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
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Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ544331A (en) | 2003-07-22 | 2010-03-26 | Arena Pharm 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 |
| CA2687721A1 (en) * | 2007-06-08 | 2008-12-18 | Arena Pharmaceuticals, Inc. | Crystalline forms of (r)-1-{2-[4'-(3-methoxy-propane-1-sulfonyl)-biphenyl-4-yl]-ethyl}-2-methyl-pyrrolidine, and compositions, and methods related thereto |
| ES2421237T7 (es) | 2007-08-15 | 2013-09-30 | Arena Pharmaceuticals, Inc. | Derivados de imidazo[1,2-a]piridin como moduladores del receptor serotoninérgico 5ht2a en el tratamiento de trastornos relacionados con el mismo |
| WO2009123714A2 (en) * | 2008-04-02 | 2009-10-08 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
| JP2011518154A (ja) * | 2008-04-16 | 2011-06-23 | アリーナ ファーマシューティカルズ， インコーポレイテッド | （ｒ）−１−｛２−［４’−（３−メトキシプロパン−１−スルホニル）−ビフェニル−４−イル］−エチル｝−２−メチル−ピロリジンの合成に有用なプロセス |
| US9126946B2 (en) | 2008-10-28 | 2015-09-08 | 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 |
| 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 |
| 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 |
| EP2943473B1 (en) * | 2013-01-09 | 2017-08-23 | Arena Pharmaceuticals, Inc. | Biphenyl-ethyl-pyrrolidine derivatives as histamine h3 receptor modulators for the treatment of cognitive disorders |
| JP2018516992A (ja) | 2015-06-12 | 2018-06-28 | アクソファント サイエンシーズ ゲーエムベーハーＡｘｏｖａｎｔ Ｓｃｉｅｎｃｅｓ Ｇｍｂｈ | レム睡眠行動障害の予防および処置のために有用なジアリールおよびアリールヘテロアリール尿素誘導体 |
| CN108472285A (zh) | 2015-07-15 | 2018-08-31 | 阿速万科学有限责任公司 | 用于预防和治疗与神经退行性疾病相关联的幻觉的二芳基和芳基杂芳基脲衍生物 |
| 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 |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE69333489T2 (de) * | 1992-09-14 | 2005-04-14 | 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 |
| US20040044029A1 (en) * | 2002-08-14 | 2004-03-04 | Dart Michael J. | Azabicyclic compounds are central nervous system active agents |
| 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 |
| CA2561628C (en) * | 2004-04-01 | 2012-05-08 | Eli Lilly And Company | Histamine h3 receptor agents, preparation and therapeutic uses |
| US20050245543A1 (en) * | 2004-04-30 | 2005-11-03 | Pfizer Inc | Histamine-3 receptor antagonists |
| 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 |
| CA2579204A1 (en) * | 2004-09-07 | 2006-03-16 | Banyu Pharmaceutical Co., Ltd. | Carbamoyl-substituted spiro derivative |
| MX2007006387A (es) * | 2004-12-03 | 2007-06-20 | Hoffmann La Roche | Derivados de piridina 3-substituidos como antagonistas h3. |
| AU2006207712A1 (en) * | 2005-01-19 | 2006-07-27 | F. Hoffmann-La Roche Ag | 5-aminoindole derivatives |
| US20060188960A1 (en) * | 2005-02-18 | 2006-08-24 | Waters Stephen M | Chimeric histamine H3 receptor |
| AU2006261162A1 (en) * | 2005-06-17 | 2006-12-28 | Janssen Pharmaceutica N.V. | Naphthyridine compounds |
| KR101336106B1 (ko) * | 2005-09-16 | 2013-12-05 | 얀센 파마슈티카 엔.브이. | 히스타민 ｈ3 수용체의 조절제로서 사이클로프로필 아민 |
| DE602006020482D1 (de) * | 2005-11-30 | 2011-04-14 | Hoffmann La Roche | 1,5-substituierte indol-2-yl amidderivative |
| AU2006331850A1 (en) * | 2005-12-21 | 2007-07-05 | Schering Corporation | Substituted aniline derivatives useful as histamine H3 antagonists |
| WO2007108936A2 (en) * | 2006-03-15 | 2007-09-27 | Wyeth | N-substituted-azacyclylamines as histamine-3 antagonists |
| CA2649913A1 (en) * | 2006-05-19 | 2007-11-29 | Wyeth | N-benzoyl- and n-benzylpyrrolidin-3-ylamines as histamine-3 antagonists |
| MX339668B (es) * | 2006-05-30 | 2016-06-02 | Janssen Pharmaceutica N V * | Compuestos de piridil amida sustituidos como moduladores del receptor h3 de la histamina. |
| EP2035372A1 (en) * | 2006-06-29 | 2009-03-18 | Arena Pharmaceuticals, Inc. | Modulators of the histamine h3-receptor useful for the treatment of disorders related thereto |
| US7648979B2 (en) * | 2007-02-07 | 2010-01-19 | Hoffmann-La Roche Inc. | 5-amido-(1H-indol-2-yl)-piperazin-1-yl-methanone derivatives |
| US7557108B2 (en) * | 2007-02-07 | 2009-07-07 | Hoffmann-La Roche Inc. | (Indol-4-yl) or (indol-5-yl)-piperazinylmethanones |
| US7507736B2 (en) * | 2007-02-07 | 2009-03-24 | Hoffmann-La Roche Inc. | Indol-2-yl-piperazin-1-yl-methanone derivatives |
| WO2008144305A1 (en) * | 2007-05-18 | 2008-11-27 | Janssen Pharmaceutica N.V. | Diaryl-substituted tetrahydroisoquinolines as histamine h3 receptor and serotonin transporter modulators |
| AR066721A1 (es) * | 2007-05-24 | 2009-09-09 | Wyeth Corp | Derivados de benzo[d]imidazol-1-il, composicion farmaceutica, proceso de preparacion y uso. |
| US20090069300A1 (en) * | 2007-09-12 | 2009-03-12 | Wyeth | Isoquinolinyl and isoindolinyl derivatives as histamine-3 antagonists |
| TW200918062A (en) * | 2007-09-12 | 2009-05-01 | Wyeth Corp | Azacyclylisoquinolinone and-isoindolinone derivatives as histamine-3 antagonists |
| WO2009067406A1 (en) * | 2007-11-20 | 2009-05-28 | Janssen Pharmaceutica N.V. | Substituted pyridyl amide compounds as modulators of the histamine h3 receptor |
| US8236792B2 (en) * | 2008-05-23 | 2012-08-07 | Janssen Pharmaceutica Nv | Substituted pyrrolidine amides as modulators of the histamine H3 receptor |
| US20100130477A1 (en) * | 2008-11-25 | 2010-05-27 | Astrazeneca Ab | Spirocyclobutyl Piperidine Derivatives |
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- 2007-09-28 TW TW096136478A patent/TW200823204A/zh unknown
- 2007-10-10 AR ARP070104474A patent/AR063226A1/es not_active Application Discontinuation
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- 2007-10-16 KR KR1020097009992A patent/KR20090069333A/ko not_active Withdrawn
- 2007-10-16 WO PCT/US2007/022086 patent/WO2008048609A1/en not_active Ceased
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- 2007-10-16 EA EA200970386A patent/EA200970386A1/ru unknown
- 2007-10-16 US US12/445,795 patent/US20100240653A1/en not_active Abandoned
- 2007-10-16 MX MX2009004071A patent/MX2009004071A/es active IP Right Grant
- 2007-10-16 AU AU2007313180A patent/AU2007313180A1/en not_active Abandoned
- 2007-10-16 PE PE2007001398A patent/PE20081462A1/es not_active Application Discontinuation
- 2007-10-16 JP JP2009533349A patent/JP2010506918A/ja not_active Withdrawn
- 2007-10-16 AT AT07852791T patent/ATE512948T1/de not_active IP Right Cessation
- 2007-10-17 PA PA20078750901A patent/PA8750901A1/es unknown
- 2007-10-17 CL CL200702977A patent/CL2007002977A1/es unknown
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2009
- 2009-04-05 IL IL197892A patent/IL197892A0/en unknown
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