DK153758B - Fremgangsmaade til fremstilling af ranitidin eller syreadditionssalte deraf samt derivat af 5-((2-aminoethyl)thiomethyl)-2-furanmethanol til brug som udgangsmateriale for fremgangsmaaden - Google Patents
Fremgangsmaade til fremstilling af ranitidin eller syreadditionssalte deraf samt derivat af 5-((2-aminoethyl)thiomethyl)-2-furanmethanol til brug som udgangsmateriale for fremgangsmaaden Download PDFInfo
- Publication number
- DK153758B DK153758B DK438485D DK438485D DK153758B DK 153758 B DK153758 B DK 153758B DK 438485 D DK438485 D DK 438485D DK 438485 D DK438485 D DK 438485D DK 153758 B DK153758 B DK 153758B
- Authority
- DK
- Denmark
- Prior art keywords
- methyl
- ranitidine
- mmol
- preparation
- thio
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- 229960000620 ranitidine Drugs 0.000 title claims description 23
- SEJFTTVTZJIVSM-UHFFFAOYSA-N [5-(2-aminoethylsulfanylmethyl)furan-2-yl]methanol Chemical class NCCSCC1=CC=C(CO)O1 SEJFTTVTZJIVSM-UHFFFAOYSA-N 0.000 title claims description 7
- 239000002253 acid Substances 0.000 title claims description 5
- 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 claims 3
- 238000002360 preparation method Methods 0.000 title description 13
- 239000000463 material Substances 0.000 title 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 14
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 8
- -1 triphenylphosphonium halide Chemical class 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- SPJRYDGGIPREOP-UHFFFAOYSA-N CNC(C[N+](=O)[O-])NCCSCC1=CC=C(O1)CO Chemical group CNC(C[N+](=O)[O-])NCCSCC1=CC=C(O1)CO SPJRYDGGIPREOP-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 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 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- OTXQUGSUXRBUTC-UHFFFAOYSA-N butan-1-ol;toluene Chemical compound CCCCO.CC1=CC=CC=C1 OTXQUGSUXRBUTC-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- NXGHEDHQXXXTTP-UHFFFAOYSA-N 1,1-bis(methylsulfanyl)-2-nitroethene Chemical group CSC(SC)=C[N+]([O-])=O NXGHEDHQXXXTTP-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical class C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- KHVAOAQBEIQFBX-UHFFFAOYSA-M dimethylamino(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(N(C)C)C1=CC=CC=C1 KHVAOAQBEIQFBX-UHFFFAOYSA-M 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 150000003573 thiols Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 3
- 244000248349 Citrus limon Species 0.000 description 3
- 235000005979 Citrus limon Nutrition 0.000 description 3
- JPOGMXPBVKSGSN-UHFFFAOYSA-M [5-(hydroxymethyl)furan-2-yl]methyl-trimethylazanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1=CC=C(CO)O1 JPOGMXPBVKSGSN-UHFFFAOYSA-M 0.000 description 3
- IASILKVDEBTERX-UHFFFAOYSA-N [5-[2-[(1-methylsulfanyl-2-nitroethenyl)amino]ethylsulfanylmethyl]furan-2-yl]methanol Chemical compound [O-][N+](=O)C=C(SC)NCCSCC1=CC=C(CO)O1 IASILKVDEBTERX-UHFFFAOYSA-N 0.000 description 3
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Natural products OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- BQRQOLQFLNSWNV-UHFFFAOYSA-N [5-[(dimethylamino)methyl]furan-2-yl]methanol Chemical compound CN(C)CC1=CC=C(CO)O1 BQRQOLQFLNSWNV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000711 cancerogenic effect Effects 0.000 description 2
- 231100000315 carcinogenic Toxicity 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- BHFRSJBIUDOLDB-UHFFFAOYSA-N dimethylamino(triphenyl)phosphanium Chemical class C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(N(C)C)C1=CC=CC=C1 BHFRSJBIUDOLDB-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000012071 phase 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
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- LFUDFHQLZYUZDC-UHFFFAOYSA-N 1-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]-n-methyl-2-nitroethenamine Chemical compound [O-][N+](=O)C=C(NC)SCC1=CC=C(CN(C)C)O1 LFUDFHQLZYUZDC-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- ZFFTZDQKIXPDAF-UHFFFAOYSA-N 2-Furanmethanethiol Chemical compound SCC1=CC=CO1 ZFFTZDQKIXPDAF-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001541 aziridines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 description 1
- 229940099500 cystamine Drugs 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N methyl bromide Substances BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- XGZVNVFLUGNOJQ-UHFFFAOYSA-N n,n-dimethylformamide;ethyl acetate Chemical compound CN(C)C=O.CCOC(C)=O XGZVNVFLUGNOJQ-UHFFFAOYSA-N 0.000 description 1
- YQFHPXZGXNYYLD-UHFFFAOYSA-N n-methyl-1-methylsulfanyl-2-nitroethenamine Chemical compound CNC(SC)=C[N+]([O-])=O YQFHPXZGXNYYLD-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 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
- C07D307/38—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- 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
- C07D307/38—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK438485 | 1985-09-27 | ||
| DK438485A DK153758C (da) | 1985-09-27 | 1985-09-27 | Fremgangsmåde til fremstilling af ranitidin eller syreadditionssalte deraf samt derivat af 5-((2-aminoethyl)thiomethyl)-2-furanmethanol til brug som udgangsmateriale for fremgangsmåden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK153758B true DK153758B (da) | 1988-08-29 |
Family
ID=8133057
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK438485D DK153758B (da) | 1985-09-27 | 1985-09-27 | Fremgangsmaade til fremstilling af ranitidin eller syreadditionssalte deraf samt derivat af 5-((2-aminoethyl)thiomethyl)-2-furanmethanol til brug som udgangsmateriale for fremgangsmaaden |
| DK438485A DK153758C (da) | 1985-09-27 | 1985-09-27 | Fremgangsmåde til fremstilling af ranitidin eller syreadditionssalte deraf samt derivat af 5-((2-aminoethyl)thiomethyl)-2-furanmethanol til brug som udgangsmateriale for fremgangsmåden |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK438485A DK153758C (da) | 1985-09-27 | 1985-09-27 | Fremgangsmåde til fremstilling af ranitidin eller syreadditionssalte deraf samt derivat af 5-((2-aminoethyl)thiomethyl)-2-furanmethanol til brug som udgangsmateriale for fremgangsmåden |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0219225B1 (de) |
| JP (2) | JPH0730063B2 (de) |
| KR (1) | KR940003296B1 (de) |
| AR (1) | AR241462A1 (de) |
| AT (1) | ATE40888T1 (de) |
| BR (1) | BR8604449A (de) |
| CA (1) | CA1263400A (de) |
| DE (1) | DE3662145D1 (de) |
| DK (2) | DK153758B (de) |
| ES (1) | ES2001804A6 (de) |
| FI (1) | FI89596C (de) |
| GR (1) | GR862445B (de) |
| IS (1) | IS3148A7 (de) |
| MA (1) | MA20777A1 (de) |
| NO (1) | NO169650C (de) |
| PT (1) | PT83420B (de) |
| SU (1) | SU1531854A3 (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5541335A (en) * | 1994-07-11 | 1996-07-30 | Torcan Chemical Ltd. | Process for preparing nizatidine |
| US5981757A (en) * | 1998-02-02 | 1999-11-09 | Torcan Chemical Ltd. | Nizatidine preparation |
| CN112028862A (zh) * | 2020-08-18 | 2020-12-04 | 北京云鹏鹏程医药科技有限公司 | 一种低ndma含量盐酸雷尼替丁的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK153841C (da) * | 1980-12-30 | 1989-02-20 | Glaxo Group Ltd | Fremgangsmaade til fremstilling af ranitidin |
-
1985
- 1985-09-27 DK DK438485D patent/DK153758B/da not_active IP Right Cessation
- 1985-09-27 DK DK438485A patent/DK153758C/da not_active IP Right Cessation
-
1986
- 1986-09-09 IS IS3148A patent/IS3148A7/is unknown
- 1986-09-10 EP EP86306998A patent/EP0219225B1/de not_active Expired
- 1986-09-10 AT AT86306998T patent/ATE40888T1/de not_active IP Right Cessation
- 1986-09-10 DE DE8686306998T patent/DE3662145D1/de not_active Expired
- 1986-09-10 FI FI863651A patent/FI89596C/fi not_active IP Right Cessation
- 1986-09-12 AR AR86305230A patent/AR241462A1/es active
- 1986-09-17 BR BR8604449A patent/BR8604449A/pt not_active Application Discontinuation
- 1986-09-18 NO NO86863735A patent/NO169650C/no unknown
- 1986-09-22 JP JP61224067A patent/JPH0730063B2/ja not_active Expired - Lifetime
- 1986-09-22 CA CA000518765A patent/CA1263400A/en not_active Expired
- 1986-09-23 KR KR1019860007929A patent/KR940003296B1/ko not_active Expired - Fee Related
- 1986-09-23 PT PT83420A patent/PT83420B/pt not_active IP Right Cessation
- 1986-09-25 GR GR862445A patent/GR862445B/el unknown
- 1986-09-26 MA MA21005A patent/MA20777A1/fr unknown
- 1986-09-26 SU SU864028187A patent/SU1531854A3/ru active
- 1986-09-26 ES ES8602232A patent/ES2001804A6/es not_active Expired
-
1994
- 1994-10-05 JP JP6240952A patent/JP2520376B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ATE40888T1 (de) | 1989-03-15 |
| NO169650C (no) | 1992-07-22 |
| FI89596C (fi) | 1993-10-25 |
| JPH07316146A (ja) | 1995-12-05 |
| KR940003296B1 (ko) | 1994-04-20 |
| JPS6272680A (ja) | 1987-04-03 |
| KR870003083A (ko) | 1987-04-15 |
| NO169650B (no) | 1992-04-13 |
| DE3662145D1 (en) | 1989-03-30 |
| EP0219225A1 (de) | 1987-04-22 |
| IS3148A7 (is) | 1987-03-28 |
| BR8604449A (pt) | 1987-05-12 |
| AR241462A1 (es) | 1992-07-31 |
| DK438485D0 (da) | 1985-09-27 |
| EP0219225B1 (de) | 1989-02-22 |
| MA20777A1 (fr) | 1987-04-01 |
| ES2001804A6 (es) | 1988-06-16 |
| DK438485A (da) | 1987-03-28 |
| PT83420B (pt) | 1989-01-17 |
| SU1531854A3 (ru) | 1989-12-23 |
| FI863651A7 (fi) | 1987-03-28 |
| NO863735D0 (no) | 1986-09-18 |
| FI89596B (fi) | 1993-07-15 |
| JPH0730063B2 (ja) | 1995-04-05 |
| FI863651A0 (fi) | 1986-09-10 |
| GR862445B (en) | 1987-01-27 |
| JP2520376B2 (ja) | 1996-07-31 |
| PT83420A (en) | 1986-10-01 |
| NO863735L (no) | 1987-03-30 |
| CA1263400A (en) | 1989-11-28 |
| DK153758C (da) | 1995-10-02 |
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