CN1061968A - 制备雷尼替丁的方法 - Google Patents
制备雷尼替丁的方法 Download PDFInfo
- Publication number
- CN1061968A CN1061968A CN91110542A CN91110542A CN1061968A CN 1061968 A CN1061968 A CN 1061968A CN 91110542 A CN91110542 A CN 91110542A CN 91110542 A CN91110542 A CN 91110542A CN 1061968 A CN1061968 A CN 1061968A
- Authority
- CN
- China
- Prior art keywords
- methylamine
- ranitidine
- reaction
- formula
- described method
- 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.)
- Pending
Links
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 title abstract description 5
- 229960000620 ranitidine Drugs 0.000 title abstract description 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 30
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 26
- -1 5-dimethylaminomethyl-2-furyl Chemical group 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 239000000243 solution Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 3
- NESLOYMMIUOLMU-UHFFFAOYSA-N 1-n'-methyl-2-nitroethene-1,1-diamine Chemical group CNC(N)=C[N+]([O-])=O NESLOYMMIUOLMU-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 5
- RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 abstract 1
- 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 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229960004756 ethanol Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- 229960001520 ranitidine hydrochloride Drugs 0.000 description 3
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical class [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 239000003814 drug Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 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
- 238000005406 washing Methods 0.000 description 2
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 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
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- WZUCWMVNONEJSO-UHFFFAOYSA-N [N+](=O)([O-])N1C=CC1 Chemical compound [N+](=O)([O-])N1C=CC1 WZUCWMVNONEJSO-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 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
- 150000002240 furans Chemical class 0.000 description 1
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000203 mixture Substances 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
- 238000001556 precipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 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
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 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)
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 (1)
| Publication Number | Publication Date |
|---|---|
| CN1061968A true CN1061968A (zh) | 1992-06-17 |
Family
ID=10972142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN91110542A Pending CN1061968A (zh) | 1990-11-09 | 1991-11-09 | 制备雷尼替丁的方法 |
Country Status (16)
| Country | Link |
|---|---|
| KR (1) | KR920009813A (cg-RX-API-DMAC10.html) |
| CN (1) | CN1061968A (cg-RX-API-DMAC10.html) |
| AR (1) | AR248017A1 (cg-RX-API-DMAC10.html) |
| AT (1) | AT400146B (cg-RX-API-DMAC10.html) |
| CA (1) | CA2055189A1 (cg-RX-API-DMAC10.html) |
| CZ (1) | CZ280197B6 (cg-RX-API-DMAC10.html) |
| DK (1) | DK184291A (cg-RX-API-DMAC10.html) |
| ES (1) | ES2036479B1 (cg-RX-API-DMAC10.html) |
| FI (1) | FI915265A7 (cg-RX-API-DMAC10.html) |
| GR (1) | GR1002225B (cg-RX-API-DMAC10.html) |
| HU (1) | HU207308B (cg-RX-API-DMAC10.html) |
| NO (1) | NO179208C (cg-RX-API-DMAC10.html) |
| PL (1) | PL166616B1 (cg-RX-API-DMAC10.html) |
| PT (1) | PT99470A (cg-RX-API-DMAC10.html) |
| RU (1) | RU2032681C1 (cg-RX-API-DMAC10.html) |
| YU (1) | YU177391A (cg-RX-API-DMAC10.html) |
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 |
| ES543966A0 (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 |
| 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 |
| 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 AT AT0220391A patent/AT400146B/de not_active IP Right Cessation
- 1991-11-06 RU SU915010152A patent/RU2032681C1/ru active
- 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 NO NO914376A patent/NO179208C/no unknown
- 1991-11-08 CZ CS913403A patent/CZ280197B6/cs 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 PL PL91292327A patent/PL166616B1/pl 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 |
|---|---|
| ES2036479B1 (es) | 1993-12-16 |
| DK184291D0 (da) | 1991-11-08 |
| RU2032681C1 (ru) | 1995-04-10 |
| ATA220391A (de) | 1995-02-15 |
| CA2055189C (cg-RX-API-DMAC10.html) | 1992-05-10 |
| PL292327A1 (en) | 1992-07-13 |
| DK184291A (da) | 1992-05-10 |
| PT99470A (pt) | 1992-10-30 |
| NO914376L (no) | 1992-05-11 |
| YU177391A (sh) | 1994-01-20 |
| HU207308B (en) | 1993-03-29 |
| NO179208C (no) | 1996-08-28 |
| GR1002225B (en) | 1996-04-18 |
| KR920009813A (ko) | 1992-06-25 |
| HU907074D0 (en) | 1991-05-28 |
| ES2036479A1 (es) | 1993-05-16 |
| AT400146B (de) | 1995-10-25 |
| NO179208B (no) | 1996-05-20 |
| HUT59916A (en) | 1992-07-28 |
| CZ280197B6 (cs) | 1995-11-15 |
| GR910100451A (el) | 1992-10-08 |
| CS340391A3 (en) | 1992-05-13 |
| NO914376D0 (no) | 1991-11-08 |
| PL166616B1 (pl) | 1995-06-30 |
| FI915265A7 (fi) | 1992-05-10 |
| CA2055189A1 (en) | 1992-05-10 |
| AR248017A1 (es) | 1995-05-31 |
| FI915265A0 (fi) | 1991-11-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| AD01 | Patent right deemed abandoned | ||
| C20 | Patent right or utility model deemed to be abandoned or is abandoned |