IL86292A - Reliable alkylene coils are transformed into a process for their preparation and pharmaceutical preparations containing them - Google Patents
Reliable alkylene coils are transformed into a process for their preparation and pharmaceutical preparations containing themInfo
- Publication number
- IL86292A IL86292A IL8629288A IL8629288A IL86292A IL 86292 A IL86292 A IL 86292A IL 8629288 A IL8629288 A IL 8629288A IL 8629288 A IL8629288 A IL 8629288A IL 86292 A IL86292 A IL 86292A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- alkyl
- mao
- dimethyl
- formula
- Prior art date
Links
- -1 silyl alkylene amines Chemical class 0.000 title claims abstract description 69
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title abstract description 49
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 230000008569 process Effects 0.000 title abstract description 5
- 102000010909 Monoamine Oxidase Human genes 0.000 claims abstract description 19
- 108010062431 Monoamine oxidase Proteins 0.000 claims abstract description 19
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 100
- 238000006243 chemical reaction Methods 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- MGIWMNVXJAUWRI-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-2-methylsilylbutan-2-amine Chemical compound FC1=C(CC(N)([SiH2]C)CC)C=CC(=C1)F MGIWMNVXJAUWRI-UHFFFAOYSA-N 0.000 claims description 2
- KASOPZUXQKEAJL-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-dimethylsilylethanamine Chemical compound ClC1=CC=C(CC(N)[SiH](C)C)C=C1 KASOPZUXQKEAJL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000011260 aqueous acid Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- VLAXMTMOFBQHNE-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-dimethylsilylethanamine Chemical compound FC1=C(CC(N)[SiH](C)C)C=CC(=C1)F VLAXMTMOFBQHNE-UHFFFAOYSA-N 0.000 claims 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 1
- 230000000648 anti-parkinson Effects 0.000 claims 1
- 239000000939 antiparkinson agent Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 9
- 230000000144 pharmacologic effect Effects 0.000 abstract description 8
- 239000000543 intermediate Substances 0.000 abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 98
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 229960004132 diethyl ether Drugs 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 150000001412 amines Chemical class 0.000 description 23
- 229910001868 water Inorganic materials 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 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 18
- 239000000047 product Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 12
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 10
- 239000011777 magnesium Substances 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229940093499 ethyl acetate Drugs 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- 229910052749 magnesium Inorganic materials 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- 150000001540 azides Chemical class 0.000 description 7
- AZFVLHQDIIJLJG-UHFFFAOYSA-N chloromethylsilane Chemical compound [SiH3]CCl AZFVLHQDIIJLJG-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 229960003732 tyramine Drugs 0.000 description 7
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 6
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 6
- 229940082992 antihypertensives mao inhibitors Drugs 0.000 description 6
- 150000003943 catecholamines Chemical class 0.000 description 6
- 235000013351 cheese Nutrition 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical group C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229960001779 pargyline Drugs 0.000 description 5
- 125000005543 phthalimide group Chemical group 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XKFPYPQQHFEXRZ-UHFFFAOYSA-N 5-methyl-N'-(phenylmethyl)-3-isoxazolecarbohydrazide Chemical compound O1C(C)=CC(C(=O)NNCC=2C=CC=CC=2)=N1 XKFPYPQQHFEXRZ-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 4
- 229910017852 NH2NH2 Inorganic materials 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 description 4
- 229940124639 Selective inhibitor Drugs 0.000 description 4
- FYTPGBJPTDQJCG-UHFFFAOYSA-N Trichloro(chloromethyl)silane Chemical compound ClC[Si](Cl)(Cl)Cl FYTPGBJPTDQJCG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 229960003638 dopamine Drugs 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 4
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
- IGLYMJRIWWIQQE-QUOODJBBSA-N (1S,2R)-2-phenylcyclopropan-1-amine (1R,2S)-2-phenylcyclopropan-1-amine Chemical compound N[C@H]1C[C@@H]1C1=CC=CC=C1.N[C@@H]1C[C@H]1C1=CC=CC=C1 IGLYMJRIWWIQQE-QUOODJBBSA-N 0.000 description 3
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 3
- 229930182837 (R)-adrenaline Natural products 0.000 description 3
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- KRXAVBPUAIKSFF-UHFFFAOYSA-N 3,4-dihydrodithiine Chemical compound C1CC=CSS1 KRXAVBPUAIKSFF-UHFFFAOYSA-N 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 3
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- 229910019567 Re Re Inorganic materials 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical class [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000150 Sympathomimetic Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 229960004217 benzyl alcohol Drugs 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- BTFHLQRNAMSNLC-UHFFFAOYSA-N clorgyline Chemical compound C#CCN(C)CCCOC1=CC=C(Cl)C=C1Cl BTFHLQRNAMSNLC-UHFFFAOYSA-N 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 229960005139 epinephrine Drugs 0.000 description 3
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 229960002672 isocarboxazid Drugs 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 230000002503 metabolic effect Effects 0.000 description 3
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 3
- 229960002748 norepinephrine Drugs 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 229960000964 phenelzine Drugs 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- YWOSGXSBVHJBEJ-UHFFFAOYSA-N silylmethanamine Chemical compound NC[SiH3] YWOSGXSBVHJBEJ-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
- 229940127230 sympathomimetic drug Drugs 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 229960003741 tranylcypromine Drugs 0.000 description 3
- WPCDOFKVQOPQLT-UHFFFAOYSA-N 1-dimethylsilyl-2-phenylethanamine hydrochloride Chemical compound Cl.C[SiH](C)C(N)CC1=CC=CC=C1 WPCDOFKVQOPQLT-UHFFFAOYSA-N 0.000 description 2
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 description 2
- FMEVAQARAVDUNY-UHFFFAOYSA-N 2-(2-aminoethyl)phenol Chemical compound NCCC1=CC=CC=C1O FMEVAQARAVDUNY-UHFFFAOYSA-N 0.000 description 2
- ICXYACHRXUEOOD-UHFFFAOYSA-N 2-(2-trimethylsilylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CC[Si](C)(C)C)C(=O)C2=C1 ICXYACHRXUEOOD-UHFFFAOYSA-N 0.000 description 2
- AINXKOKFDMEBKC-UHFFFAOYSA-N 2-[[benzyl(dimethyl)silyl]methyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C[Si](C)(C)CC1=CC=CC=C1 AINXKOKFDMEBKC-UHFFFAOYSA-N 0.000 description 2
- QYNHSWILQDJWQQ-UHFFFAOYSA-N 2-trimethylsilylpropan-1-amine Chemical compound NCC(C)[Si](C)(C)C QYNHSWILQDJWQQ-UHFFFAOYSA-N 0.000 description 2
- DXICVLABVQYHKX-UHFFFAOYSA-N 2-trimethylsilylpropan-1-ol Chemical compound OCC(C)[Si](C)(C)C DXICVLABVQYHKX-UHFFFAOYSA-N 0.000 description 2
- WGTASENVNYJZBK-UHFFFAOYSA-N 3,4,5-trimethoxyamphetamine Chemical compound COC1=CC(CC(C)N)=CC(OC)=C1OC WGTASENVNYJZBK-UHFFFAOYSA-N 0.000 description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LUVSNVIOOGISMS-UHFFFAOYSA-N CC(C)(C)OC(=O)NC([SiH](C)C)CC1=CC=C(F)C=C1F Chemical compound CC(C)(C)OC(=O)NC([SiH](C)C)CC1=CC=C(F)C=C1F LUVSNVIOOGISMS-UHFFFAOYSA-N 0.000 description 2
- GLBNRQAUFYTMCS-UHFFFAOYSA-N Cl.CC(C)(N)[SiH2]Cc1cccc(F)c1 Chemical compound Cl.CC(C)(N)[SiH2]Cc1cccc(F)c1 GLBNRQAUFYTMCS-UHFFFAOYSA-N 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- DFFLKWSXKQMYPL-UHFFFAOYSA-N FC=1C=C(CC(N)[SiH](C)C)C=CC1F Chemical compound FC=1C=C(CC(N)[SiH](C)C)C=CC1F DFFLKWSXKQMYPL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- ITKVLPYNJQOCPW-UHFFFAOYSA-N chloro-(chloromethyl)-dimethylsilane Chemical compound C[Si](C)(Cl)CCl ITKVLPYNJQOCPW-UHFFFAOYSA-N 0.000 description 2
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 2
- KKDMRASJCMNJJV-UHFFFAOYSA-N chloromethyl-[(4-fluorophenyl)methyl]-dimethylsilane Chemical compound ClC[Si](C)(C)CC1=CC=C(F)C=C1 KKDMRASJCMNJJV-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- YUXZQHVHUIOTBL-UHFFFAOYSA-N dimethylsilylmethanamine Chemical compound NC[SiH](C)C YUXZQHVHUIOTBL-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 2
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000007788 liquid 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
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229960002523 mercuric chloride Drugs 0.000 description 2
- 229940101209 mercuric oxide Drugs 0.000 description 2
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000002858 neurotransmitter agent Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
- 230000002315 pressor effect Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- CQVVPZKXDRZYBM-UHFFFAOYSA-N 1-(4-nitrophenyl)propan-2-amine Chemical compound CC(N)CC1=CC=C([N+]([O-])=O)C=C1 CQVVPZKXDRZYBM-UHFFFAOYSA-N 0.000 description 1
- IZXWCDITFDNEBY-UHFFFAOYSA-N 1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C=C1 IZXWCDITFDNEBY-UHFFFAOYSA-N 0.000 description 1
- LHCJFGFOEQKUDC-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethylsilyl]propan-1-amine Chemical compound C(C)C(N)[SiH2]CCC1=CC=C(C=C1)F LHCJFGFOEQKUDC-UHFFFAOYSA-N 0.000 description 1
- WZBFSVLGNSEAKV-UHFFFAOYSA-N 1-dimethylsilyl-2-(4-fluorophenyl)ethanamine Chemical compound FC1=CC=C(CC(N)[SiH](C)C)C=C1 WZBFSVLGNSEAKV-UHFFFAOYSA-N 0.000 description 1
- WEKFRLOKGMLVOJ-UHFFFAOYSA-N 1-dimethylsilylethanamine Chemical compound C[SiH](C)C(C)N WEKFRLOKGMLVOJ-UHFFFAOYSA-N 0.000 description 1
- AKZAIECMGWDNRN-UHFFFAOYSA-N 1-silylethanamine Chemical class CC(N)[SiH3] AKZAIECMGWDNRN-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical class C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 1
- LOEMVLKMGFODJJ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)ethyl-dimethylsilane azide Chemical compound [N-]=[N+]=[N-].FC1=C(CC[SiH](C)C)C=CC(=C1)F LOEMVLKMGFODJJ-UHFFFAOYSA-N 0.000 description 1
- FXQZBKBXTSGNOF-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-2-triethylsilylethanamine Chemical compound CC[Si](CC)(CC)C(CN)C1=CC=C(F)C(F)=C1 FXQZBKBXTSGNOF-UHFFFAOYSA-N 0.000 description 1
- JBMTWVXNUPYART-UHFFFAOYSA-N 2-(pyridin-3-ylmethylsilyl)propan-2-amine Chemical compound CC(C)(N)[SiH2]CC1=CC=CN=C1 JBMTWVXNUPYART-UHFFFAOYSA-N 0.000 description 1
- PYSDOECVWDSXBT-UHFFFAOYSA-N 2-[(4-fluorophenyl)methylsilyl]propan-2-amine Chemical compound CC(C)(N)[SiH2]Cc1ccc(F)cc1 PYSDOECVWDSXBT-UHFFFAOYSA-N 0.000 description 1
- UYQKYVIKNCRKLJ-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methylsilyl]propan-2-amine Chemical compound COc1ccc(C[SiH2]C(C)(C)N)cc1 UYQKYVIKNCRKLJ-UHFFFAOYSA-N 0.000 description 1
- YCMNFDRCDZGLTL-UHFFFAOYSA-N 2-[(4-nitrophenyl)methylsilyl]propan-2-amine Chemical compound CC(C)(N)[SiH2]Cc1ccc(cc1)[N+]([O-])=O YCMNFDRCDZGLTL-UHFFFAOYSA-N 0.000 description 1
- SJCRFYLXXKGHIV-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)ethylsilyl]butan-2-amine Chemical compound CCC(C)(N)[SiH2]CCc1ccc(F)cc1 SJCRFYLXXKGHIV-UHFFFAOYSA-N 0.000 description 1
- RMSOAYBERYVZFJ-UHFFFAOYSA-N 2-[[4-(trifluoromethyl)phenyl]methylsilyl]propan-2-amine Chemical compound CC(N)([SiH2]CC1=CC=C(C=C1)C(F)(F)F)C RMSOAYBERYVZFJ-UHFFFAOYSA-N 0.000 description 1
- OEWZJQHLYSWZLK-UHFFFAOYSA-N 2-[benzyl(dimethyl)silyl]ethanamine;hydrochloride Chemical compound Cl.NCC[Si](C)(C)CC1=CC=CC=C1 OEWZJQHLYSWZLK-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([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
- NIBXVTMWHMMKGV-UHFFFAOYSA-N 2-trimethylsilylethanamine Chemical compound C[Si](C)(C)CCN NIBXVTMWHMMKGV-UHFFFAOYSA-N 0.000 description 1
- ZNGINKJHQQQORD-UHFFFAOYSA-N 2-trimethylsilylethanol Chemical compound C[Si](C)(C)CCO ZNGINKJHQQQORD-UHFFFAOYSA-N 0.000 description 1
- OECFYIVZLPNYAX-UHFFFAOYSA-N 2-trimethylsilylethylazanium;chloride Chemical compound Cl.C[Si](C)(C)CCN OECFYIVZLPNYAX-UHFFFAOYSA-N 0.000 description 1
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 description 1
- NZZZMYZBHWOCFI-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-1-dimethylsilylpropan-1-amine Chemical compound C[SiH](C)C(N)CCC1=CC=C(F)C=C1F NZZZMYZBHWOCFI-UHFFFAOYSA-N 0.000 description 1
- SJMQVCMOLVYDAE-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-1-ethylsilylpropan-1-amine Chemical compound FC1=C(CCC(N)[SiH2]CC)C=CC(=C1)F SJMQVCMOLVYDAE-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 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
- TXQWRUFYUHCPJM-UHFFFAOYSA-N 4-(2-aminopropan-2-ylsilylmethyl)benzonitrile Chemical compound CC(C)(N)[SiH2]Cc1ccc(cc1)C#N TXQWRUFYUHCPJM-UHFFFAOYSA-N 0.000 description 1
- IGGWNCKACDGUJG-UHFFFAOYSA-N 4-(3-amino-2-triethylsilylpropyl)phenol Chemical compound CC[Si](CC)(CC)C(CN)CC1=CC=C(O)C=C1 IGGWNCKACDGUJG-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
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 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 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- BEXFLSVOPTVPEQ-UHFFFAOYSA-N C(C1=CC=CC=C1)[Mg]C[SiH](C)C Chemical compound C(C1=CC=CC=C1)[Mg]C[SiH](C)C BEXFLSVOPTVPEQ-UHFFFAOYSA-N 0.000 description 1
- SJAZOSRNSVRGIT-UHFFFAOYSA-N CC(C)(N)[SiH2]Cc1ccccc1F Chemical compound CC(C)(N)[SiH2]Cc1ccccc1F SJAZOSRNSVRGIT-UHFFFAOYSA-N 0.000 description 1
- JSIUEYNHRVYHKT-UHFFFAOYSA-N CC[SiH](CC)CN Chemical compound CC[SiH](CC)CN JSIUEYNHRVYHKT-UHFFFAOYSA-N 0.000 description 1
- WHESLGBSASYCEE-UHFFFAOYSA-N C[SiH](C)C(N)CC1=CC=C(Cl)C(Cl)=C1 Chemical compound C[SiH](C)C(N)CC1=CC=C(Cl)C(Cl)=C1 WHESLGBSASYCEE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JKQAEFCAYKLRPY-UHFFFAOYSA-N Cl.C(C)C(N)[SiH2]CCC1=CC=C(C=C1)F Chemical compound Cl.C(C)C(N)[SiH2]CCC1=CC=C(C=C1)F JKQAEFCAYKLRPY-UHFFFAOYSA-N 0.000 description 1
- ARXISKQMEBJXEA-UHFFFAOYSA-N Cl.FC1=C(CC(N)[SiH](C)C)C(=CC=C1)F Chemical compound Cl.FC1=C(CC(N)[SiH](C)C)C(=CC=C1)F ARXISKQMEBJXEA-UHFFFAOYSA-N 0.000 description 1
- UEKQAJAPSFDBTK-UHFFFAOYSA-N Cl.FC=1C=C(CC(N)[SiH](C)C)C=CC1F Chemical compound Cl.FC=1C=C(CC(N)[SiH](C)C)C=CC1F UEKQAJAPSFDBTK-UHFFFAOYSA-N 0.000 description 1
- QCUBESKZPNHXFQ-UHFFFAOYSA-N ClC[Si](CC1=CC=C(C=C1)F)(C)C.C[Si](CC1=CC=C(C=C1)F)(C)CN1C(C=2C(C1=O)=CC=CC2)=O Chemical compound ClC[Si](CC1=CC=C(C=C1)F)(C)C.C[Si](CC1=CC=C(C=C1)F)(C)CN1C(C=2C(C1=O)=CC=CC2)=O QCUBESKZPNHXFQ-UHFFFAOYSA-N 0.000 description 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 description 1
- 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 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000000023 Kugelrohr distillation Methods 0.000 description 1
- 101710096582 L-tyrosine decarboxylase Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000906091 Lethrinus miniatus Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000006751 Mitsunobu reaction Methods 0.000 description 1
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- JPMKVWILKRAMON-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethylsilylpropan-2-amine Chemical compound CC[SiH2]C(C)(C)NCC1=CC=C(F)C=C1F JPMKVWILKRAMON-UHFFFAOYSA-N 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 229910003910 SiCl4 Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 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 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- BKPRVQDIOGQWTG-ICOOEGOYSA-N [(1s,2r)-2-phenylcyclopropyl]azanium;[(1r,2s)-2-phenylcyclopropyl]azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.[NH3+][C@H]1C[C@@H]1C1=CC=CC=C1.[NH3+][C@@H]1C[C@H]1C1=CC=CC=C1 BKPRVQDIOGQWTG-ICOOEGOYSA-N 0.000 description 1
- WXNVDQWUGUEUMO-UHFFFAOYSA-N [1-(4-fluorophenyl)-2-methylpropan-2-yl]azanium;chloride Chemical compound Cl.CC(C)(N)CC1=CC=C(F)C=C1 WXNVDQWUGUEUMO-UHFFFAOYSA-N 0.000 description 1
- BZJZYTJKRCKFKD-UHFFFAOYSA-M [Cl-].FC1=CC=C(C[Mg+])C(F)=C1 Chemical compound [Cl-].FC1=CC=C(C[Mg+])C(F)=C1 BZJZYTJKRCKFKD-UHFFFAOYSA-M 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000005902 aminomethylation reaction Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 1
- MEMDIECPWPQFCX-UHFFFAOYSA-N benzyl-(chloromethyl)-dimethylsilane Chemical compound ClC[Si](C)(C)CC1=CC=CC=C1 MEMDIECPWPQFCX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- NKTIPHQNEHWHMS-UHFFFAOYSA-N bis[dimethyl(2-phenylethyl)silyl]methanone Chemical compound C=1C=CC=CC=1CC[Si](C)(C)C(=O)[Si](C)(C)CCC1=CC=CC=C1 NKTIPHQNEHWHMS-UHFFFAOYSA-N 0.000 description 1
- 210000000133 brain stem Anatomy 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229960004205 carbidopa Drugs 0.000 description 1
- TZFNLOMSOLWIDK-JTQLQIEISA-N carbidopa (anhydrous) Chemical compound NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 TZFNLOMSOLWIDK-JTQLQIEISA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- NDYMCIJMGAEPPZ-UHFFFAOYSA-N chloro-(chloromethyl)-ethyl-methylsilane Chemical compound CC[Si](C)(Cl)CCl NDYMCIJMGAEPPZ-UHFFFAOYSA-N 0.000 description 1
- PBPJXYHXZXZDNN-UHFFFAOYSA-N chloromethyl-[(2,6-difluorophenyl)methyl]-dimethylsilane Chemical compound ClC[Si](C)(C)CC1=C(F)C=CC=C1F PBPJXYHXZXZDNN-UHFFFAOYSA-N 0.000 description 1
- WVIMLLNELCZNGQ-UHFFFAOYSA-N chloromethyl-[(2-fluorophenyl)methyl]-dimethylsilane Chemical compound ClC[Si](C)(C)CC1=CC=CC=C1F WVIMLLNELCZNGQ-UHFFFAOYSA-N 0.000 description 1
- ZFMOROZWCVRHRB-UHFFFAOYSA-N chloromethyl-[(3,4-difluorophenyl)methyl]-dimethylsilane Chemical compound ClC[Si](C)(C)CC1=CC=C(F)C(F)=C1 ZFMOROZWCVRHRB-UHFFFAOYSA-N 0.000 description 1
- AIBTZRWSQSRYTI-UHFFFAOYSA-N chloromethyl-[(3-fluorophenyl)methyl]-dimethylsilane Chemical compound ClC[Si](C)(C)CC1=CC=CC(F)=C1 AIBTZRWSQSRYTI-UHFFFAOYSA-N 0.000 description 1
- ZLGORJNWAUDTIV-UHFFFAOYSA-N chloromethyl-dimethyl-(2-phenylethyl)silane Chemical compound ClC[Si](C)(C)CCC1=CC=CC=C1 ZLGORJNWAUDTIV-UHFFFAOYSA-N 0.000 description 1
- MTKRRLVQKUMBJM-UHFFFAOYSA-N chloromethyl-ethyl-[2-(4-fluorophenyl)ethyl]silane Chemical compound CC[SiH](CCl)CCC1=CC=C(F)C=C1 MTKRRLVQKUMBJM-UHFFFAOYSA-N 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000006482 condensation reaction 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
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- JAYBZWYBCUJLNQ-UHFFFAOYSA-N dichloro-(chloromethyl)-methylsilane Chemical compound C[Si](Cl)(Cl)CCl JAYBZWYBCUJLNQ-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002192 heptalenyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- JHMNJUQVLPODJN-UHFFFAOYSA-M magnesium;1-fluoro-4-methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=C(F)C=C1 JHMNJUQVLPODJN-UHFFFAOYSA-M 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- DHZDXXLCWXHNOB-UHFFFAOYSA-M magnesium;ethylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]CC1=CC=CC=C1 DHZDXXLCWXHNOB-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940110127 marplan Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229940087524 nardil Drugs 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007833 oxidative deamination reaction Methods 0.000 description 1
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 229940087824 parnate Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- XZPVPNZTYPUODG-UHFFFAOYSA-M sodium;chloride;dihydrate Chemical compound O.O.[Na+].[Cl-] XZPVPNZTYPUODG-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical class CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4784787A | 1987-05-08 | 1987-05-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL86292A0 IL86292A0 (en) | 1988-11-15 |
| IL86292A true IL86292A (en) | 1996-03-31 |
Family
ID=21951325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL8629288A IL86292A (en) | 1987-05-08 | 1988-05-05 | Reliable alkylene coils are transformed into a process for their preparation and pharmaceutical preparations containing them |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0291787B1 (es) |
| JP (1) | JP2640670B2 (es) |
| KR (1) | KR950009194B1 (es) |
| CN (1) | CN1023485C (es) |
| AT (1) | ATE102947T1 (es) |
| AU (1) | AU611683B2 (es) |
| CA (1) | CA1341025C (es) |
| DE (1) | DE3888391T2 (es) |
| DK (1) | DK172834B1 (es) |
| ES (1) | ES2052635T3 (es) |
| FI (1) | FI89803C (es) |
| HU (1) | HU199850B (es) |
| IE (1) | IE61213B1 (es) |
| IL (1) | IL86292A (es) |
| NO (1) | NO179209C (es) |
| NZ (1) | NZ224502A (es) |
| PH (1) | PH26977A (es) |
| PT (1) | PT87433B (es) |
| ZA (1) | ZA883144B (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU206725B (en) * | 1990-07-27 | 1992-12-28 | Richter Gedeon Vegyeszet | Process for producing new organosilane derivatives and pharmaceutical compositions containing them |
| US5220047A (en) * | 1990-09-17 | 1993-06-15 | Union Carbide Chemicals & Plastics Technology Corporation | Carbamate silicon compounds as latent coupling agents and process for preparation and use |
| US5159095A (en) * | 1991-06-07 | 1992-10-27 | Abbott Laboratories | Substituted silyl alcohols |
| DE102004059378A1 (de) * | 2004-12-09 | 2006-06-22 | Consortium für elektrochemische Industrie GmbH | Alpha-Aminomethyl-alkoxysilane mit hoher Reaktivität und verbesserter Stabilität |
| UA110703C2 (uk) | 2010-06-03 | 2016-02-10 | Байєр Кропсайнс Аг | Фунгіцидні похідні n-[(тризаміщений силіл)метил]-карбоксаміду |
| CN103958531B (zh) | 2011-11-21 | 2016-12-28 | 拜耳知识产权有限责任公司 | 杀真菌剂n‑[(三取代的甲硅烷基)甲基]‑羧酰胺衍生物 |
| KR101595730B1 (ko) * | 2014-10-01 | 2016-02-22 | 포항공과대학교 산학협력단 | 알파-실릴메틸 아자이드 화합물로부터 알파-실릴아민 화합물을 제조하는 방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1210319B (it) * | 1987-03-06 | 1989-09-14 | Donegani Guido Ist | Composto silanico o silossanico con processo per la produzione di untenente almeno un anello cicloalchilico |
-
1988
- 1988-05-03 ZA ZA883144A patent/ZA883144B/xx unknown
- 1988-05-03 CA CA000565813A patent/CA1341025C/en not_active Expired - Fee Related
- 1988-05-04 FI FI882072A patent/FI89803C/fi not_active IP Right Cessation
- 1988-05-04 PH PH36891A patent/PH26977A/en unknown
- 1988-05-05 NZ NZ224502A patent/NZ224502A/xx unknown
- 1988-05-05 IL IL8629288A patent/IL86292A/en not_active IP Right Cessation
- 1988-05-05 AU AU15643/88A patent/AU611683B2/en not_active Ceased
- 1988-05-06 ES ES88107312T patent/ES2052635T3/es not_active Expired - Lifetime
- 1988-05-06 PT PT87433A patent/PT87433B/pt not_active IP Right Cessation
- 1988-05-06 IE IE137888A patent/IE61213B1/en not_active IP Right Cessation
- 1988-05-06 NO NO881991A patent/NO179209C/no not_active IP Right Cessation
- 1988-05-06 JP JP63111345A patent/JP2640670B2/ja not_active Expired - Lifetime
- 1988-05-06 HU HU882318A patent/HU199850B/hu not_active IP Right Cessation
- 1988-05-06 DE DE3888391T patent/DE3888391T2/de not_active Expired - Fee Related
- 1988-05-06 EP EP88107312A patent/EP0291787B1/en not_active Expired - Lifetime
- 1988-05-06 AT AT88107312T patent/ATE102947T1/de not_active IP Right Cessation
- 1988-05-06 KR KR1019880005241A patent/KR950009194B1/ko not_active IP Right Cessation
- 1988-05-06 DK DK198802492A patent/DK172834B1/da not_active IP Right Cessation
- 1988-05-07 CN CN88102628A patent/CN1023485C/zh not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR0179661B1 (ko) | N-페닐알킬 치환된 알파-아미노 카복스아미드 유도체 및 이를 포함하는 약제학적 조성물 및 이의 제조방법 | |
| KR890002756B1 (ko) | 알릴아민 mao 억제제의 제조 방법 | |
| CA2164303C (en) | Aromatic acetylcholinesterase inhibitors | |
| CA2007117A1 (en) | Beta-adrenergic agonists | |
| JP3516955B2 (ja) | シリル化アセチルコリンエステラーゼ阻害剤 | |
| JP3116364B2 (ja) | エンイン誘導体の製造法 | |
| EP0291787B1 (en) | Novel substituted silyl alkylene amines | |
| GB2046259A (en) | Amino-alcohol derivatives and pharmaceutical compositions containing them | |
| CA1265818A (en) | Nonaromatic fluoroallylamine mao inhibitors | |
| US3946060A (en) | Acetylene derivatives | |
| US5529988A (en) | Substituted silyl alkylene amines | |
| FR2708609A1 (fr) | Dérivés de méthylguanidine, leurs procédés de préparation ainsi que les compositions en contenant. | |
| Huc et al. | Organogermanium dendrimers | |
| DK172113B1 (da) | 5-Substituerede ornithinderivater samt farmaceutisk præparat heraf | |
| US4587359A (en) | Amine-carbamoylborane adducts | |
| KR910003711B1 (ko) | 2-(n-피롤리디노)-3-이소부톡시-n-치환된 페닐-n-벤질-프로필아민의 제조방법 | |
| Picard et al. | An improved preparation of enamines of acylsilanes, a new synthesis of acylsilanes | |
| JPH02713A (ja) | 光学活性アルコール、シアノヒドリンおよびこれらの製造方法 | |
| FR2572075A1 (fr) | Nouveaux derives de la 4-dioxino-(4,5-c)-pyridine et leur procede de preparation | |
| KR19990015037A (ko) | 클로로하이드로실란 유도체 및 이의 제조방법 | |
| JPS6230779A (ja) | 新規化合物，その製法及びそれを含む医薬組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees | ||
| HC | Change of name of proprietor(s) |
Owner name: AVENTIS INC. Free format text: FORMER NAME:MERRELL PHARMACEUTICALS INC. |