NZ569630A - Cycloalkylamines as monoamine reuptake inhibitors - Google Patents
Cycloalkylamines as monoamine reuptake inhibitorsInfo
- Publication number
- NZ569630A NZ569630A NZ569630A NZ56963007A NZ569630A NZ 569630 A NZ569630 A NZ 569630A NZ 569630 A NZ569630 A NZ 569630A NZ 56963007 A NZ56963007 A NZ 56963007A NZ 569630 A NZ569630 A NZ 569630A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- substituted
- pharmaceutically acceptable
- disorder
- solvate
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title description 7
- 230000000407 monoamine reuptake Effects 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 184
- 150000003839 salts Chemical class 0.000 claims abstract description 69
- 239000012453 solvate Substances 0.000 claims abstract description 33
- 208000002193 Pain Diseases 0.000 claims abstract description 21
- 208000015114 central nervous system disease Diseases 0.000 claims abstract description 19
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 16
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims abstract description 11
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims abstract description 9
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 9
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 9
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims abstract description 8
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 7
- 208000001640 Fibromyalgia Diseases 0.000 claims abstract description 6
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 6
- 230000036506 anxiety Effects 0.000 claims abstract description 6
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims abstract description 6
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 6
- 208000028173 post-traumatic stress disease Diseases 0.000 claims abstract description 5
- 208000019116 sleep disease Diseases 0.000 claims abstract description 5
- 206010013954 Dysphoria Diseases 0.000 claims abstract description 4
- 208000005793 Restless legs syndrome Diseases 0.000 claims abstract description 4
- 230000007278 cognition impairment Effects 0.000 claims abstract description 4
- 208000020685 sleep-wake disease Diseases 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 326
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 85
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 101710164184 Synaptic vesicular amine transporter Proteins 0.000 claims description 40
- 102100034333 Synaptic vesicular amine transporter Human genes 0.000 claims description 40
- 230000000694 effects Effects 0.000 claims description 31
- 239000003814 drug Substances 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 238000011282 treatment Methods 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 24
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 230000005764 inhibitory process Effects 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 12
- 208000024714 major depressive disease Diseases 0.000 claims description 11
- 102000006441 Dopamine Plasma Membrane Transport Proteins Human genes 0.000 claims description 10
- 108010044266 Dopamine Plasma Membrane Transport Proteins Proteins 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 102000008092 Norepinephrine Plasma Membrane Transport Proteins Human genes 0.000 claims description 9
- 108010049586 Norepinephrine Plasma Membrane Transport Proteins Proteins 0.000 claims description 9
- 102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 claims description 9
- 108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 claims description 9
- 208000012672 seasonal affective disease Diseases 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000003981 vehicle Substances 0.000 claims description 7
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 6
- 208000004296 neuralgia Diseases 0.000 claims description 6
- 208000024732 dysthymic disease Diseases 0.000 claims description 5
- 208000021722 neuropathic pain Diseases 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 208000020925 Bipolar disease Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 208000020401 Depressive disease Diseases 0.000 claims description 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 3
- 201000002859 sleep apnea Diseases 0.000 claims description 3
- 201000003104 endogenous depression Diseases 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 230000009182 swimming Effects 0.000 claims description 2
- 230000009194 climbing Effects 0.000 claims 1
- 230000003137 locomotive effect Effects 0.000 claims 1
- 238000001543 one-way ANOVA Methods 0.000 claims 1
- -1 cycloalkane amine Chemical class 0.000 abstract description 153
- 150000001412 amines Chemical class 0.000 abstract description 55
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 270
- 238000000034 method Methods 0.000 description 249
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 201
- 238000005481 NMR spectroscopy Methods 0.000 description 191
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 187
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 132
- 101150041968 CDC13 gene Proteins 0.000 description 129
- 230000015572 biosynthetic process Effects 0.000 description 129
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 128
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 125
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 124
- 239000000243 solution Substances 0.000 description 111
- 238000004128 high performance liquid chromatography Methods 0.000 description 110
- 238000003786 synthesis reaction Methods 0.000 description 108
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 85
- 235000019439 ethyl acetate Nutrition 0.000 description 83
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 80
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 80
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 73
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 64
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 62
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
- 239000002904 solvent Substances 0.000 description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- 239000003921 oil Substances 0.000 description 51
- 235000019198 oils Nutrition 0.000 description 50
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 229910001868 water Inorganic materials 0.000 description 46
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 44
- 238000010898 silica gel chromatography Methods 0.000 description 44
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 43
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 41
- 230000000875 corresponding effect Effects 0.000 description 41
- 239000007787 solid Substances 0.000 description 41
- 230000014759 maintenance of location Effects 0.000 description 40
- 150000003141 primary amines Chemical class 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 239000012043 crude product Substances 0.000 description 38
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 38
- 125000001424 substituent group Chemical group 0.000 description 37
- 238000006722 reduction reaction Methods 0.000 description 33
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 31
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 31
- 239000012044 organic layer Substances 0.000 description 31
- 230000009467 reduction Effects 0.000 description 31
- 150000001408 amides Chemical class 0.000 description 29
- 235000019441 ethanol Nutrition 0.000 description 29
- 150000002825 nitriles Chemical class 0.000 description 28
- 239000000047 product Substances 0.000 description 28
- 229910000085 borane Inorganic materials 0.000 description 25
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 24
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 24
- 229940079593 drug Drugs 0.000 description 24
- 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 23
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 22
- 235000019253 formic acid Nutrition 0.000 description 22
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 21
- 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 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 239000012267 brine Substances 0.000 description 21
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 21
- 229960002748 norepinephrine Drugs 0.000 description 21
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 19
- 239000004480 active ingredient Substances 0.000 description 19
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 19
- 239000000543 intermediate Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 16
- 239000002552 dosage form Substances 0.000 description 16
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 16
- 150000003335 secondary amines Chemical class 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 238000009472 formulation Methods 0.000 description 15
- 239000003446 ligand Substances 0.000 description 15
- 239000012071 phase Substances 0.000 description 15
- 229910000104 sodium hydride Inorganic materials 0.000 description 15
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 13
- 239000003826 tablet Substances 0.000 description 13
- GDLOOQFSFHLRKT-UHFFFAOYSA-N 1-methylcyclohexane-1-carboxamide Chemical compound NC(=O)C1(C)CCCCC1 GDLOOQFSFHLRKT-UHFFFAOYSA-N 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- 125000000753 cycloalkyl group Chemical group 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 208000024891 symptom Diseases 0.000 description 12
- 230000029936 alkylation Effects 0.000 description 11
- 238000005804 alkylation reaction Methods 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 11
- 238000004296 chiral HPLC Methods 0.000 description 11
- 229960003638 dopamine Drugs 0.000 description 11
- 230000002401 inhibitory effect Effects 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- 238000004007 reversed phase HPLC Methods 0.000 description 11
- 229940076279 serotonin Drugs 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 230000001225 therapeutic effect Effects 0.000 description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 10
- 230000027455 binding Effects 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 238000013270 controlled release Methods 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 238000006268 reductive amination reaction Methods 0.000 description 10
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 10
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 239000012279 sodium borohydride Substances 0.000 description 10
- 229910000033 sodium borohydride Inorganic materials 0.000 description 10
- 241000282414 Homo sapiens Species 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000009471 action Effects 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 239000012458 free base Substances 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 9
- 150000002596 lactones Chemical class 0.000 description 9
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- 150000003973 alkyl amines Chemical class 0.000 description 8
- 238000003556 assay Methods 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 8
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 208000020016 psychiatric disease Diseases 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- 230000002441 reversible effect Effects 0.000 description 8
- 150000003512 tertiary amines Chemical class 0.000 description 8
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 7
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 7
- 238000003821 enantio-separation Methods 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 230000000946 synaptic effect Effects 0.000 description 7
- BSMNRYCSBFHEMQ-KCJUWKMLSA-N (1r,5s)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(Cl)C(Cl)=CC=C1[C@]1(CNC2)[C@@H]2C1 BSMNRYCSBFHEMQ-KCJUWKMLSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 239000000935 antidepressant agent Substances 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 125000002560 nitrile group Chemical group 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000002953 preparative HPLC Methods 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 238000004808 supercritical fluid chromatography Methods 0.000 description 6
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 6
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 6
- 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 6
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 5
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 5
- 208000024827 Alzheimer disease Diseases 0.000 description 5
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 description 5
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 5
- 108010010803 Gelatin Proteins 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 229930006000 Sucrose Natural products 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000008186 active pharmaceutical agent Substances 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- 210000003169 central nervous system Anatomy 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 229940088679 drug related substance Drugs 0.000 description 5
- 125000001207 fluorophenyl group Chemical group 0.000 description 5
- 229960002464 fluoxetine Drugs 0.000 description 5
- 239000008273 gelatin Substances 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 235000011852 gelatine desserts Nutrition 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 125000004474 heteroalkylene group Chemical group 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 238000001990 intravenous administration Methods 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- 210000005036 nerve Anatomy 0.000 description 5
- 210000002569 neuron Anatomy 0.000 description 5
- 239000002858 neurotransmitter agent Substances 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 235000015320 potassium carbonate Nutrition 0.000 description 5
- 239000000651 prodrug Substances 0.000 description 5
- 229940002612 prodrug Drugs 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000005720 sucrose Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 238000002560 therapeutic procedure Methods 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- XNQYQTCZUDFGJQ-UHFFFAOYSA-N [1-(3,4-dichlorophenyl)cyclobutyl]methanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CN)CCC1 XNQYQTCZUDFGJQ-UHFFFAOYSA-N 0.000 description 4
- AWFDYLNQFMKXDE-UHFFFAOYSA-N [1-(3,4-difluorophenyl)cyclohexyl]methanamine;hydrochloride Chemical compound Cl.C=1C=C(F)C(F)=CC=1C1(CN)CCCCC1 AWFDYLNQFMKXDE-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000010171 animal model Methods 0.000 description 4
- 229940005513 antidepressants Drugs 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- RHJVIGLEIFVHIJ-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1[CH]CCCC1 RHJVIGLEIFVHIJ-UHFFFAOYSA-N 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 230000007812 deficiency Effects 0.000 description 4
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 4
- 125000004188 dichlorophenyl group Chemical group 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 4
- 239000002502 liposome Substances 0.000 description 4
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- 239000012038 nucleophile Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 238000007911 parenteral administration Methods 0.000 description 4
- 229960002296 paroxetine Drugs 0.000 description 4
- 239000006187 pill Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- 150000008163 sugars Chemical class 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 4
- XWHBDOLRNWCIGO-UHFFFAOYSA-N (1-naphthalen-1-ylcyclohexyl)methanamine Chemical compound C=1C=CC2=CC=CC=C2C=1C1(CN)CCCCC1 XWHBDOLRNWCIGO-UHFFFAOYSA-N 0.000 description 3
- VAIVCJJEERBYIM-UHFFFAOYSA-N (1-phenylcyclohexyl)methanamine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(CN)CCCCC1 VAIVCJJEERBYIM-UHFFFAOYSA-N 0.000 description 3
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 3
- UFFRBOMGNQGCAY-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)cyclohexyl]-n,n-dimethylmethanamine Chemical compound C=1C=C(Cl)C=CC=1C1(CN(C)C)CCCCC1 UFFRBOMGNQGCAY-UHFFFAOYSA-N 0.000 description 3
- PXJDTWINCCFEMX-UHFFFAOYSA-N 3-(aminomethyl)-3-(3,4-dichlorophenyl)cyclohexan-1-ol Chemical class C=1C=C(Cl)C(Cl)=CC=1C1(CN)CCCC(O)C1 PXJDTWINCCFEMX-UHFFFAOYSA-N 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- 208000000044 Amnesia Diseases 0.000 description 3
- 241000416162 Astragalus gummifer Species 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- DYHSDKLCOJIUFX-UHFFFAOYSA-N Di-tert-butyl dicarbonate Substances CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 3
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 3
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 206010021639 Incontinence Diseases 0.000 description 3
- 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 3
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 3
- 240000007472 Leucaena leucocephala Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 208000019695 Migraine disease Diseases 0.000 description 3
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 3
- 229920002732 Polyanhydride Polymers 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229920001615 Tragacanth Polymers 0.000 description 3
- NMFAKPRDDDKVBP-UHFFFAOYSA-N [1-(3,4-dichlorophenyl)cycloheptyl]methanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CN)CCCCCC1 NMFAKPRDDDKVBP-UHFFFAOYSA-N 0.000 description 3
- LCHCBXNMUHCZMY-UHFFFAOYSA-N [1-(3-chlorophenyl)cyclohexyl]methanamine;hydrochloride Chemical compound Cl.C=1C=CC(Cl)=CC=1C1(CN)CCCCC1 LCHCBXNMUHCZMY-UHFFFAOYSA-N 0.000 description 3
- YZSUPDYMUSVHAR-UHFFFAOYSA-N [1-(4-fluoronaphthalen-1-yl)cyclohexyl]methanamine Chemical compound C=1C=C(F)C2=CC=CC=C2C=1C1(CN)CCCCC1 YZSUPDYMUSVHAR-UHFFFAOYSA-N 0.000 description 3
- 230000005856 abnormality Effects 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 235000010419 agar Nutrition 0.000 description 3
- 235000010443 alginic acid Nutrition 0.000 description 3
- 229920000615 alginic acid Polymers 0.000 description 3
- 150000004781 alginic acids Chemical class 0.000 description 3
- 230000001430 anti-depressive effect Effects 0.000 description 3
- 150000001499 aryl bromides Chemical class 0.000 description 3
- 230000033228 biological regulation Effects 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 210000004958 brain cell Anatomy 0.000 description 3
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
- 239000007894 caplet Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 235000010980 cellulose Nutrition 0.000 description 3
- 238000010568 chiral column chromatography Methods 0.000 description 3
- 230000019771 cognition Effects 0.000 description 3
- 150000003946 cyclohexylamines Chemical class 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 150000004656 dimethylamines Chemical class 0.000 description 3
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000012048 forced swim test Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229940093915 gynecological organic acid Drugs 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000007918 intramuscular administration Methods 0.000 description 3
- 229960004592 isopropanol Drugs 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 239000002207 metabolite Substances 0.000 description 3
- 150000003956 methylamines Chemical class 0.000 description 3
- 206010027599 migraine Diseases 0.000 description 3
- 230000036651 mood Effects 0.000 description 3
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 description 3
- OJPUSWIDKBVLFU-UHFFFAOYSA-N n-[[1-(3,4-dichlorophenyl)cyclohexyl]methyl]ethanamine;hydrochloride Chemical compound Cl.C=1C=C(Cl)C(Cl)=CC=1C1(CNCC)CCCCC1 OJPUSWIDKBVLFU-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 230000001242 postsynaptic effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 230000009183 running Effects 0.000 description 3
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 3
- 230000001568 sexual effect Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 235000010487 tragacanth Nutrition 0.000 description 3
- 239000000196 tragacanth Substances 0.000 description 3
- 229940116362 tragacanth Drugs 0.000 description 3
- 229960004688 venlafaxine Drugs 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- SAARGPSTPXUSIL-UHFFFAOYSA-N (1-naphthalen-2-ylcyclohexyl)methanamine Chemical compound C=1C=C2C=CC=CC2=CC=1C1(CN)CCCCC1 SAARGPSTPXUSIL-UHFFFAOYSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- LTSYNZQYIYTKNW-UHFFFAOYSA-N (6-fluoronaphthalen-2-yl)methanol Chemical compound C1=C(F)C=CC2=CC(CO)=CC=C21 LTSYNZQYIYTKNW-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- VKXUOQVDGXTZTH-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)cyclopent-3-en-1-yl]-n-methylmethanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CNC)CC=CC1 VKXUOQVDGXTZTH-UHFFFAOYSA-N 0.000 description 2
- RBTTVTNVCSFPKD-UHFFFAOYSA-N 1-[1-(3,4-difluorophenyl)cyclohexyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.C=1C=C(F)C(F)=CC=1C1(CN(C)C)CCCCC1 RBTTVTNVCSFPKD-UHFFFAOYSA-N 0.000 description 2
- FLAQOJMPRHHQFA-UHFFFAOYSA-N 1-[1-(3-chloro-4-fluorophenyl)cyclohexyl]-n-methylmethanamine Chemical compound C=1C=C(F)C(Cl)=CC=1C1(CNC)CCCCC1 FLAQOJMPRHHQFA-UHFFFAOYSA-N 0.000 description 2
- OQRNBXLNDRHWAT-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)cyclohexyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.C=1C=CC(Cl)=CC=1C1(CN(C)C)CCCCC1 OQRNBXLNDRHWAT-UHFFFAOYSA-N 0.000 description 2
- RZOBDKWPVHNHIC-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]cyclohexane-1-carbonitrile Chemical compound C1=CC(C(F)(F)F)=CC=C1C1(C#N)CCCCC1 RZOBDKWPVHNHIC-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- FUJSJWRORKKPAI-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1Cl FUJSJWRORKKPAI-UHFFFAOYSA-N 0.000 description 2
- IHCSARCBLKAYDN-UHFFFAOYSA-N 2-(6-fluoronaphthalen-2-yl)acetonitrile Chemical compound C1=C(CC#N)C=CC2=CC(F)=CC=C21 IHCSARCBLKAYDN-UHFFFAOYSA-N 0.000 description 2
- FQNISYMJARSLPX-UHFFFAOYSA-N 2-(bromomethyl)-6-fluoronaphthalene Chemical compound C1=C(CBr)C=CC2=CC(F)=CC=C21 FQNISYMJARSLPX-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- GWOMMAUEYXPNRP-UHFFFAOYSA-N 2-[[1-(3,4-dichlorophenyl)cyclohexyl]methylamino]cyclopentan-1-ol Chemical compound OC1CCCC1NCC1(C=2C=C(Cl)C(Cl)=CC=2)CCCCC1 GWOMMAUEYXPNRP-UHFFFAOYSA-N 0.000 description 2
- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
- NAENGEZVKXADGC-UHFFFAOYSA-N 3-(aminomethyl)-3-(3,4-dichlorophenyl)-1-methylcyclohexan-1-ol Chemical compound C1C(C)(O)CCCC1(CN)C1=CC=C(Cl)C(Cl)=C1 NAENGEZVKXADGC-UHFFFAOYSA-N 0.000 description 2
- PIXYARPXLBNXJR-UHFFFAOYSA-N 4,4-dimethylcyclohexane-1-carboxamide Chemical compound CC1(C)CCC(C(N)=O)CC1 PIXYARPXLBNXJR-UHFFFAOYSA-N 0.000 description 2
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 2
- 241000349731 Afzelia bipindensis Species 0.000 description 2
- 208000007848 Alcoholism Diseases 0.000 description 2
- 208000031091 Amnestic disease Diseases 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 108010078791 Carrier Proteins Proteins 0.000 description 2
- 208000001387 Causalgia Diseases 0.000 description 2
- 208000000094 Chronic Pain Diseases 0.000 description 2
- RXMFXKQKIJQIFC-UHFFFAOYSA-N Cl.C=1C=C(Cl)C(Cl)=CC=1C1(CN(C)CC)CCCCC1 Chemical compound Cl.C=1C=C(Cl)C(Cl)=CC=1C1(CN(C)CC)CCCCC1 RXMFXKQKIJQIFC-UHFFFAOYSA-N 0.000 description 2
- 208000023890 Complex Regional Pain Syndromes Diseases 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 206010012289 Dementia Diseases 0.000 description 2
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 241000206672 Gelidium Species 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 208000004454 Hyperalgesia Diseases 0.000 description 2
- 208000035154 Hyperesthesia Diseases 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- 229910020667 PBr3 Inorganic materials 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 208000006262 Psychological Sexual Dysfunctions Diseases 0.000 description 2
- 208000028017 Psychotic disease Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 201000001880 Sexual dysfunction Diseases 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 206010066218 Stress Urinary Incontinence Diseases 0.000 description 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
- KROLLEKHYZYOIF-UHFFFAOYSA-N [1-(2,4-dichlorophenyl)cyclohexyl]methanamine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C1(CN)CCCCC1 KROLLEKHYZYOIF-UHFFFAOYSA-N 0.000 description 2
- SVGMBLIFYWKNDC-UHFFFAOYSA-N [1-(3,4-dichlorophenyl)-3,3-difluorocyclohexyl]methanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CN)CCCC(F)(F)C1 SVGMBLIFYWKNDC-UHFFFAOYSA-N 0.000 description 2
- CTUZLMXCSKURAB-UHFFFAOYSA-N [1-(3,4-dichlorophenyl)cyclopentyl]methanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CN)CCCC1 CTUZLMXCSKURAB-UHFFFAOYSA-N 0.000 description 2
- VPDDMTHLPLVCMM-UHFFFAOYSA-N [1-(4-fluorophenyl)cyclohexyl]methanamine Chemical compound C=1C=C(F)C=CC=1C1(CN)CCCCC1 VPDDMTHLPLVCMM-UHFFFAOYSA-N 0.000 description 2
- XZUTVZVXEKNHHN-UHFFFAOYSA-N [1-(6-fluoronaphthalen-2-yl)cyclohexyl]methanamine Chemical compound C=1C=C2C=C(F)C=CC2=CC=1C1(CN)CCCCC1 XZUTVZVXEKNHHN-UHFFFAOYSA-N 0.000 description 2
- MILNRKCCACSUTQ-UHFFFAOYSA-N [2-(3,4-dichlorophenyl)-2-(ethylaminomethyl)cyclohexyl]methanol Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CNCC)CCCCC1CO MILNRKCCACSUTQ-UHFFFAOYSA-N 0.000 description 2
- DQTMXLZZAPRYGV-UHFFFAOYSA-K [diacetyloxy-(4-chlorophenyl)plumbyl] acetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)C1=CC=C(Cl)C=C1 DQTMXLZZAPRYGV-UHFFFAOYSA-K 0.000 description 2
- VGOLOFUVYIGQBD-UHFFFAOYSA-K [diacetyloxy-(4-methoxyphenyl)plumbyl] acetate Chemical compound COC1=CC=C([Pb](OC(C)=O)(OC(C)=O)OC(C)=O)C=C1 VGOLOFUVYIGQBD-UHFFFAOYSA-K 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000001800 adrenalinergic effect Effects 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
- 229960001126 alginic acid Drugs 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 238000010976 amide bond formation reaction Methods 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000003868 ammonium compounds Chemical class 0.000 description 2
- 230000008503 anti depressant like effect Effects 0.000 description 2
- 235000019789 appetite Nutrition 0.000 description 2
- 230000036528 appetite Effects 0.000 description 2
- 150000001543 aryl boronic acids Chemical class 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 235000012216 bentonite Nutrition 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229920002988 biodegradable polymer Polymers 0.000 description 2
- 239000004621 biodegradable polymer Substances 0.000 description 2
- 230000000035 biogenic effect Effects 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- 210000005013 brain tissue Anatomy 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 208000014439 complex regional pain syndrome type 2 Diseases 0.000 description 2
- 239000007891 compressed tablet Substances 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- GTBRTGPZZALPNS-MXHVRSFHSA-N cyanoketone Chemical compound C1C=C2C(C)(C)C(=O)[C@H](C#N)C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GTBRTGPZZALPNS-MXHVRSFHSA-N 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical class NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- SIIJRCRHAIMFNT-UHFFFAOYSA-N cyclopropanamine;hydrochloride Chemical compound Cl.NC1CC1 SIIJRCRHAIMFNT-UHFFFAOYSA-N 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000001212 derivatisation Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 125000005265 dialkylamine group Chemical group 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- BSMNRYCSBFHEMQ-UHFFFAOYSA-N dov-216,303 Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(CNC2)C2C1 BSMNRYCSBFHEMQ-UHFFFAOYSA-N 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 238000002651 drug therapy Methods 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- ZLYUKPJOVIEBGA-UHFFFAOYSA-N ethyl 1-(3-chlorophenyl)-2-hydroxycyclohexane-1-carboxylate Chemical compound C=1C=CC(Cl)=CC=1C1(C(=O)OCC)CCCCC1O ZLYUKPJOVIEBGA-UHFFFAOYSA-N 0.000 description 2
- GWYIZUQYPMYOSI-UHFFFAOYSA-N ethyl 1-(4-chloro-3-fluorophenyl)-2-hydroxycyclohexane-1-carboxylate Chemical compound C=1C=C(Cl)C(F)=CC=1C1(C(=O)OCC)CCCCC1O GWYIZUQYPMYOSI-UHFFFAOYSA-N 0.000 description 2
- DNSAVXQJMXTVRC-UHFFFAOYSA-N ethyl 2-hydroxy-1-[4-(trifluoromethyl)phenyl]cyclohexane-1-carboxylate Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1(C(=O)OCC)CCCCC1O DNSAVXQJMXTVRC-UHFFFAOYSA-N 0.000 description 2
- FGSGHBPKHFDJOP-UHFFFAOYSA-N ethyl 2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCCC1=O FGSGHBPKHFDJOP-UHFFFAOYSA-N 0.000 description 2
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 2
- 229940093471 ethyl oleate Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 206010016256 fatigue Diseases 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 2
- 238000006197 hydroboration reaction Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 150000001261 hydroxy acids Chemical class 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- ZCYVEMRRCGMTRW-YPZZEJLDSA-N iodine-125 Chemical compound [125I] ZCYVEMRRCGMTRW-YPZZEJLDSA-N 0.000 description 2
- 229940070765 laurate Drugs 0.000 description 2
- 239000008297 liquid dosage form Substances 0.000 description 2
- 239000000314 lubricant Substances 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
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 239000004530 micro-emulsion Substances 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- UTQLEVQLADDVHS-UHFFFAOYSA-N n,n-dimethyl-1-(1-naphthalen-1-ylcyclohexyl)methanamine Chemical compound C=1C=CC2=CC=CC=C2C=1C1(CN(C)C)CCCCC1 UTQLEVQLADDVHS-UHFFFAOYSA-N 0.000 description 2
- AWEAQYLFGOXJHA-UHFFFAOYSA-N n,n-dimethyl-1-[1-(4-methylsulfanylphenyl)cyclohexyl]methanamine Chemical compound C1=CC(SC)=CC=C1C1(CN(C)C)CCCCC1 AWEAQYLFGOXJHA-UHFFFAOYSA-N 0.000 description 2
- SYDXJSKTVHXBGQ-UHFFFAOYSA-N n,n-dimethyl-1-[1-[3-(trifluoromethyl)phenyl]cyclohexyl]methanamine Chemical compound C=1C=CC(C(F)(F)F)=CC=1C1(CN(C)C)CCCCC1 SYDXJSKTVHXBGQ-UHFFFAOYSA-N 0.000 description 2
- QIYANFXIRPCCFR-UHFFFAOYSA-N n,n-dimethyl-1-[1-[4-(trifluoromethyl)phenyl]cyclohexyl]methanamine Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1(CN(C)C)CCCCC1 QIYANFXIRPCCFR-UHFFFAOYSA-N 0.000 description 2
- ZZRHLICOWQQNJL-UHFFFAOYSA-N n-[[1-(3,4-dichlorophenyl)cyclohexyl]methyl]-n-methylethanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CN(C)CC)CCCCC1 ZZRHLICOWQQNJL-UHFFFAOYSA-N 0.000 description 2
- MWCFXXYOMLDMRG-UHFFFAOYSA-N n-[[1-(3,4-dichlorophenyl)cyclohexyl]methyl]cyclopropanamine;hydrochloride Chemical compound Cl.C1=C(Cl)C(Cl)=CC=C1C1(CNC2CC2)CCCCC1 MWCFXXYOMLDMRG-UHFFFAOYSA-N 0.000 description 2
- WQBHQWJJWWMKPS-UHFFFAOYSA-N n-methyl-1-(1-naphthalen-1-ylcyclohexyl)methanamine Chemical compound C=1C=CC2=CC=CC=C2C=1C1(CNC)CCCCC1 WQBHQWJJWWMKPS-UHFFFAOYSA-N 0.000 description 2
- WISXSHNMYCUZHH-UHFFFAOYSA-N n-methyl-1-(1-naphthalen-2-ylcyclohexyl)ethanamine Chemical compound C=1C=C2C=CC=CC2=CC=1C1(C(C)NC)CCCCC1 WISXSHNMYCUZHH-UHFFFAOYSA-N 0.000 description 2
- KRFDIGOXPVUJOM-UHFFFAOYSA-N n-methyl-1-(1-thiophen-2-ylcyclohexyl)ethanamine Chemical compound C=1C=CSC=1C1(C(C)NC)CCCCC1 KRFDIGOXPVUJOM-UHFFFAOYSA-N 0.000 description 2
- YNJHBZUBKJKAEC-UHFFFAOYSA-N n-methyl-1-[1-[3-(trifluoromethyl)phenyl]cyclohexyl]methanamine Chemical compound C=1C=CC(C(F)(F)F)=CC=1C1(CNC)CCCCC1 YNJHBZUBKJKAEC-UHFFFAOYSA-N 0.000 description 2
- ZZZAXWVNEPCNQE-UHFFFAOYSA-N n-methyl-1-[1-[4-(trifluoromethoxy)phenyl]cyclohexyl]ethanamine Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C1(C(C)NC)CCCCC1 ZZZAXWVNEPCNQE-UHFFFAOYSA-N 0.000 description 2
- OMEZNRIAKKKRHT-UHFFFAOYSA-N n-methyl-1-[1-[4-(trifluoromethyl)phenyl]cyclohexyl]methanamine Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1(CNC)CCCCC1 OMEZNRIAKKKRHT-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 210000004498 neuroglial cell Anatomy 0.000 description 2
- 239000012457 nonaqueous media Substances 0.000 description 2
- 230000001473 noxious effect Effects 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 208000033808 peripheral neuropathy Diseases 0.000 description 2
- 239000008177 pharmaceutical agent Substances 0.000 description 2
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 2
- 230000004962 physiological condition Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 208000026961 psychosexual disease Diseases 0.000 description 2
- 150000003235 pyrrolidines Chemical class 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000000862 serotonergic effect Effects 0.000 description 2
- 230000013275 serotonin uptake Effects 0.000 description 2
- 229960002073 sertraline Drugs 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- 231100000872 sexual dysfunction Toxicity 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000007909 solid dosage form Substances 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 239000002594 sorbent Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 210000003568 synaptosome Anatomy 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 125000005309 thioalkoxy group Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- UFXIRMVZNARBDL-UHFFFAOYSA-N trifluoro(morpholin-4-yl)-$l^{4}-sulfane Chemical compound FS(F)(F)N1CCOCC1 UFXIRMVZNARBDL-UHFFFAOYSA-N 0.000 description 2
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 2
- 239000003174 triple reuptake inhibitor Substances 0.000 description 2
- 229910052722 tritium Inorganic materials 0.000 description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-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
- IFTGEZOPUAJVMG-UHFFFAOYSA-N 1,1-dibromobut-1-ene Chemical compound CCC=C(Br)Br IFTGEZOPUAJVMG-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-NMQOAUCRSA-N 1,2-dideuteriooxyethane Chemical compound [2H]OCCO[2H] LYCAIKOWRPUZTN-NMQOAUCRSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical class BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- ORRFNEKJIRYORQ-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-methoxycyclohexane-1-carbonitrile Chemical compound C1C(OC)CCCC1(C#N)C1=CC=C(Cl)C(Cl)=C1 ORRFNEKJIRYORQ-UHFFFAOYSA-N 0.000 description 1
- NOKIGWPDUSAWBX-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-n,n-dimethylcyclohexane-1-carboxamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(C(=O)N(C)C)CCCCC1 NOKIGWPDUSAWBX-UHFFFAOYSA-N 0.000 description 1
- SJDWWUWLHXKFKC-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-n-methylcyclohexane-1-carboxamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(C(=O)NC)CCCCC1 SJDWWUWLHXKFKC-UHFFFAOYSA-N 0.000 description 1
- QEGCUNHOEAACFK-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)cyclohexane-1-carboxylic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(C(=O)O)CCCCC1 QEGCUNHOEAACFK-UHFFFAOYSA-N 0.000 description 1
- OSHOYPXOCQTDGJ-UHFFFAOYSA-N 1-(4-chlorophenyl)cyclohexane-1-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C1(C#N)CCCCC1 OSHOYPXOCQTDGJ-UHFFFAOYSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- MSRLFKAAHSYYJT-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)cyclohexyl]-n,n-dimethylmethanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CN(C)C)CCCCC1 MSRLFKAAHSYYJT-UHFFFAOYSA-N 0.000 description 1
- SPDFAGCVWXSLAU-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)cyclohexyl]propan-1-ol Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(C(O)CC)CCCCC1 SPDFAGCVWXSLAU-UHFFFAOYSA-N 0.000 description 1
- WBMNVGKXODDUFS-UHFFFAOYSA-N 1-[1-(3,4-difluorophenyl)cyclohexyl]-n-methylmethanamine;hydrochloride Chemical compound Cl.C=1C=C(F)C(F)=CC=1C1(CNC)CCCCC1 WBMNVGKXODDUFS-UHFFFAOYSA-N 0.000 description 1
- QSIUSSGCDXBSAQ-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)cyclohexyl]-n-methylmethanamine;hydrochloride Chemical compound Cl.C=1C=CC(Cl)=CC=1C1(CNC)CCCCC1 QSIUSSGCDXBSAQ-UHFFFAOYSA-N 0.000 description 1
- JCPLIJBMSKJFQE-UHFFFAOYSA-N 1-[1-(3-fluorophenyl)cyclohexyl]-n-methylmethanamine Chemical compound C=1C=CC(F)=CC=1C1(CNC)CCCCC1 JCPLIJBMSKJFQE-UHFFFAOYSA-N 0.000 description 1
- IVLZRBHUBNRBAH-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)cyclohexyl]-n-methylmethanamine;hydrochloride Chemical compound Cl.C=1C=C(Cl)C=CC=1C1(CNC)CCCCC1 IVLZRBHUBNRBAH-UHFFFAOYSA-N 0.000 description 1
- HVKCZUVMQPUWSX-UHFFFAOYSA-N 1-bromo-2,3-dichlorobenzene Chemical compound ClC1=CC=CC(Br)=C1Cl HVKCZUVMQPUWSX-UHFFFAOYSA-N 0.000 description 1
- LJIDJMVSECDENB-UHFFFAOYSA-N 1-cyclopropylcyclohexane-1-carboxamide Chemical compound C1CC1C1(C(=O)N)CCCCC1 LJIDJMVSECDENB-UHFFFAOYSA-N 0.000 description 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical class CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- RAFAUZBNXUAQRT-UHFFFAOYSA-N 1-ethyl-n-methylcyclohexane-1-carboxamide Chemical compound CNC(=O)C1(CC)CCCCC1 RAFAUZBNXUAQRT-UHFFFAOYSA-N 0.000 description 1
- BPOVRAAUERBWFK-UHFFFAOYSA-N 1-hydroxycyclohexane-1-carboxylic acid Chemical compound OC(=O)C1(O)CCCCC1 BPOVRAAUERBWFK-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- CHNMUXHAGUGWJF-UHFFFAOYSA-N 1-phenylcyclohexane-1-carbaldehyde Chemical compound C=1C=CC=CC=1C1(C=O)CCCCC1 CHNMUXHAGUGWJF-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 1
- QWZNCAFWRZZJMA-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)acetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1Cl QWZNCAFWRZZJMA-UHFFFAOYSA-N 0.000 description 1
- DEJPYROXSVVWIE-UHFFFAOYSA-N 2-(3-fluorophenyl)acetonitrile Chemical compound FC1=CC=CC(CC#N)=C1 DEJPYROXSVVWIE-UHFFFAOYSA-N 0.000 description 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- WFBPCVXJUKWTBA-UHFFFAOYSA-N 2-hydroxy-1-(4-methoxyphenyl)-n-methylcyclohexane-1-carboxamide Chemical compound C=1C=C(OC)C=CC=1C1(C(=O)NC)CCCCC1O WFBPCVXJUKWTBA-UHFFFAOYSA-N 0.000 description 1
- JNODDICFTDYODH-UHFFFAOYSA-N 2-hydroxytetrahydrofuran Chemical compound OC1CCCO1 JNODDICFTDYODH-UHFFFAOYSA-N 0.000 description 1
- LPCWDVLDJVZIHA-UHFFFAOYSA-N 2-naphthalen-2-ylacetonitrile Chemical compound C1=CC=CC2=CC(CC#N)=CC=C21 LPCWDVLDJVZIHA-UHFFFAOYSA-N 0.000 description 1
- RWMVCOUKVCLWIC-UHFFFAOYSA-N 2-oxocyclohexane-1-carbonitrile Chemical compound O=C1CCCCC1C#N RWMVCOUKVCLWIC-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- NTIGNJOEVBTPJJ-UHFFFAOYSA-N 3,3-dibromopentane Chemical compound CCC(Br)(Br)CC NTIGNJOEVBTPJJ-UHFFFAOYSA-N 0.000 description 1
- VAQNIUDWPOLHBT-UHFFFAOYSA-N 3,3-difluorocyclohexan-1-amine Chemical compound NC1CCCC(F)(F)C1 VAQNIUDWPOLHBT-UHFFFAOYSA-N 0.000 description 1
- KNKMSUDZFYUEBQ-UHFFFAOYSA-N 3,4-dichloro-n-cyclohexylaniline Chemical class C1=C(Cl)C(Cl)=CC=C1NC1CCCCC1 KNKMSUDZFYUEBQ-UHFFFAOYSA-N 0.000 description 1
- WXMSDLQBZMGSLY-UHFFFAOYSA-N 3,4-diphenylcyclohexan-1-amine Chemical compound C1C(N)CCC(C=2C=CC=CC=2)C1C1=CC=CC=C1 WXMSDLQBZMGSLY-UHFFFAOYSA-N 0.000 description 1
- ACEHPFMVELBCNI-UHFFFAOYSA-N 3-(aminomethyl)-3-(3,4-dichlorophenyl)cyclopentan-1-ol Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CN)CCC(O)C1 ACEHPFMVELBCNI-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- JWCFJPLIRVYENQ-UHFFFAOYSA-N 3-ethoxycyclohex-2-en-1-one Chemical compound CCOC1=CC(=O)CCC1 JWCFJPLIRVYENQ-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- JQGZGROVQGEGIO-UHFFFAOYSA-N 3-methoxycyclohexan-1-amine Chemical class COC1CCCC(N)C1 JQGZGROVQGEGIO-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- WLYUMBPDHPMKHM-UHFFFAOYSA-N 3a,4,5,6,7,7a-hexahydro-3h-2-benzofuran-1-one Chemical compound C1CCCC2C(=O)OCC21 WLYUMBPDHPMKHM-UHFFFAOYSA-N 0.000 description 1
- CPOPXARYEANNSX-UHFFFAOYSA-N 4,6-dimethoxytriazine Chemical compound COC1=CC(OC)=NN=N1 CPOPXARYEANNSX-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-M 4-aminobenzenesulfonate Chemical compound NC1=CC=C(S([O-])(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-M 0.000 description 1
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical class NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 1
- DEWIOKQDRWFLFW-UHFFFAOYSA-N 4-fluoronaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(F)C2=C1 DEWIOKQDRWFLFW-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- QIWQJGMBIABGRX-UHFFFAOYSA-N 4-oxocyclohexane-1-carbonitrile Chemical compound O=C1CCC(C#N)CC1 QIWQJGMBIABGRX-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- WUZCGLBJMGGJMO-UHFFFAOYSA-N 4a-(3,4-dichlorophenyl)-3-methyl-4,5,6,7,8,8a-hexahydro-2h-benzo[e][1,3]oxazine Chemical compound C1N(C)COC2CCCCC21C1=CC=C(Cl)C(Cl)=C1 WUZCGLBJMGGJMO-UHFFFAOYSA-N 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- CYKDCZRPLWJEKA-UHFFFAOYSA-N 6-fluoronaphthalene-2-carboxylic acid Chemical compound C1=C(F)C=CC2=CC(C(=O)O)=CC=C21 CYKDCZRPLWJEKA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VQPXZVKBTCCGRL-UHFFFAOYSA-N 7a-(3,4-dichlorophenyl)-3,3a,4,5,6,7-hexahydro-2-benzofuran-1-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(C(OC2)=O)C2CCCC1 VQPXZVKBTCCGRL-UHFFFAOYSA-N 0.000 description 1
- PDLDXOXJUWPJAN-UHFFFAOYSA-N 7a-phenyl-3,3a,4,5,6,7-hexahydro-2-benzofuran-1-one Chemical compound O=C1OCC2CCCCC12C1=CC=CC=C1 PDLDXOXJUWPJAN-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 108060003345 Adrenergic Receptor Proteins 0.000 description 1
- 102000017910 Adrenergic receptor Human genes 0.000 description 1
- 208000017194 Affective disease Diseases 0.000 description 1
- 206010001488 Aggression Diseases 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 208000007415 Anhedonia Diseases 0.000 description 1
- 235000003276 Apios tuberosa Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000010744 Arachis villosulicarpa Nutrition 0.000 description 1
- 208000036487 Arthropathies Diseases 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 206010003805 Autism Diseases 0.000 description 1
- 208000020706 Autistic disease Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- RDVAIIPFSISBIJ-UHFFFAOYSA-N CC(CC(C1)O)CC1(CN)C(C=C1)=CC(Cl)=C1Cl Chemical compound CC(CC(C1)O)CC1(CN)C(C=C1)=CC(Cl)=C1Cl RDVAIIPFSISBIJ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010058019 Cancer Pain Diseases 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 208000001573 Cataplexy Diseases 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- 206010010144 Completed suicide Diseases 0.000 description 1
- 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Natural products NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- 206010012374 Depressed mood Diseases 0.000 description 1
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-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
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 238000006228 Dieckmann condensation reaction Methods 0.000 description 1
- 102000015554 Dopamine receptor Human genes 0.000 description 1
- 108050004812 Dopamine receptor Proteins 0.000 description 1
- 206010013886 Dysaesthesia Diseases 0.000 description 1
- 208000004483 Dyspareunia Diseases 0.000 description 1
- 241000283073 Equus caballus Species 0.000 description 1
- 208000010228 Erectile Dysfunction Diseases 0.000 description 1
- 238000006824 Eschweiler-Clarke methylation reaction Methods 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 108010015899 Glycopeptides Proteins 0.000 description 1
- 102000002068 Glycopeptides Human genes 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- 102000000543 Histamine Receptors Human genes 0.000 description 1
- 108010002059 Histamine Receptors Proteins 0.000 description 1
- 208000033830 Hot Flashes Diseases 0.000 description 1
- 206010060800 Hot flush Diseases 0.000 description 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010020651 Hyperkinesia Diseases 0.000 description 1
- 208000000269 Hyperkinesis Diseases 0.000 description 1
- 206010065952 Hyperpathia Diseases 0.000 description 1
- 206010065390 Inflammatory pain Diseases 0.000 description 1
- 241000581650 Ivesia Species 0.000 description 1
- 208000012659 Joint disease Diseases 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 201000006792 Lennox-Gastaut syndrome Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 208000030431 Male orgasmic disease Diseases 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 102000003939 Membrane transport proteins Human genes 0.000 description 1
- 108090000301 Membrane transport proteins Proteins 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- DUGOZIWVEXMGBE-UHFFFAOYSA-N Methylphenidate Chemical group C=1C=CC=CC=1C(C(=O)OC)C1CCCCN1 DUGOZIWVEXMGBE-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 238000006751 Mitsunobu reaction Methods 0.000 description 1
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 1
- 208000019022 Mood disease Diseases 0.000 description 1
- 208000016285 Movement disease Diseases 0.000 description 1
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 1
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 1
- RTHCYVBBDHJXIQ-UHFFFAOYSA-N N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)OC1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 208000001294 Nociceptive Pain Diseases 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 208000004983 Phantom Limb Diseases 0.000 description 1
- 206010056238 Phantom pain Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920000954 Polyglycolide Polymers 0.000 description 1
- 229920001710 Polyorthoester Polymers 0.000 description 1
- 206010062519 Poor quality sleep Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010036618 Premenstrual syndrome Diseases 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 201000001947 Reflex Sympathetic Dystrophy Diseases 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 229910007161 Si(CH3)3 Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 206010042458 Suicidal ideation Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 208000000921 Urge Urinary Incontinence Diseases 0.000 description 1
- 206010046543 Urinary incontinence Diseases 0.000 description 1
- 206010047791 Vulvovaginal dryness Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- FVUNYNAPGFKYRV-UHFFFAOYSA-N [1-(3-fluorophenyl)cyclohexyl]methanamine Chemical compound C=1C=CC(F)=CC=1C1(CN)CCCCC1 FVUNYNAPGFKYRV-UHFFFAOYSA-N 0.000 description 1
- PGGTUNCWXAFOIJ-UHFFFAOYSA-N [1-[4-(trifluoromethyl)phenyl]cyclohexyl]methanamine Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1(CN)CCCCC1 PGGTUNCWXAFOIJ-UHFFFAOYSA-N 0.000 description 1
- JDWSDFASVMDEMI-UHFFFAOYSA-K [diacetyloxy(naphthalen-2-yl)plumbyl] acetate Chemical compound C1=CC=CC2=CC([Pb](OC(C)=O)(OC(C)=O)OC(=O)C)=CC=C21 JDWSDFASVMDEMI-UHFFFAOYSA-K 0.000 description 1
- RGJJUSDSGRRSJC-UHFFFAOYSA-K [diacetyloxy-(4-chloro-3-fluorophenyl)plumbyl] acetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)C1=CC=C(Cl)C(F)=C1 RGJJUSDSGRRSJC-UHFFFAOYSA-K 0.000 description 1
- UVHXKDREOOMOPF-UHFFFAOYSA-K [diacetyloxy-[4-(trifluoromethoxy)phenyl]plumbyl] acetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)C1=CC=C(OC(F)(F)F)C=C1 UVHXKDREOOMOPF-UHFFFAOYSA-K 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000003655 absorption accelerator Substances 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 208000012761 aggressive behavior Diseases 0.000 description 1
- 230000016571 aggressive behavior Effects 0.000 description 1
- 206010001584 alcohol abuse Diseases 0.000 description 1
- 201000007930 alcohol dependence Diseases 0.000 description 1
- 208000025746 alcohol use disease Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000005237 alkyleneamino group Chemical group 0.000 description 1
- 125000005238 alkylenediamino group Chemical group 0.000 description 1
- 125000005530 alkylenedioxy group Chemical group 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 206010053552 allodynia Diseases 0.000 description 1
- 102000030619 alpha-1 Adrenergic Receptor Human genes 0.000 description 1
- 108020004102 alpha-1 Adrenergic Receptor Proteins 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 229940126575 aminoglycoside Drugs 0.000 description 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
- 229960000836 amitriptyline Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000006986 amnesia Effects 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000037007 arousal Effects 0.000 description 1
- 125000005165 aryl thioxy group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 238000002820 assay format Methods 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 238000002306 biochemical method Methods 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
- 125000005620 boronic acid group Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 1
- 229960001058 bupropion Drugs 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000009084 cardiovascular function Effects 0.000 description 1
- 208000003295 carpal tunnel syndrome Diseases 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 150000003943 catecholamines Chemical class 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000012069 chiral reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 150000008371 chromenes Chemical class 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229960001653 citalopram Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000002493 climbing effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000001149 cognitive effect Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 238000011461 current therapy Methods 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 208000026725 cyclothymic disease Diseases 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 229960003914 desipramine Drugs 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
- OHCJAUNDJHZDGL-UHFFFAOYSA-N dimethyl 3-cyano-3-naphthalen-2-ylhexanedioate Chemical compound C1=CC=CC2=CC(C(CC(=O)OC)(C#N)CCC(=O)OC)=CC=C21 OHCJAUNDJHZDGL-UHFFFAOYSA-N 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000010249 dopaminergic function Effects 0.000 description 1
- 210000005064 dopaminergic neuron Anatomy 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 229940098766 effexor Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000008451 emotion Effects 0.000 description 1
- 230000006397 emotional response Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-L ethane-1,2-disulfonate Chemical compound [O-]S(=O)(=O)CCS([O-])(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 description 1
- ZRSDQBKGDNPFLT-UHFFFAOYSA-N ethanol;oxolane Chemical compound CCO.C1CCOC1 ZRSDQBKGDNPFLT-UHFFFAOYSA-N 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- TVKVOZGAYKOEOL-UHFFFAOYSA-N ethyl 1-(3,4-dichlorophenyl)-2-hydroxycyclohexane-1-carboxylate Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(C(=O)OCC)CCCCC1O TVKVOZGAYKOEOL-UHFFFAOYSA-N 0.000 description 1
- VUDTWTPENKPJEI-UHFFFAOYSA-N ethyl 1-(3,4-dichlorophenyl)-2-oxocyclohexane-1-carboxylate Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(C(=O)OCC)CCCCC1=O VUDTWTPENKPJEI-UHFFFAOYSA-N 0.000 description 1
- QSPHWBKYTDCTCH-UHFFFAOYSA-N ethyl 1-(3-chlorophenyl)-2-oxocyclohexane-1-carboxylate Chemical compound C=1C=CC(Cl)=CC=1C1(C(=O)OCC)CCCCC1=O QSPHWBKYTDCTCH-UHFFFAOYSA-N 0.000 description 1
- UWDYDEAUFUFJHO-UHFFFAOYSA-N ethyl 1-(4-chloro-3-fluorophenyl)-2-oxocyclohexane-1-carboxylate Chemical compound C=1C=C(Cl)C(F)=CC=1C1(C(=O)OCC)CCCCC1=O UWDYDEAUFUFJHO-UHFFFAOYSA-N 0.000 description 1
- QHSADIBDGOJZPT-UHFFFAOYSA-N ethyl 1-(4-chlorophenyl)-2-hydroxycyclohexane-1-carboxylate Chemical compound C=1C=C(Cl)C=CC=1C1(C(=O)OCC)CCCCC1O QHSADIBDGOJZPT-UHFFFAOYSA-N 0.000 description 1
- HIXDBCNUDXMJON-UHFFFAOYSA-N ethyl 1-(4-chlorophenyl)-2-oxocyclohexane-1-carboxylate Chemical compound C=1C=C(Cl)C=CC=1C1(C(=O)OCC)CCCCC1=O HIXDBCNUDXMJON-UHFFFAOYSA-N 0.000 description 1
- MXHSUAJIDRSFFU-UHFFFAOYSA-N ethyl 1-(4-methoxyphenyl)-2-oxocyclohexane-1-carboxylate Chemical compound C=1C=C(OC)C=CC=1C1(C(=O)OCC)CCCCC1=O MXHSUAJIDRSFFU-UHFFFAOYSA-N 0.000 description 1
- JCHLUYUWWQDLJJ-UHFFFAOYSA-N ethyl 1-naphthalen-2-yl-2-oxocyclohexane-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1C1(C(=O)OCC)CCCCC1=O JCHLUYUWWQDLJJ-UHFFFAOYSA-N 0.000 description 1
- VTAZHEFAWKETOM-UHFFFAOYSA-N ethyl 2-hydroxy-1-(4-methoxyphenyl)cyclohexane-1-carboxylate Chemical compound C=1C=C(OC)C=CC=1C1(C(=O)OCC)CCCCC1O VTAZHEFAWKETOM-UHFFFAOYSA-N 0.000 description 1
- LOKKXMFGOSWRPE-UHFFFAOYSA-N ethyl 2-hydroxy-1-naphthalen-2-ylcyclohexane-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1C1(C(=O)OCC)CCCCC1O LOKKXMFGOSWRPE-UHFFFAOYSA-N 0.000 description 1
- OAZGDZNXYPGAOK-UHFFFAOYSA-N ethyl 2-oxo-1-[4-(trifluoromethyl)phenyl]cyclohexane-1-carboxylate Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1(C(=O)OCC)CCCCC1=O OAZGDZNXYPGAOK-UHFFFAOYSA-N 0.000 description 1
- ACKIWGDNDSOAHU-UHFFFAOYSA-N ethyl 4-hydroxy-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-5-carboxylate Chemical compound OC1C(C(=O)OCC)CCC2OCOC21 ACKIWGDNDSOAHU-UHFFFAOYSA-N 0.000 description 1
- DMFBDVLUFAYFBX-UHFFFAOYSA-N ethyl 4-oxo-5,6,7,7a-tetrahydro-3aH-1,3-benzodioxole-5-carboxylate Chemical compound O=C1C(C(=O)OCC)CCC2OCOC21 DMFBDVLUFAYFBX-UHFFFAOYSA-N 0.000 description 1
- AEARPZNULDFPNQ-UHFFFAOYSA-N ethyl-carbamic acid methyl ester Chemical compound CCNC(=O)OC AEARPZNULDFPNQ-UHFFFAOYSA-N 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000013265 extended release Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 230000009760 functional impairment Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000007897 gelcap Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000003400 hallucinatory effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- JUMYIBMBTDDLNG-OJERSXHUSA-N hydron;methyl (2r)-2-phenyl-2-[(2r)-piperidin-2-yl]acetate;chloride Chemical compound Cl.C([C@@H]1[C@H](C(=O)OC)C=2C=CC=CC=2)CCCN1 JUMYIBMBTDDLNG-OJERSXHUSA-N 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 201000004197 inhibited female orgasm Diseases 0.000 description 1
- 201000000068 inhibited male orgasm Diseases 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000000185 intracerebroventricular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229940044173 iodine-125 Drugs 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229940099584 lactobionate Drugs 0.000 description 1
- JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- QBZXOWQOWPHHRA-UHFFFAOYSA-N lithium;ethane Chemical compound [Li+].[CH2-]C QBZXOWQOWPHHRA-UHFFFAOYSA-N 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 231100000863 loss of memory Toxicity 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- RMXGWLUCCKWPGK-UHFFFAOYSA-M magnesium;1,2-dichlorobenzene-5-ide;bromide Chemical compound [Mg+2].[Br-].ClC1=CC=[C-]C=C1Cl RMXGWLUCCKWPGK-UHFFFAOYSA-M 0.000 description 1
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
- RYEXTBOQKFUPOE-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].CC[CH2-] RYEXTBOQKFUPOE-UHFFFAOYSA-M 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 208000015421 male orgasm disease Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000006984 memory degeneration Effects 0.000 description 1
- 208000023060 memory loss Diseases 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- QSRRZKPKHJHIRB-UHFFFAOYSA-N methyl 4-[(2,5-dichloro-4-methylthiophen-3-yl)sulfonylamino]-2-hydroxybenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1NS(=O)(=O)C1=C(Cl)SC(Cl)=C1C QSRRZKPKHJHIRB-UHFFFAOYSA-N 0.000 description 1
- YKCRXOONSJLXJF-UHFFFAOYSA-N methyl 5-cyano-2-hydroxy-5-naphthalen-2-ylcyclohexene-1-carboxylate Chemical compound C1C(C(=O)OC)=C(O)CCC1(C#N)C1=CC=C(C=CC=C2)C2=C1 YKCRXOONSJLXJF-UHFFFAOYSA-N 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229960001344 methylphenidate Drugs 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 125000006682 monohaloalkyl group Chemical group 0.000 description 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 230000008450 motivation Effects 0.000 description 1
- 230000003551 muscarinic effect Effects 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- ROFHPDIVEBIITO-UHFFFAOYSA-N n,n-dimethyl-1-(1-naphthalen-1-ylcyclohexyl)ethanamine Chemical compound C=1C=CC2=CC=CC=C2C=1C1(C(N(C)C)C)CCCCC1 ROFHPDIVEBIITO-UHFFFAOYSA-N 0.000 description 1
- DIOWQSMFSBKMCS-UHFFFAOYSA-N n,n-dimethyl-1-(1-naphthalen-2-ylcyclohexyl)ethanamine Chemical compound C=1C=C2C=CC=CC2=CC=1C1(C(N(C)C)C)CCCCC1 DIOWQSMFSBKMCS-UHFFFAOYSA-N 0.000 description 1
- VECQSYDTGJGEFK-UHFFFAOYSA-N n,n-dimethyl-1-(1-phenylcyclohexyl)methanamine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(CN(C)C)CCCCC1 VECQSYDTGJGEFK-UHFFFAOYSA-N 0.000 description 1
- ISMSDKKDVZFDPK-UHFFFAOYSA-N n,n-dimethyl-1-phenylcyclohexane-1-carboxamide Chemical compound C=1C=CC=CC=1C1(C(=O)N(C)C)CCCCC1 ISMSDKKDVZFDPK-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- JZPODXHMQOJDHR-UHFFFAOYSA-N n-methyl-1-(1-naphthalen-1-ylcyclohexyl)ethanamine Chemical compound C=1C=CC2=CC=CC=C2C=1C1(C(C)NC)CCCCC1 JZPODXHMQOJDHR-UHFFFAOYSA-N 0.000 description 1
- QEDWSHUUJKHLMG-UHFFFAOYSA-N n-methyl-1-(1-phenylcyclohexyl)methanamine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(CNC)CCCCC1 QEDWSHUUJKHLMG-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 201000003631 narcolepsy Diseases 0.000 description 1
- 230000003955 neuronal function Effects 0.000 description 1
- 230000003982 neuronal uptake Effects 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 230000001962 neuropharmacologic effect Effects 0.000 description 1
- 206010029410 night sweats Diseases 0.000 description 1
- 230000036565 night sweats Effects 0.000 description 1
- ITJNARMNRKSWTA-UHFFFAOYSA-N nisoxetine Chemical compound C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1OC ITJNARMNRKSWTA-UHFFFAOYSA-N 0.000 description 1
- 229950004211 nisoxetine Drugs 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000002474 noradrenergic effect Effects 0.000 description 1
- 230000000966 norepinephrine reuptake Effects 0.000 description 1
- 230000012154 norepinephrine uptake Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OIPZNTLJVJGRCI-UHFFFAOYSA-M octadecanoyloxyaluminum;dihydrate Chemical compound O.O.CCCCCCCCCCCCCCCCCC(=O)O[Al] OIPZNTLJVJGRCI-UHFFFAOYSA-M 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 239000002997 ophthalmic solution Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 208000024449 overflow incontinence Diseases 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 208000035824 paresthesia Diseases 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000005897 peptide coupling reaction Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000000505 pernicious effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 125000004351 phenylcyclohexyl group Chemical group C1(=CC=CC=C1)C1(CCCCC1)* 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- DAPIMSMZSXHIOD-UHFFFAOYSA-N potassium;2-methylpropan-2-olate;methylsulfinylmethane Chemical compound [K+].CS(C)=O.CC(C)(C)[O-] DAPIMSMZSXHIOD-UHFFFAOYSA-N 0.000 description 1
- VBKNTGMWIPUCRF-UHFFFAOYSA-M potassium;fluoride;hydrofluoride Chemical compound F.[F-].[K+] VBKNTGMWIPUCRF-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 206010036596 premature ejaculation Diseases 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 229940035613 prozac Drugs 0.000 description 1
- 201000002274 psychologic vaginismus Diseases 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000029865 regulation of blood pressure Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 229940099204 ritalin Drugs 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000036186 satiety Effects 0.000 description 1
- 235000019627 satiety Nutrition 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000000698 schizophrenic effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 230000009155 sensory pathway Effects 0.000 description 1
- 239000003775 serotonin noradrenalin reuptake inhibitor Substances 0.000 description 1
- 230000000697 serotonin reuptake Effects 0.000 description 1
- 230000035946 sexual desire Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 230000016160 smooth muscle contraction Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 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
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 208000027765 speech disease Diseases 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 201000009032 substance abuse Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- OBCFIAREDRGTQB-UHFFFAOYSA-N tert-butyl n-[1-(3,4-dichlorophenyl)-2-methylcyclohexyl]-n-methylcarbamate Chemical compound CC1CCCCC1(N(C)C(=O)OC(C)(C)C)C1=CC=C(Cl)C(Cl)=C1 OBCFIAREDRGTQB-UHFFFAOYSA-N 0.000 description 1
- LJAHDVHDYCSTPV-UHFFFAOYSA-N tert-butyl n-[1-(3,4-dichlorophenyl)-3-hydroxy-3-methylcyclohexyl]-n-methylcarbamate Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(N(C(=O)OC(C)(C)C)C)CCCC(C)(O)C1 LJAHDVHDYCSTPV-UHFFFAOYSA-N 0.000 description 1
- PVJAMJWGEFXJLP-UHFFFAOYSA-N tert-butyl n-[[1-(3,4-dichlorophenyl)-2-methylcyclohexyl]methyl]-n-ethylcarbamate Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CN(CC)C(=O)OC(C)(C)C)CCCCC1C PVJAMJWGEFXJLP-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- CMJCEVKJYRZMIA-UHFFFAOYSA-M thallium(i) iodide Chemical compound [Tl]I CMJCEVKJYRZMIA-UHFFFAOYSA-M 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000006211 transdermal dosage form Substances 0.000 description 1
- 102000040811 transporter activity Human genes 0.000 description 1
- 108091092194 transporter activity Proteins 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- 206010046494 urge incontinence Diseases 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 230000001457 vasomotor Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- QUSLQENMLDRCTO-YJNKXOJESA-N win 35428 Chemical compound C1([C@H]2C[C@@H]3CC[C@@H](N3C)[C@H]2C(=O)OC)=CC=C(F)C=C1 QUSLQENMLDRCTO-YJNKXOJESA-N 0.000 description 1
- 229940020965 zoloft Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
-
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- C07C211/16—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings other than six-membered aromatic rings
- C07C211/17—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings other than six-membered aromatic rings containing only non-condensed rings
-
- 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
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/40—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing only non-condensed rings
-
- 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
- C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same 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
- C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/44—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton bound to carbon atoms of the same ring or condensed ring system
-
- 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
- C07C217/52—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same 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
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified 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
- C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified 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 rings other than six-membered aromatic rings being part of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
-
- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/06—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 no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- 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
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
-
- 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
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
-
- 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
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Epidemiology (AREA)
- Gynecology & Obstetrics (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Anesthesiology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75655006P | 2006-01-06 | 2006-01-06 | |
| PCT/US2007/000376 WO2007081857A2 (en) | 2006-01-06 | 2007-01-05 | Cycloalkylamines as monoamine reuptake inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ569630A true NZ569630A (en) | 2011-09-30 |
Family
ID=38256951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ569630A NZ569630A (en) | 2006-01-06 | 2007-01-05 | Cycloalkylamines as monoamine reuptake inhibitors |
Country Status (14)
| Country | Link |
|---|---|
| US (4) | US20070203111A1 (enExample) |
| EP (1) | EP1976513B1 (enExample) |
| JP (2) | JP5432526B2 (enExample) |
| KR (1) | KR101294014B1 (enExample) |
| CN (1) | CN101394847B (enExample) |
| AU (1) | AU2007205114B2 (enExample) |
| BR (1) | BRPI0706365A2 (enExample) |
| CA (1) | CA2636324C (enExample) |
| ES (1) | ES2594156T3 (enExample) |
| IL (1) | IL192613A (enExample) |
| NZ (1) | NZ569630A (enExample) |
| RU (2) | RU2430913C2 (enExample) |
| WO (1) | WO2007081857A2 (enExample) |
| ZA (1) | ZA200806145B (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005066135A2 (en) * | 2003-12-29 | 2005-07-21 | Sepracor Inc. | Pyrrole and pyrazole daao inhibitors |
| CA2957667A1 (en) | 2005-07-06 | 2007-01-11 | Sepracor Inc. | Combinations of eszopiclone and trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-n-methyl-1-napthalenamine or trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine, and methods of treatment of menopause and mood, anxiety, and cognitive disorders |
| JP5432526B2 (ja) * | 2006-01-06 | 2014-03-05 | サノビオン ファーマシューティカルズ インク | モノアミン再取り込み阻害剤としてのシクロアルキルアミン |
| CA2636275C (en) | 2006-01-06 | 2013-02-12 | Sepracor Inc. | Tetralone-based monoamine reuptake inhibitors |
| US8097760B2 (en) | 2006-03-31 | 2012-01-17 | Sunovion Pharmacuticals Inc. | Preparation of chiral amides and amines |
| EP2007723A2 (en) | 2006-04-11 | 2008-12-31 | Novartis AG | Organic compounds |
| US7884124B2 (en) * | 2006-06-30 | 2011-02-08 | Sepracor Inc. | Fluoro-substituted inhibitors of D-amino acid oxidase |
| US7579370B2 (en) * | 2006-06-30 | 2009-08-25 | Sepracor Inc. | Fused heterocycles |
| US8604244B2 (en) | 2010-07-02 | 2013-12-10 | Reviva Pharmaceuticals, Inc. | Compositions, synthesis, and methods of using cycloalkylmethylamine derivatives |
| RU2462451C2 (ru) | 2006-09-15 | 2012-09-27 | Ривайва Фармасьютикалс, Инк. | Способ получения, способы применения и композиции циклоалкилметиламинов |
| US20080082066A1 (en) * | 2006-10-02 | 2008-04-03 | Weyerhaeuser Co. | Crosslinked carboxyalkyl cellulose fibers having non-permanent and temporary crosslinks |
| CN101610761A (zh) * | 2006-12-22 | 2009-12-23 | 诺瓦提斯公司 | 作为ddp-iv抑制剂的1-氨基甲基-l-苯基-环己烷衍生物 |
| US7902252B2 (en) * | 2007-01-18 | 2011-03-08 | Sepracor, Inc. | Inhibitors of D-amino acid oxidase |
| JP2010516697A (ja) * | 2007-01-18 | 2010-05-20 | セプラコール インク. | D−アミノ酸オキシダーゼ阻害剤 |
| EP3296289A3 (en) | 2007-05-31 | 2018-06-20 | Sunovion Pharmaceuticals Inc. | Phenyl substituted cycloalkylamines as monoamine reuptake inhibitors |
| US20100120740A1 (en) * | 2008-08-07 | 2010-05-13 | Sepracor Inc. | Prodrugs of fused heterocyclic inhibitors of d-amino acid oxidase |
| CN102340992B (zh) * | 2009-02-09 | 2014-11-05 | 桑诺维恩药品公司 | 吡咯烷三重再摄取抑制剂 |
| US20110021928A1 (en) * | 2009-07-23 | 2011-01-27 | The Boards Of Trustees Of The Leland Stanford Junior University | Methods and system of determining cardio-respiratory parameters |
| WO2011017634A2 (en) * | 2009-08-07 | 2011-02-10 | Sepracore Inc. | Prodrugs of fused heterocyclic inhibitors of d-amino acid oxidase |
| SG186885A1 (en) | 2010-06-04 | 2013-02-28 | Albany Molecular Res Inc | Glycine transporter-1 inhibitors, methods of making them, and uses thereof |
| WO2012142067A2 (en) * | 2011-04-13 | 2012-10-18 | Sunovion Pharmaceuticals Inc. | Formulations, salts, and solid forms of substituted cyclohexylmethanamines, processes for preparation, and uses thereof |
| IN2014MN01407A (enExample) * | 2011-12-30 | 2015-07-03 | Reviva Pharmaceuticals Inc | |
| TWI613182B (zh) | 2013-02-21 | 2018-02-01 | 必治妥美雅史谷比公司 | 雙環化合物 |
| WO2014141110A2 (en) * | 2013-03-14 | 2014-09-18 | Curadev Pharma Pvt. Ltd. | Aminonitriles as kynurenine pathway inhibitors |
| WO2015027058A2 (en) * | 2013-08-21 | 2015-02-26 | Prexa Pharmaceuticals, Inc. | Cyclolkyl amine compounds |
| US9840482B2 (en) * | 2014-04-19 | 2017-12-12 | Sunshine Lake Pharma Co., Ltd. | Sulfonamide derivatives and pharmaceutical applications thereof |
| TWI689487B (zh) | 2014-08-20 | 2020-04-01 | 美商必治妥美雅史谷比公司 | 經取代雙環化合物 |
| CN104387279B (zh) * | 2014-10-29 | 2016-04-06 | 河南师范大学 | 一种简便合成3,3-二氟环己基甲胺的方法 |
| RU2637928C2 (ru) * | 2016-02-08 | 2017-12-08 | Закрытое Акционерное Общество "Вертекс" | Производные арилциклоалкиламинов, нейропротектор (варианты), вещество, обладающее сочетанным нейропротекторным, анальгетическим и антидепрессивным действием, фармацевтические композиции на его основе |
| CN110343050B (zh) | 2018-04-04 | 2021-09-24 | 上海键合医药科技有限公司 | 芳香类化合物及其制备方法和用途 |
| CN120842114A (zh) * | 2019-10-29 | 2025-10-28 | 株式会社Api | 高纯度2-萘乙腈及其生产方法 |
| CA3233930A1 (en) * | 2021-10-19 | 2023-04-27 | Justin KIRKLAND | Mesembrine derivatives |
| WO2024191676A2 (en) * | 2023-03-13 | 2024-09-19 | Miralogx Llc | Antidepressant compounds, pharmaceutical compositions, and methods of treating depression and other disorders |
| WO2025122822A1 (en) * | 2023-12-06 | 2025-06-12 | Sensorium Therapeutics, Inc. | Therapeutic alkaloid compounds |
Family Cites Families (150)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE112485C (enExample) | ||||
| BE616646A (enExample) | ||||
| US1124485A (en) * | 1913-07-08 | 1915-01-12 | Standard Knitting Mills Company | Undergarment. |
| DE1124485B (de) * | 1960-02-12 | 1962-03-01 | Hoechst Ag | Verfahren zur Herstellung von analeptisch wirksamen Phenylcycloalkylmethylaminen |
| DE1518545A1 (de) * | 1965-04-01 | 1970-01-15 | Boehringer Mannheim Gmbh | Verfahren zur Herstellung neuer Phenylcyclohexylalkylamine und ihrer Salze |
| US4105762A (en) | 1975-02-05 | 1978-08-08 | Rohm And Haas Company | Metal salt complexes of 1-substituted aralkyl imidazoles, and methods and compositions for controlling phytopathogenic fungi using them |
| SE7600674L (sv) | 1975-02-05 | 1976-08-06 | Rohm & Haas | Fungicider |
| US4065573A (en) * | 1976-06-03 | 1977-12-27 | The Upjohn Company | 4-Amino-4-phenylcyclohexanone ketal compositions and process of use |
| JPS6033106B2 (ja) | 1977-10-07 | 1985-08-01 | 住友化学工業株式会社 | カルボン酸エステル、その製造法およびそれを有効成分とする殺虫、殺ダニ剤 |
| US4369184A (en) * | 1980-01-24 | 1983-01-18 | Janssen Pharmaceutica N.V. | 1-(Cyclohexyl)-4-aryl-4-piperidinecarboxylic acid derivatives |
| ZA817261B (en) | 1980-10-23 | 1982-09-29 | Schering Corp | Carboxyalkyl dipeptides,processes for their production and pharmaceutical compositions containing them |
| US4540690A (en) | 1982-02-09 | 1985-09-10 | The Upjohn Company | 2-(Phenylmethylene)cycloalkylamines and -azetidines |
| JPS58177915A (ja) | 1982-04-12 | 1983-10-18 | Green Cross Corp:The | 抗血栓剤 |
| EP0100426A1 (en) * | 1982-07-28 | 1984-02-15 | American Cyanamid Company | 3a-(substituted-phenyl)-hexaloctahydro-4,7-alkanoisoindoles |
| EP0190224A1 (en) | 1984-07-30 | 1986-08-13 | Schering Corporation | PROCESS FOR THE PREPARATION OF CIS, ENDOOCTAHYDROCYCLOPENTA [b] PYRROLE-2-CARBOXYLATE |
| DE3431541A1 (de) | 1984-08-28 | 1986-03-06 | Hoechst Ag, 6230 Frankfurt | Cis,endo-2-azabicycloalkan-3-carbonsaeure-derivate, verfahren zu deren herstellung, deren verwendung sowie zwischenprodukte bei deren herstellung |
| US4738709A (en) | 1985-01-10 | 1988-04-19 | Ppg Industries, Inc. | Herbicidally active substituted benzisoxazoles |
| US5015644A (en) * | 1987-06-02 | 1991-05-14 | Warner-Lambert Company | Antihyperlipidemic and antiatherosclerotic urea and carbamate compounds |
| JPS6416786A (en) | 1987-07-09 | 1989-01-20 | Sumitomo Chemical Co | Thienopyrrolopyrroles and preparation thereof |
| US4751231A (en) | 1987-09-16 | 1988-06-14 | Merck & Co., Inc. | Substituted thieno[2,3-b]pyrrole-5-sulfonamides as antiglaucoma agents |
| JPH01172388A (ja) | 1987-12-25 | 1989-07-07 | Sumitomo Chem Co Ltd | チエノ〔3,2−b〕ピロロ〔2,3−d〕ピロール類およびその製法 |
| ATE103910T1 (de) * | 1988-06-14 | 1994-04-15 | Searle & Co | 1,2-diarylethylamine zur behandlung neurotoxischer verletzungen. |
| US4981870A (en) | 1989-03-07 | 1991-01-01 | Pfizer Inc. | Use of 4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine derivatives in the treatment of psychosis, inflammation and as immunosuppressants |
| PT93943A (pt) | 1989-05-05 | 1991-02-08 | Searle & Co | Processo para a preparacao de composicoes contendo compostos indole-2-carboxilato para tratamento de perturbacoes do snc |
| KR100195656B1 (ko) | 1989-05-31 | 1999-06-15 | 로버트 에이.아미테이지 | 치료학적으로 유용한 2-아미노테트랄린 유도체 |
| JPH0477476A (ja) | 1990-07-19 | 1992-03-11 | Sankyo Co Ltd | 抗潰瘍剤 |
| US5086054A (en) * | 1990-07-31 | 1992-02-04 | Sri International | Novel arylcycloalkanepolyalkylamines |
| CA2133439C (en) * | 1992-04-02 | 2005-07-26 | Siegfried Benjamin Christensen, Iv | Compounds useful for treating allergic and inflammatory diseases |
| GB9208492D0 (en) | 1992-04-16 | 1992-06-03 | Glaxo Spa | Heterocyclic compounds |
| CA2146755A1 (en) | 1992-10-28 | 1994-05-11 | Kenji Takeda | Novel 1,2-benzoisoxazole derivative or its salt and brain-protecting agent comprising the same |
| GB9304500D0 (en) | 1993-03-05 | 1993-04-21 | Glaxo Spa | Heterocyclic compounds |
| ES2081747B1 (es) | 1993-09-07 | 1997-01-16 | Esteve Labor Dr | Amidas derivadas de tienopirroles, su preparacion y su aplicacion como medicamentos. |
| GB9321221D0 (en) | 1993-10-14 | 1993-12-01 | Glaxo Spa | Heterocyclic compounds |
| GB9326284D0 (en) | 1993-12-23 | 1994-02-23 | Erba Carlo Spa | Pyrrolydenemethyl-derivatives and process for their preparation |
| CN1047384C (zh) | 1994-07-28 | 1999-12-15 | 北京大学 | 雷米普利的合成方法 |
| CA2198457A1 (en) | 1994-08-30 | 1996-03-07 | Koichi Kojima | Isoxazole derivatives |
| US5484763A (en) | 1995-02-10 | 1996-01-16 | American Cyanamid Company | Substituted benzisoxazole and benzisothiazole herbicidal agents |
| US5620997A (en) | 1995-05-31 | 1997-04-15 | Warner-Lambert Company | Isothiazolones |
| US5859042A (en) | 1995-09-27 | 1999-01-12 | Ono Pharmaceutical Co., Ltd. | Five membered heterocyclic compounds |
| NZ332334A (en) * | 1996-04-19 | 2000-06-23 | Akzo Nobel Nv | Substituted benzylamines and their use for the treatment of depression and other neurologically related disorders |
| EP0920424B1 (en) * | 1996-08-22 | 2005-11-30 | Warner-Lambert Company Llc | Non-peptide bombesin receptor antagonists |
| GB9619757D0 (en) * | 1996-09-21 | 1996-11-06 | Knoll Ag | Chemical process |
| GB9705428D0 (en) * | 1997-03-15 | 1997-04-30 | Knoll Ag | Therapeutic agents |
| DE19711785A1 (de) | 1997-03-21 | 1998-09-24 | Merck Patent Gmbh | Endothelin-Rezeptor-Antagonisten |
| EP0884640A1 (en) * | 1997-06-13 | 1998-12-16 | Eastman Kodak Company | Processing of photographic elements using N,N-dialkylhydroxylamine antioxidants in photographic color developers |
| US6080760A (en) * | 1997-06-18 | 2000-06-27 | Merck & Co., Inc. | Alpha 1A adrenergic receptor antagonists |
| GB9717804D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| AU9275498A (en) | 1997-10-03 | 1999-04-27 | Chirotech Technology Limited | Chiral amines |
| GB9803226D0 (en) | 1998-02-17 | 1998-04-08 | Zeneca Ltd | Chemical compounds |
| GB9803228D0 (en) | 1998-02-17 | 1998-04-08 | Zeneca Ltd | Chemical compounds |
| EP1066257A2 (en) | 1998-03-26 | 2001-01-10 | Sugen, Inc. | Heterocylic classes of compounds for the modulating tyrosine protein kinase |
| US6476078B2 (en) * | 1999-08-11 | 2002-11-05 | Sepracor, Inc. | Methods of using sibutramine metabolites in combination with a phosphodiesterase inhibitor to treat sexual dysfunction |
| US6632836B1 (en) * | 1998-10-30 | 2003-10-14 | Merck & Co., Inc. | Carbocyclic potassium channel inhibitors |
| US6828460B2 (en) | 1999-03-22 | 2004-12-07 | Pfizer Inc. | Resorcinol derivatives |
| US20020058606A1 (en) * | 1999-05-10 | 2002-05-16 | Gonzalez Maria Isabel | Treatment of sexual dysfunction |
| FR2795733B1 (fr) | 1999-06-30 | 2001-09-07 | Aventis Pharma Sa | Derives de streptogramines, leur preparation et les compositions qui les contiennent |
| DK1088824T3 (da) | 1999-09-30 | 2004-04-13 | Pfizer Prod Inc | Bicykliske pyrrolylamider som glycogen phosphorylase inhibitorer |
| EP1391460A1 (en) | 1999-09-30 | 2004-02-25 | Pfizer Products Inc. | Tricyclic pyrrolyl amides as glycogen phosphorylase inhibitors |
| PE20010635A1 (es) | 1999-10-08 | 2001-08-15 | Smithkline Beecham Corp | Inhibidores de fab i utiles para el tratamiento de infecciones bacterianas |
| DE19960917A1 (de) | 1999-12-17 | 2001-06-21 | Bayer Ag | Neue 3-Oxo-2,1-benzisoxazol-1(3H)-carboxamide zur Behandlung von ZNS-Erkrankungen |
| US6632417B2 (en) * | 2000-03-07 | 2003-10-14 | Chevron U.S.A. Inc. | Process for preparing zeolites |
| JP2001247462A (ja) | 2000-03-07 | 2001-09-11 | Otsuka Pharmaceut Co Ltd | ウレアーゼ阻害剤 |
| EP1136071A3 (en) | 2000-03-22 | 2003-03-26 | Pfizer Products Inc. | Use of glycogen phosphorylase inhibitors |
| WO2001079208A1 (en) | 2000-04-19 | 2001-10-25 | Kaneka Corporation | Novel azetidine derivative and process for preparation thereof |
| GB0012214D0 (en) * | 2000-05-19 | 2000-07-12 | Merck Sharp & Dohme | Therapeutic agents |
| JP5089003B2 (ja) * | 2000-05-31 | 2012-12-05 | シェブロン ユー.エス.エー. インコーポレイテッド | ゼオライトssz−53 |
| RU2233839C1 (ru) * | 2000-07-13 | 2004-08-10 | Санкио Компани, Лимитед | Производные аминоспиртов, фармацевтическая композиция, способ профилактики или лечения, промежуточные соединения и способ получения промежуточных соединений |
| US6395762B1 (en) * | 2000-07-17 | 2002-05-28 | American Home Products Corporation | Phenyl amino squarate and thiadiazole dioxide beta-3 adrenergic receptor agonists |
| RU2272030C2 (ru) * | 2000-08-01 | 2006-03-20 | Оно Фармасьютикал Ко., Лтд. | Производные 3,4-дигидроизохинолина и фармацевтический агент, включающий его в качестве активного ингредиента |
| WO2002012249A2 (en) | 2000-08-04 | 2002-02-14 | Eli Lilly And Company | Substituted pyrrole compounds and their use as spla2 inhibitors |
| GB0021831D0 (en) | 2000-09-06 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| EP1318988A2 (en) * | 2000-09-11 | 2003-06-18 | Sepracor, Inc. | Ligands for monoamine receptors and transporters, and methods of use thereof (neurotransmission) |
| FR2814073B1 (fr) | 2000-09-21 | 2005-06-24 | Yang Ji Chemical Company Ltd | Composition pharmaceutique antifongique et/ou antiparasitaire et nouveaux derives de l'indole a titre de principes actifs d'une telle composition |
| CA2424987A1 (en) | 2000-10-06 | 2002-04-18 | Smithkline Beecham Corporation | Methods of agonizing and antagonizing fabk |
| TWI283575B (en) | 2000-10-31 | 2007-07-11 | Eisai Co Ltd | Medicinal compositions for concomitant use as anticancer agent |
| EP1333824B1 (en) * | 2000-11-17 | 2005-09-07 | Warner-Lambert Company LLC | Treatment of sexual dysfunction with bombesin receptor antagonists |
| DE10063992A1 (de) | 2000-12-21 | 2002-07-04 | Max Planck Gesellschaft | Tryptophan-Analoga in Proteinen, Peptiden und peptidischen Leitstrukturen |
| US6372919B1 (en) | 2001-01-11 | 2002-04-16 | Dov Pharmaceutical, Inc. | (+)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane, compositions thereof, and uses as an anti-depressant agent |
| US20020123490A1 (en) | 2001-03-01 | 2002-09-05 | Pfizer Inc. | Combination treatment for anxiety, depression, obsessive compulsive disorder and psychosis |
| DE10110051C2 (de) * | 2001-03-02 | 2003-07-03 | Clariant Gmbh | Verfahren zur Herstellung von Boron- und Borinsäuren |
| WO2003016302A1 (en) | 2001-08-09 | 2003-02-27 | Daiichi Pharmaceutical Co., Ltd. | Diamine derivatives |
| US7365205B2 (en) | 2001-06-20 | 2008-04-29 | Daiichi Sankyo Company, Limited | Diamine derivatives |
| IL158923A0 (en) * | 2001-06-27 | 2004-05-12 | Smithkline Beecham Corp | Fluoropyrrolidines as dipeptidyl peptidase inhibitors |
| US6603000B2 (en) | 2001-07-11 | 2003-08-05 | Boehringer Ingelheim Pharmaceuticals, Inc. | Synthesis for heteroarylamine compounds |
| US6464956B1 (en) * | 2001-07-13 | 2002-10-15 | Chevron U.S.A. Inc. | Zeolite SSZ-59 composition of matter and synthesis thereof |
| US7045543B2 (en) | 2001-11-05 | 2006-05-16 | Enzrel Inc. | Covalent conjugates of biologically-active compounds with amino acids and amino acid derivatives for targeting to physiologically-protected sites |
| WO2003039540A2 (en) | 2001-11-09 | 2003-05-15 | Sepracor Inc. | D-amino acid oxidase inhibitors for learning and memory |
| US6780891B2 (en) | 2001-11-30 | 2004-08-24 | Sepracor Inc. | Tramadol analogs and uses thereof |
| TW200307539A (en) | 2002-02-01 | 2003-12-16 | Bristol Myers Squibb Co | Cycloalkyl inhibitors of potassium channel function |
| DE10303638B4 (de) * | 2002-02-28 | 2018-10-04 | Merck Patent Gmbh | Axial substituiertes Cyclohexylenderivat und flüssigkristallines Medium |
| GB0205170D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| GB0205165D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| US6995144B2 (en) | 2002-03-14 | 2006-02-07 | Eisai Co., Ltd. | Nitrogen containing heterocyclic compounds and medicines containing the same |
| AU2003227360A1 (en) | 2002-04-25 | 2003-11-10 | Yamanouchi Pharmaceutical Co., Ltd. | Novel amide derivatives or salts thereof |
| CA2484582A1 (en) | 2002-05-03 | 2003-11-13 | Warner-Lambert Company Llc | Bombesin antagonists |
| AU2003252299A1 (en) | 2002-07-31 | 2004-02-16 | Eisai Co., Ltd. | Novel physiologically active substance |
| AU2003272285A1 (en) | 2002-09-06 | 2004-03-29 | Janssen Pharmaceutica, N.V. | Thienopyrrolyl and furanopyrrolyl compounds and their use as histamine h4 receptor ligands |
| JP2006504693A (ja) | 2002-09-16 | 2006-02-09 | セプラコア インコーポレーテッド | トランス4−(3,4−ジクロロフェニル)−1,2,3,4−テトラヒドロ−n−メチル−1−ナフタレンアミンによるcns障害の治療 |
| WO2004024669A1 (en) | 2002-09-16 | 2004-03-25 | Sepracor, Inc. | Treatment of cns disorders with trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine and its formamide |
| AU2003284005B2 (en) | 2002-10-03 | 2009-12-17 | Forest Laboratories Holdings Limited | Dosage escalation and divided daily dose of anti-depressants to treat neurological disorders |
| GB0222909D0 (en) | 2002-10-03 | 2002-11-13 | Astrazeneca Ab | Novel process and intermediates |
| GB0222912D0 (en) | 2002-10-03 | 2002-11-13 | Astrazeneca Ab | Novel process and intermediates |
| US20040097554A1 (en) | 2002-10-30 | 2004-05-20 | Pfizer Inc | Heteroaryl-hexanoic acid amide derivatives as immonomodulatory agents |
| BR0316099A (pt) | 2002-11-07 | 2005-09-27 | Pfizer Prod Inc | Agentes antidiabéticos |
| EP1569647B1 (en) * | 2002-12-13 | 2008-08-20 | Smithkline Beecham Corporation | Cyclohexyl compounds as ccr5 antagonists |
| CA2514191C (en) | 2003-01-31 | 2011-10-11 | Sanwa Kagaku Kenkyusho Co., Ltd. | Compound inhibiting dipeptidyl peptidase iv |
| DE602004027171D1 (de) | 2003-04-11 | 2010-06-24 | High Point Pharmaceuticals Llc | Verbindungen mit Aktivität an der 11Beta-Hydroxasteroiddehydrogenase |
| CA2521962A1 (en) | 2003-04-30 | 2004-11-11 | Pfizer Products Inc. | Anti-diabetic agents |
| WO2004113345A1 (ja) | 2003-06-20 | 2004-12-29 | Japan Tobacco Inc. | 縮合ピロール化合物及びその医薬用途 |
| EP1362864B1 (fr) | 2003-06-30 | 2007-04-25 | Les Laboratoires Servier | Nouveau procédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables |
| JP4745226B2 (ja) | 2003-07-07 | 2011-08-10 | チバ ホールディング インコーポレーテッド | フロピロールの製造法 |
| JP2005060375A (ja) * | 2003-07-28 | 2005-03-10 | Kyowa Hakko Kogyo Co Ltd | 含酸素複素環化合物 |
| KR20120116991A (ko) | 2003-07-29 | 2012-10-23 | 시그너쳐 알 앤드 디 홀딩스, 엘엘씨 | 아미노산 프로드럭 |
| GB0318463D0 (en) | 2003-08-07 | 2003-09-10 | Astrazeneca Ab | Chemical compounds |
| GB0319759D0 (en) | 2003-08-22 | 2003-09-24 | Astrazeneca Ab | Chemical compounds |
| WO2005020986A1 (en) | 2003-08-29 | 2005-03-10 | Astrazeneca Ab | Heterocyclic amide derivatives which posses glycogen phosphorylase inhibitory activity |
| GB0320422D0 (en) | 2003-08-30 | 2003-10-01 | Astrazeneca Ab | Chemical compounds |
| NZ546365A (en) * | 2003-10-08 | 2010-01-29 | Vertex Pharma | Modulators of ATP-binding cassette transporters containing cycloalkyl or pyranyl groups |
| US7396940B2 (en) | 2003-10-23 | 2008-07-08 | Hoffmann-La Roche Inc. | Combinatorial library of 3-aryl-1H-indole-2-carboxylic acid |
| PT1420028E (pt) | 2003-11-19 | 2007-05-31 | Servier Lab | Processo de síntese do perindopril e dos seus sais farmacêuticamente aceitáveis. |
| WO2005066135A2 (en) | 2003-12-29 | 2005-07-21 | Sepracor Inc. | Pyrrole and pyrazole daao inhibitors |
| ZA200605384B (en) | 2003-12-29 | 2007-10-31 | Sepracor Inc | Benzo[D]isoxazol-3-OL DAAO inhibitors |
| CN100556904C (zh) * | 2004-01-23 | 2009-11-04 | 三共农业株式会社 | 3-(二氢(四氢)异喹啉-1-基)喹啉化合物 |
| EP1746991A2 (en) | 2004-03-16 | 2007-01-31 | Janssen Pharmaceutica N.V. | Daao inhibiting benzisoxazoles for treating mental disorders |
| EP1736467A4 (en) * | 2004-04-06 | 2009-07-01 | Dainippon Sumitomo Pharma Co | NEW SULFONIC ACID AMID DERIVATIVE |
| US7772232B2 (en) * | 2004-04-15 | 2010-08-10 | Bristol-Myers Squibb Company | Quinazolinyl compounds as inhibitors of potassium channel function |
| BRPI0510664B8 (pt) | 2004-05-07 | 2021-05-25 | Warner Lambert Co | derivados de fenol e tiofenol 3 ou 4-monosubstituído, composição farmacêutica, combinação e uso dos compostos para tratamento de doenças relacionadas ao h3, incluindo transtornos do sistema nervoso central e transtornos inflamatórios |
| US20050261327A1 (en) * | 2004-05-20 | 2005-11-24 | Bock Mark G | 2-(Bicyclo)alkylamino-derivatives as mediatores of chronic pain and inflammation |
| EP1753740A2 (en) | 2004-05-21 | 2007-02-21 | Merck & Co., Inc. | Amino cyclopentyl heterocyclic and carbocyclic modulators of chemokine receptor activity |
| BRPI0511504A (pt) | 2004-05-26 | 2008-01-22 | Eisai R&D Man Co Ltd | composto ou um sal farmaceuticamente aceitável do mesmo, e, agente preventivo ou terapêutico para uma doença resultante de beta-amilóides |
| WO2005123677A1 (en) | 2004-06-16 | 2005-12-29 | Actelion Pharmaceuticals Ltd | 4-carbonyl substituted 1,1,2-trimethyl-1a,4,5,5a-tetrahydro-1h-4-aza-cyclopropa'a!pentalene derivatives as agonists for the g-protein-coupled receptor s1p1/edg1 and immunosuppressive agents |
| PT1775298E (pt) | 2004-07-01 | 2013-06-12 | Daiichi Sankyo Co Ltd | Derivado de tienopirazol com atividade inibidora da pde 7 |
| US7276631B2 (en) | 2004-07-20 | 2007-10-02 | Bristol-Myers Squibb Company | Cyclopentylamine and cyclohexylamine derivatives as NK-1/SSRI antagonists |
| JO2629B1 (en) | 2004-08-19 | 2012-06-24 | افينتيس فارما سوتيكالز انك | Branched carboxylic acid amides containing thienobirol, carboxylic acid amides containing pyrolithiazole, and the like as kinase inhibitors casein epsilon |
| JP2008527032A (ja) | 2005-01-19 | 2008-07-24 | バイオリポックス エービー | 炎症の治療に有用なチエノピロール |
| CN100391945C (zh) | 2005-05-31 | 2008-06-04 | 浙江大学 | 一种s-(-)-吲哚啉-2-羧酸的合成方法 |
| WO2007039773A1 (en) | 2005-10-06 | 2007-04-12 | Merck Sharp & Dohme Limited | Use of fused pyrrole carboxylic acids for the treatment of neurodegenerative and psychiatric diseases as d-amino acid oxidase inhibitors |
| UA95788C2 (en) | 2005-12-15 | 2011-09-12 | Ф. Хоффманн-Ля Рош Аг | Fused pyrrole derivatives |
| CA2636275C (en) | 2006-01-06 | 2013-02-12 | Sepracor Inc. | Tetralone-based monoamine reuptake inhibitors |
| JP5432526B2 (ja) | 2006-01-06 | 2014-03-05 | サノビオン ファーマシューティカルズ インク | モノアミン再取り込み阻害剤としてのシクロアルキルアミン |
| US8097760B2 (en) | 2006-03-31 | 2012-01-17 | Sunovion Pharmacuticals Inc. | Preparation of chiral amides and amines |
| US20080058395A1 (en) | 2006-06-30 | 2008-03-06 | Sepracor Inc. | Fused heterocyclic inhibitors of D-amino acid oxidase |
| US7884124B2 (en) | 2006-06-30 | 2011-02-08 | Sepracor Inc. | Fluoro-substituted inhibitors of D-amino acid oxidase |
| BRPI0713216A2 (pt) | 2006-06-30 | 2012-12-04 | Sepracor Inc | inibiadores heterocìclos fundidos da d-aminoácido oxidase |
| US7579370B2 (en) | 2006-06-30 | 2009-08-25 | Sepracor Inc. | Fused heterocycles |
| CN1962656A (zh) | 2006-11-29 | 2007-05-16 | 沈阳药科大学 | 吲哚美辛5-氟尿嘧啶甲酯药用化合物及其制剂和制备方法 |
| US7902252B2 (en) | 2007-01-18 | 2011-03-08 | Sepracor, Inc. | Inhibitors of D-amino acid oxidase |
| JP2010516697A (ja) | 2007-01-18 | 2010-05-20 | セプラコール インク. | D−アミノ酸オキシダーゼ阻害剤 |
| EP3296289A3 (en) | 2007-05-31 | 2018-06-20 | Sunovion Pharmaceuticals Inc. | Phenyl substituted cycloalkylamines as monoamine reuptake inhibitors |
| US20100120740A1 (en) | 2008-08-07 | 2010-05-13 | Sepracor Inc. | Prodrugs of fused heterocyclic inhibitors of d-amino acid oxidase |
-
2007
- 2007-01-05 JP JP2008549588A patent/JP5432526B2/ja not_active Expired - Fee Related
- 2007-01-05 CN CN200780008105.XA patent/CN101394847B/zh not_active Expired - Fee Related
- 2007-01-05 ES ES07716419.2T patent/ES2594156T3/es active Active
- 2007-01-05 NZ NZ569630A patent/NZ569630A/en not_active IP Right Cessation
- 2007-01-05 AU AU2007205114A patent/AU2007205114B2/en not_active Ceased
- 2007-01-05 WO PCT/US2007/000376 patent/WO2007081857A2/en not_active Ceased
- 2007-01-05 RU RU2008132320A patent/RU2430913C2/ru active
- 2007-01-05 US US11/649,927 patent/US20070203111A1/en not_active Abandoned
- 2007-01-05 CA CA2636324A patent/CA2636324C/en active Active
- 2007-01-05 KR KR1020087019131A patent/KR101294014B1/ko not_active Expired - Fee Related
- 2007-01-05 EP EP07716419.2A patent/EP1976513B1/en active Active
- 2007-01-05 BR BRPI0706365-2A patent/BRPI0706365A2/pt not_active Application Discontinuation
- 2007-02-05 ZA ZA200806145A patent/ZA200806145B/xx unknown
-
2008
- 2008-07-03 IL IL192613A patent/IL192613A/en active IP Right Grant
-
2010
- 2010-01-15 US US12/688,474 patent/US8877975B2/en active Active
-
2011
- 2011-05-18 RU RU2011119990/04A patent/RU2011119990A/ru not_active Application Discontinuation
-
2013
- 2013-05-10 JP JP2013100267A patent/JP2013209390A/ja not_active Withdrawn
-
2014
- 2014-09-30 US US14/502,532 patent/US9868718B2/en active Active
-
2017
- 2017-12-08 US US15/836,261 patent/US10562878B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP1976513B1 (en) | 2016-08-24 |
| KR101294014B1 (ko) | 2013-08-09 |
| KR20080083201A (ko) | 2008-09-16 |
| US10562878B2 (en) | 2020-02-18 |
| US20100190861A1 (en) | 2010-07-29 |
| JP2013209390A (ja) | 2013-10-10 |
| US20180230120A1 (en) | 2018-08-16 |
| CN101394847A (zh) | 2009-03-25 |
| ZA200806145B (en) | 2010-02-24 |
| US20150126511A1 (en) | 2015-05-07 |
| RU2430913C2 (ru) | 2011-10-10 |
| IL192613A (en) | 2015-11-30 |
| BRPI0706365A2 (pt) | 2011-03-22 |
| CA2636324A1 (en) | 2007-07-19 |
| JP5432526B2 (ja) | 2014-03-05 |
| US9868718B2 (en) | 2018-01-16 |
| US20070203111A1 (en) | 2007-08-30 |
| ES2594156T3 (es) | 2016-12-16 |
| RU2011119990A (ru) | 2012-11-27 |
| CA2636324C (en) | 2012-03-20 |
| EP1976513A4 (en) | 2012-04-18 |
| EP1976513A2 (en) | 2008-10-08 |
| CN101394847B (zh) | 2017-05-24 |
| US8877975B2 (en) | 2014-11-04 |
| IL192613A0 (en) | 2009-09-22 |
| RU2008132320A (ru) | 2010-02-20 |
| WO2007081857A2 (en) | 2007-07-19 |
| AU2007205114B2 (en) | 2012-11-08 |
| AU2007205114A1 (en) | 2007-07-19 |
| JP2009531277A (ja) | 2009-09-03 |
| WO2007081857A3 (en) | 2007-11-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10562878B2 (en) | Cycloalkylamines as monoamine reuptake inhibitors | |
| CA2688493C (en) | Phenyl substituted cycloalkylamines as monoamine reuptake inhibitors | |
| CA2636275C (en) | Tetralone-based monoamine reuptake inhibitors | |
| US9505716B2 (en) | Pyrrolidine triple reuptake inhibitors | |
| MX2008008807A (en) | Cycloalkylamines as monoamine reuptake inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| S883 | Correction of error according to section 88(3) (mistake in register caused on part of patentee or applicant) |
Free format text: THE INVENTORS (72) SHOULD HAVE APPEARED AS THE APPLICANT (71) AT THE TIME OF FILING, THE PATENT APPLICATION HAS SUBSEQUENTLY BEEN ASSIGNED |
|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 3 YEARS UNTIL 05 JAN 2017 BY CPA GLOBAL Effective date: 20131212 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 05 JAN 2018 BY COMPUTER PACKAGES INC Effective date: 20161220 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 05 JAN 2019 BY COMPUTER PACKAGES INC Effective date: 20171219 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 05 JAN 2020 BY COMPUTER PACKAGES INC Effective date: 20181218 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 05 JAN 2021 BY COMPUTER PACKAGES INC Effective date: 20191218 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 05 JAN 2022 BY COMPUTER PACKAGES INC Effective date: 20201218 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 05 JAN 2023 BY COMPUTER PACKAGES INC Effective date: 20211217 |
|
| LAPS | Patent lapsed |