FI66858C - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara sulfoximider och salter daerav - Google Patents
Foerfarande foer framstaellning av nya terapeutiskt anvaendbara sulfoximider och salter daerav Download PDFInfo
- Publication number
- FI66858C FI66858C FI784009A FI784009A FI66858C FI 66858 C FI66858 C FI 66858C FI 784009 A FI784009 A FI 784009A FI 784009 A FI784009 A FI 784009A FI 66858 C FI66858 C FI 66858C
- Authority
- FI
- Finland
- Prior art keywords
- thienyl
- sulfoximide
- phenyl
- general formula
- diethylaminoethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 6
- 125000005555 sulfoximide group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 1
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- 239000000155 melt Substances 0.000 description 19
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- LXFQSRIDYRFTJW-UHFFFAOYSA-M 2,4,6-trimethylbenzenesulfonate Chemical compound CC1=CC(C)=C(S([O-])(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-M 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 7
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- -1 halide ion Chemical class 0.000 description 5
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- CURCMGVZNYCRNY-UHFFFAOYSA-N trimethylazanium;iodide Chemical compound I.CN(C)C CURCMGVZNYCRNY-UHFFFAOYSA-N 0.000 description 4
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- AAYSYRDMYHUBOQ-UHFFFAOYSA-N imino-oxo-phenyl-thiophen-3-yl-$l^{6}-sulfane Chemical compound C=1C=CC=CC=1S(=O)(=N)C=1C=CSC=1 AAYSYRDMYHUBOQ-UHFFFAOYSA-N 0.000 description 3
- PNOONZAHOCKLFS-UHFFFAOYSA-N imino-phenyl-thiophen-2-yl-$l^{4}-sulfane;2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1.C=1C=CC=CC=1S(=N)C1=CC=CS1 PNOONZAHOCKLFS-UHFFFAOYSA-N 0.000 description 3
- 230000000968 intestinal effect Effects 0.000 description 3
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- 230000008018 melting Effects 0.000 description 3
- GNGDKKKOIFKUFI-UHFFFAOYSA-N n,n-diethyl-2-[(furan-2-yl-oxo-phenyl-$l^{6}-sulfanylidene)amino]ethanamine Chemical compound C=1C=CC=CC=1S(=O)(=NCCN(CC)CC)C1=CC=CO1 GNGDKKKOIFKUFI-UHFFFAOYSA-N 0.000 description 3
- XJBNJAGGPWDWJA-UHFFFAOYSA-N n,n-diethyl-2-[(oxo-thiophen-2-yl-thiophen-3-yl-$l^{6}-sulfanylidene)amino]ethanamine Chemical compound C=1C=CSC=1S(=O)(=NCCN(CC)CC)C=1C=CSC=1 XJBNJAGGPWDWJA-UHFFFAOYSA-N 0.000 description 3
- FYRWTOMMNKUDPI-UHFFFAOYSA-N n,n-diethyl-2-[[oxo(dithiophen-2-yl)-$l^{6}-sulfanylidene]amino]ethanamine Chemical compound C=1C=CSC=1S(=O)(=NCCN(CC)CC)C1=CC=CS1 FYRWTOMMNKUDPI-UHFFFAOYSA-N 0.000 description 3
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
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- 239000005457 ice water Substances 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- MWWOQCGYDYOJKI-UHFFFAOYSA-N imino-phenyl-thiophen-3-yl-$l^{4}-sulfane Chemical compound C=1C=CC=CC=1S(=N)C=1C=CSC=1 MWWOQCGYDYOJKI-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- GRSZTUFRSFNCTA-UHFFFAOYSA-N n,n-dimethyl-3-[(oxo-phenyl-thiophen-2-yl-$l^{6}-sulfanylidene)amino]propan-1-amine Chemical compound C=1C=CC=CC=1S(=O)(=NCCCN(C)C)C1=CC=CS1 GRSZTUFRSFNCTA-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- IKVKJCYGNQAGDB-UHFFFAOYSA-N oxo-(2-piperidin-1-ylethylimino)-dithiophen-2-yl-$l^{6}-sulfane Chemical compound C=1C=CSC=1S(C=1SC=CC=1)(=O)=NCCN1CCCCC1 IKVKJCYGNQAGDB-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/64—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2758613A DE2758613C2 (de) | 1977-12-29 | 1977-12-29 | Sulfoximide, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| DE2758613 | 1977-12-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI784009A7 FI784009A7 (fi) | 1979-06-30 |
| FI66858B FI66858B (fi) | 1984-08-31 |
| FI66858C true FI66858C (fi) | 1984-12-10 |
Family
ID=6027591
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI784009A FI66858C (fi) | 1977-12-29 | 1978-12-28 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara sulfoximider och salter daerav |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4294838A (de) |
| AT (1) | AT371119B (de) |
| CH (1) | CH637940A5 (de) |
| DE (1) | DE2758613C2 (de) |
| FI (1) | FI66858C (de) |
| FR (1) | FR2413384A1 (de) |
| GB (1) | GB2011404B (de) |
| IT (1) | IT1110883B (de) |
| NL (1) | NL7812548A (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1568734C3 (de) * | 1966-12-22 | 1974-03-28 | Goedecke Ag, 1000 Berlin | N-Dialkyl-aminoalkyl-S-diphenylsulfoximine und ihre Salze sowie Verfahren zu ihrer Herstellung |
| GB1168700A (en) * | 1966-12-22 | 1969-10-29 | Warner Lambert Pharmaceutical | N-Substituted Aminoalkyl-S, S-Diphenyl-Sulfoximines and Process for Their Production. |
| US3637664A (en) * | 1966-12-22 | 1972-01-25 | Warner Lambert Co | N-substituted aminoalkyl-s s-diphenyl-sulfoximines and process for their production |
-
1977
- 1977-12-29 DE DE2758613A patent/DE2758613C2/de not_active Expired
-
1978
- 1978-12-21 GB GB7849567A patent/GB2011404B/en not_active Expired
- 1978-12-27 NL NL7812548A patent/NL7812548A/xx not_active Application Discontinuation
- 1978-12-28 CH CH1321578A patent/CH637940A5/de not_active IP Right Cessation
- 1978-12-28 IT IT52479/78A patent/IT1110883B/it active
- 1978-12-28 FI FI784009A patent/FI66858C/fi not_active IP Right Cessation
- 1978-12-29 AT AT0937378A patent/AT371119B/de not_active IP Right Cessation
- 1978-12-29 FR FR7836811A patent/FR2413384A1/fr active Granted
-
1980
- 1980-05-15 US US06/150,119 patent/US4294838A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ATA937378A (de) | 1982-10-15 |
| FI784009A7 (fi) | 1979-06-30 |
| IT7852479A0 (it) | 1978-12-28 |
| DE2758613C2 (de) | 1982-07-15 |
| CH637940A5 (de) | 1983-08-31 |
| GB2011404B (en) | 1982-04-21 |
| NL7812548A (nl) | 1979-07-03 |
| FR2413384B1 (de) | 1983-04-01 |
| FI66858B (fi) | 1984-08-31 |
| AT371119B (de) | 1983-06-10 |
| US4294838A (en) | 1981-10-13 |
| DE2758613A1 (de) | 1979-07-05 |
| GB2011404A (en) | 1979-07-11 |
| IT1110883B (it) | 1986-01-06 |
| FR2413384A1 (fr) | 1979-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: WARNER-LAMBERT COMPANY |