hoffmann La Roche | compostos; processo para a fabricação de compostos; composições farmacêuticas; método para o tratamento ou prevenção de doenças que são associadas com a modulação de receptores h3; método para o tratamento ou prevenção de obesidade em um ser humano ou animal; método de tratamento ou prevenção de diabetes tipo ii em um ser humano ou animal e usos de compostos |
| US20060188960A1 (en) * | 2005-02-18 | 2006-08-24 | Waters Stephen M | Chimeric histamine H3 receptor |
| DE602006002894D1 (de) * | 2005-06-17 | 2008-11-06 | Janssen Pharmaceutica Nv | Naphthyridinverbindungen |
| PL1948607T3 (pl) * | 2005-09-16 | 2010-09-30 | Janssen Pharmaceutica Nv | Cyklopropyloaminy jako modulatory receptora histaminowego H3 |
| WO2007062999A2 (en) * | 2005-11-30 | 2007-06-07 | F. Hoffmann-La Roche Ag | 1,5-substituted indol-2-yl amide derivatives |
| JP2009521451A (ja) * | 2005-12-21 | 2009-06-04 | シェーリング コーポレイション | ヒスタミンｈ３アンタゴニストとして有用な置換アニリン誘導体 |
| JP2009530274A (ja) * | 2006-03-15 | 2009-08-27 | ワイス | ヒスタミン−３アンタゴニストとしてのｎ−置換−アザシクリルアミン化合物 |
| EP2027086B1 (en) * | 2006-05-19 | 2011-11-16 | Wyeth LLC | N-benzoyl-pyrrolidin-3-ylamines as histamine-3 antagonists |
| KR101372941B1 (ko) * | 2006-05-30 | 2014-03-14 | 얀센 파마슈티카 엔.브이. | 히스타민 ｈ３ 수용체 조절제로서의 치환된 피리딜 아미드 화합물 |
| WO2008005338A1 (en) * | 2006-06-29 | 2008-01-10 | Arena Pharmaceuticals, Inc. | Modulators of the histamine h3-receptor useful for the treatment of disorders related thereto |
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| US7507736B2 (en) * | 2007-02-07 | 2009-03-24 | Hoffmann-La Roche Inc. | Indol-2-yl-piperazin-1-yl-methanone derivatives |
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| AR066721A1 (es) * | 2007-05-24 | 2009-09-09 | Wyeth Corp | Derivados de benzo[d]imidazol-1-il, composicion farmaceutica, proceso de preparacion y uso. |
| TW200918062A (en) * | 2007-09-12 | 2009-05-01 | Wyeth Corp | Azacyclylisoquinolinone and-isoindolinone derivatives as histamine-3 antagonists |
| AP2010005202A0 (en) * | 2007-09-12 | 2010-04-30 | Wyeth Llc | Isoquinolinyl and isoindolinyl derivatives as histamines-3 antagonists |
| US20090131417A1 (en) * | 2007-11-20 | 2009-05-21 | Letavic Michael A | Substituted pyridyl amide compounds as modulators of the histamine h3 receptor |
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| US20100130477A1 (en) * | 2008-11-25 | 2010-05-27 | Astrazeneca Ab | Spirocyclobutyl Piperidine Derivatives |
-
2007
- 2007-09-28 TW TW096136478A patent/TW200823204A/zh unknown
- 2007-10-10 AR ARP070104474A patent/AR063226A1/es not_active Application Discontinuation
- 2007-10-16 AT AT07852791T patent/ATE512948T1/de not_active IP Right Cessation
- 2007-10-16 MX MX2009004071A patent/MX2009004071A/es active IP Right Grant
- 2007-10-16 CA CA002665204A patent/CA2665204A1/en not_active Abandoned
- 2007-10-16 US US12/445,795 patent/US20100240653A1/en not_active Abandoned
- 2007-10-16 WO PCT/US2007/022086 patent/WO2008048609A1/en not_active Ceased
- 2007-10-16 PE PE2007001398A patent/PE20081462A1/es not_active Application Discontinuation
- 2007-10-16 EA EA200970386A patent/EA200970386A1/ru unknown
- 2007-10-16 KR KR1020097009992A patent/KR20090069333A/ko not_active Withdrawn
- 2007-10-16 AU AU2007313180A patent/AU2007313180A1/en not_active Abandoned
- 2007-10-16 JP JP2009533349A patent/JP2010506918A/ja not_active Withdrawn
- 2007-10-16 EP EP07852791A patent/EP2074086B1/en active Active
- 2007-10-17 CL CL200702977A patent/CL2007002977A1/es unknown
- 2007-10-17 PA PA20078750901A patent/PA8750901A1/es unknown
-
2009
- 2009-04-05 IL IL197892A patent/IL197892A0/en unknown
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