FI89803B - Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara substituerade silylalkylenaminer - Google Patents
Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara substituerade silylalkylenaminer Download PDFInfo
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- FI89803B FI89803B FI882072A FI882072A FI89803B FI 89803 B FI89803 B FI 89803B FI 882072 A FI882072 A FI 882072A FI 882072 A FI882072 A FI 882072A FI 89803 B FI89803 B FI 89803B
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- -1 silyl alkylene amines Chemical class 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 21
- 230000008569 process Effects 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 49
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 26
- 238000010992 reflux Methods 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 4
- 239000005695 Ammonium acetate Substances 0.000 claims description 4
- 235000019257 ammonium acetate Nutrition 0.000 claims description 4
- 229940043376 ammonium acetate Drugs 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 4
- 239000011260 aqueous acid Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- PYSDOECVWDSXBT-UHFFFAOYSA-N 2-[(4-fluorophenyl)methylsilyl]propan-2-amine Chemical compound CC(C)(N)[SiH2]Cc1ccc(F)cc1 PYSDOECVWDSXBT-UHFFFAOYSA-N 0.000 claims description 2
- NAGHEFSYCFYFEI-UHFFFAOYSA-N 3-[(4-fluorophenyl)methylsilyl]pentan-3-amine Chemical compound CCC(N)(CC)[SiH2]Cc1ccc(F)cc1 NAGHEFSYCFYFEI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 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 description 2
- 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 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
- 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 1
- 102000010909 Monoamine Oxidase Human genes 0.000 abstract description 13
- 108010062431 Monoamine oxidase Proteins 0.000 abstract description 13
- 230000000144 pharmacologic effect Effects 0.000 abstract description 6
- 239000003112 inhibitor Substances 0.000 abstract description 5
- 208000018737 Parkinson disease Diseases 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 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 12
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 238000004587 chromatography analysis Methods 0.000 description 11
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 10
- 238000001914 filtration Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- MEMDIECPWPQFCX-UHFFFAOYSA-N benzyl-(chloromethyl)-dimethylsilane Chemical compound ClC[Si](C)(C)CC1=CC=CC=C1 MEMDIECPWPQFCX-UHFFFAOYSA-N 0.000 description 8
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 229940082992 antihypertensives mao inhibitors Drugs 0.000 description 7
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 235000013351 cheese Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 229960003732 tyramine Drugs 0.000 description 6
- 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 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 229960001779 pargyline Drugs 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical group C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- YUIOPHXTILULQC-UHFFFAOYSA-N 1,4-Dithiane-2,5-diol Chemical compound OC1CSC(O)CS1 YUIOPHXTILULQC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 229940124639 Selective inhibitor Drugs 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000001540 azides Chemical class 0.000 description 4
- 150000003943 catecholamines Chemical class 0.000 description 4
- 229960003638 dopamine Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 230000003389 potentiating effect Effects 0.000 description 4
- 239000000843 powder Substances 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
- 239000000758 substrate Substances 0.000 description 4
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 208000020401 Depressive disease Diseases 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 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
- 239000000706 filtrate Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 229960002672 isocarboxazid Drugs 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- 125000005543 phthalimide group Chemical group 0.000 description 3
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 2
- 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 2
- 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
- UWCYCARIMVPAMX-UHFFFAOYSA-N 1-phenyl-2-trimethylsilylethanamine Chemical compound C[Si](C)(C)CC(N)C1=CC=CC=C1 UWCYCARIMVPAMX-UHFFFAOYSA-N 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
- BIPSCIJNOZWJCA-UHFFFAOYSA-N 2-[[(4-fluorophenyl)methyl-dimethylsilyl]methyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C[Si](C)(C)CC1=CC=C(F)C=C1 BIPSCIJNOZWJCA-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
- GZDZMXHQEBYPRU-UHFFFAOYSA-N 2-[benzyl(dimethyl)silyl]ethanol Chemical compound OCC[Si](C)(C)CC1=CC=CC=C1 GZDZMXHQEBYPRU-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-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
- 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 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229910017852 NH2NH2 Inorganic materials 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 208000027089 Parkinsonian disease Diseases 0.000 description 2
- 206010034010 Parkinsonism Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910003902 SiCl 4 Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000150 Sympathomimetic Substances 0.000 description 2
- FYTPGBJPTDQJCG-UHFFFAOYSA-N Trichloro(chloromethyl)silane Chemical compound ClC[Si](Cl)(Cl)Cl FYTPGBJPTDQJCG-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- VIMWARQCQBIUHZ-UHFFFAOYSA-N benzyl n-(1-phenyl-2-trimethylsilylethyl)carbamate Chemical compound C=1C=CC=CC=1C(C[Si](C)(C)C)NC(=O)OCC1=CC=CC=C1 VIMWARQCQBIUHZ-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 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
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 2
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 2
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 238000009533 lab test Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- DWAWYEUJUWLESO-UHFFFAOYSA-N trichloromethylsilane Chemical compound [SiH3]C(Cl)(Cl)Cl DWAWYEUJUWLESO-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 238000010626 work up procedure 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)
Claims (8)
1. Förfarande för framställning av nya, terapeu-tiskt användbara silylalkylenaminer med formeln (I) eller 5 farmaceutiskt godtagbara salter därav, R4 Vfi-(CH2)nNH2 (I) R6 10 där n är ett heltal 1 eller 2, R4 är Ci.jQ-alkyl, R5 är C1.10-alkyl eller -(CH2)B-(X,Y-substltuerad fenyl), R6 är cyklohexylmetyl eller -(CH2)B-(X, Y-substituerad fe-15 nyl), varvid X och Y är H, OH, halogen, C1.6-alkyl, C1.6-alkoxl, CF3, CN eller N02, och m är ett heltal 1-4, för- utsatt, att R5-^l-R6 är annan än bensyldimetylsilyl, (3-klorbensyl)dimetylsilyl eller bensyldietylsilyl, k ä n -20 netecknat därav, att a) en förenlng, som har formeln O
25 R5-si-(CH2)n-N^jf^j (B) O omsätts med hydrazln, som är företrädesvis i hydratform, i 30 ett lämpligt lösningsmedel, företrädesvis etanol, och den bildade mellanprodukten behandlas med en vattenhaltig sy-ra, företrädesvis vattenhaltig klorvätesyra, varvid nämnda reaktioner utförs vid ungefär rektionsblandningens reflu-xeringstemperatur, eller 35 32 ‘13 303 b) en förening, som har formeln R. H I 4 I R5-Si-CHNHCOOt-butyl (D) K omsätts med gasformig klorvätesyra i ett vattenfritt lös-ningsmedel, företrädesvis eter, vid ungefär rumstempera-tur, eller c) en förening, som har formeln R4 R5-Si-(F) ' R6 X° ) amineras reduktivt genom att omsätta ketonen (F) med nat-riumcyanoborohydrid och ammoniumacetat i ett lämpligt vattenfritt lösningsmedel, företrädesvis metanol, vid ungefär rumstemperatur. 3 2. Förfarande enligt patentkravet 1, känne- t e c k n a t därav, att man framställer dimetyl-4-fluor-bensylsilylmetanamin.
3. Förfarande enligt patentkravet 1, känne- t e c k n a t därav, att man framställer dimetyl(3-pyri-5 dylmetylJsilylmetanamin.
4. Förfarande enligt patentkravet 1, känne- t e c k n a t därav, att man framställer B-(dimetyl-4-fluorbensylsilyl)etanamin.
5. Förfarande enligt patentkravet 1, känne- 0 tecknat därav, att man framställer 4-klorbensyldi- metylsilylmetanamin.
6. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer (2,4-difluorben-syl)etylmetylsilylmetanamin. ,5 i 33 .-::)8 03
7. Förfarande enligt patentkravet 1, känne- t e c k n a t därav, att man framställer (2,4-difluorben-syl)dimetylsilylmetanamin.
8. Förfarande enligt patentkravet 1, känne- 5 tecknat därav, att man framställer dietyl-4-fluor-bensylsilylmetanamin.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4784787A | 1987-05-08 | 1987-05-08 | |
| US4784787 | 1987-05-08 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI882072A0 FI882072A0 (fi) | 1988-05-04 |
| FI882072A FI882072A (fi) | 1988-11-09 |
| FI89803B true FI89803B (fi) | 1993-08-13 |
| FI89803C FI89803C (sv) | 1993-11-25 |
Family
ID=21951325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI882072A FI89803C (sv) | 1987-05-08 | 1988-05-04 | Förfarande för framställning av nya, terapeutiskt användbara substitue rade silylalkylenaminer |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0291787B1 (sv) |
| JP (1) | JP2640670B2 (sv) |
| KR (1) | KR950009194B1 (sv) |
| CN (1) | CN1023485C (sv) |
| AT (1) | ATE102947T1 (sv) |
| AU (1) | AU611683B2 (sv) |
| CA (1) | CA1341025C (sv) |
| DE (1) | DE3888391T2 (sv) |
| DK (1) | DK172834B1 (sv) |
| ES (1) | ES2052635T3 (sv) |
| FI (1) | FI89803C (sv) |
| HU (1) | HU199850B (sv) |
| IE (1) | IE61213B1 (sv) |
| IL (1) | IL86292A (sv) |
| NO (1) | NO179209C (sv) |
| NZ (1) | NZ224502A (sv) |
| PH (1) | PH26977A (sv) |
| PT (1) | PT87433B (sv) |
| ZA (1) | ZA883144B (sv) |
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 |
| MX2014005976A (es) | 2011-11-21 | 2014-08-27 | Bayer Ip Gmbh | Derivados de n-[(silil trisustituido)metil]-carboxamida fungicidas. |
| 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/sv not_active IP Right Cessation
- 1988-05-04 PH PH36891A patent/PH26977A/en 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
- 1988-05-05 NZ NZ224502A patent/NZ224502A/xx unknown
- 1988-05-06 KR KR1019880005241A patent/KR950009194B1/ko not_active IP Right Cessation
- 1988-05-06 AT AT88107312T patent/ATE102947T1/de not_active IP Right Cessation
- 1988-05-06 IE IE137888A patent/IE61213B1/en not_active IP Right Cessation
- 1988-05-06 EP EP88107312A patent/EP0291787B1/en not_active Expired - Lifetime
- 1988-05-06 HU HU882318A patent/HU199850B/hu not_active IP Right Cessation
- 1988-05-06 JP JP63111345A patent/JP2640670B2/ja not_active Expired - Lifetime
- 1988-05-06 DK DK198802492A patent/DK172834B1/da not_active IP Right Cessation
- 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 DE DE3888391T patent/DE3888391T2/de not_active Expired - Fee Related
- 1988-05-06 NO NO881991A patent/NO179209C/no not_active IP Right Cessation
- 1988-05-07 CN CN88102628A patent/CN1023485C/zh not_active Expired - Fee Related
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| MM | Patent lapsed |
Owner name: MERRELL DOW PHARMACEUTICALS INC. |