CH620203A5 - - Google Patents
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- Publication number
- CH620203A5 CH620203A5 CH589877A CH589877A CH620203A5 CH 620203 A5 CH620203 A5 CH 620203A5 CH 589877 A CH589877 A CH 589877A CH 589877 A CH589877 A CH 589877A CH 620203 A5 CH620203 A5 CH 620203A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- ethanol
- lower alkyl
- imidazoline
- compound
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 21
- 125000000217 alkyl group Chemical group 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 239000002253 acid Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000008105 immune reaction Effects 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- -1 dialkylaminoalkyl halide Chemical class 0.000 description 2
- 150000002462 imidazolines Chemical class 0.000 description 2
- 230000001506 immunosuppresive effect Effects 0.000 description 2
- 150000002541 isothioureas Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- VFLQQZCRHPIGJU-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine;hydron;chloride Chemical compound Cl.ClCCN1CCCCC1 VFLQQZCRHPIGJU-UHFFFAOYSA-N 0.000 description 1
- 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 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
- BVCBJBVDMXCOJC-UHFFFAOYSA-N 3-(dimethylamino)propyl n,n'-dimethylcarbamimidothioate Chemical compound CNC(=NC)SCCCN(C)C BVCBJBVDMXCOJC-UHFFFAOYSA-N 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- 206010036030 Polyarthritis Diseases 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
- AMNIXZXHVQGDCK-XYOKQWHBSA-N [(e)-1-(1-methylcyclohexyl)ethylideneamino]thiourea Chemical compound NC(=S)N\N=C(/C)C1(C)CCCCC1 AMNIXZXHVQGDCK-XYOKQWHBSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000003111 delayed effect Effects 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
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Transplantation (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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 |
|---|---|
| CH620203A5 true CH620203A5 (da) | 1980-11-14 |
Family
ID=10138568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH589877A CH620203A5 (da) | 1976-05-14 | 1977-05-11 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4294854A (da) |
| JP (1) | JPS532420A (da) |
| AR (1) | AR218872A1 (da) |
| AT (1) | AT359521B (da) |
| AU (1) | AU509573B2 (da) |
| BE (1) | BE854553A (da) |
| CA (1) | CA1086758A (da) |
| CH (1) | CH620203A5 (da) |
| DE (1) | DE2721830A1 (da) |
| DK (1) | DK211277A (da) |
| ES (1) | ES458756A1 (da) |
| FI (1) | FI771400A (da) |
| FR (2) | FR2351098A1 (da) |
| GB (1) | GB1592453A (da) |
| HU (1) | HU174978B (da) |
| IE (1) | IE45144B1 (da) |
| IL (1) | IL52011A (da) |
| LU (1) | LU77332A1 (da) |
| NL (1) | NL7705331A (da) |
| NO (1) | NO771697L (da) |
| PT (1) | PT66509B (da) |
| SE (1) | SE7705658L (da) |
| ZA (1) | ZA772612B (da) |
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 |
| WO1994028897A2 (en) * | 1993-06-07 | 1994-12-22 | The Government Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services | 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 AU AU25079/77A patent/AU509573B2/en not_active Expired
- 1977-05-11 JP JP5483077A patent/JPS532420A/ja active Pending
- 1977-05-11 CH CH589877A patent/CH620203A5/fr not_active IP Right Cessation
- 1977-05-12 BE BE177510A patent/BE854553A/xx not_active IP Right Cessation
- 1977-05-13 DK DK211277A patent/DK211277A/da not_active Application Discontinuation
- 1977-05-13 AR AR267623A patent/AR218872A1/es active
- 1977-05-13 FR FR7714766A patent/FR2351098A1/fr active Granted
- 1977-05-13 LU LU77332A patent/LU77332A1/xx unknown
- 1977-05-13 HU HU77SI1576A patent/HU174978B/hu unknown
- 1977-05-13 NL NL7705331A patent/NL7705331A/xx not_active Application Discontinuation
- 1977-05-13 CA CA278,412A patent/CA1086758A/en not_active Expired
- 1977-05-13 DE DE19772721830 patent/DE2721830A1/de not_active Withdrawn
- 1977-05-13 NO NO771697A patent/NO771697L/no unknown
- 1977-05-13 ES ES458756A patent/ES458756A1/es not_active Expired
- 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 |
|---|---|
| CA1086758A (en) | 1980-09-30 |
| JPS532420A (en) | 1978-01-11 |
| FR2351098B1 (da) | 1982-06-18 |
| IE45144L (en) | 1977-11-14 |
| NO771697L (no) | 1977-11-15 |
| AU509573B2 (en) | 1980-05-15 |
| ZA772612B (en) | 1978-04-26 |
| IL52011A (en) | 1982-05-31 |
| US4294854A (en) | 1981-10-13 |
| AT359521B (de) | 1980-11-10 |
| LU77332A1 (da) | 1977-08-29 |
| FR2351098A1 (fr) | 1977-12-09 |
| ES458756A1 (es) | 1978-03-01 |
| GB1592453A (en) | 1981-07-08 |
| IE45144B1 (en) | 1982-06-30 |
| DK211277A (da) | 1977-11-15 |
| FI771400A (da) | 1977-11-15 |
| AR218872A1 (es) | 1980-07-15 |
| HU174978B (hu) | 1980-04-28 |
| AU2507977A (en) | 1978-11-16 |
| SE7705658L (sv) | 1977-11-15 |
| BE854553A (fr) | 1977-11-14 |
| ATA318277A (de) | 1980-04-15 |
| NL7705331A (nl) | 1977-11-16 |
| PT66509A (en) | 1977-06-01 |
| FR2472935A1 (fr) | 1981-07-10 |
| DE2721830A1 (de) | 1977-11-24 |
| PT66509B (en) | 1978-10-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |