NO771697L - Fremgangsm}te for fremstilling av fysiologisk aktive isotiourinstoffer - Google Patents
Fremgangsm}te for fremstilling av fysiologisk aktive isotiourinstofferInfo
- Publication number
- NO771697L NO771697L NO771697A NO771697A NO771697L NO 771697 L NO771697 L NO 771697L NO 771697 A NO771697 A NO 771697A NO 771697 A NO771697 A NO 771697A NO 771697 L NO771697 L NO 771697L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- lower alkyl
- preparation
- compound
- ethanol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000126 substance Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000002541 isothioureas Chemical class 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 230000008105 immune reaction Effects 0.000 description 3
- KMFBOMKUKPBRBH-UHFFFAOYSA-N 3-(4,5-dihydro-1h-imidazol-2-ylsulfanyl)-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCSC1=NCCN1 KMFBOMKUKPBRBH-UHFFFAOYSA-N 0.000 description 2
- BVCBJBVDMXCOJC-UHFFFAOYSA-N 3-(dimethylamino)propyl n,n'-dimethylcarbamimidothioate Chemical compound CNC(=NC)SCCCN(C)C BVCBJBVDMXCOJC-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 230000001506 immunosuppresive effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- VFLQQZCRHPIGJU-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine;hydron;chloride Chemical compound Cl.ClCCN1CCCCC1 VFLQQZCRHPIGJU-UHFFFAOYSA-N 0.000 description 1
- FSNGFFWICFYWQC-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine;hydron;chloride Chemical compound Cl.ClCCN1CCCC1 FSNGFFWICFYWQC-UHFFFAOYSA-N 0.000 description 1
- MTDFNKHFIYPIFF-UHFFFAOYSA-N 3-(4,5-dihydro-1h-imidazol-2-ylsulfanyl)-n,n-dimethylpropan-1-amine;dihydrochloride Chemical compound Cl.Cl.CN(C)CCCSC1=NCCN1 MTDFNKHFIYPIFF-UHFFFAOYSA-N 0.000 description 1
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 1
- LJQNMDZRCXJETK-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine;hydron;chloride Chemical compound Cl.CN(C)CCCCl LJQNMDZRCXJETK-UHFFFAOYSA-N 0.000 description 1
- NBJHDLKSWUDGJG-UHFFFAOYSA-N 4-(2-chloroethyl)morpholin-4-ium;chloride Chemical compound Cl.ClCCN1CCOCC1 NBJHDLKSWUDGJG-UHFFFAOYSA-N 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- -1 dialkylaminoalkyl halide Chemical class 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 208000027930 type IV hypersensitivity disease Diseases 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
- C07D295/08—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 bound oxygen or sulfur atoms
- C07D295/084—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/32—Isothioureas having sulfur atoms of isothiourea groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/42—Sulfur atoms
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB19994/76A GB1592453A (en) | 1976-05-14 | 1976-05-14 | Aminoalkyl esters of carbarimidothioic acid and compositions having immunosuppressant activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO771697L true NO771697L (no) | 1977-11-15 |
Family
ID=10138568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO771697A NO771697L (no) | 1976-05-14 | 1977-05-13 | Fremgangsm}te for fremstilling av fysiologisk aktive isotiourinstoffer |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4294854A (fi) |
| JP (1) | JPS532420A (fi) |
| AR (1) | AR218872A1 (fi) |
| AT (1) | AT359521B (fi) |
| AU (1) | AU509573B2 (fi) |
| BE (1) | BE854553A (fi) |
| CA (1) | CA1086758A (fi) |
| CH (1) | CH620203A5 (fi) |
| DE (1) | DE2721830A1 (fi) |
| DK (1) | DK211277A (fi) |
| ES (1) | ES458756A1 (fi) |
| FI (1) | FI771400A (fi) |
| FR (2) | FR2351098A1 (fi) |
| GB (1) | GB1592453A (fi) |
| HU (1) | HU174978B (fi) |
| IE (1) | IE45144B1 (fi) |
| IL (1) | IL52011A (fi) |
| LU (1) | LU77332A1 (fi) |
| NL (1) | NL7705331A (fi) |
| NO (1) | NO771697L (fi) |
| PT (1) | PT66509B (fi) |
| SE (1) | SE7705658L (fi) |
| ZA (1) | ZA772612B (fi) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0672244B2 (ja) * | 1984-12-12 | 1994-09-14 | 三菱マテリアル株式会社 | 貴金属造粒装置 |
| AU695120B2 (en) * | 1993-06-07 | 1998-08-06 | Baylor College Of Medicine | Use of an MHC class I suppressor drug for the treatment of autoimmune diseases and transplantation rejection |
| EP0776886A4 (en) * | 1994-08-18 | 1999-05-12 | Chugai Pharmaceutical Co Ltd | AMINO ACID DERIVATIVE WITH NITROGEN MONOXIDE SYNTHETASE INHIBITING ACTIVITY |
| US7645873B2 (en) * | 2003-03-20 | 2010-01-12 | The Scripps Research Institute | 6″-amino-6″-deoxygalactosylceramides |
| EP2058011A1 (en) * | 2007-11-07 | 2009-05-13 | Wittycell | Nkt cell activating gycolipids covalently bound antigens and/or drug |
| MX338827B (es) * | 2008-10-08 | 2016-05-03 | Vincent Serra | Composicion de vacuna para uso contra influenza. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2648710A (en) * | 1950-09-22 | 1953-08-11 | Hoffmann La Roche | Bis-quaternary salts of 1:10-bis-(dialkylamino)-5:6-dithia-decane |
| US2813102A (en) * | 1956-04-10 | 1957-11-12 | American Home Prod | 2-(di-lower alkylaminoethylmercapto)-imidazolines and their acid addition salts and preparation thereof |
| US4152453A (en) * | 1975-12-01 | 1979-05-01 | Smith Kline & French Laboratories Limited | Pharmacologically active compounds and compositions and methods of use |
-
1976
- 1976-05-14 GB GB19994/76A patent/GB1592453A/en not_active Expired
-
1977
- 1977-05-02 ZA ZA00772612A patent/ZA772612B/xx unknown
- 1977-05-03 FI FI771400A patent/FI771400A/fi not_active Application Discontinuation
- 1977-05-04 IL IL52011A patent/IL52011A/xx unknown
- 1977-05-04 PT PT66509A patent/PT66509B/pt unknown
- 1977-05-04 AT AT318277A patent/AT359521B/de not_active IP Right Cessation
- 1977-05-10 IE IE947/77A patent/IE45144B1/en unknown
- 1977-05-11 CH CH589877A patent/CH620203A5/fr not_active IP Right Cessation
- 1977-05-11 JP JP5483077A patent/JPS532420A/ja active Pending
- 1977-05-11 AU AU25079/77A patent/AU509573B2/en not_active Expired
- 1977-05-12 BE BE177510A patent/BE854553A/xx not_active IP Right Cessation
- 1977-05-13 HU HU77SI1576A patent/HU174978B/hu unknown
- 1977-05-13 AR AR267623A patent/AR218872A1/es active
- 1977-05-13 DE DE19772721830 patent/DE2721830A1/de not_active Withdrawn
- 1977-05-13 FR FR7714766A patent/FR2351098A1/fr active Granted
- 1977-05-13 NL NL7705331A patent/NL7705331A/xx not_active Application Discontinuation
- 1977-05-13 DK DK211277A patent/DK211277A/da not_active Application Discontinuation
- 1977-05-13 CA CA278,412A patent/CA1086758A/en not_active Expired
- 1977-05-13 NO NO771697A patent/NO771697L/no unknown
- 1977-05-13 ES ES458756A patent/ES458756A1/es not_active Expired
- 1977-05-13 LU LU77332A patent/LU77332A1/xx unknown
- 1977-05-16 SE SE7705658A patent/SE7705658L/xx unknown
-
1979
- 1979-10-09 US US06/082,836 patent/US4294854A/en not_active Expired - Lifetime
-
1980
- 1980-11-17 FR FR8024334A patent/FR2472935A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE2721830A1 (de) | 1977-11-24 |
| GB1592453A (en) | 1981-07-08 |
| LU77332A1 (fi) | 1977-08-29 |
| AR218872A1 (es) | 1980-07-15 |
| AU2507977A (en) | 1978-11-16 |
| SE7705658L (sv) | 1977-11-15 |
| DK211277A (da) | 1977-11-15 |
| HU174978B (hu) | 1980-04-28 |
| IE45144B1 (en) | 1982-06-30 |
| NL7705331A (nl) | 1977-11-16 |
| PT66509A (en) | 1977-06-01 |
| ATA318277A (de) | 1980-04-15 |
| CA1086758A (en) | 1980-09-30 |
| ZA772612B (en) | 1978-04-26 |
| IE45144L (en) | 1977-11-14 |
| AT359521B (de) | 1980-11-10 |
| CH620203A5 (fi) | 1980-11-14 |
| FR2351098A1 (fr) | 1977-12-09 |
| US4294854A (en) | 1981-10-13 |
| IL52011A (en) | 1982-05-31 |
| FI771400A (fi) | 1977-11-15 |
| JPS532420A (en) | 1978-01-11 |
| FR2472935A1 (fr) | 1981-07-10 |
| ES458756A1 (es) | 1978-03-01 |
| AU509573B2 (en) | 1980-05-15 |
| FR2351098B1 (fi) | 1982-06-18 |
| PT66509B (en) | 1978-10-16 |
| BE854553A (fr) | 1977-11-14 |
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