DK172834B1 - Benzyldimethylsilylmethanaminer og farmaceutisk acceptable salte deraf - Google Patents
Benzyldimethylsilylmethanaminer og farmaceutisk acceptable salte deraf Download PDFInfo
- Publication number
- DK172834B1 DK172834B1 DK198802492A DK249288A DK172834B1 DK 172834 B1 DK172834 B1 DK 172834B1 DK 198802492 A DK198802492 A DK 198802492A DK 249288 A DK249288 A DK 249288A DK 172834 B1 DK172834 B1 DK 172834B1
- Authority
- DK
- Denmark
- Prior art keywords
- mao
- compounds
- dimethyl
- yield
- inhibitors
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims description 6
- VFAHGRJJCYCNTG-UHFFFAOYSA-N 1-dimethylsilyl-2-phenylethanamine Chemical class C[SiH](C)C(N)CC1=CC=CC=C1 VFAHGRJJCYCNTG-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 27
- 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
- PYSDOECVWDSXBT-UHFFFAOYSA-N 2-[(4-fluorophenyl)methylsilyl]propan-2-amine Chemical group CC(C)(N)[SiH2]Cc1ccc(F)cc1 PYSDOECVWDSXBT-UHFFFAOYSA-N 0.000 claims 1
- 102000010909 Monoamine Oxidase Human genes 0.000 abstract description 19
- 108010062431 Monoamine oxidase Proteins 0.000 abstract description 19
- 239000003112 inhibitor Substances 0.000 abstract description 9
- -1 silyl alkylene amines Chemical class 0.000 abstract description 6
- 208000018737 Parkinson disease Diseases 0.000 abstract description 4
- 230000000144 pharmacologic effect Effects 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 9
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 229960003732 tyramine Drugs 0.000 description 7
- 150000003943 catecholamines Chemical class 0.000 description 6
- 235000013351 cheese Nutrition 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 229940082992 antihypertensives mao inhibitors Drugs 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 4
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 4
- 229940124639 Selective inhibitor Drugs 0.000 description 4
- 229960003638 dopamine Drugs 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229960001779 pargyline Drugs 0.000 description 4
- 230000002093 peripheral effect Effects 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
- 239000002904 solvent Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 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
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 229960005139 epinephrine Drugs 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000002503 metabolic effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
- 230000003389 potentiating effect Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000002560 therapeutic procedure Methods 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 2
- FMEVAQARAVDUNY-UHFFFAOYSA-N 2-(2-aminoethyl)phenol Chemical compound NCCC1=CC=CC=C1O FMEVAQARAVDUNY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-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
- RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 description 2
- 239000000150 Sympathomimetic Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 235000013305 food Nutrition 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
- 229960002672 isocarboxazid Drugs 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
- 239000002858 neurotransmitter agent Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229960000964 phenelzine Drugs 0.000 description 2
- 229940117803 phenethylamine Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229940127230 sympathomimetic drug Drugs 0.000 description 2
- 229960003741 tranylcypromine Drugs 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical class C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- 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 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
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 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
- 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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229930006000 Sucrose Natural products 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
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 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
- 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
- 239000011230 binding agent Substances 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 210000000133 brain stem Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 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 1
- 229940127232 direct-acting sympathomimetic drug Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 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
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 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
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002315 pressor effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000003381 stabilizer Substances 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
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000036962 time dependent Effects 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4784787A | 1987-05-08 | 1987-05-08 | |
| US4784787 | 1987-05-08 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK249288D0 DK249288D0 (da) | 1988-05-06 |
| DK249288A DK249288A (da) | 1988-11-09 |
| DK172834B1 true DK172834B1 (da) | 1999-08-09 |
Family
ID=21951325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK198802492A DK172834B1 (da) | 1987-05-08 | 1988-05-06 | Benzyldimethylsilylmethanaminer og farmaceutisk acceptable salte deraf |
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 |
| EP2782920B1 (en) | 2011-11-21 | 2016-12-21 | Bayer Intellectual Property GmbH | Fungicide n-[(trisubstitutedsilyl)methyl]-carboxamide derivatives |
| 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 CA CA000565813A patent/CA1341025C/en not_active Expired - Fee Related
- 1988-05-03 ZA ZA883144A patent/ZA883144B/xx unknown
- 1988-05-04 PH PH36891A patent/PH26977A/en unknown
- 1988-05-04 FI FI882072A patent/FI89803C/fi not_active IP Right Cessation
- 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 EP EP88107312A patent/EP0291787B1/en not_active Expired - Lifetime
- 1988-05-06 DE DE3888391T patent/DE3888391T2/de not_active Expired - Fee Related
- 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 PT PT87433A patent/PT87433B/pt 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 NO NO881991A patent/NO179209C/no not_active IP Right Cessation
- 1988-05-06 HU HU882318A patent/HU199850B/hu not_active IP Right Cessation
- 1988-05-06 ES ES88107312T patent/ES2052635T3/es not_active Expired - Lifetime
- 1988-05-07 CN CN88102628A patent/CN1023485C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DK249288D0 (da) | 1988-05-06 |
| PH26977A (en) | 1992-12-28 |
| PT87433B (pt) | 1992-08-31 |
| DE3888391D1 (de) | 1994-04-21 |
| NO179209B (no) | 1996-05-20 |
| FI882072A0 (fi) | 1988-05-04 |
| PT87433A (pt) | 1989-05-31 |
| JP2640670B2 (ja) | 1997-08-13 |
| NZ224502A (en) | 1990-09-26 |
| KR880013953A (ko) | 1988-12-22 |
| HU199850B (en) | 1990-03-28 |
| DE3888391T2 (de) | 1994-06-23 |
| ES2052635T3 (es) | 1994-07-16 |
| KR950009194B1 (ko) | 1995-08-16 |
| CN1023485C (zh) | 1994-01-12 |
| ATE102947T1 (de) | 1994-04-15 |
| NO881991L (no) | 1988-11-09 |
| FI89803C (fi) | 1993-11-25 |
| NO179209C (no) | 1996-08-28 |
| DK249288A (da) | 1988-11-09 |
| JPS63287786A (ja) | 1988-11-24 |
| IE61213B1 (en) | 1994-10-19 |
| IL86292A (en) | 1996-03-31 |
| EP0291787A1 (en) | 1988-11-23 |
| HUT47122A (en) | 1989-01-30 |
| FI882072A (fi) | 1988-11-09 |
| NO881991D0 (no) | 1988-05-06 |
| AU1564388A (en) | 1988-11-10 |
| EP0291787B1 (en) | 1994-03-16 |
| IE881378L (en) | 1988-11-08 |
| FI89803B (fi) | 1993-08-13 |
| AU611683B2 (en) | 1991-06-20 |
| IL86292A0 (en) | 1988-11-15 |
| CA1341025C (en) | 2000-06-13 |
| ZA883144B (en) | 1988-11-08 |
| CN88102628A (zh) | 1988-11-30 |
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| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |
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