CA2055189A1 - Process for preparing 1-{2-¬ (5-dimethyllaminomethyl-2-furyl) -methylthio)-ethyl)-amino-1-methylamino-2-nitroethylene - Google Patents
Process for preparing 1-{2-¬ (5-dimethyllaminomethyl-2-furyl) -methylthio)-ethyl)-amino-1-methylamino-2-nitroethyleneInfo
- Publication number
- CA2055189A1 CA2055189A1 CA002055189A CA2055189A CA2055189A1 CA 2055189 A1 CA2055189 A1 CA 2055189A1 CA 002055189 A CA002055189 A CA 002055189A CA 2055189 A CA2055189 A CA 2055189A CA 2055189 A1 CA2055189 A1 CA 2055189A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- furyl
- methylthio
- ethyl
- nitroethylene
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 21
- -1 diketene imine Chemical class 0.000 claims abstract description 14
- PZUSILGYGJONKA-UHFFFAOYSA-N 4-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]-2-n-methyl-1-nitrobut-1-ene-1,2-diamine Chemical group [O-][N+](=O)C(N)=C(NC)CCSCC1=CC=C(CN(C)C)O1 PZUSILGYGJONKA-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000243 solution Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229960000620 ranitidine Drugs 0.000 abstract description 12
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 abstract 2
- VMXUWOKSQNHOCA-UKTHLTGXSA-N ranitidine Chemical compound [O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-UKTHLTGXSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 description 3
- 229960001520 ranitidine hydrochloride Drugs 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical class C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 101000654316 Centruroides limpidus Beta-toxin Cll2 Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 230000001944 accentuation Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008395 clarifying agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D307/36—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU7074/90 | 1990-11-09 | ||
| HU907074A HU207308B (en) | 1990-11-09 | 1990-11-09 | Process for producing 1- /2-/5-/dimethyl-amino-methyl/-2-/furyl-methyl-thio/-ethyl//- -amino-1-/methyl-amino-2-nitro-ethylene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2055189C CA2055189C (h) | 1992-05-10 |
| CA2055189A1 true CA2055189A1 (en) | 1992-05-10 |
Family
ID=10972142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002055189A Granted CA2055189A1 (en) | 1990-11-09 | 1991-11-08 | Process for preparing 1-{2-¬ (5-dimethyllaminomethyl-2-furyl) -methylthio)-ethyl)-amino-1-methylamino-2-nitroethylene |
Country Status (16)
| Country | Link |
|---|---|
| KR (1) | KR920009813A (h) |
| CN (1) | CN1061968A (h) |
| AR (1) | AR248017A1 (h) |
| AT (1) | AT400146B (h) |
| CA (1) | CA2055189A1 (h) |
| CZ (1) | CZ280197B6 (h) |
| DK (1) | DK184291A (h) |
| ES (1) | ES2036479B1 (h) |
| FI (1) | FI915265A7 (h) |
| GR (1) | GR1002225B (h) |
| HU (1) | HU207308B (h) |
| NO (1) | NO179208C (h) |
| PL (1) | PL166616B1 (h) |
| PT (1) | PT99470A (h) |
| RU (1) | RU2032681C1 (h) |
| YU (1) | YU177391A (h) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2115111B (en) * | 1982-01-25 | 1987-01-14 | Ava Int Corp | Fail safe gate valves and actuators therefor |
| YU42819B (en) * | 1982-11-22 | 1988-12-31 | Lek Tovarna Farmacevtskih | Process for preparing n-/2-///5-(dimethyl-amino)-methyl-2-furanyl/methyl/thio/ethyl-n'-methyl-2-nitro-1,1-ethene diamine |
| ES8604917A3 (es) * | 1982-11-22 | 1986-03-01 | Medichem Sa | Procedimiento para la preparacion de la n-(2-(((5-(dimetila-mino)-metil-2-furanil)metil)tio)etil)-n'-metil-2-nitro-1,1- etendiamina |
| PT79699B (en) * | 1983-12-22 | 1986-12-10 | Pfizer | Process for preparing quinolone inotropic agents |
| HU196979B (en) * | 1985-01-11 | 1989-02-28 | Gyogyszerkutato Intezet | Process for producing basic thioether and salt |
| ES8603706A1 (es) * | 1985-06-12 | 1986-01-16 | Medichem Sa | Procedimiento para la preparacion de la n-(2-(((5-(dimetila-mino)metil-2-furanil)metil)tio)etil)-n'-metil-2-nitro-1,1- etilendiamina |
-
1990
- 1990-11-09 HU HU907074A patent/HU207308B/hu not_active IP Right Cessation
-
1991
- 1991-11-06 RU SU915010152A patent/RU2032681C1/ru active
- 1991-11-06 AT AT0220391A patent/AT400146B/de not_active IP Right Cessation
- 1991-11-07 YU YU177391A patent/YU177391A/sh unknown
- 1991-11-07 GR GR910100451A patent/GR1002225B/el unknown
- 1991-11-08 FI FI915265A patent/FI915265A7/fi not_active Application Discontinuation
- 1991-11-08 CZ CS913403A patent/CZ280197B6/cs unknown
- 1991-11-08 PL PL91292327A patent/PL166616B1/pl unknown
- 1991-11-08 NO NO914376A patent/NO179208C/no unknown
- 1991-11-08 ES ES9102480A patent/ES2036479B1/es not_active Expired - Lifetime
- 1991-11-08 DK DK184291A patent/DK184291A/da unknown
- 1991-11-08 PT PT99470A patent/PT99470A/pt not_active Application Discontinuation
- 1991-11-08 AR AR91321118A patent/AR248017A1/es active
- 1991-11-08 CA CA002055189A patent/CA2055189A1/en active Granted
- 1991-11-09 CN CN91110542A patent/CN1061968A/zh active Pending
- 1991-11-09 KR KR1019910019914A patent/KR920009813A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| YU177391A (sh) | 1994-01-20 |
| NO179208B (no) | 1996-05-20 |
| NO914376D0 (no) | 1991-11-08 |
| AT400146B (de) | 1995-10-25 |
| CA2055189C (h) | 1992-05-10 |
| ES2036479A1 (es) | 1993-05-16 |
| AR248017A1 (es) | 1995-05-31 |
| HUT59916A (en) | 1992-07-28 |
| PL166616B1 (pl) | 1995-06-30 |
| PL292327A1 (en) | 1992-07-13 |
| NO914376L (no) | 1992-05-11 |
| ATA220391A (de) | 1995-02-15 |
| NO179208C (no) | 1996-08-28 |
| DK184291A (da) | 1992-05-10 |
| FI915265A0 (fi) | 1991-11-08 |
| HU907074D0 (en) | 1991-05-28 |
| HU207308B (en) | 1993-03-29 |
| CS340391A3 (en) | 1992-05-13 |
| GR910100451A (el) | 1992-10-08 |
| CN1061968A (zh) | 1992-06-17 |
| FI915265A7 (fi) | 1992-05-10 |
| RU2032681C1 (ru) | 1995-04-10 |
| KR920009813A (ko) | 1992-06-25 |
| CZ280197B6 (cs) | 1995-11-15 |
| DK184291D0 (da) | 1991-11-08 |
| PT99470A (pt) | 1992-10-30 |
| GR1002225B (en) | 1996-04-18 |
| ES2036479B1 (es) | 1993-12-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |