NO314724B1 - Terapeutisk aktive diarylpropylaminer samt fremstilling og anvendelse derav - Google Patents
Terapeutisk aktive diarylpropylaminer samt fremstilling og anvendelse derav Download PDFInfo
- Publication number
- NO314724B1 NO314724B1 NO19994438A NO994438A NO314724B1 NO 314724 B1 NO314724 B1 NO 314724B1 NO 19994438 A NO19994438 A NO 19994438A NO 994438 A NO994438 A NO 994438A NO 314724 B1 NO314724 B1 NO 314724B1
- Authority
- NO
- Norway
- Prior art keywords
- diisopropyl
- hydroxy
- phenyl
- phenylpropanamine
- mmol
- Prior art date
Links
- -1 diaryl propylamines Chemical class 0.000 title claims description 59
- 238000002360 preparation method Methods 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 106
- 239000000203 mixture Substances 0.000 claims description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 239000001257 hydrogen Substances 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 150000001412 amines Chemical class 0.000 claims description 25
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000002971 oxazolyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 5
- 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 description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- DPFSNUNXCJRDOM-UHFFFAOYSA-N 2-[3-[di(propan-2-yl)amino]-1-thiophen-2-ylpropyl]-4-methylphenol Chemical compound C=1C(C)=CC=C(O)C=1C(CCN(C(C)C)C(C)C)C1=CC=CS1 DPFSNUNXCJRDOM-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 3
- 230000001078 anti-cholinergic effect Effects 0.000 claims description 3
- 239000000812 cholinergic antagonist Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- XDVMDFKKDYVSHW-UHFFFAOYSA-N 1-[3-[3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxyphenyl]ethanone Chemical compound C=1C(C(C)=O)=CC=C(O)C=1C(CCN(C(C)C)C(C)C)C1=CC=CC=C1 XDVMDFKKDYVSHW-UHFFFAOYSA-N 0.000 claims description 2
- ITAGCYAEFDQKNU-UHFFFAOYSA-N 2-[3-[cyclobutyl(methyl)amino]-1-phenylpropyl]phenol Chemical compound C1CCC1N(C)CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1 ITAGCYAEFDQKNU-UHFFFAOYSA-N 0.000 claims description 2
- HNOIEYVHTFAEHF-UHFFFAOYSA-N 2-[3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(1-hydroxyethyl)phenol Chemical compound C=1C(C(C)O)=CC=C(O)C=1C(CCN(C(C)C)C(C)C)C1=CC=CC=C1 HNOIEYVHTFAEHF-UHFFFAOYSA-N 0.000 claims description 2
- MXJPFOKHIBZVBU-UHFFFAOYSA-N 2-[3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(3-hydroxypropyl)phenol Chemical compound C=1C(CCCO)=CC=C(O)C=1C(CCN(C(C)C)C(C)C)C1=CC=CC=C1 MXJPFOKHIBZVBU-UHFFFAOYSA-N 0.000 claims description 2
- OJHQCRKOQXACNW-UHFFFAOYSA-N 2-[3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(6-hydroxyhexyl)phenol Chemical compound C=1C(CCCCCCO)=CC=C(O)C=1C(CCN(C(C)C)C(C)C)C1=CC=CC=C1 OJHQCRKOQXACNW-UHFFFAOYSA-N 0.000 claims description 2
- IOAGZOSRHBAGLF-UHFFFAOYSA-N 2-[3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(ethoxymethyl)phenol Chemical compound CCOCC1=CC=C(O)C(C(CCN(C(C)C)C(C)C)C=2C=CC=CC=2)=C1 IOAGZOSRHBAGLF-UHFFFAOYSA-N 0.000 claims description 2
- QVMRSIJFYBWKPV-UHFFFAOYSA-N 3-(2-fluorophenyl)-3-phenyl-n,n-di(propan-2-yl)propan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=C(F)C=1C(CCN(C(C)C)C(C)C)C1=CC=CC=C1 QVMRSIJFYBWKPV-UHFFFAOYSA-N 0.000 claims description 2
- RYBZMVRTONWJJF-UHFFFAOYSA-N 3-[3-[3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxyphenyl]propanenitrile Chemical compound C=1C(CCC#N)=CC=C(O)C=1C(CCN(C(C)C)C(C)C)C1=CC=CC=C1 RYBZMVRTONWJJF-UHFFFAOYSA-N 0.000 claims description 2
- DHTHWYZNJZNTIT-UHFFFAOYSA-N 3-[3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxybenzaldehyde Chemical compound C=1C(C=O)=CC=C(O)C=1C(CCN(C(C)C)C(C)C)C1=CC=CC=C1 DHTHWYZNJZNTIT-UHFFFAOYSA-N 0.000 claims description 2
- CQWFSQJROMJICT-UHFFFAOYSA-N 4-(3-aminopropyl)-2-[3-[di(propan-2-yl)amino]-1-phenylpropyl]phenol Chemical compound C=1C(CCCN)=CC=C(O)C=1C(CCN(C(C)C)C(C)C)C1=CC=CC=C1 CQWFSQJROMJICT-UHFFFAOYSA-N 0.000 claims description 2
- QYNLTNFESGCQMB-UHFFFAOYSA-N 4-amino-2-[3-[di(propan-2-yl)amino]-1-phenylpropyl]phenol Chemical compound C=1C(N)=CC=C(O)C=1C(CCN(C(C)C)C(C)C)C1=CC=CC=C1 QYNLTNFESGCQMB-UHFFFAOYSA-N 0.000 claims description 2
- SCZILZULKYLKCS-UHFFFAOYSA-N 4-azido-2-[3-[di(propan-2-yl)amino]-1-phenylpropyl]phenol Chemical compound C=1C(N=[N+]=[N-])=CC=C(O)C=1C(CCN(C(C)C)C(C)C)C1=CC=CC=C1 SCZILZULKYLKCS-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 2
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- BVDJSAWIASTWBI-UHFFFAOYSA-N n-[3-[3-[3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxyphenyl]propyl]acetamide Chemical compound C=1C(CCCNC(C)=O)=CC=C(O)C=1C(CCN(C(C)C)C(C)C)C1=CC=CC=C1 BVDJSAWIASTWBI-UHFFFAOYSA-N 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- KYWHDMMYBSEIAF-UHFFFAOYSA-N 2-[3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(2-hydroxyethyl)phenol Chemical compound C=1C(CCO)=CC=C(O)C=1C(CCN(C(C)C)C(C)C)C1=CC=CC=C1 KYWHDMMYBSEIAF-UHFFFAOYSA-N 0.000 claims 1
- HGJKQYUDOTVXQV-UHFFFAOYSA-N 2-[3-[di(propan-2-yl)amino]-1-thiophen-2-ylpropyl]phenol Chemical compound C=1C=CC=C(O)C=1C(CCN(C(C)C)C(C)C)C1=CC=CS1 HGJKQYUDOTVXQV-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- LAPCBEFVTNSDFY-UHFFFAOYSA-N methyl 3-[3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C(C(CCN(C(C)C)C(C)C)C=2C=CC=CC=2)=C1 LAPCBEFVTNSDFY-UHFFFAOYSA-N 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 366
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 117
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 114
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 102
- 239000000243 solution Substances 0.000 description 85
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 81
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 79
- 239000002904 solvent Substances 0.000 description 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
- 239000000377 silicon dioxide Substances 0.000 description 50
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 44
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 44
- 239000013078 crystal Substances 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000003921 oil Substances 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 239000007858 starting material Substances 0.000 description 32
- 239000012074 organic phase Substances 0.000 description 30
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 29
- 229910052799 carbon Inorganic materials 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000012043 crude product Substances 0.000 description 23
- 239000012044 organic layer Substances 0.000 description 23
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 239000008346 aqueous phase Substances 0.000 description 18
- 239000012280 lithium aluminium hydride Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 238000010992 reflux Methods 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 239000003208 petroleum Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- UCYJWCSOSZIQLQ-AREMUKBSSA-N (3r)-3-(5-bromo-2-phenylmethoxyphenyl)-3-phenyl-n,n-di(propan-2-yl)propan-1-amine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(Br)C=2)OCC=2C=CC=CC=2)=CC=CC=C1 UCYJWCSOSZIQLQ-AREMUKBSSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- NTEUNCALHORCCY-UHFFFAOYSA-N n,n-diethylethanamine;toluene Chemical compound CCN(CC)CC.CC1=CC=CC=C1 NTEUNCALHORCCY-UHFFFAOYSA-N 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
- VPJXQGSRWJZDOB-UHFFFAOYSA-O 2-carbamoyloxyethyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCOC(N)=O VPJXQGSRWJZDOB-UHFFFAOYSA-O 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 229960004484 carbachol Drugs 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 6
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 6
- 206010046543 Urinary incontinence Diseases 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 4
- KISZTEOELCMZPY-UHFFFAOYSA-N 3,3-diphenylpropylamine Chemical group C=1C=CC=CC=1C(CCN)C1=CC=CC=C1 KISZTEOELCMZPY-UHFFFAOYSA-N 0.000 description 4
- DHTHWYZNJZNTIT-HXUWFJFHSA-N 3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxybenzaldehyde Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=O)C=2)O)=CC=CC=C1 DHTHWYZNJZNTIT-HXUWFJFHSA-N 0.000 description 4
- GXNUYRLWHSRKTG-UHFFFAOYSA-N 3-[3-[benzyl(propan-2-yl)amino]-1-phenylpropyl]-4-phenylmethoxybenzoic acid Chemical compound C=1C=CC=CC=1CN(C(C)C)CCC(C=1C(=CC=C(C=1)C(O)=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 GXNUYRLWHSRKTG-UHFFFAOYSA-N 0.000 description 4
- FSXFWVUDKCDJEX-UHFFFAOYSA-N 4-[di(propan-2-yl)amino]-2-phenylbutanethioamide Chemical compound CC(C)N(C(C)C)CCC(C(N)=S)C1=CC=CC=C1 FSXFWVUDKCDJEX-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- WCYMWQIUHPXBKM-UHFFFAOYSA-N n,n-diethylethanamine;ethoxyethane Chemical compound CCOCC.CCN(CC)CC WCYMWQIUHPXBKM-UHFFFAOYSA-N 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 4
- BZLCHRVOOOPPRV-MUUNZHRXSA-N (3r)-3-(5-ethenyl-2-phenylmethoxyphenyl)-3-phenyl-n,n-di(propan-2-yl)propan-1-amine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=C)C=2)OCC=2C=CC=CC=2)=CC=CC=C1 BZLCHRVOOOPPRV-MUUNZHRXSA-N 0.000 description 3
- ORQJTDRXCBMXOA-MUUNZHRXSA-N 1-[3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-phenylmethoxyphenyl]ethanone Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=2)C(C)=O)OCC=2C=CC=CC=2)=CC=CC=C1 ORQJTDRXCBMXOA-MUUNZHRXSA-N 0.000 description 3
- DIAWHHLLHVAPED-NDEPHWFRSA-N 2-[3-[(1s)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-phenylmethoxyphenyl]ethanol Chemical compound C1([C@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CCO)C=2)OCC=2C=CC=CC=2)=CC=CC=C1 DIAWHHLLHVAPED-NDEPHWFRSA-N 0.000 description 3
- XWAPRYPNWHAJAV-UHFFFAOYSA-N 3-(1,3-oxazol-5-yl)-3-phenyl-n,n-di(propan-2-yl)propanamide Chemical compound C=1C=CC=CC=1C(CC(=O)N(C(C)C)C(C)C)C1=CN=CO1 XWAPRYPNWHAJAV-UHFFFAOYSA-N 0.000 description 3
- OMBFFHYKWKZZHQ-UHFFFAOYSA-N 3-(2-fluorophenyl)-3-phenyl-n,n-di(propan-2-yl)propanamide Chemical compound C=1C=CC=C(F)C=1C(CC(=O)N(C(C)C)C(C)C)C1=CC=CC=C1 OMBFFHYKWKZZHQ-UHFFFAOYSA-N 0.000 description 3
- PSYHZGWUOHTDQO-UHFFFAOYSA-N 3-(2-methoxyphenyl)-n,n-di(propan-2-yl)-3-pyridin-3-ylpropanamide Chemical compound COC1=CC=CC=C1C(CC(=O)N(C(C)C)C(C)C)C1=CC=CN=C1 PSYHZGWUOHTDQO-UHFFFAOYSA-N 0.000 description 3
- SDTLSOIVVRHNFT-UHFFFAOYSA-N 3-(5-bromo-2-phenylmethoxyphenyl)-3-phenylpropanal Chemical compound C=1C=CC=CC=1C(CC=O)C1=CC(Br)=CC=C1OCC1=CC=CC=C1 SDTLSOIVVRHNFT-UHFFFAOYSA-N 0.000 description 3
- PSNQHGJVGCUGBC-HHHXNRCGSA-N 3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-phenylmethoxybenzaldehyde Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=O)C=2)OCC=2C=CC=CC=2)=CC=CC=C1 PSNQHGJVGCUGBC-HHHXNRCGSA-N 0.000 description 3
- KZBMPKPZDVBLGS-GDLZYMKVSA-N 3-[3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-phenylmethoxyphenyl]prop-2-enenitrile Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=CC#N)C=2)OCC=2C=CC=CC=2)=CC=CC=C1 KZBMPKPZDVBLGS-GDLZYMKVSA-N 0.000 description 3
- WADDJQCUERYFPL-UHFFFAOYSA-N 3-phenyl-n,n-di(propan-2-yl)-3-[2-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=CC=C(C(F)(F)F)C=1C(CC(=O)N(C(C)C)C(C)C)C1=CC=CC=C1 WADDJQCUERYFPL-UHFFFAOYSA-N 0.000 description 3
- QYNLTNFESGCQMB-LJQANCHMSA-N 4-amino-2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]phenol Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(N)C=2)O)=CC=CC=C1 QYNLTNFESGCQMB-LJQANCHMSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical class Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 3
- DTRKHFIILOKLIC-HSZRJFAPSA-N ethyl 3-[3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxyphenyl]propanoate Chemical compound CCOC(=O)CCC1=CC=C(O)C([C@H](CCN(C(C)C)C(C)C)C=2C=CC=CC=2)=C1 DTRKHFIILOKLIC-HSZRJFAPSA-N 0.000 description 3
- WKVJVVGZQUOUOY-UHFFFAOYSA-N ethyl 4-[di(propan-2-yl)amino]-2-phenylbutanoate Chemical compound CC(C)N(C(C)C)CCC(C(=O)OCC)C1=CC=CC=C1 WKVJVVGZQUOUOY-UHFFFAOYSA-N 0.000 description 3
- 235000011087 fumaric acid Nutrition 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- GGVNYSNKHHBQOA-UHFFFAOYSA-N n-[3-(5-bromo-2-phenylmethoxyphenyl)-3-phenylpropyl]-n-methylcyclopentanamine Chemical compound C1CCCC1N(C)CCC(C=1C(=CC=C(Br)C=1)OCC=1C=CC=CC=1)C1=CC=CC=C1 GGVNYSNKHHBQOA-UHFFFAOYSA-N 0.000 description 3
- LRWJZYCOTQEAHV-UHFFFAOYSA-N n-cycloheptyl-3-(2-hydroxy-5-methylphenyl)-n-methyl-3-phenylpropanamide Chemical compound C=1C=CC=CC=1C(C=1C(=CC=C(C)C=1)O)CC(=O)N(C)C1CCCCCC1 LRWJZYCOTQEAHV-UHFFFAOYSA-N 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- MDXUQVAIHMJKOR-AREMUKBSSA-N (3r)-3-(5-azido-2-phenylmethoxyphenyl)-3-phenyl-n,n-di(propan-2-yl)propan-1-amine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=2)N=[N+]=[N-])OCC=2C=CC=CC=2)=CC=CC=C1 MDXUQVAIHMJKOR-AREMUKBSSA-N 0.000 description 2
- GFYVDGHZCVTQSF-UUWRZZSWSA-N (3r)-3-[5-[2-[di(propan-2-yl)amino]ethyl]-2-phenylmethoxyphenyl]-3-phenyl-n,n-di(propan-2-yl)propan-1-amine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CCN(C(C)C)C(C)C)C=2)OCC=2C=CC=CC=2)=CC=CC=C1 GFYVDGHZCVTQSF-UUWRZZSWSA-N 0.000 description 2
- UCYJWCSOSZIQLQ-SANMLTNESA-N (3s)-3-(5-bromo-2-phenylmethoxyphenyl)-3-phenyl-n,n-di(propan-2-yl)propan-1-amine Chemical compound C1([C@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(Br)C=2)OCC=2C=CC=CC=2)=CC=CC=C1 UCYJWCSOSZIQLQ-SANMLTNESA-N 0.000 description 2
- BZLCHRVOOOPPRV-NDEPHWFRSA-N (3s)-3-(5-ethenyl-2-phenylmethoxyphenyl)-3-phenyl-n,n-di(propan-2-yl)propan-1-amine Chemical compound C1([C@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=C)C=2)OCC=2C=CC=CC=2)=CC=CC=C1 BZLCHRVOOOPPRV-NDEPHWFRSA-N 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
- DUDBRFQIUYLGGA-ITCMONMYSA-N 1-[3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-phenylmethoxyphenyl]ethanol Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=2)C(C)O)OCC=2C=CC=CC=2)=CC=CC=C1 DUDBRFQIUYLGGA-ITCMONMYSA-N 0.000 description 2
- HTDQSWDEWGSAMN-UHFFFAOYSA-N 1-bromo-2-methoxybenzene Chemical compound COC1=CC=CC=C1Br HTDQSWDEWGSAMN-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- TZHLMTIOWMWDAQ-AREMUKBSSA-N 2-[(1R)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-[(4-methylphenyl)diazenyl]phenol Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=2)N=NC=2C=CC(C)=CC=2)O)=CC=CC=C1 TZHLMTIOWMWDAQ-AREMUKBSSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- KVFCUUUXBJCRLN-UHFFFAOYSA-N 3-(1-methylpyrrol-2-yl)-3-phenyl-n,n-di(propan-2-yl)propanamide Chemical compound C=1C=CC=CC=1C(CC(=O)N(C(C)C)C(C)C)C1=CC=CN1C KVFCUUUXBJCRLN-UHFFFAOYSA-N 0.000 description 2
- KLONVMNJUGIBLL-UHFFFAOYSA-N 3-(2-hydroxyphenyl)-n,n-di(propan-2-yl)-3-thiophen-2-ylpropanamide Chemical compound C=1C=CC=C(O)C=1C(CC(=O)N(C(C)C)C(C)C)C1=CC=CS1 KLONVMNJUGIBLL-UHFFFAOYSA-N 0.000 description 2
- FGJUWHXXVOMQDE-UHFFFAOYSA-N 3-(2-methoxyphenyl)-n,n-di(propan-2-yl)-3-thiophen-2-ylpropanamide Chemical compound COC1=CC=CC=C1C(CC(=O)N(C(C)C)C(C)C)C1=CC=CS1 FGJUWHXXVOMQDE-UHFFFAOYSA-N 0.000 description 2
- VATYLQAEVSNONV-UHFFFAOYSA-N 3-phenyl-n,n-di(propan-2-yl)-3-[2-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C=1C=CC=C(C(F)(F)F)C=1C(=CC(=O)N(C(C)C)C(C)C)C1=CC=CC=C1 VATYLQAEVSNONV-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- ZAETYTPFTJNPQR-UHFFFAOYSA-N 4-[di(propan-2-yl)amino]-2-phenylbutanenitrile Chemical compound CC(C)N(C(C)C)CCC(C#N)C1=CC=CC=C1 ZAETYTPFTJNPQR-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- RQOMVMAPQOHTMY-JGCGQSQUSA-N 6-[3-[(1R)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-phenylmethoxyphenyl]hex-5-en-1-ol Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=CCCCCO)C=2)OCC=2C=CC=CC=2)=CC=CC=C1 RQOMVMAPQOHTMY-JGCGQSQUSA-N 0.000 description 2
- AMKGKYQBASDDJB-UHFFFAOYSA-N 9$l^{2}-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1[B]2 AMKGKYQBASDDJB-UHFFFAOYSA-N 0.000 description 2
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Substances C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DUXZAXCGJSBGDW-HXUWFJFHSA-N Desfesoterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CO)C=2)O)=CC=CC=C1 DUXZAXCGJSBGDW-HXUWFJFHSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 229910004373 HOAc Inorganic materials 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229910010082 LiAlH Inorganic materials 0.000 description 2
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- TYKZXWURWDNYTB-UHFFFAOYSA-N [2-[(4-hydroxy-3,5-dimethylphenyl)diazenyl]phenyl]-phenylmethanone Chemical compound CC1=C(O)C(C)=CC(N=NC=2C(=CC=CC=2)C(=O)C=2C=CC=CC=2)=C1 TYKZXWURWDNYTB-UHFFFAOYSA-N 0.000 description 2
- MNROXPXLYMUQRN-UHFFFAOYSA-N [4-[(2-benzoylphenyl)diazenyl]-2,6-dimethylphenyl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=C(C)C=C(N=NC=2C(=CC=CC=2)C(=O)C=2C=CC=CC=2)C=C1C MNROXPXLYMUQRN-UHFFFAOYSA-N 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- DFGXLIGEPDCRFU-UHFFFAOYSA-N bis[2-(2-methoxyphenyl)pyridin-3-yl]methanone Chemical compound COC1=CC=CC=C1C1=NC=CC=C1C(=O)C1=CC=CN=C1C1=CC=CC=C1OC DFGXLIGEPDCRFU-UHFFFAOYSA-N 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 230000009989 contractile response Effects 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 2
- BTRHEJSPFCGKBZ-SSEXGKCCSA-N ethyl 3-[3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-phenylmethoxyphenyl]propanoate Chemical compound C1([C@H](CCN(C(C)C)C(C)C)C=2C=CC=CC=2)=CC(CCC(=O)OCC)=CC=C1OCC1=CC=CC=C1 BTRHEJSPFCGKBZ-SSEXGKCCSA-N 0.000 description 2
- NBIRTCJKAMQURV-UHFFFAOYSA-N ethyl 4-[di(propan-2-yl)amino]-4-oxo-2-phenylbutanoate Chemical compound CC(C)N(C(C)C)C(=O)CC(C(=O)OCC)C1=CC=CC=C1 NBIRTCJKAMQURV-UHFFFAOYSA-N 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 2
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- PFCFKYSBIQBHAO-UHFFFAOYSA-N lithium;methoxybenzene Chemical compound [Li+].COC1=CC=CC=[C-]1 PFCFKYSBIQBHAO-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- WQDJYZFWACDLMK-UHFFFAOYSA-N n,n-diethylethanamine;ethanol;hexane Chemical compound CCO.CCCCCC.CCN(CC)CC WQDJYZFWACDLMK-UHFFFAOYSA-N 0.000 description 2
- CSYNQJPENMOLHR-UHFFFAOYSA-N n,n-diethylethanamine;ethyl acetate Chemical compound CCOC(C)=O.CCN(CC)CC CSYNQJPENMOLHR-UHFFFAOYSA-N 0.000 description 2
- OFSOKSWHXLWYOO-UHFFFAOYSA-N n-[2-(2-hydroxyethoxy)ethyl]-3-(2-hydroxy-5-methylphenyl)-3-phenyl-n-propan-2-ylpropanamide Chemical compound C=1C(C)=CC=C(O)C=1C(CC(=O)N(CCOCCO)C(C)C)C1=CC=CC=C1 OFSOKSWHXLWYOO-UHFFFAOYSA-N 0.000 description 2
- GUPGSAPWDQPAQE-UHFFFAOYSA-N n-[3-(5-bromo-2-phenylmethoxyphenyl)-3-phenylpropyl]-n-methylcyclobutanamine Chemical compound C1CCC1N(C)CCC(C=1C(=CC=C(Br)C=1)OCC=1C=CC=CC=1)C1=CC=CC=C1 GUPGSAPWDQPAQE-UHFFFAOYSA-N 0.000 description 2
- IWECAIYMBGQJEA-UHFFFAOYSA-N n-[3-(5-bromo-2-phenylmethoxyphenyl)-3-phenylpropyl]cyclobutanamine Chemical compound C1CCC1NCCC(C=1C=CC=CC=1)C1=CC(Br)=CC=C1OCC1=CC=CC=C1 IWECAIYMBGQJEA-UHFFFAOYSA-N 0.000 description 2
- XARPFTFWUFOLEV-UHFFFAOYSA-N n-[3-(5-bromo-2-phenylmethoxyphenyl)-3-phenylpropyl]cyclopentanamine Chemical compound C1CCCC1NCCC(C=1C=CC=CC=1)C1=CC(Br)=CC=C1OCC1=CC=CC=C1 XARPFTFWUFOLEV-UHFFFAOYSA-N 0.000 description 2
- QOZZDKPFJCKXEW-UHFFFAOYSA-N n-benzyl-3-(5-bromo-2-phenylmethoxyphenyl)-3-phenyl-n-propan-2-ylpropan-1-amine Chemical compound C=1C=CC=CC=1CN(C(C)C)CCC(C=1C(=CC=C(Br)C=1)OCC=1C=CC=CC=1)C1=CC=CC=C1 QOZZDKPFJCKXEW-UHFFFAOYSA-N 0.000 description 2
- VTLPWIRIZXMUIT-UHFFFAOYSA-N o-ethyl 4-amino-2-phenylbutanethioate;n-propan-2-ylpropan-2-amine Chemical compound CC(C)NC(C)C.CCOC(=S)C(CCN)C1=CC=CC=C1 VTLPWIRIZXMUIT-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- JXIWJBWMQXDALU-UHFFFAOYSA-N phenyl-[2-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)C1=CC=CC=C1 JXIWJBWMQXDALU-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000000284 resting effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- KQERVIARWMHFOS-UHFFFAOYSA-N (4-dimethylsilylphenyl)-dimethylsilane Chemical compound C[SiH](C)C1=CC=C([SiH](C)C)C=C1 KQERVIARWMHFOS-UHFFFAOYSA-N 0.000 description 1
- NQKKAGIVNUMNFM-UHFFFAOYSA-N (5-methyl-2-phenylmethoxyphenyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1=CC(C)=CC=C1OCC1=CC=CC=C1 NQKKAGIVNUMNFM-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- KTNPVCWCOHPAOV-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-(3-phenyl-3-thiophen-2-ylpropyl)pyrrolidine Chemical compound OC(=O)\C=C\C(O)=O.C=1C=CSC=1C(C=1C=CC=CC=1)CCN1CCCC1 KTNPVCWCOHPAOV-WLHGVMLRSA-N 0.000 description 1
- ZHJXCVNOGPFUEA-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-methyl-2-(1-phenyl-3-pyrrolidin-1-ylpropyl)pyrrole Chemical compound OC(=O)\C=C\C(O)=O.CN1C=CC=C1C(C=1C=CC=CC=1)CCN1CCCC1 ZHJXCVNOGPFUEA-WLHGVMLRSA-N 0.000 description 1
- KTFZGOQKDYOZNJ-SGPREKLPSA-N (e)-but-2-enedioic acid;2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(1-hydroxyethyl)phenol Chemical compound OC(=O)\C=C\C(O)=O.C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=2)C(C)O)O)=CC=CC=C1 KTFZGOQKDYOZNJ-SGPREKLPSA-N 0.000 description 1
- AMJYTLVCEBIPLE-WLHGVMLRSA-N (e)-but-2-enedioic acid;3-(1-methylpyrrol-2-yl)-3-phenyl-n,n-di(propan-2-yl)propan-1-amine Chemical compound OC(=O)\C=C\C(O)=O.C=1C=CC=CC=1C(CCN(C(C)C)C(C)C)C1=CC=CN1C AMJYTLVCEBIPLE-WLHGVMLRSA-N 0.000 description 1
- PDQVDBGCCCOPFX-WLHGVMLRSA-N (e)-but-2-enedioic acid;3-(2,4-dimethoxyphenyl)-n,n-di(propan-2-yl)-3-thiophen-2-ylpropan-1-amine Chemical compound OC(=O)\C=C\C(O)=O.COC1=CC(OC)=CC=C1C(CCN(C(C)C)C(C)C)C1=CC=CS1 PDQVDBGCCCOPFX-WLHGVMLRSA-N 0.000 description 1
- RSUUQMWGWNNINY-WLHGVMLRSA-N (e)-but-2-enedioic acid;3-(2-methoxyphenyl)-n-methyl-n-propan-2-yl-3-thiophen-2-ylpropan-1-amine Chemical compound OC(=O)\C=C\C(O)=O.COC1=CC=CC=C1C(CCN(C)C(C)C)C1=CC=CS1 RSUUQMWGWNNINY-WLHGVMLRSA-N 0.000 description 1
- LTNBOIOUWAAAJC-WLHGVMLRSA-N (e)-but-2-enedioic acid;n,n-diethyl-3-phenyl-3-thiophen-2-ylpropan-1-amine Chemical compound OC(=O)\C=C\C(O)=O.C=1C=CC=CC=1C(CCN(CC)CC)C1=CC=CS1 LTNBOIOUWAAAJC-WLHGVMLRSA-N 0.000 description 1
- UDRRCRDRXXSVIX-UHFFFAOYSA-N 1-(3-phenyl-3-thiophen-2-ylpropyl)piperidine;hydrochloride Chemical compound Cl.C=1C=CSC=1C(C=1C=CC=CC=1)CCN1CCCCC1 UDRRCRDRXXSVIX-UHFFFAOYSA-N 0.000 description 1
- OUKQTRFCDKSEPL-UHFFFAOYSA-N 1-Methyl-2-pyrrolecarboxaldehyde Chemical compound CN1C=CC=C1C=O OUKQTRFCDKSEPL-UHFFFAOYSA-N 0.000 description 1
- KMWPSVTVAXBXCN-MPPNBAAUSA-N 1-[3-[(1R)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-phenylmethoxyphenyl]ethanol 1-[3-[(1R)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-phenylmethoxyphenyl]ethanone Chemical compound C(C)(C)N(CC[C@H](C1=CC=CC=C1)C1=C(C=CC(=C1)C(C)=O)OCC1=CC=CC=C1)C(C)C.C(C)(C)N(CC[C@H](C1=CC=CC=C1)C1=C(C=CC(=C1)C(C)O)OCC1=CC=CC=C1)C(C)C KMWPSVTVAXBXCN-MPPNBAAUSA-N 0.000 description 1
- XSFMWVZHXKHBQL-ZMBIFBSDSA-N 1-[3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxyphenyl]ethanone;hydrochloride Chemical compound Cl.C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=2)C(C)=O)O)=CC=CC=C1 XSFMWVZHXKHBQL-ZMBIFBSDSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- FMRWQLAJBBKXDM-UHFFFAOYSA-N 2,2,5,5-tetramethylpyrrolidine Chemical compound CC1(C)CCC(C)(C)N1 FMRWQLAJBBKXDM-UHFFFAOYSA-N 0.000 description 1
- LLCKGEYSQVLXAX-ZMBIFBSDSA-N 2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(2-hydroxyethyl)phenol;hydrochloride Chemical compound Cl.C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CCO)C=2)O)=CC=CC=C1 LLCKGEYSQVLXAX-ZMBIFBSDSA-N 0.000 description 1
- QPPNORSBENMRSB-VZYDHVRKSA-N 2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(3-hydroxypropyl)phenol;hydrochloride Chemical compound Cl.C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CCCO)C=2)O)=CC=CC=C1 QPPNORSBENMRSB-VZYDHVRKSA-N 0.000 description 1
- IOAGZOSRHBAGLF-JOCHJYFZSA-N 2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(ethoxymethyl)phenol Chemical compound CCOCC1=CC=C(O)C([C@H](CCN(C(C)C)C(C)C)C=2C=CC=CC=2)=C1 IOAGZOSRHBAGLF-JOCHJYFZSA-N 0.000 description 1
- IEKNHKFBHBENMC-LJQANCHMSA-N 2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]phenol Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=CC=2)O)=CC=CC=C1 IEKNHKFBHBENMC-LJQANCHMSA-N 0.000 description 1
- LLCKGEYSQVLXAX-BOXHHOBZSA-N 2-[(1s)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(2-hydroxyethyl)phenol;hydrochloride Chemical compound Cl.C1([C@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CCO)C=2)O)=CC=CC=C1 LLCKGEYSQVLXAX-BOXHHOBZSA-N 0.000 description 1
- RBZQLPFPTPQBEI-UHFFFAOYSA-N 2-[2-(propan-2-ylamino)ethoxy]ethanol Chemical compound CC(C)NCCOCCO RBZQLPFPTPQBEI-UHFFFAOYSA-N 0.000 description 1
- ZNCHSPXWBPWDOM-UHFFFAOYSA-N 2-[2-[1-[di(propan-2-yl)amino]propyl]thiophen-3-yl]-4-methylphenol Chemical compound S1C=CC(C=2C(=CC=C(C)C=2)O)=C1C(N(C(C)C)C(C)C)CC ZNCHSPXWBPWDOM-UHFFFAOYSA-N 0.000 description 1
- ZTPYAGYKKXNHLK-MUUNZHRXSA-N 2-[3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-phenylmethoxyphenyl]acetaldehyde Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CC=O)C=2)OCC=2C=CC=CC=2)=CC=CC=C1 ZTPYAGYKKXNHLK-MUUNZHRXSA-N 0.000 description 1
- DIAWHHLLHVAPED-MUUNZHRXSA-N 2-[3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-phenylmethoxyphenyl]ethanol Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CCO)C=2)OCC=2C=CC=CC=2)=CC=CC=C1 DIAWHHLLHVAPED-MUUNZHRXSA-N 0.000 description 1
- NEZKOIVRRLJDAZ-UHFFFAOYSA-N 2-[3-[benzyl(propan-2-yl)amino]-1-phenylpropyl]phenol;hydrochloride Chemical compound Cl.C=1C=CC=CC=1CN(C(C)C)CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1 NEZKOIVRRLJDAZ-UHFFFAOYSA-N 0.000 description 1
- RKGNOXGYQLBEGY-UHFFFAOYSA-N 2-[3-[cyclobutyl(methyl)amino]-1-phenylpropyl]phenol;hydrochloride Chemical compound Cl.C1CCC1N(C)CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1 RKGNOXGYQLBEGY-UHFFFAOYSA-N 0.000 description 1
- MKBHOGSRAJZLKZ-UHFFFAOYSA-N 2-[3-[cyclohexyl(methyl)amino]-1-phenylpropyl]-4-methylphenol;hydrochloride Chemical compound Cl.C1CCCCC1N(C)CCC(C=1C(=CC=C(C)C=1)O)C1=CC=CC=C1 MKBHOGSRAJZLKZ-UHFFFAOYSA-N 0.000 description 1
- VZRANWRZJVGBEL-UHFFFAOYSA-N 2-[3-[cyclopentyl(methyl)amino]-1-phenylpropyl]phenol;hydrochloride Chemical compound Cl.C1CCCC1N(C)CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1 VZRANWRZJVGBEL-UHFFFAOYSA-N 0.000 description 1
- NELGVYWSJCGCMA-UHFFFAOYSA-N 2-[3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(ethylaminomethyl)phenol Chemical compound CCNCC1=CC=C(O)C(C(CCN(C(C)C)C(C)C)C=2C=CC=CC=2)=C1 NELGVYWSJCGCMA-UHFFFAOYSA-N 0.000 description 1
- CZPAEHUEZNMIDC-UHFFFAOYSA-N 2-[3-[di(propan-2-yl)amino]-1-phenylpropyl]aniline;hydrochloride Chemical compound Cl.C=1C=CC=C(N)C=1C(CCN(C(C)C)C(C)C)C1=CC=CC=C1 CZPAEHUEZNMIDC-UHFFFAOYSA-N 0.000 description 1
- IWYAUOFQYHWNTO-UHFFFAOYSA-N 2-[3-[di(propan-2-yl)amino]-1-phenylpropyl]benzoic acid;hydrochloride Chemical compound Cl.C=1C=CC=C(C(O)=O)C=1C(CCN(C(C)C)C(C)C)C1=CC=CC=C1 IWYAUOFQYHWNTO-UHFFFAOYSA-N 0.000 description 1
- LQLMPDOVHVTBGB-UHFFFAOYSA-N 2-[3-[di(propan-2-yl)amino]-1-thiophen-2-ylpropyl]-4-methylphenol;hydrochloride Chemical compound Cl.C=1C(C)=CC=C(O)C=1C(CCN(C(C)C)C(C)C)C1=CC=CS1 LQLMPDOVHVTBGB-UHFFFAOYSA-N 0.000 description 1
- FHUABAPZGBGMLA-UHFFFAOYSA-N 2-amino-2-ethoxyethanol Chemical compound CCOC(N)CO FHUABAPZGBGMLA-UHFFFAOYSA-N 0.000 description 1
- BOVSDOOOPYUOQT-UHFFFAOYSA-N 3-(1,3-benzoxazol-2-yl)-3-phenyl-n,n-di(propan-2-yl)propan-1-amine;hydrochloride Chemical compound Cl.N=1C2=CC=CC=C2OC=1C(CCN(C(C)C)C(C)C)C1=CC=CC=C1 BOVSDOOOPYUOQT-UHFFFAOYSA-N 0.000 description 1
- BSSXVAYOSSAQEY-UHFFFAOYSA-N 3-(1,3-oxazol-2-yl)-3-phenyl-n,n-di(propan-2-yl)propan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCN(C(C)C)C(C)C)C1=NC=CO1 BSSXVAYOSSAQEY-UHFFFAOYSA-N 0.000 description 1
- BVNNSRJSRADLEH-UHFFFAOYSA-N 3-(1,3-oxazol-5-yl)-3-phenyl-n,n-di(propan-2-yl)propan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCN(C(C)C)C(C)C)C1=CN=CO1 BVNNSRJSRADLEH-UHFFFAOYSA-N 0.000 description 1
- ZBLMXLBLBDYCSD-UHFFFAOYSA-N 3-(1-methylpyrrol-2-yl)-n,n-di(propan-2-yl)prop-2-enamide Chemical compound CC(C)N(C(C)C)C(=O)C=CC1=CC=CN1C ZBLMXLBLBDYCSD-UHFFFAOYSA-N 0.000 description 1
- MPYKUEGGMSTVRH-UHFFFAOYSA-N 3-(3-methoxyphenyl)-n,n-di(propan-2-yl)-3-thiophen-2-ylpropan-1-amine;hydrochloride Chemical compound Cl.COC1=CC=CC(C(CCN(C(C)C)C(C)C)C=2SC=CC=2)=C1 MPYKUEGGMSTVRH-UHFFFAOYSA-N 0.000 description 1
- WNJAGPYUDAOEBZ-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n,n-di(propan-2-yl)-3-thiophen-2-ylpropan-1-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C(CCN(C(C)C)C(C)C)C1=CC=CS1 WNJAGPYUDAOEBZ-UHFFFAOYSA-N 0.000 description 1
- SCXQJJQXVRVRPW-UHFFFAOYSA-N 3-(4-methyl-1,3-thiazol-2-yl)-3-phenyl-n,n-di(propan-2-yl)propan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCN(C(C)C)C(C)C)C1=NC(C)=CS1 SCXQJJQXVRVRPW-UHFFFAOYSA-N 0.000 description 1
- AESIFZBFAKULOJ-UHFFFAOYSA-N 3-(furan-2-yl)-3-phenyl-n,n-di(propan-2-yl)propan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCN(C(C)C)C(C)C)C1=CC=CO1 AESIFZBFAKULOJ-UHFFFAOYSA-N 0.000 description 1
- KHFWQOYQXGSMED-UHFFFAOYSA-N 3-(furan-2-yl)-n,n-di(propan-2-yl)prop-2-enamide Chemical compound CC(C)N(C(C)C)C(=O)C=CC1=CC=CO1 KHFWQOYQXGSMED-UHFFFAOYSA-N 0.000 description 1
- IPDKEUGHBKQTSH-VEIFNGETSA-N 3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxybenzaldehyde;hydrochloride Chemical compound Cl.C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=O)C=2)O)=CC=CC=C1 IPDKEUGHBKQTSH-VEIFNGETSA-N 0.000 description 1
- ABKAAQNSTLSMSI-UHFFFAOYSA-N 3-[2-[(4-hydroxy-3,5-dimethylphenyl)diazenyl]phenyl]-3-phenyl-N,N-di(propan-2-yl)prop-2-enamide Chemical compound C=1C=CC=C(N=NC=2C=C(C)C(O)=C(C)C=2)C=1C(=CC(=O)N(C(C)C)C(C)C)C1=CC=CC=C1 ABKAAQNSTLSMSI-UHFFFAOYSA-N 0.000 description 1
- KAUNKKOHFWTFBD-OAQYLSRUSA-N 3-[3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxyphenyl]propanamide Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CCC(N)=O)C=2)O)=CC=CC=C1 KAUNKKOHFWTFBD-OAQYLSRUSA-N 0.000 description 1
- HICVNWLIMJRFNJ-ZMBIFBSDSA-N 3-[3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxyphenyl]propanamide;hydrochloride Chemical compound Cl.C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CCC(N)=O)C=2)O)=CC=CC=C1 HICVNWLIMJRFNJ-ZMBIFBSDSA-N 0.000 description 1
- RYBZMVRTONWJJF-JOCHJYFZSA-N 3-[3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxyphenyl]propanenitrile Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CCC#N)C=2)O)=CC=CC=C1 RYBZMVRTONWJJF-JOCHJYFZSA-N 0.000 description 1
- DNLCSYCFCIVCQT-VZYDHVRKSA-N 3-[3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxyphenyl]propanenitrile;hydrochloride Chemical compound Cl.C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CCC#N)C=2)O)=CC=CC=C1 DNLCSYCFCIVCQT-VZYDHVRKSA-N 0.000 description 1
- MQMUPFNBTZAHAJ-ZMBIFBSDSA-N 3-[3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxyphenyl]propanoic acid;hydrochloride Chemical compound Cl.C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CCC(O)=O)C=2)O)=CC=CC=C1 MQMUPFNBTZAHAJ-ZMBIFBSDSA-N 0.000 description 1
- LXXCVBXNPJGWGC-UHFFFAOYSA-N 3-cyano-3-phenyl-N,N-di(propan-2-yl)propanamide 3-cyano-3-phenylpropanoic acid Chemical compound C(#N)C(CC(=O)O)C1=CC=CC=C1.C(C)(C)N(C(CC(C1=CC=CC=C1)C#N)=O)C(C)C LXXCVBXNPJGWGC-UHFFFAOYSA-N 0.000 description 1
- OJNHEPLKBNQATC-UHFFFAOYSA-N 3-cyano-3-phenyl-n,n-di(propan-2-yl)propanamide;2-phenyl-n',n'-di(propan-2-yl)butanediamide Chemical compound CC(C)N(C(C)C)C(=O)CC(C#N)C1=CC=CC=C1.CC(C)N(C(C)C)C(=O)CC(C(N)=O)C1=CC=CC=C1 OJNHEPLKBNQATC-UHFFFAOYSA-N 0.000 description 1
- GMPNSKPTQXVWAF-UHFFFAOYSA-N 3-cyano-3-phenylpropanoic acid Chemical compound OC(=O)CC(C#N)C1=CC=CC=C1 GMPNSKPTQXVWAF-UHFFFAOYSA-N 0.000 description 1
- RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 1
- UTBSGBPARBUSQW-UHFFFAOYSA-N 3-phenyl-N,N-di(propan-2-yl)-3-thiophen-2-ylpropan-1-amine hydrochloride Chemical compound Cl.C(C)(C)N(CCC(C=1SC=CC1)C1=CC=CC=C1)C(C)C UTBSGBPARBUSQW-UHFFFAOYSA-N 0.000 description 1
- TXGCFBQOZQASDR-UHFFFAOYSA-N 3-phenyl-n,n-di(propan-2-yl)-3-(1,3-thiazol-2-yl)propan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCN(C(C)C)C(C)C)C1=NC=CS1 TXGCFBQOZQASDR-UHFFFAOYSA-N 0.000 description 1
- QSQXCESJBWSDOE-UHFFFAOYSA-N 3-phenyl-n,n-di(propan-2-yl)-3-(1,3-thiazol-5-yl)propan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCN(C(C)C)C(C)C)C1=CN=CS1 QSQXCESJBWSDOE-UHFFFAOYSA-N 0.000 description 1
- JNHWMIKNCIRXFO-UHFFFAOYSA-N 3-phenyl-n,n-di(propan-2-yl)-3-[2-(trifluoromethyl)phenyl]propan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=C(C(F)(F)F)C=1C(CCN(C(C)C)C(C)C)C1=CC=CC=C1 JNHWMIKNCIRXFO-UHFFFAOYSA-N 0.000 description 1
- WVAUXZZPKMRRBE-UHFFFAOYSA-N 3-phenyl-n,n-di(propan-2-yl)-3-thiophen-3-ylpropan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCN(C(C)C)C(C)C)C=1C=CSC=1 WVAUXZZPKMRRBE-UHFFFAOYSA-N 0.000 description 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
- CQWFSQJROMJICT-JOCHJYFZSA-N 4-(3-aminopropyl)-2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]phenol Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CCCN)C=2)O)=CC=CC=C1 CQWFSQJROMJICT-JOCHJYFZSA-N 0.000 description 1
- ZDLOGUJIIFKYMH-GJICFQLNSA-N 4-(3-aminopropyl)-2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]phenol;dihydrochloride Chemical compound Cl.Cl.C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CCCN)C=2)O)=CC=CC=C1 ZDLOGUJIIFKYMH-GJICFQLNSA-N 0.000 description 1
- BSFNMJAZQOYYHB-HZPIKELBSA-N 4-[2-[di(propan-2-yl)amino]ethyl]-2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]phenol;hydrochloride Chemical compound Cl.C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CCN(C(C)C)C(C)C)C=2)O)=CC=CC=C1 BSFNMJAZQOYYHB-HZPIKELBSA-N 0.000 description 1
- YCTHNQPOTPIFTQ-UHFFFAOYSA-N 4-[3-[di(propan-2-yl)amino]-1-thiophen-2-ylpropyl]benzene-1,3-diol Chemical compound C=1C=C(O)C=C(O)C=1C(CCN(C(C)C)C(C)C)C1=CC=CS1 YCTHNQPOTPIFTQ-UHFFFAOYSA-N 0.000 description 1
- SZPVBJHNOFWCDK-UHFFFAOYSA-N 4-[di(propan-2-yl)amino]-2-phenylbutanamide Chemical compound CC(C)N(C(C)C)CCC(C(N)=O)C1=CC=CC=C1 SZPVBJHNOFWCDK-UHFFFAOYSA-N 0.000 description 1
- UDYYBQFPNPVIKM-UHFFFAOYSA-N 4-[di(propan-2-yl)amino]-2-phenylbutanamide ethyl 4-[di(propan-2-yl)amino]-2-phenylbutanoate Chemical compound C(C)(C)N(CCC(C1=CC=CC=C1)C(N)=O)C(C)C.C(C)(C)N(CCC(C1=CC=CC=C1)C(=O)OCC)C(C)C UDYYBQFPNPVIKM-UHFFFAOYSA-N 0.000 description 1
- MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 description 1
- WQQCLUUXZXDTMS-WJOKGBTCSA-N 6-[3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-phenylmethoxyphenyl]hex-5-enoic acid Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=CCCCC(O)=O)C=2)OCC=2C=CC=CC=2)=CC=CC=C1 WQQCLUUXZXDTMS-WJOKGBTCSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- RKMINRRVKFFUJD-UHFFFAOYSA-N BrC=1SC=CC1.C(C)(C)N(C(C=CC=1SC=CC1)=O)C(C)C Chemical compound BrC=1SC=CC1.C(C)(C)N(C(C=CC=1SC=CC1)=O)C(C)C RKMINRRVKFFUJD-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JKEHQQGRKOOCAV-UHFFFAOYSA-N C(C)(C)N(CCC(C1=CC=CC=C1)C#N)C(C)C.C(C)(C)N(CCC(C1=CC=CC=C1)C(N)=O)C(C)C Chemical compound C(C)(C)N(CCC(C1=CC=CC=C1)C#N)C(C)C.C(C)(C)N(CCC(C1=CC=CC=C1)C(N)=O)C(C)C JKEHQQGRKOOCAV-UHFFFAOYSA-N 0.000 description 1
- GUHXDVGQEHGMGH-WXXKFALUSA-N C(\C=C\C(=O)O)(=O)O.COC1=C(C=CC=C1)C(CCN)C=1SC=CC1.C(C)(C)NC(C)C Chemical compound C(\C=C\C(=O)O)(=O)O.COC1=C(C=CC=C1)C(CCN)C=1SC=CC1.C(C)(C)NC(C)C GUHXDVGQEHGMGH-WXXKFALUSA-N 0.000 description 1
- JEUNKORWLZWLRG-UHFFFAOYSA-N CC(C)N(C(C)C)C(=O)C=C(c1ccccc1)c1ccccc1N.CC(C)N(C(C)C)C(=O)C=C(c1ccccc1)c1ccccc1N=Nc1cc(C)c(O)c(C)c1 Chemical compound CC(C)N(C(C)C)C(=O)C=C(c1ccccc1)c1ccccc1N.CC(C)N(C(C)C)C(=O)C=C(c1ccccc1)c1ccccc1N=Nc1cc(C)c(O)c(C)c1 JEUNKORWLZWLRG-UHFFFAOYSA-N 0.000 description 1
- PJYKHNYACSTLLS-UHFFFAOYSA-N CCOP(=O)OCC.CC(C)N(C(C)C)C(C)=O Chemical compound CCOP(=O)OCC.CC(C)N(C(C)C)C(C)=O PJYKHNYACSTLLS-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- QLTIKURIPRNYLZ-FSRHSHDFSA-N Cl.C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=2)N=[N+]=[N-])O)=CC=CC=C1 Chemical compound Cl.C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=2)N=[N+]=[N-])O)=CC=CC=C1 QLTIKURIPRNYLZ-FSRHSHDFSA-N 0.000 description 1
- QASFUMOKHFSJGL-LAFRSMQTSA-N Cyclopamine Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H](CC2=C3C)[C@@H]1[C@@H]2CC[C@@]13O[C@@H]2C[C@H](C)CN[C@H]2[C@H]1C QASFUMOKHFSJGL-LAFRSMQTSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KBEBGUQPQBELIU-CMDGGOBGSA-N Ethyl cinnamate Chemical compound CCOC(=O)\C=C\C1=CC=CC=C1 KBEBGUQPQBELIU-CMDGGOBGSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000001358 L(+)-tartaric acid Substances 0.000 description 1
- 235000011002 L(+)-tartaric acid Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 229940121743 Muscarinic receptor agonist Drugs 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000000921 Urge Urinary Incontinence Diseases 0.000 description 1
- SEEPTNSKENXPBS-UHFFFAOYSA-N [4-[[2-[3-[di(propan-2-yl)amino]-3-oxo-1-phenylprop-1-enyl]phenyl]diazenyl]-2,6-dimethylphenyl] 4-methylbenzenesulfonate Chemical compound C=1C=CC=C(N=NC=2C=C(C)C(OS(=O)(=O)C=3C=CC(C)=CC=3)=C(C)C=2)C=1C(=CC(=O)N(C(C)C)C(C)C)C1=CC=CC=C1 SEEPTNSKENXPBS-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012925 biological evaluation Methods 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- WDJQAYUPVJEQJW-UHFFFAOYSA-N chloroform;n,n-diethylethanamine;methanol Chemical compound OC.ClC(Cl)Cl.CCN(CC)CC WDJQAYUPVJEQJW-UHFFFAOYSA-N 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- KBEBGUQPQBELIU-UHFFFAOYSA-N cinnamic acid ethyl ester Natural products CCOC(=O)C=CC1=CC=CC=C1 KBEBGUQPQBELIU-UHFFFAOYSA-N 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 150000004691 decahydrates Chemical class 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- 235000019700 dicalcium phosphate Nutrition 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- ZRKSVHFXTRFQFL-UHFFFAOYSA-N isocyanomethane Chemical compound C[N+]#[C-] ZRKSVHFXTRFQFL-UHFFFAOYSA-N 0.000 description 1
- LYBKPDDZTNUNNM-UHFFFAOYSA-N isopropylbenzylamine Chemical compound CC(C)NCC1=CC=CC=C1 LYBKPDDZTNUNNM-UHFFFAOYSA-N 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229960001375 lactose Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- RILWVYLDCFYYGU-VEIFNGETSA-N methyl 3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxybenzoate;hydrochloride Chemical compound Cl.COC(=O)C1=CC=C(O)C([C@H](CCN(C(C)C)C(C)C)C=2C=CC=CC=2)=C1 RILWVYLDCFYYGU-VEIFNGETSA-N 0.000 description 1
- YRJYQILAWNHFTB-HHHXNRCGSA-N methyl 3-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-phenylmethoxybenzoate Chemical compound C1([C@H](CCN(C(C)C)C(C)C)C=2C=CC=CC=2)=CC(C(=O)OC)=CC=C1OCC1=CC=CC=C1 YRJYQILAWNHFTB-HHHXNRCGSA-N 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000000472 muscarinic agonist Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- UOYMWALYYNKJJD-UHFFFAOYSA-N n,n-di(propan-2-yl)-3-thiophen-2-ylprop-2-enamide Chemical compound CC(C)N(C(C)C)C(=O)C=CC1=CC=CS1 UOYMWALYYNKJJD-UHFFFAOYSA-N 0.000 description 1
- ZYWWDMKBDWSFGT-UHFFFAOYSA-N n,n-di(propan-2-yl)-3-thiophen-3-ylprop-2-enamide Chemical compound CC(C)N(C(C)C)C(=O)C=CC=1C=CSC=1 ZYWWDMKBDWSFGT-UHFFFAOYSA-N 0.000 description 1
- YHOSNAAUPKDRMI-UHFFFAOYSA-N n,n-di(propan-2-yl)prop-2-enamide Chemical compound CC(C)N(C(C)C)C(=O)C=C YHOSNAAUPKDRMI-UHFFFAOYSA-N 0.000 description 1
- YMWUQUCSXBOUTD-UHFFFAOYSA-N n,n-diethylethanamine;hexane Chemical compound CCCCCC.CCN(CC)CC YMWUQUCSXBOUTD-UHFFFAOYSA-N 0.000 description 1
- DBVADBHSJCWFKI-UHFFFAOYSA-N n-(2-chloroethyl)-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)CCCl DBVADBHSJCWFKI-UHFFFAOYSA-N 0.000 description 1
- RUBSSNLSMUUSEW-UHFFFAOYSA-N n-benzyl-3-phenyl-3-(2-phenylmethoxyphenyl)-n-propan-2-ylpropan-1-amine Chemical compound C=1C=CC=CC=1CN(C(C)C)CCC(C=1C(=CC=CC=1)OCC=1C=CC=CC=1)C1=CC=CC=C1 RUBSSNLSMUUSEW-UHFFFAOYSA-N 0.000 description 1
- OQJUXUOBLLMNHN-UHFFFAOYSA-N n-methyl-3-phenyl-n-propan-2-yl-3-thiophen-2-ylpropan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCN(C)C(C)C)C1=CC=CS1 OQJUXUOBLLMNHN-UHFFFAOYSA-N 0.000 description 1
- VQZMQDJGUUFPNA-UHFFFAOYSA-N n-methyl-n-(3-phenyl-3-thiophen-2-ylpropyl)cyclohexanamine;hydrochloride Chemical compound Cl.C1CCCCC1N(C)CCC(C=1C=CC=CC=1)C1=CC=CS1 VQZMQDJGUUFPNA-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- QNEGFNAKVDHTEG-UHFFFAOYSA-N o-ethyl 4-[di(propan-2-yl)amino]-2-phenylbutanethioate Chemical compound CC(C)N(C(C)C)CCC(C(=S)OCC)C1=CC=CC=C1 QNEGFNAKVDHTEG-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 206010046494 urge incontinence Diseases 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/03—Monoamines
- C07C211/06—Monoamines containing only n- or iso-propyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
- C07C215/80—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring containing at least two amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/48—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C223/00—Compounds containing amino and —CHO groups bound to the same carbon skeleton
- C07C223/02—Compounds containing amino and —CHO groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- C07C247/16—Compounds containing azido groups with azido groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
- C07C255/43—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9701144A SE9701144D0 (sv) | 1997-03-27 | 1997-03-27 | Novel compounds, their use and preparation |
PCT/SE1998/000556 WO1998043942A1 (en) | 1997-03-27 | 1998-03-26 | Novel compounds, their use and preparation |
Publications (3)
Publication Number | Publication Date |
---|---|
NO994438D0 NO994438D0 (no) | 1999-09-13 |
NO994438L NO994438L (no) | 1999-11-26 |
NO314724B1 true NO314724B1 (no) | 2003-05-12 |
Family
ID=20406354
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19994438A NO314724B1 (no) | 1997-03-27 | 1999-09-13 | Terapeutisk aktive diarylpropylaminer samt fremstilling og anvendelse derav |
Country Status (26)
Country | Link |
---|---|
US (1) | US6313132B1 (ko) |
EP (1) | EP1019358B2 (ko) |
JP (1) | JP4187274B2 (ko) |
KR (1) | KR100774692B1 (ko) |
CN (2) | CN1251569A (ko) |
AR (1) | AR014868A1 (ko) |
AT (1) | ATE239693T1 (ko) |
AU (1) | AU739186B2 (ko) |
BR (2) | BR9808069B8 (ko) |
CA (1) | CA2284977C (ko) |
DE (2) | DE69814431T3 (ko) |
DK (1) | DK1019358T4 (ko) |
ES (1) | ES2199433T5 (ko) |
FR (1) | FR07C0049I2 (ko) |
HK (1) | HK1078561A1 (ko) |
LU (1) | LU91368I2 (ko) |
MY (1) | MY129473A (ko) |
NL (1) | NL300295I2 (ko) |
NO (1) | NO314724B1 (ko) |
NZ (1) | NZ337967A (ko) |
PT (1) | PT1019358E (ko) |
SE (1) | SE9701144D0 (ko) |
SI (1) | SI1019358T2 (ko) |
TW (1) | TW555735B (ko) |
WO (1) | WO1998043942A1 (ko) |
ZA (1) | ZA982478B (ko) |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0957073A1 (en) * | 1998-05-12 | 1999-11-17 | Schwarz Pharma Ag | Novel derivatives of 3,3-diphenylpropylamines |
DE19955190A1 (de) * | 1999-11-16 | 2001-06-21 | Sanol Arznei Schwarz Gmbh | Stabile Salze neuartiger Derivate von 3,3-Diphenylpropylaminen |
AU4274401A (en) | 2000-03-24 | 2001-10-03 | Meiji Seika Kaisha | Diphenylalkylamine derivatives useful as opioid delta receptor agonists |
DE10028443C1 (de) * | 2000-06-14 | 2002-05-29 | Sanol Arznei Schwarz Gmbh | Verfahren zur Herstellung von 3,3-Diarylpropylaminen, (R,S)- und (R)-4-Phenyl-2-chromanon-6-carbonsäure sowie (R)-4-Phenyl-2-chromanon-carbonsäure-cinchonidinsalz und deren Verwendung zur Herstellung eines rechtsdrehenden Hydroxybenzylalkohols und von pharmazeutischen Zusammensetzungen |
WO2002096855A2 (en) * | 2001-04-03 | 2002-12-05 | Aryx Therapeutics | Anticholinergic compounds and methods of use |
US20030027856A1 (en) * | 2001-06-29 | 2003-02-06 | Aberg A.K. Gunnar | Tolterodine metabolites |
JP3981357B2 (ja) | 2001-10-26 | 2007-09-26 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | 第4級アンモニウム化合物および抗ムスカリン剤としてのそれらの使用 |
WO2003039524A1 (en) * | 2001-11-09 | 2003-05-15 | Pharmacia Ab | Anti-muscarinic agent and estrogen-agonist for treating unstable or overactive bladder |
DE10315917A1 (de) | 2003-04-08 | 2004-11-18 | Schwarz Pharma Ag | Hochreine Basen von 3,3-Diphenylpropylaminmonoestern |
ATE545627T1 (de) * | 2003-05-23 | 2012-03-15 | Bridge Pharma Inc | Glattmuskelspasmolytika |
WO2005012227A2 (en) * | 2003-08-05 | 2005-02-10 | Ranbaxy Laboratories Limited | Process for preparation of 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethyl-phenol, a metabolite of tolterodine |
ES2235648B1 (es) * | 2003-12-22 | 2006-11-01 | Ragactives, S.L. | Procedimiento para la obtencion de tolterodina. |
CA2569238A1 (en) * | 2004-06-01 | 2005-12-15 | F. Hoffmann-La Roche Ag | Monoamine reuptake inhibitor |
AU2006319229B2 (en) | 2005-11-30 | 2011-09-15 | F. Hoffmann-La Roche Ag | Methods for synthesis of 3-amino-1-arylpropyl indoles |
WO2007062996A1 (en) | 2005-11-30 | 2007-06-07 | F. Hoffmann-La Roche Ag | 3-amino-1-arylpropyl indoles and aza-substituted indoles |
RU2008120141A (ru) | 2005-11-30 | 2010-01-10 | Ф. Хоффманн-Ля Рош Аг (Ch) | 3-амино-2-арилпропилазаиндолы и их применения |
CN101454273B (zh) * | 2006-05-31 | 2013-08-21 | 施瓦茨制药有限公司 | 取代的羟甲基苯酚的合成方法 |
CA2648333C (en) | 2006-06-09 | 2014-04-29 | Schwarz Pharma Ltd | Synthesis of phenolic esters of hydroxymethyl phenols |
CA2647990C (en) | 2006-06-12 | 2014-02-04 | Claus Meese | New chiral intermediate, process for producing the same and its use in the manufacture of tolterodine, fesoterodine, or the active metabolite thereof |
BRPI0713314A2 (pt) | 2006-06-20 | 2012-03-06 | Lek Pharmaceuticals D.D. | Processo para a preparação de 3-(2-hidróxi-5-fenil substituído)-n-alquil-3-fenilpropilaminas |
WO2010113813A1 (ja) | 2009-03-31 | 2010-10-07 | 大日本印刷株式会社 | 塩基発生剤、感光性樹脂組成物、当該感光性樹脂組成物からなるパターン形成用材料、当該感光性樹脂組成物を用いたパターン形成方法並びに物品 |
EP2281801B1 (en) * | 2009-07-27 | 2014-01-08 | Crystal Pharma, S.A.U. | Process for obtaining 3,3-diphenylpropylamines |
WO2011048409A1 (en) | 2009-10-20 | 2011-04-28 | Astrazeneca Ab | Cyclic amine derivatives having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
EP2364966A1 (en) * | 2010-03-09 | 2011-09-14 | LEK Pharmaceuticals d.d. | Process for preparation of 3-(2-hydroxy-5-substituted phenyl)-3-phenylpropylamines, intermediates for making hydroxytolterodine |
CZ2010997A3 (cs) * | 2010-12-30 | 2012-02-08 | Zentiva, K.S. | Zpusob výroby (2R,3R)-N,N-dimethyl-3-(3-hydroxyfenyl)-2-methylpentylaminu (tapentadolu) |
EP2508175A1 (en) | 2011-04-08 | 2012-10-10 | LEK Pharmaceuticals d.d. | Pharmaceutical composition comprising fesoterodine or a salt or a solvate thereof |
EP2508173A1 (en) | 2011-04-08 | 2012-10-10 | LEK Pharmaceuticals d.d. | Stabilized pharmaceutical composition comprising fesoterodine |
CZ2014400A3 (cs) | 2014-06-09 | 2015-12-16 | Zentiva, K.S. | Stabilizovaná formulace fesoterodinu |
CN110372571B (zh) | 2018-04-12 | 2022-11-15 | 中国科学院大连化学物理研究所 | 一种2-(2,2-二芳基乙基)-环胺衍生物或盐及合成和应用与组合物 |
CN111559992B (zh) * | 2020-05-29 | 2022-04-08 | 华中科技大学 | 一种2-芳基-γ-氨基丁酸衍生物的制备方法 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL271270A (ko) * | 1960-11-10 | |||
US3238242A (en) * | 1962-05-24 | 1966-03-01 | Chinoin Gyogyszer Es Vegyeszet | Process for the preparation of phenyl (meta-and para-tolyl)-propionitriles |
NL296693A (ko) * | 1962-08-16 | |||
DK111894A (ko) | 1962-11-15 | |||
GB1169944A (en) | 1966-08-25 | 1969-11-05 | Geistlich Soehne Ag | Novel 3,3-Diphenylpropylamines and processes for the preparation thereof |
GB1169945A (en) | 1966-08-25 | 1969-11-05 | Geistlich Soehne Ag | Pharmaceutical Compositions containing Diphenylalkyl-amine Derivatives |
HU200591B (en) * | 1986-07-11 | 1990-07-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing new diphenyl propylamine derivatives and pharmaceutical compositions comprising such compounds |
JPH02500108A (ja) | 1987-07-09 | 1990-01-18 | ザ ダウ ケミカル カンパニー | ビス(アミン含有)ベンゼンジオールの製造 |
SE8800207D0 (sv) * | 1988-01-22 | 1988-01-22 | Kabivitrum Ab | Nya aminer, deras anvendning och framstellning |
US5382600A (en) * | 1988-01-22 | 1995-01-17 | Pharmacia Aktiebolag | 3,3-diphenylpropylamines and pharmaceutical compositions thereof |
SE9203318D0 (sv) * | 1992-11-06 | 1992-11-06 | Kabi Pharmacia Ab | Novel 3,3-diphenylpropylamines, their use and preparation |
EP1423700A2 (en) † | 2001-09-04 | 2004-06-02 | Pfizer Limited | Affinity-assay for the human erg potassium channel |
CN1251569C (zh) * | 2003-09-25 | 2006-04-19 | 中国科学院西北高原生物研究所 | 花锚植物的引种栽培技术 |
-
1997
- 1997-03-27 SE SE9701144A patent/SE9701144D0/xx unknown
-
1998
- 1998-03-24 ZA ZA982478A patent/ZA982478B/xx unknown
- 1998-03-25 MY MYPI98001287A patent/MY129473A/en unknown
- 1998-03-26 BR BRPI9808069A patent/BR9808069B8/pt not_active IP Right Cessation
- 1998-03-26 WO PCT/SE1998/000556 patent/WO1998043942A1/en active IP Right Grant
- 1998-03-26 BR BRPI9808069A patent/BRPI9808069B8/pt unknown
- 1998-03-26 CA CA002284977A patent/CA2284977C/en not_active Expired - Lifetime
- 1998-03-26 SI SI9830486T patent/SI1019358T2/sl unknown
- 1998-03-26 AT AT98912864T patent/ATE239693T1/de active
- 1998-03-26 DK DK98912864T patent/DK1019358T4/da active
- 1998-03-26 JP JP54154898A patent/JP4187274B2/ja not_active Expired - Lifetime
- 1998-03-26 DE DE69814431T patent/DE69814431T3/de not_active Expired - Lifetime
- 1998-03-26 AR ARP980101393A patent/AR014868A1/es active IP Right Grant
- 1998-03-26 CN CN98803764A patent/CN1251569A/zh active Pending
- 1998-03-26 AU AU67552/98A patent/AU739186B2/en not_active Expired
- 1998-03-26 KR KR1019997008415A patent/KR100774692B1/ko not_active IP Right Cessation
- 1998-03-26 DE DE122007000067C patent/DE122007000067I1/de active Pending
- 1998-03-26 PT PT98912864T patent/PT1019358E/pt unknown
- 1998-03-26 ES ES98912864T patent/ES2199433T5/es not_active Expired - Lifetime
- 1998-03-26 NZ NZ337967A patent/NZ337967A/xx not_active IP Right Cessation
- 1998-03-26 US US09/381,868 patent/US6313132B1/en not_active Expired - Lifetime
- 1998-03-26 EP EP98912864A patent/EP1019358B2/en not_active Expired - Lifetime
- 1998-03-26 CN CNB2004100952769A patent/CN100482635C/zh not_active Expired - Lifetime
- 1998-04-09 TW TW087105376A patent/TW555735B/zh not_active IP Right Cessation
-
1999
- 1999-09-13 NO NO19994438A patent/NO314724B1/no not_active IP Right Cessation
-
2005
- 2005-11-18 HK HK05110397.3A patent/HK1078561A1/xx not_active IP Right Cessation
-
2007
- 2007-09-25 NL NL300295C patent/NL300295I2/nl unknown
- 2007-09-26 LU LU91368C patent/LU91368I2/fr unknown
- 2007-10-12 FR FR07C0049C patent/FR07C0049I2/fr active Active
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO314724B1 (no) | Terapeutisk aktive diarylpropylaminer samt fremstilling og anvendelse derav | |
AU2006242950B2 (en) | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3 -receptor ligands | |
EP1254895B1 (en) | Nitrogenous cyclic compounds and pharmaceutical compositions containing the same | |
AU781141B2 (en) | Novel use of phenylheteroalkylamine derivatives | |
RU2503660C2 (ru) | Замещенные производные 4-аминоциклогексана | |
US7005432B2 (en) | Substituted imidazol-pyridazine derivatives | |
KR101861942B1 (ko) | 신경 발생을 자극할 수 있는 n-페닐-락탐 유도체 및 이의 신경 장애 치료에서의 용도 | |
HUT66319A (en) | Benzanilide derivatives and pharmaceutical compositions containing them | |
NO329617B1 (no) | Tiazolderivater med CB1-antagonistisk, agonistisk eller partiell agonistisk aktivitet | |
WO2007079931A1 (de) | Substituierte oxadiazol-derivate und ihre verwendung als opioid-rezeptor liganden | |
US20150175534A1 (en) | Alpha-7 NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS AND USES THEROF-I | |
JP2007523179A (ja) | アセチレン系ピペラジン化合物、および、代謝型グルタミン酸受容体アンタゴニストとしてのそれらの使用 | |
JP2008542365A (ja) | 新規なmchr1アンタゴニスト並びにmchr1媒介状態及び障害の処置のためのそれらの使用 | |
KR20170100585A (ko) | 괴사 억제제 | |
EP1963288A1 (de) | Substituierte oxazol-derivate mit analgetischer wirkung | |
EP1963278A1 (de) | Substituierte imidazolin-derivate | |
JP2018138566A (ja) | 組成物、合成およびフェニルシクロアルキルメチルアミン誘導体を使用する方法 | |
JP3966693B2 (ja) | 含窒素環化合物およびそれらを含んでなる医薬組成物 | |
KR20190121664A (ko) | 신규한 hdac6 억제제를 이용한 치매 또는 인지장애 예방 또는 치료용 약학적 조성물 | |
JPH10251224A (ja) | 新規なチオカルバミン酸誘導体 | |
CZ272599A3 (cs) | Sulfonamidové deriváty | |
AU2009333620A1 (en) | N-(1-phenyl-2-arylethyl)-4,5-dihydro-3H-pyrrol-2-amine compounds as subtype selective modulators of alpha2B or alpha2B and alpha2C adrenoceptors |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MK1K | Patent expired |