HU207308B - Process for producing 1- /2-/5-/dimethyl-amino-methyl/-2-/furyl-methyl-thio/-ethyl//- -amino-1-/methyl-amino-2-nitro-ethylene - Google Patents
Process for producing 1- /2-/5-/dimethyl-amino-methyl/-2-/furyl-methyl-thio/-ethyl//- -amino-1-/methyl-amino-2-nitro-ethylene Download PDFInfo
- Publication number
- HU207308B HU207308B HU907074A HU707490A HU207308B HU 207308 B HU207308 B HU 207308B HU 907074 A HU907074 A HU 907074A HU 707490 A HU707490 A HU 707490A HU 207308 B HU207308 B HU 207308B
- Authority
- HU
- Hungary
- Prior art keywords
- methyl
- amino
- ethyl
- nitro
- methylamine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 title description 4
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 title description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 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
- 229960000620 ranitidine Drugs 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- -1 methylthio nitro Chemical class 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 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 2
- 229960001520 ranitidine hydrochloride Drugs 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
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical class C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- YMZHHNXFDGLNIA-UHFFFAOYSA-N azanium;ethyl acetate;propan-2-one;hydroxide Chemical compound [NH4+].[OH-].CC(C)=O.CCOC(C)=O YMZHHNXFDGLNIA-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- ZUKSLMGYYPZZJD-UHFFFAOYSA-N ethenimine Chemical compound C=C=N ZUKSLMGYYPZZJD-UHFFFAOYSA-N 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229960003299 ketamine Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- SVIDAEJFBAYABG-UHFFFAOYSA-N n-methyl-2-nitroethenamine Chemical group CNC=C[N+]([O-])=O SVIDAEJFBAYABG-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003573 thiols Chemical class 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)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
| SU915010152A RU2032681C1 (ru) | 1990-11-09 | 1991-11-06 | Способ получения 1-(2-[(5-диметиламинометил-2-фурил) -метилтио]-этил)-амино-1- метиламино-2-нитроэтилена |
| AT0220391A AT400146B (de) | 1990-11-09 | 1991-11-06 | Verfahren zur herstellung von 1-(2-((5- |
| YU177391A YU177391A (sh) | 1990-11-09 | 1991-11-07 | Postupak za dobivanje 1-/2-/(5-dimetil-aminometil-2-furil)-metiltio/-etil/-amino-1-metil -amino-2-nitroetilen |
| GR910100451A GR1002225B (en) | 1990-11-09 | 1991-11-07 | Preparation method of 1-{2-£(5-dimethylaminomethyl-2-fouryl)-methylthio|-ethyl}-amino-1 methylamino-2-nitroethylen |
| FI915265A FI915265A7 (fi) | 1990-11-09 | 1991-11-08 | Foerfarande foer framstaellning av 1-( 2-((5-dimetylaminometyl-2-fenyl)-metyltio)-etyl)-amino-1-metylamino-2 -nitroeten. |
| ES9102480A ES2036479B1 (es) | 1990-11-09 | 1991-11-08 | Procedimiento para preparar 1-(-2-((5-dimetilaminometil-2-furil)-metiltio)-amino-1-metilamino-2-nitroetileno. |
| NO914376A NO179208C (no) | 1990-11-09 | 1991-11-08 | Fremgangsmåte for fremstilling av 1-æ2-[(5-diametylaminometyl-2-furyl)-metyltioÅ-etylå-amino-1-metylamino-2-nitroetylen (ranitidin) |
| PT99470A PT99470A (pt) | 1990-11-09 | 1991-11-08 | Processo para a preparacao de 1-{2-{(5-dimetilaminometil-2-furil)-metiltio}-etil}-amino-1-metilamino-2-nitroetileno (ranitidina) |
| DK184291A DK184291A (da) | 1990-11-09 | 1991-11-08 | Furanderivat |
| CS913403A CZ280197B6 (cs) | 1990-11-09 | 1991-11-08 | Způsob přípravy 1-(2-/(5-dimethylaminoethyl-2-fu ryl)-methylthio/-ethyl)-amino-1-methylamino-2 -nitroethylenu |
| CA002055189A CA2055189A1 (en) | 1990-11-09 | 1991-11-08 | Process for preparing 1-{2-¬ (5-dimethyllaminomethyl-2-furyl) -methylthio)-ethyl)-amino-1-methylamino-2-nitroethylene |
| AR91321118A AR248017A1 (es) | 1990-11-09 | 1991-11-08 | Procedimiento para preparar 1 1 1 1 1 |
| PL91292327A PL166616B1 (pl) | 1990-11-09 | 1991-11-08 | metyloamino-2-nttroetylenu PL |
| CN91110542A CN1061968A (zh) | 1990-11-09 | 1991-11-09 | 制备雷尼替丁的方法 |
| KR1019910019914A KR920009813A (ko) | 1990-11-09 | 1991-11-09 | 1-{2-[(5-디메틸아미노메틸-2-푸릴)-메틸티오]-에틸}-아미노-1-메틸아미노-2-니트로에틸렌의 제조방법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (3)
| Publication Number | Publication Date |
|---|---|
| HU907074D0 HU907074D0 (en) | 1991-05-28 |
| HUT59916A HUT59916A (en) | 1992-07-28 |
| HU207308B true HU207308B (en) | 1993-03-29 |
Family
ID=10972142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
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 |
| CA2055189A1 (en) | 1992-05-10 |
| 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 |
| 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 |
|---|---|---|---|
| HMM4 | Cancellation of final prot. due to non-payment of fee |