CH627740A5 - Verfahren zur herstellung von substituierten sulfoximidsalzen. - Google Patents
Verfahren zur herstellung von substituierten sulfoximidsalzen. Download PDFInfo
- Publication number
- CH627740A5 CH627740A5 CH1050876A CH1050876A CH627740A5 CH 627740 A5 CH627740 A5 CH 627740A5 CH 1050876 A CH1050876 A CH 1050876A CH 1050876 A CH1050876 A CH 1050876A CH 627740 A5 CH627740 A5 CH 627740A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- formula
- sulfoximide
- atoms
- compound
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 5
- -1 methoxy, ethoxy, propoxy Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000007975 iminium salts Chemical class 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 150000001449 anionic compounds Chemical class 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 150000002891 organic anions Chemical class 0.000 claims description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000005555 sulfoximide group Chemical group 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 239000000010 aprotic solvent Substances 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 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 claims 1
- 235000011054 acetic acid Nutrition 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 239000001630 malic acid Substances 0.000 claims 1
- 235000011090 malic acid Nutrition 0.000 claims 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 235000011007 phosphoric acid Nutrition 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229960001340 histamine Drugs 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 101150041968 CDC13 gene Proteins 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000008098 formaldehyde solution Substances 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 229940102396 methyl bromide Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000002048 spasmolytic effect Effects 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 229930003347 Atropine Natural products 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-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
- XQGOFKFATFKSFH-UHFFFAOYSA-N N-ethyl-N-[[[oxo(diphenyl)-lambda6-sulfanylidene]amino]methyl]ethanamine Chemical compound C(C)N(CC)CN=S(=O)(C1=CC=CC=C1)C1=CC=CC=C1 XQGOFKFATFKSFH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 238000005273 aeration Methods 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
- 239000002585 base Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- YRBWBVBBWHYPJE-UHFFFAOYSA-N oxo-diphenyl-(piperidin-1-ylmethylimino)-lambda6-sulfane Chemical compound N1(CCCCC1)CN=S(=O)(C1=CC=CC=C1)C1=CC=CC=C1 YRBWBVBBWHYPJE-UHFFFAOYSA-N 0.000 description 2
- 208000009079 Bronchial Spasm Diseases 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QAJAPCKYJKXVOR-UHFFFAOYSA-N ClC1=CC=C(S(=N)=O)C=C1 Chemical compound ClC1=CC=C(S(=N)=O)C=C1 QAJAPCKYJKXVOR-UHFFFAOYSA-N 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 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
- 229940098165 atrovent Drugs 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
- 230000001813 broncholytic effect Effects 0.000 description 1
- 229940088506 buscopan Drugs 0.000 description 1
- HOZOZZFCZRXYEK-GSWUYBTGSA-M butylscopolamine bromide Chemical compound [Br-].C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)CCCC)=CC=CC=C1 HOZOZZFCZRXYEK-GSWUYBTGSA-M 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- KEWHKYJURDBRMN-XSAPEOHZSA-M chembl2134724 Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-XSAPEOHZSA-M 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 229960000520 diphenhydramine Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-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
- MSWZGWJZZCNBPR-UHFFFAOYSA-N oxo-diphenyl-(pyrrolidin-1-ylmethylimino)-lambda6-sulfane Chemical compound N1(CCCC1)CN=S(=O)(C1=CC=CC=C1)C1=CC=CC=C1 MSWZGWJZZCNBPR-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 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)
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 |
|---|---|
| CH627740A5 true CH627740A5 (de) | 1982-01-29 |
Family
ID=5955519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1050876A CH627740A5 (de) | 1975-09-03 | 1976-08-18 | Verfahren zur herstellung von substituierten sulfoximidsalzen. |
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) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5531856A (en) * | 1978-08-28 | 1980-03-06 | Achilles Corp | Resin composition for electroconductive shoe |
| GB9000303D0 (en) * | 1990-01-06 | 1990-03-07 | Pfizer Ltd | Therapeutic agents |
| 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
Also Published As
| Publication number | Publication date |
|---|---|
| IL50399A0 (en) | 1976-11-30 |
| PT65544B (de) | 1978-03-24 |
| US4105795A (en) | 1978-08-08 |
| DE2539220A1 (de) | 1977-03-17 |
| 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 |
| 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 |
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