AT400146B - Verfahren zur herstellung von 1-(2-((5- - Google Patents
Verfahren zur herstellung von 1-(2-((5- Download PDFInfo
- Publication number
- AT400146B AT400146B AT0220391A AT220391A AT400146B AT 400146 B AT400146 B AT 400146B AT 0220391 A AT0220391 A AT 0220391A AT 220391 A AT220391 A AT 220391A AT 400146 B AT400146 B AT 400146B
- Authority
- AT
- Austria
- Prior art keywords
- methylthio
- ethyl
- furyl
- formula
- derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- VMXUWOKSQNHOCA-UHFFFAOYSA-N N1'-[2-[[5-[(dimethylamino)methyl]-2-furanyl]methylthio]ethyl]-N1-methyl-2-nitroethene-1,1-diamine Chemical group [O-][N+](=O)C=C(NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-UHFFFAOYSA-N 0.000 title 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 239000000243 solution Substances 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- -1 5-dimethylaminomethyl-2-furyl Chemical group 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 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 claims description 3
- 229960001520 ranitidine hydrochloride Drugs 0.000 claims description 3
- 229960000620 ranitidine Drugs 0.000 abstract description 12
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 abstract description 4
- 229940097265 cysteamine hydrochloride Drugs 0.000 abstract description 4
- 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 1
- 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 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 150000002828 nitro derivatives Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NXGHEDHQXXXTTP-UHFFFAOYSA-N 1,1-bis(methylsulfanyl)-2-nitroethene Chemical compound CSC(SC)=C[N+]([O-])=O NXGHEDHQXXXTTP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000003932 ketenimines Chemical group 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000008395 clarifying agent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 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
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 208000000718 duodenal ulcer Diseases 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
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- MAPYMMOMOBHYDY-UHFFFAOYSA-N methylsulfanyloxysulfanylmethane Chemical compound CSOSC MAPYMMOMOBHYDY-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 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
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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 (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 (2)
| Publication Number | Publication Date |
|---|---|
| ATA220391A ATA220391A (de) | 1995-02-15 |
| AT400146B true AT400146B (de) | 1995-10-25 |
Family
ID=10972142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0220391A AT400146B (de) | 1990-11-09 | 1991-11-06 | Verfahren zur herstellung von 1-(2-((5- |
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) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8603863A1 (es) * | 1983-12-22 | 1986-01-01 | Pfizer | Un procedimiento para la preparacion de agentes inotropicos de quinolona. |
| 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 |
| GB2169063A (en) * | 1982-01-25 | 1986-07-02 | Ava Int Corp | Fail safe gate valves and actuators therefor |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| HU196979B (en) * | 1985-01-11 | 1989-02-28 | Gyogyszerkutato Intezet | Process for producing basic thioether and salt |
-
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
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2169063A (en) * | 1982-01-25 | 1986-07-02 | Ava Int Corp | Fail safe gate valves and actuators therefor |
| ES8603863A1 (es) * | 1983-12-22 | 1986-01-01 | Pfizer | Un procedimiento para la preparacion de agentes inotropicos de quinolona. |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| YU177391A (sh) | 1994-01-20 |
| NO179208B (no) | 1996-05-20 |
| NO914376D0 (no) | 1991-11-08 |
| 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 |
| 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 |
|---|---|---|---|
| ELJ | Ceased due to non-payment of the annual fee | ||
| RER | Ceased as to paragraph 5 lit. 3 law introducing patent treaties |