FI58325C - Foerfarande foer framstaellning av farmakologiskt vaerdefulla sulfamider - Google Patents
Foerfarande foer framstaellning av farmakologiskt vaerdefulla sulfamider Download PDFInfo
- Publication number
- FI58325C FI58325C FI915/72A FI91572A FI58325C FI 58325 C FI58325 C FI 58325C FI 915/72 A FI915/72 A FI 915/72A FI 91572 A FI91572 A FI 91572A FI 58325 C FI58325 C FI 58325C
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- Finland
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- group
- chr
- formula
- hydroxy
- hydrogen
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- 230000000144 pharmacologic effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 47
- -1 phenoxy, hydroxyphenyl Chemical group 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 230000002829 reductive effect Effects 0.000 claims description 4
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 claims 1
- 101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 description 9
- 239000012279 sodium borohydride Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000007868 Raney catalyst Substances 0.000 description 6
- 229910000564 Raney nickel Inorganic materials 0.000 description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 230000010412 perfusion Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 230000002093 peripheral effect Effects 0.000 description 4
- 230000024883 vasodilation Effects 0.000 description 4
- VLJAEEVNYSRKHM-UHFFFAOYSA-N 2-(dimethylsulfamoylamino)-1-hydroxy-4-[1-hydroxy-2-(2-phenoxypropan-2-ylamino)ethyl]benzene Chemical compound C1=C(O)C(NS(=O)(=O)N(C)C)=CC(C(O)CNC(C)(C)OC=2C=CC=CC=2)=C1 VLJAEEVNYSRKHM-UHFFFAOYSA-N 0.000 description 3
- JABCEAMBQLYGJQ-UHFFFAOYSA-N OC1=C(C=C(C=C1)C(CNC(CCC1=CC=CC=C1)(C)C)O)NS(=O)(=O)N(C)C Chemical compound OC1=C(C=C(C=C1)C(CNC(CCC1=CC=CC=C1)(C)C)O)NS(=O)(=O)N(C)C JABCEAMBQLYGJQ-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000002373 hemiacetals Chemical class 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BMUKKTUHUDJSNZ-UHFFFAOYSA-N 4-[1-hydroxy-2-(1-phenoxypropan-2-ylamino)propyl]phenol Chemical compound C=1C=C(O)C=CC=1C(O)C(C)NC(C)COC1=CC=CC=C1 BMUKKTUHUDJSNZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 210000003141 lower extremity Anatomy 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- QWAVNXZAQASOML-UHFFFAOYSA-N 1-phenoxypropan-2-one Chemical compound CC(=O)COC1=CC=CC=C1 QWAVNXZAQASOML-UHFFFAOYSA-N 0.000 description 1
- CKJRKLKVCHMWLV-UHFFFAOYSA-N 2-(2-methoxyphenoxy)ethanamine Chemical compound COC1=CC=CC=C1OCCN CKJRKLKVCHMWLV-UHFFFAOYSA-N 0.000 description 1
- HTELNSZFICFFDY-UHFFFAOYSA-N 2-(dimethylsulfamoylamino)-1-hydroxy-4-(2-oxopropyl)benzene Chemical compound OC1=C(C=C(C=C1)CC(C)=O)NS(=O)(=O)N(C)C HTELNSZFICFFDY-UHFFFAOYSA-N 0.000 description 1
- OOVNXQIFYLNPHP-UHFFFAOYSA-N 2-(dimethylsulfamoylamino)-1-hydroxy-4-[1-hydroxy-2-[2-(2-methoxyphenoxy)ethylamino]ethyl]benzene Chemical compound OC1=C(C=C(C=C1)C(CNCCOC1=C(C=CC=C1)OC)O)NS(=O)(=O)N(C)C OOVNXQIFYLNPHP-UHFFFAOYSA-N 0.000 description 1
- WUIRWZPQAFRYMR-UHFFFAOYSA-N 2-(dimethylsulfamoylamino)-4-[1-hydroxy-2-[2-(2-methoxyphenoxy)ethylamino]ethyl]-1-phenylmethoxybenzene Chemical compound C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C(CNCCOC1=C(C=CC=C1)OC)O)NS(=O)(=O)N(C)C WUIRWZPQAFRYMR-UHFFFAOYSA-N 0.000 description 1
- PRJWYFPDHWJLEV-UHFFFAOYSA-N 2-methyl-4-phenylbutan-2-amine Chemical compound CC(C)(N)CCC1=CC=CC=C1 PRJWYFPDHWJLEV-UHFFFAOYSA-N 0.000 description 1
- RYPTUTPKWGZXCY-UHFFFAOYSA-N 2-phenoxypropan-2-amine Chemical compound CC(C)(N)OC1=CC=CC=C1 RYPTUTPKWGZXCY-UHFFFAOYSA-N 0.000 description 1
- XLGIKRNKRPTKHL-UHFFFAOYSA-N 2-phenoxypropan-2-amine;hydrobromide Chemical compound Br.CC(C)(N)OC1=CC=CC=C1 XLGIKRNKRPTKHL-UHFFFAOYSA-N 0.000 description 1
- MDIPBCCAQUVZND-UHFFFAOYSA-N 4-(2-amino-1-hydroxypropyl)-2-(dimethylsulfamoylamino)-1-hydroxybenzene Chemical compound OC1=C(C=C(C=C1)C(C(C)N)O)NS(=O)(=O)N(C)C MDIPBCCAQUVZND-UHFFFAOYSA-N 0.000 description 1
- YUDIYDJTADRDEN-UHFFFAOYSA-N 4-(2-aminopropyl)-2-(dimethylsulfamoylamino)-1-hydroxybenzene Chemical compound OC1=C(C=C(C=C1)CC(C)N)NS(=O)(=O)N(C)C YUDIYDJTADRDEN-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KJVVHPCHTVCYOL-UHFFFAOYSA-N CC(C(C1=CC(=CC=C1)N(O)S(=O)(=O)N(C)C)O)N Chemical compound CC(C(C1=CC(=CC=C1)N(O)S(=O)(=O)N(C)C)O)N KJVVHPCHTVCYOL-UHFFFAOYSA-N 0.000 description 1
- XKFPXTYVEUGHIC-UHFFFAOYSA-N CCC(C(C)N)C(C=C1)=CC(NS(N(C)C)(=O)=O)=C1O Chemical compound CCC(C(C)N)C(C=C1)=CC(NS(N(C)C)(=O)=O)=C1O XKFPXTYVEUGHIC-UHFFFAOYSA-N 0.000 description 1
- WBOOXLVECGMZJN-UHFFFAOYSA-N CCNCC(C1=CC(=C(C=C1)O)NS(=O)(=O)N(C)C)O Chemical compound CCNCC(C1=CC(=C(C=C1)O)NS(=O)(=O)N(C)C)O WBOOXLVECGMZJN-UHFFFAOYSA-N 0.000 description 1
- GCDUWHMRDFJARZ-UHFFFAOYSA-N CN(C)S(=O)(=O)N(C1=CC=CC(=C1)C(CN)O)O Chemical compound CN(C)S(=O)(=O)N(C1=CC=CC(=C1)C(CN)O)O GCDUWHMRDFJARZ-UHFFFAOYSA-N 0.000 description 1
- QJHPMTKYBWJLGS-UHFFFAOYSA-N CN(C)S(=O)(=O)NC1=C(C=CC(=C1)C(CNC(CC=O)C2=CC=CC=C2)O)O Chemical compound CN(C)S(=O)(=O)NC1=C(C=CC(=C1)C(CNC(CC=O)C2=CC=CC=C2)O)O QJHPMTKYBWJLGS-UHFFFAOYSA-N 0.000 description 1
- 101100532690 Caenorhabditis elegans mau-2 gene Proteins 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 102100036309 MAU2 chromatid cohesion factor homolog Human genes 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- ATFVEZSSZDYHBL-UHFFFAOYSA-N [chlorosulfonyloxy(methyl)amino]methane Chemical compound CN(C)OS(Cl)(=O)=O ATFVEZSSZDYHBL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- LXWZZBDWWCCJDU-UHFFFAOYSA-N benzoic acid;ethane Chemical compound CC.OC(=O)C1=CC=CC=C1 LXWZZBDWWCCJDU-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- GPOMTENHXXIXEG-UHFFFAOYSA-N ethyl(2-hydroxyethyl)azanium;chloride Chemical compound Cl.CCNCCO GPOMTENHXXIXEG-UHFFFAOYSA-N 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000001976 hemiacetal group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229960004819 isoxsuprine Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UMFZHZYVMPUKIM-UHFFFAOYSA-N n-benzyl-n-bromoethanamine Chemical compound CCN(Br)CC1=CC=CC=C1 UMFZHZYVMPUKIM-UHFFFAOYSA-N 0.000 description 1
- HVAAHUDGWQAAOJ-UHFFFAOYSA-N n-benzylethanamine Chemical compound CCNCC1=CC=CC=C1 HVAAHUDGWQAAOJ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2115926A DE2115926C3 (de) | 1971-04-01 | 1971-04-01 | 1 -(4-Hydroxy-3-dimethylaminosuIfamidophenyI)-2-aminoäthanderivate, Verfahren zu ihrer Herstellung und diese enthaltende Mittel |
| DE2115926 | 1971-04-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI58325B FI58325B (fi) | 1980-09-30 |
| FI58325C true FI58325C (fi) | 1981-01-12 |
Family
ID=5803592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI915/72A FI58325C (fi) | 1971-04-01 | 1972-03-30 | Foerfarande foer framstaellning av farmakologiskt vaerdefulla sulfamider |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4038314A (es) |
| JP (3) | JPS5735193B1 (es) |
| AR (6) | AR204905A1 (es) |
| AT (7) | AT321888B (es) |
| AU (1) | AU470838B2 (es) |
| BE (1) | BE781542A (es) |
| CH (6) | CH580069A5 (es) |
| DE (1) | DE2115926C3 (es) |
| DK (1) | DK140836B (es) |
| ES (4) | ES401332A1 (es) |
| FI (1) | FI58325C (es) |
| FR (1) | FR2132372B1 (es) |
| GB (1) | GB1381184A (es) |
| IE (1) | IE36240B1 (es) |
| IL (1) | IL39110A (es) |
| NL (1) | NL170850C (es) |
| NO (1) | NO135247C (es) |
| PH (1) | PH14121A (es) |
| SE (1) | SE393106B (es) |
| ZA (1) | ZA722177B (es) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1435721A (en) * | 1972-05-18 | 1976-05-12 | Lilly Industries Ltd | Benzoxazole derivatives |
| CA1147342A (en) * | 1977-10-12 | 1983-05-31 | Kazuo Imai | Process of producing novel phenylethanolamine derivatives |
| JPS56110665A (en) * | 1980-02-08 | 1981-09-01 | Yamanouchi Pharmaceut Co Ltd | Sulfamoyl-substituted phenetylamine derivative and its preparation |
| US4558156A (en) * | 1980-02-08 | 1985-12-10 | Yamanouchi Pharmaceutical Co., Ltd. | Sulfamoyl-substituted phenethylamine derivatives |
| DE3220598A1 (de) * | 1982-06-01 | 1983-12-01 | Boehringer Ingelheim KG, 6507 Ingelheim | Lipolytische zusammensetzungen und mittel zur behandlung der fettsucht |
| GB8322178D0 (en) * | 1983-08-17 | 1983-09-21 | Sterwin Ag | Preparing aerosol compositions |
| GB8502892D0 (en) * | 1985-02-05 | 1985-03-06 | Sterwin Ag | Aerosol composition |
| IE883400L (en) * | 1987-11-13 | 1989-05-13 | Fuisz Technologies Ltd | Phenethanolamine derivatives |
| US20040127733A1 (en) | 2002-10-31 | 2004-07-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | New beta-agonists, processes for preparing them and their use as pharmaceutical compositions |
| DE10251170A1 (de) * | 2002-10-31 | 2004-05-13 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Beta-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| DE102004021779A1 (de) | 2004-04-30 | 2005-11-24 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Beta-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| DE102005052127A1 (de) | 2005-10-28 | 2007-05-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue indol-haltige Beta-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| US7718822B2 (en) * | 2007-08-28 | 2010-05-18 | Sepracor Inc. | Carbamate Stereoisomer |
| CN109535007A (zh) * | 2018-11-07 | 2019-03-29 | 万华化学集团股份有限公司 | 一种二氨基二环己基甲烷同分异构体分离方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3804834A (en) * | 1967-10-16 | 1974-04-16 | Boehringer Sohn Ingelheim | 1-(2',3',4'-trisubstituted-phenyl)-2-amino-alkanols-(1)and salts thereof |
| US3701808A (en) * | 1967-12-21 | 1972-10-31 | Allen & Hanburys Ltd | Phenylethanolamines |
| US3574741A (en) * | 1969-04-14 | 1971-04-13 | Mead Johnson & Co | Sulfonamidophenalkylamines |
| US3711545A (en) * | 1971-02-23 | 1973-01-16 | Smith Kline French Lab | Alpha-aminoalkyl-4-hydroxy-3-sulfamoylaminobenzyl alcohols |
| BE794414A (fr) * | 1972-01-25 | 1973-07-23 | Sandoz Sa | Nouveaux amino-alcools, leur preparation et leur application comme medicament |
-
1971
- 1971-04-01 DE DE2115926A patent/DE2115926C3/de not_active Expired
-
1972
- 1972-01-01 AR AR244859A patent/AR204905A1/es active
- 1972-03-28 NO NO1061/72A patent/NO135247C/no unknown
- 1972-03-29 ES ES401332A patent/ES401332A1/es not_active Expired
- 1972-03-29 PH PH13398A patent/PH14121A/en unknown
- 1972-03-29 DK DK154772AA patent/DK140836B/da not_active IP Right Cessation
- 1972-03-29 IL IL39110A patent/IL39110A/xx unknown
- 1972-03-30 FI FI915/72A patent/FI58325C/fi active
- 1972-03-30 GB GB1515672A patent/GB1381184A/en not_active Expired
- 1972-03-30 NL NLAANVRAGE7204316,A patent/NL170850C/xx not_active IP Right Cessation
- 1972-03-30 CH CH1390475A patent/CH580069A5/xx not_active IP Right Cessation
- 1972-03-30 ZA ZA722177A patent/ZA722177B/xx unknown
- 1972-03-30 CH CH1647576A patent/CH587237A5/xx not_active IP Right Cessation
- 1972-03-30 AU AU40592/72A patent/AU470838B2/en not_active Expired
- 1972-03-30 CH CH1390375A patent/CH580068A5/xx not_active IP Right Cessation
- 1972-03-30 IE IE415/72A patent/IE36240B1/xx unknown
- 1972-03-30 SE SE7204239A patent/SE393106B/xx unknown
- 1972-03-30 CH CH1056976A patent/CH590219A5/xx not_active IP Right Cessation
- 1972-03-30 CH CH1390275A patent/CH572905A5/xx not_active IP Right Cessation
- 1972-03-30 CH CH482372A patent/CH587236A5/xx not_active IP Right Cessation
- 1972-03-31 JP JP3180472A patent/JPS5735193B1/ja active Pending
- 1972-03-31 AT AT89474*A patent/AT321888B/de not_active IP Right Cessation
- 1972-03-31 AT AT00895/74A patent/AT320613B/de not_active IP Right Cessation
- 1972-03-31 FR FR7211614A patent/FR2132372B1/fr not_active Expired
- 1972-03-31 BE BE781542A patent/BE781542A/xx not_active IP Right Cessation
- 1972-03-31 AT AT915174*1A patent/ATA915174A/de unknown
- 1972-03-31 AT AT284472A patent/AT326628B/de not_active IP Right Cessation
- 1972-03-31 AT AT915074*7A patent/AT327173B/de not_active IP Right Cessation
- 1972-03-31 AT AT915174*7A patent/AT327174B/de active
- 1972-10-27 AR AR244860A patent/AR200116A1/es active
- 1972-10-27 AR AR244858A patent/AR200002A1/es active
-
1973
- 1973-10-25 ES ES419936A patent/ES419936A1/es not_active Expired
- 1973-10-25 ES ES419934A patent/ES419934A1/es not_active Expired
- 1973-10-25 ES ES419935A patent/ES419935A1/es not_active Expired
- 1973-11-26 AR AR251171A patent/AR209268A1/es active
- 1973-11-26 AR AR251169A patent/AR199809A1/es active
- 1973-11-26 AR AR251170A patent/AR210055A1/es active
-
1974
- 1974-03-21 US US05/453,438 patent/US4038314A/en not_active Expired - Lifetime
- 1974-03-31 AT AT89674*A patent/AT321889B/de not_active IP Right Cessation
-
1981
- 1981-05-25 JP JP56078169A patent/JPS5929190B2/ja not_active Expired
- 1981-05-25 JP JP56078170A patent/JPS5929191B2/ja not_active Expired
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