DE2539220A1 - Substituierte sulfoximide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel - Google Patents
Substituierte sulfoximide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittelInfo
- Publication number
- DE2539220A1 DE2539220A1 DE19752539220 DE2539220A DE2539220A1 DE 2539220 A1 DE2539220 A1 DE 2539220A1 DE 19752539220 DE19752539220 DE 19752539220 DE 2539220 A DE2539220 A DE 2539220A DE 2539220 A1 DE2539220 A1 DE 2539220A1
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- sulfoximides
- radicals
- groups
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title 1
- 229940126601 medicinal product Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 150000003254 radicals Chemical class 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000005555 sulfoximide group Chemical group 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical group C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 150000001449 anionic compounds Chemical group 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 150000007975 iminium salts Chemical class 0.000 claims description 3
- 150000002891 organic anions Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical group C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 11
- -1 η-butyl Chemical group 0.000 description 10
- 239000003921 oil Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000007717 exclusion Effects 0.000 description 6
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- SKAOERQLLZRKGY-UHFFFAOYSA-N 1-methylpiperidin-1-ium;bromide Chemical compound [Br-].C[NH+]1CCCCC1 SKAOERQLLZRKGY-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229930003347 Atropine Natural products 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 2
- 229960000396 atropine Drugs 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 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 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229940102396 methyl bromide Drugs 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- JBYHSSAVUBIJMK-UHFFFAOYSA-N 1,4-oxathiane Chemical compound C1CSCCO1 JBYHSSAVUBIJMK-UHFFFAOYSA-N 0.000 description 1
- LRKYLKBLUJXTFL-UHFFFAOYSA-N 1-(piperidin-1-ylmethyl)piperidine Chemical compound C1CCCCN1CN1CCCCC1 LRKYLKBLUJXTFL-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- ZZQUQFZVCJWSER-UHFFFAOYSA-N 3,4-dihydro-1h-isothiochromene Chemical compound C1=CC=C2CSCCC2=C1 ZZQUQFZVCJWSER-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WXICWQGWDGVMIP-UHFFFAOYSA-N 4-methylmorpholin-4-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[NH+]1CCOCC1 WXICWQGWDGVMIP-UHFFFAOYSA-N 0.000 description 1
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- DGKDUSLEYDJDHE-UHFFFAOYSA-N C(S(=O)=N)S(=O)=N Chemical compound C(S(=O)=N)S(=O)=N DGKDUSLEYDJDHE-UHFFFAOYSA-N 0.000 description 1
- VWEWZGXRVCOTLK-UHFFFAOYSA-N CC1=CC=C(S(=N)=O)C=C1 Chemical compound CC1=CC=C(S(=N)=O)C=C1 VWEWZGXRVCOTLK-UHFFFAOYSA-N 0.000 description 1
- AXYZTWMGRALTCR-UHFFFAOYSA-N COC1=CC=C(S(=N)=O)C=C1 Chemical compound COC1=CC=C(S(=N)=O)C=C1 AXYZTWMGRALTCR-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 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
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- GBTSVRPLKGEMIU-UHFFFAOYSA-N aminomethylidene(diethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)=CN GBTSVRPLKGEMIU-UHFFFAOYSA-N 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000001813 broncholytic effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- JHPVVOXKINUOSC-UHFFFAOYSA-N diethyl(methyl)azanium;iodide Chemical compound [I-].CC[NH+](C)CC JHPVVOXKINUOSC-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- QDUXDCXILAPLAG-UHFFFAOYSA-N hydron;1-methylpiperidine;chloride Chemical compound Cl.CN1CCCCC1 QDUXDCXILAPLAG-UHFFFAOYSA-N 0.000 description 1
- YFYIDTVGWCYSEO-UHFFFAOYSA-N imino-methyl-oxo-phenyl-$l^{6}-sulfane Chemical compound CS(=N)(=O)C1=CC=CC=C1 YFYIDTVGWCYSEO-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 230000003170 musculotropic effect Effects 0.000 description 1
- WKJPWARSTZJWDU-UHFFFAOYSA-N n-ethyl-n-[[(1-methylcyclohexyl)-oxo-phenyl-$l^{6}-sulfanylidene]amino]ethanamine Chemical compound C1CCCCC1(C)S(=O)(=NN(CC)CC)C1=CC=CC=C1 WKJPWARSTZJWDU-UHFFFAOYSA-N 0.000 description 1
- INFSYNLQBZDWRI-UHFFFAOYSA-N n-ethyl-n-methylethanamine;hydrobromide Chemical compound [Br-].CC[NH+](C)CC INFSYNLQBZDWRI-UHFFFAOYSA-N 0.000 description 1
- 230000002276 neurotropic effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752539220 DE2539220A1 (de) | 1975-09-03 | 1975-09-03 | Substituierte sulfoximide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| CH1050876A CH627740A5 (de) | 1975-09-03 | 1976-08-18 | Verfahren zur herstellung von substituierten sulfoximidsalzen. |
| ZA765176A ZA765176B (en) | 1975-09-03 | 1976-08-30 | New substituted sulphoximides a process for their peparation and pharmaceutical compositions containing these compounds |
| NL7609598A NL7609598A (nl) | 1975-09-03 | 1976-08-30 | Werkwijze ter bereiding van een geneesmiddel, zo gevormd geneesmiddel en werkwijze ter be- reiding van daarvoor geschikte geneeskrachtige verbindingen. |
| IL50399A IL50399A (en) | 1975-09-03 | 1976-09-01 | Substituted sulphoximides,a process for their preparation and pharmaceutical compositions containing these compounds |
| AU17350/76A AU1735076A (en) | 1975-09-03 | 1976-09-01 | Substituted sulfoximides |
| GR51596A GR65990B (enExample) | 1975-09-03 | 1976-09-01 | |
| AT649576A AT352724B (de) | 1975-09-03 | 1976-09-01 | Verfahren zur herstellung von neuen substi- tuierten sulfoximiden und deren salzen |
| US05/719,970 US4105795A (en) | 1975-09-03 | 1976-09-02 | Antispasmodic substituted sulphoximides |
| AR264572A AR216058A1 (es) | 1975-09-03 | 1976-09-02 | Procedimiento de preparacion de sulfoximidas sustituidas,y sus sales |
| CA260,429A CA1102808A (en) | 1975-09-03 | 1976-09-02 | Substituted sulphoximides, a process for their preparation and pharmaceutical compositions containing these compounds |
| PT65544A PT65544B (de) | 1975-09-03 | 1976-09-02 | Substituierte sulfoximide verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| GB36589/76A GB1526996A (en) | 1975-09-03 | 1976-09-03 | Substituted sulphoximides a process for their preparation and pharmaceutical compositions containing these compound |
| FR7626691A FR2322589A1 (fr) | 1975-09-03 | 1976-09-03 | Sulfoximides substitues, procede pour leur production et medicaments contenant ces composes |
| HU76HE719A HU176675B (en) | 1975-09-03 | 1976-09-03 | Process for preparing substituted sulphoximides and pharmaceutical nreparations containing such active material |
| MX764883U MX3845E (es) | 1975-09-03 | 1976-09-03 | Procedimiento para la preparacion de sulfoximidas substituidas y sus sales |
| BE170357A BE845856A (fr) | 1975-09-03 | 1976-09-03 | Sulfoximides substitues, procede pour leur production et medicaments contenant ces composes |
| JP51106198A JPS5239625A (en) | 1975-09-03 | 1976-09-03 | New substituted sulfoxyimides and salts thereof and process for manufacture thereof |
| ES451209A ES451209A1 (es) | 1975-09-03 | 1976-09-03 | Procedimiento de fabricacion de sulfoximidas sustituidas y sus sales medicamentosas. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752539220 DE2539220A1 (de) | 1975-09-03 | 1975-09-03 | Substituierte sulfoximide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2539220A1 true DE2539220A1 (de) | 1977-03-17 |
Family
ID=5955519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752539220 Withdrawn DE2539220A1 (de) | 1975-09-03 | 1975-09-03 | Substituierte sulfoximide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4105795A (enExample) |
| JP (1) | JPS5239625A (enExample) |
| AR (1) | AR216058A1 (enExample) |
| AT (1) | AT352724B (enExample) |
| AU (1) | AU1735076A (enExample) |
| BE (1) | BE845856A (enExample) |
| CA (1) | CA1102808A (enExample) |
| CH (1) | CH627740A5 (enExample) |
| DE (1) | DE2539220A1 (enExample) |
| ES (1) | ES451209A1 (enExample) |
| FR (1) | FR2322589A1 (enExample) |
| GB (1) | GB1526996A (enExample) |
| GR (1) | GR65990B (enExample) |
| HU (1) | HU176675B (enExample) |
| IL (1) | IL50399A (enExample) |
| MX (1) | MX3845E (enExample) |
| NL (1) | NL7609598A (enExample) |
| PT (1) | PT65544B (enExample) |
| ZA (1) | ZA765176B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991010648A1 (en) * | 1990-01-06 | 1991-07-25 | Pfizer Limited | Diphenylsulphoximine muscarinic receptor antagonists |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5531856A (en) * | 1978-08-28 | 1980-03-06 | Achilles Corp | Resin composition for electroconductive shoe |
| US5187189A (en) * | 1991-01-22 | 1993-02-16 | American Home Products Corporation | S-aminoalkyl-s-arylsulfoximines as antiarrhythmic agents |
| US5140026A (en) * | 1991-05-09 | 1992-08-18 | A. H. Robins Company, Incorporated | N-aminoalkyl-S-aryl-S-alkyl (or substituted alkyl) sulfoximines as antiarrhythmic agents |
| CN101528674B (zh) * | 2006-10-25 | 2015-04-29 | 汉高知识产权及控股有限公司 | 亚胺*盐和使用该新的亚胺*盐制备缺电子烯烃的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3637664A (en) * | 1966-12-22 | 1972-01-25 | Warner Lambert Co | N-substituted aminoalkyl-s s-diphenyl-sulfoximines and process for their production |
-
1975
- 1975-09-03 DE DE19752539220 patent/DE2539220A1/de not_active Withdrawn
-
1976
- 1976-08-18 CH CH1050876A patent/CH627740A5/de not_active IP Right Cessation
- 1976-08-30 ZA ZA765176A patent/ZA765176B/xx unknown
- 1976-08-30 NL NL7609598A patent/NL7609598A/xx not_active Application Discontinuation
- 1976-09-01 AT AT649576A patent/AT352724B/de not_active IP Right Cessation
- 1976-09-01 IL IL50399A patent/IL50399A/xx unknown
- 1976-09-01 AU AU17350/76A patent/AU1735076A/en not_active Expired
- 1976-09-01 GR GR51596A patent/GR65990B/el unknown
- 1976-09-02 CA CA260,429A patent/CA1102808A/en not_active Expired
- 1976-09-02 PT PT65544A patent/PT65544B/pt unknown
- 1976-09-02 US US05/719,970 patent/US4105795A/en not_active Expired - Lifetime
- 1976-09-02 AR AR264572A patent/AR216058A1/es active
- 1976-09-03 JP JP51106198A patent/JPS5239625A/ja active Pending
- 1976-09-03 HU HU76HE719A patent/HU176675B/hu unknown
- 1976-09-03 GB GB36589/76A patent/GB1526996A/en not_active Expired
- 1976-09-03 MX MX764883U patent/MX3845E/es unknown
- 1976-09-03 BE BE170357A patent/BE845856A/xx not_active IP Right Cessation
- 1976-09-03 ES ES451209A patent/ES451209A1/es not_active Expired
- 1976-09-03 FR FR7626691A patent/FR2322589A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991010648A1 (en) * | 1990-01-06 | 1991-07-25 | Pfizer Limited | Diphenylsulphoximine muscarinic receptor antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| IL50399A0 (en) | 1976-11-30 |
| PT65544B (de) | 1978-03-24 |
| US4105795A (en) | 1978-08-08 |
| JPS5239625A (en) | 1977-03-28 |
| PT65544A (de) | 1976-10-01 |
| ES451209A1 (es) | 1977-12-16 |
| AU1735076A (en) | 1978-03-09 |
| ZA765176B (en) | 1977-08-31 |
| AR216058A1 (es) | 1979-11-30 |
| IL50399A (en) | 1981-10-30 |
| FR2322589B1 (enExample) | 1980-04-18 |
| CH627740A5 (de) | 1982-01-29 |
| HU176675B (en) | 1981-04-28 |
| MX3845E (es) | 1981-08-18 |
| FR2322589A1 (fr) | 1977-04-01 |
| NL7609598A (nl) | 1977-03-07 |
| ATA649576A (de) | 1979-03-15 |
| GB1526996A (en) | 1978-10-04 |
| AT352724B (de) | 1979-10-10 |
| CA1102808A (en) | 1981-06-09 |
| BE845856A (fr) | 1976-12-31 |
| GR65990B (enExample) | 1981-01-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH653989A5 (de) | Cyclobutendion-verbindungen. | |
| DE2065236B2 (de) | Phosphonsäuresalze, ihre Herstellung und Verwendung | |
| DE3522579A1 (de) | Neue 1,4-dihydropyridin-derivate und salze derselben, verfahren zur herstellung derselben und pharmazeutische mittel mit einem gehalt derselben | |
| DE2818947C2 (enExample) | ||
| DE69224507T2 (de) | Beta-Oxo-Beta-Benzenepropanthioamidderivate | |
| DE3109794A1 (de) | "bluthochdruck senkende amine" | |
| DE2539220A1 (de) | Substituierte sulfoximide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| CH621772A5 (enExample) | ||
| EP0534904B1 (de) | Imidazolylmethyl-Pyridine | |
| US3479346A (en) | N-acyl-n- (and n,n-bis-) ((1-piperidyl)-lower-alkyl)amines | |
| GB1565647A (en) | Pharmacologically active compounds 4-substituted-imidazole-5-methanols | |
| DD243491A5 (de) | Verfahren zur herstellung neuer 3-phenyl-2-propanamin-derivate | |
| DE2514334A1 (de) | Neue pyridinderivate, verfahren zu deren herstellung und ihre verwendung in pharmazeutischen zusammensetzungen | |
| DE3889208T2 (de) | Thioformamid-Derivate. | |
| DE2303822C2 (de) | 1-Cyclopropyl-1-phenyl-ω-amino-1-alkanol-Derivate und deren Ester, Verfahren zu ihrer Herstellung und pharmazeutische Präparate auf deren Basis | |
| DE2331721A1 (de) | Verfahren zur herstellung neuer heterocyclischer verbindungen | |
| DE2543031A1 (de) | 2(1h)-pyridinyliden-guanidin-derivate, ihre salze, verfahren zu ihrer herstellung, zwischenprodukte und arzneimittel | |
| DE2520230A1 (de) | Substituierte sulfodiimide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| EP0363869B1 (de) | Substituierte thienylethylamine und Verfahren zu deren Herstellung | |
| US2528306A (en) | Thenylamines | |
| DE2554863C2 (de) | Thiazolinylidenaminophenylpropionsäure-Derivate, ihre Salze, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE3513184A1 (de) | 1,3,4-thiadiazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| EP0180754A2 (de) | 3,4-Diazolderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE1124496B (de) | Verfahren zur Herstellung von tertiaeren Aminen, ihren Saeureadditionssalzen und quaternaeren Ammoniumverbindungen | |
| DE3535930A1 (de) | Neue 2-substituierte ergolinderivate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8130 | Withdrawal |