SU461504A3 - Способ получени производных изотиазола - Google Patents
Способ получени производных изотиазолаInfo
- Publication number
- SU461504A3 SU461504A3 SU1814223A SU1814223A SU461504A3 SU 461504 A3 SU461504 A3 SU 461504A3 SU 1814223 A SU1814223 A SU 1814223A SU 1814223 A SU1814223 A SU 1814223A SU 461504 A3 SU461504 A3 SU 461504A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- salts
- mixture
- residue
- water
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 8
- 150000003854 isothiazoles Chemical class 0.000 title description 3
- 150000003839 salts Chemical class 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- -1 alkyl isothioureas Chemical class 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- LYMODTFHYVEPSH-UHFFFAOYSA-N (3-methyl-1,2-thiazol-4-yl)methanamine Chemical compound CC1=NSC=C1CN LYMODTFHYVEPSH-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- FJGCCKCEAWBXCV-UHFFFAOYSA-N 1,2-thiazol-3-ylmethanamine Chemical compound NCC=1C=CSN=1 FJGCCKCEAWBXCV-UHFFFAOYSA-N 0.000 description 1
- QEAVLAWZVQEIEK-UHFFFAOYSA-N 2-(1,2-thiazol-3-ylmethyl)guanidine Chemical compound S1N=C(C=C1)CNC(=N)N QEAVLAWZVQEIEK-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- DMSDCBKFWUBTKX-UHFFFAOYSA-N 2-methyl-1-nitrosoguanidine Chemical compound CN=C(N)NN=O DMSDCBKFWUBTKX-UHFFFAOYSA-N 0.000 description 1
- WTLKTXIHIHFSGU-UHFFFAOYSA-N 2-nitrosoguanidine Chemical compound NC(N)=NN=O WTLKTXIHIHFSGU-UHFFFAOYSA-N 0.000 description 1
- FVJGRFFQOBEQSX-UHFFFAOYSA-N 3-(bromomethyl)-1,2-thiazole Chemical compound BrCC=1C=CSN=1 FVJGRFFQOBEQSX-UHFFFAOYSA-N 0.000 description 1
- NAQCBYNVOXNMLO-UHFFFAOYSA-N 4-(chloromethyl)-3-methyl-1,2-thiazole Chemical compound CC1=NSC=C1CCl NAQCBYNVOXNMLO-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical class [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical class [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- BPMPPVUBRPXMNX-UHFFFAOYSA-N butyl carbamimidothioate Chemical compound CCCCSC(N)=N BPMPPVUBRPXMNX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001912 cyanamides Chemical class 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- HEFJCHKCDAWHDQ-UHFFFAOYSA-N ethyl carbamimidate Chemical compound CCOC(N)=N HEFJCHKCDAWHDQ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
- MCLITRXWHZUNCQ-UHFFFAOYSA-N methylcyanamide Chemical compound CNC#N MCLITRXWHZUNCQ-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UCQFSGCWHRTMGG-UHFFFAOYSA-N pyrazole-1-carboximidamide Chemical class NC(=N)N1C=CC=N1 UCQFSGCWHRTMGG-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229910052709 silver Chemical class 0.000 description 1
- 239000004332 silver Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- IOIOILDYKMQXSF-UHFFFAOYSA-N sulfuric acid;thiourea Chemical compound NC(N)=S.OS(O)(=O)=O IOIOILDYKMQXSF-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1041371A CH552001A (de) | 1971-07-15 | 1971-07-15 | Verfahren zur herstellung von isothiazolyl-verbindungen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU461504A3 true SU461504A3 (ru) | 1975-02-25 |
Family
ID=4362957
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1814223A SU461504A3 (ru) | 1971-07-15 | 1972-07-14 | Способ получени производных изотиазола |
| SU1982236A SU541434A3 (ru) | 1971-07-15 | 1974-01-03 | "Способ получени производных изотиазола или их солей |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1982236A SU541434A3 (ru) | 1971-07-15 | 1974-01-03 | "Способ получени производных изотиазола или их солей |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3838161A (en:Method) |
| AR (2) | AR205324A1 (en:Method) |
| AT (2) | AT315167B (en:Method) |
| AU (1) | AU471856B2 (en:Method) |
| BE (1) | BE786305A (en:Method) |
| CA (1) | CA1003422A (en:Method) |
| CH (1) | CH552001A (en:Method) |
| CS (2) | CS174850B2 (en:Method) |
| DD (1) | DD101407A5 (en:Method) |
| DE (1) | DE2233114A1 (en:Method) |
| EG (1) | EG11134A (en:Method) |
| ES (1) | ES404879A1 (en:Method) |
| FR (1) | FR2145632B1 (en:Method) |
| GB (1) | GB1395360A (en:Method) |
| HU (1) | HU167425B (en:Method) |
| IE (1) | IE36517B1 (en:Method) |
| IL (1) | IL39792A0 (en:Method) |
| NL (1) | NL7209400A (en:Method) |
| PL (2) | PL96495B1 (en:Method) |
| SE (1) | SE391524B (en:Method) |
| SU (2) | SU461504A3 (en:Method) |
| ZA (1) | ZA724523B (en:Method) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4088769A (en) * | 1969-10-29 | 1978-05-09 | Smith Kline & French Laboratories Limited | Method of inhibiting histamine activity with guanidine compounds |
| GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
| US4287198A (en) * | 1971-03-09 | 1981-09-01 | Smith Kline & French Laboratories Limited | Pharmacologically active guanidine compounds |
| US4070475A (en) * | 1972-02-03 | 1978-01-24 | Smith Kline & French Laboratories Limited | Pharmacologically active guanidine compounds as H-2 histamine receptor inhibitors |
| US4221802A (en) * | 1972-02-03 | 1980-09-09 | Smith Kline & French Laboratories Limited | Pharmacologically active guanidine compounds for inhibiting H-2 histamine receptors |
| CN117510431A (zh) * | 2023-11-08 | 2024-02-06 | 浙江雅辰药物科技股份有限公司 | 一种异噻唑-3-酮及其衍生物、合成方法 |
-
0
- BE BE786305D patent/BE786305A/xx unknown
-
1971
- 1971-07-15 CH CH1041371A patent/CH552001A/xx not_active IP Right Cessation
-
1972
- 1972-01-01 AR AR243078A patent/AR205324A1/es active
- 1972-06-29 IL IL39792A patent/IL39792A0/xx unknown
- 1972-06-29 SE SE7208550A patent/SE391524B/xx unknown
- 1972-06-30 ZA ZA724523A patent/ZA724523B/xx unknown
- 1972-06-30 IE IE922/72A patent/IE36517B1/xx unknown
- 1972-07-05 NL NL7209400A patent/NL7209400A/xx unknown
- 1972-07-06 DE DE2233114A patent/DE2233114A1/de active Pending
- 1972-07-11 CA CA146,812A patent/CA1003422A/en not_active Expired
- 1972-07-11 US US00270754A patent/US3838161A/en not_active Expired - Lifetime
- 1972-07-12 CS CS7158A patent/CS174850B2/cs unknown
- 1972-07-12 CS CS4940A patent/CS174836B2/cs unknown
- 1972-07-12 FR FR7225248A patent/FR2145632B1/fr not_active Expired
- 1972-07-13 GB GB3274472A patent/GB1395360A/en not_active Expired
- 1972-07-13 DD DD164411A patent/DD101407A5/xx unknown
- 1972-07-13 AU AU44524/72A patent/AU471856B2/en not_active Expired
- 1972-07-13 PL PL1972187256A patent/PL96495B1/pl unknown
- 1972-07-13 EG EG297/72A patent/EG11134A/xx active
- 1972-07-13 PL PL1972156671A patent/PL93968B1/pl unknown
- 1972-07-14 AT AT609172A patent/AT315167B/de not_active IP Right Cessation
- 1972-07-14 SU SU1814223A patent/SU461504A3/ru active
- 1972-07-14 AT AT470673A patent/AT320640B/de not_active IP Right Cessation
- 1972-07-14 ES ES404879A patent/ES404879A1/es not_active Expired
- 1972-07-14 HU HUCI1252A patent/HU167425B/hu unknown
-
1973
- 1973-01-01 AR AR248266A patent/AR204310A1/es active
-
1974
- 1974-01-03 SU SU1982236A patent/SU541434A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| SU541434A3 (ru) | 1976-12-30 |
| FR2145632B1 (en:Method) | 1975-06-20 |
| SE391524B (sv) | 1977-02-21 |
| DE2233114A1 (de) | 1973-01-25 |
| EG11134A (en) | 1976-12-31 |
| PL96495B1 (pl) | 1977-12-31 |
| DD101407A5 (en:Method) | 1973-11-05 |
| AR205324A1 (es) | 1976-04-30 |
| CH552001A (de) | 1974-07-31 |
| AT320640B (de) | 1975-02-25 |
| HU167425B (en:Method) | 1975-10-28 |
| FR2145632A1 (en:Method) | 1973-02-23 |
| PL93968B1 (en:Method) | 1977-07-30 |
| IE36517L (en) | 1973-01-15 |
| AU4452472A (en) | 1974-01-17 |
| AR204310A1 (es) | 1975-12-22 |
| BE786305A (fr) | 1973-01-15 |
| IL39792A0 (en) | 1972-08-30 |
| CA1003422A (en) | 1977-01-11 |
| AT315167B (de) | 1974-05-10 |
| US3838161A (en) | 1974-09-24 |
| IE36517B1 (en) | 1976-11-24 |
| CS174850B2 (en:Method) | 1977-04-29 |
| ZA724523B (en) | 1973-03-28 |
| NL7209400A (en:Method) | 1973-01-17 |
| AU471856B2 (en) | 1976-05-06 |
| ES404879A1 (es) | 1975-06-16 |
| GB1395360A (en) | 1975-05-29 |
| CS174836B2 (en:Method) | 1977-04-29 |
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