SU680647A3 - Способ получени производных -(бензтиазолил-2)-оксаминовой кислоты, или ее эфиров, или ее солей - Google Patents
Способ получени производных -(бензтиазолил-2)-оксаминовой кислоты, или ее эфиров, или ее солейInfo
- Publication number
- SU680647A3 SU680647A3 SU772550552A SU2550552A SU680647A3 SU 680647 A3 SU680647 A3 SU 680647A3 SU 772550552 A SU772550552 A SU 772550552A SU 2550552 A SU2550552 A SU 2550552A SU 680647 A3 SU680647 A3 SU 680647A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mol
- acid
- solution
- acids
- salts
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 18
- 239000002253 acid Substances 0.000 title description 9
- 150000002148 esters Chemical class 0.000 title description 5
- 150000003839 salts Chemical class 0.000 title description 3
- 150000007513 acids Chemical class 0.000 title description 2
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical class NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims description 10
- UXWAJSLYHVAVKJ-UHFFFAOYSA-N 2-hydrazinyl-2-oxoacetic acid Chemical class NNC(=O)C(O)=O UXWAJSLYHVAVKJ-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- 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
- 238000001914 filtration Methods 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- UYCUMNRCCJNSBR-UHFFFAOYSA-N 2-ethoxy-2-oxoacetic acid;hydrochloride Chemical compound Cl.CCOC(=O)C(O)=O UYCUMNRCCJNSBR-UHFFFAOYSA-N 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- -1 thiocane compound Chemical class 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical class C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 2
- YEBCRAVYUWNFQT-UHFFFAOYSA-N 4-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=CC2=C1N=C(N)S2 YEBCRAVYUWNFQT-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 150000002912 oxalic acid derivatives Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NSNUZLNQTHADKD-UHFFFAOYSA-N 2-(2-methylpentan-2-yloxy)-2-oxoacetic acid Chemical compound CCCC(C)(C)OC(=O)C(O)=O NSNUZLNQTHADKD-UHFFFAOYSA-N 0.000 description 1
- DCMUUSUYVZEYNG-UHFFFAOYSA-N 2-methoxy-5-propan-2-ylaniline Chemical compound COC1=CC=C(C(C)C)C=C1N DCMUUSUYVZEYNG-UHFFFAOYSA-N 0.000 description 1
- HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 1
- OMIHQJBWAPWLBO-UHFFFAOYSA-N 5-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2SC(N)=NC2=C1 OMIHQJBWAPWLBO-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- KZHGPDSVHSDCMX-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2N=C(N)SC2=C1 KZHGPDSVHSDCMX-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000000160 carbon, hydrogen and nitrogen elemental analysis Methods 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- RZMZBHSKPLVQCP-UHFFFAOYSA-N ethyl 2-amino-2-oxoacetate Chemical compound CCOC(=O)C(N)=O RZMZBHSKPLVQCP-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
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Immunology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762656468 DE2656468A1 (de) | 1976-12-14 | 1976-12-14 | N-(benzthiazol-2-yl)-oxamidsaeure- derivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU680647A3 true SU680647A3 (ru) | 1979-08-15 |
Family
ID=5995427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772550552A SU680647A3 (ru) | 1976-12-14 | 1977-12-07 | Способ получени производных -(бензтиазолил-2)-оксаминовой кислоты, или ее эфиров, или ее солей |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5377058A (cg-RX-API-DMAC7.html) |
| AR (1) | AR216496A1 (cg-RX-API-DMAC7.html) |
| AT (1) | AT360523B (cg-RX-API-DMAC7.html) |
| AU (1) | AU510730B2 (cg-RX-API-DMAC7.html) |
| BE (1) | BE861794A (cg-RX-API-DMAC7.html) |
| CS (1) | CS203179B2 (cg-RX-API-DMAC7.html) |
| DD (1) | DD133329A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2656468A1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES465034A1 (cg-RX-API-DMAC7.html) |
| FI (1) | FI57594C (cg-RX-API-DMAC7.html) |
| FR (1) | FR2374317A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1538822A (cg-RX-API-DMAC7.html) |
| HU (1) | HU175340B (cg-RX-API-DMAC7.html) |
| NL (1) | NL7713580A (cg-RX-API-DMAC7.html) |
| SE (1) | SE7714074L (cg-RX-API-DMAC7.html) |
| SU (1) | SU680647A3 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA777236B (cg-RX-API-DMAC7.html) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2676775A (en) * | 1949-10-24 | 1954-04-27 | Gustav O Schulz | Electric flatiron cord holder |
| DE3017976A1 (de) * | 1980-05-10 | 1981-11-19 | Dr. Karl Thomae Gmbh, 7950 Biberach | Substituierte 2-amino-5-halogen-benzothiazole, verfahen zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4321372A (en) | 1980-06-16 | 1982-03-23 | Pfizer Inc. | Antiulcer thiazol-2-ylcarbamoyl-carboxylic acids, esters and amides |
| DE3027527A1 (de) | 1980-07-19 | 1982-02-18 | Basf Ag, 6700 Ludwigshafen | Neue oxamidsaeure-derivate, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
| GB2090826B (en) * | 1981-01-09 | 1985-06-12 | Usv Pharma Corp | New heterocyclic compounds useful as anti-allergie agents |
| DE3135250A1 (de) * | 1981-09-05 | 1983-03-17 | Basf Ag, 6700 Ludwigshafen | Tricyclische thiazolyloxamate, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
| US4826860A (en) * | 1987-03-16 | 1989-05-02 | Warner-Lambert Company | Substituted 2-aminobenzothiazoles and derivatives useful as cerebrovascular agents |
| FI91859C (fi) * | 1987-06-17 | 1994-08-25 | Eisai Co Ltd | Analogiamenetelmä antiallergisena aineena aktiivisen bentsotiatsolijohdannaisen valmistamiseksi |
| ATE385794T1 (de) | 2000-06-21 | 2008-03-15 | Hoffmann La Roche | Benzothiazolderivate zur behandlung von alzheimer und parkinson |
| US7087761B2 (en) | 2003-01-07 | 2006-08-08 | Hoffmann-La Roche Inc. | Cyclization process for substituted benzothiazole derivatives |
| ATE382619T1 (de) | 2004-05-24 | 2008-01-15 | Hoffmann La Roche | 4-hydroxy-4-methylpiperidin-1-carbonsäure-(4- methoxy-7-morpholin-4-ylbenzothiazol-2-yl)-amid |
| CN101056857B (zh) | 2004-11-05 | 2010-12-01 | 弗·哈夫曼-拉罗切有限公司 | 异烟酸衍生物的制备方法 |
| MX2007011483A (es) | 2005-03-23 | 2007-10-12 | Hoffmann La Roche | Derivados de acetilenil-pirazolo-pirimidina como antagonistas de glutamato metabotropico 2. |
| AU2006298829B2 (en) | 2005-09-27 | 2011-03-03 | F. Hoffmann-La Roche Ag | Oxadiazolyl pyrazolo-pyrimidines as mGluR2 antagonists |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4150140A (en) * | 1976-12-23 | 1979-04-17 | The Upjohn Company | Benzothiazolyl oxanic acids, esters and salts |
-
1976
- 1976-12-14 DE DE19762656468 patent/DE2656468A1/de not_active Withdrawn
-
1977
- 1977-12-03 HU HU77BO1695A patent/HU175340B/hu unknown
- 1977-12-05 ZA ZA00777236A patent/ZA777236B/xx unknown
- 1977-12-07 SU SU772550552A patent/SU680647A3/ru active
- 1977-12-07 CS CS778173A patent/CS203179B2/cs unknown
- 1977-12-07 AR AR270289A patent/AR216496A1/es active
- 1977-12-07 GB GB50911/77A patent/GB1538822A/en not_active Expired
- 1977-12-08 NL NL7713580A patent/NL7713580A/xx not_active Application Discontinuation
- 1977-12-08 AU AU31377/77A patent/AU510730B2/en not_active Expired
- 1977-12-08 DD DD7700202483A patent/DD133329A5/xx unknown
- 1977-12-12 SE SE7714074A patent/SE7714074L/xx not_active Application Discontinuation
- 1977-12-12 FI FI773738A patent/FI57594C/fi not_active IP Right Cessation
- 1977-12-13 FR FR7737467A patent/FR2374317A1/fr active Granted
- 1977-12-13 BE BE183407A patent/BE861794A/xx unknown
- 1977-12-13 AT AT890777A patent/AT360523B/de not_active IP Right Cessation
- 1977-12-14 JP JP15041777A patent/JPS5377058A/ja active Pending
- 1977-12-14 ES ES465034A patent/ES465034A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5377058A (en) | 1978-07-08 |
| DE2656468A1 (de) | 1978-06-15 |
| NL7713580A (nl) | 1978-06-16 |
| AU510730B2 (en) | 1980-07-10 |
| CS203179B2 (en) | 1981-02-27 |
| FI57594C (fi) | 1980-09-10 |
| FR2374317A1 (fr) | 1978-07-13 |
| ZA777236B (en) | 1978-11-29 |
| BE861794A (fr) | 1978-06-13 |
| AR216496A1 (es) | 1979-12-28 |
| AT360523B (de) | 1981-01-12 |
| SE7714074L (sv) | 1978-06-15 |
| DD133329A5 (de) | 1978-12-27 |
| FI773738A7 (fi) | 1978-06-15 |
| ES465034A1 (es) | 1978-09-01 |
| FI57594B (fi) | 1980-05-30 |
| AU3137777A (en) | 1979-06-14 |
| HU175340B (hu) | 1980-07-28 |
| GB1538822A (en) | 1979-01-24 |
| FR2374317B1 (cg-RX-API-DMAC7.html) | 1980-11-07 |
| ATA890777A (de) | 1980-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU680647A3 (ru) | Способ получени производных -(бензтиазолил-2)-оксаминовой кислоты, или ее эфиров, или ее солей | |
| US5416215A (en) | Process to preparing 2,2,6,6-tetra-methylpiperidine-n-oxyl and its 4-position substituted derivatives | |
| CN113788766A (zh) | 一种阿托伐他汀钙中间体的制备方法 | |
| SU784766A3 (ru) | Способ получени бенз-ацил-бензимидазол(2)-производных | |
| JPS648616B2 (cg-RX-API-DMAC7.html) | ||
| US4113733A (en) | Process for making 5-amino-1,2,3-thiadiazoles | |
| BG63116B1 (bg) | Метод за получаване на о-(3-амино-2-хидрокси-пропил)- хидроксимови ацилхалогениди | |
| US4086420A (en) | Thioprene or furan derivatives and process for preparation thereof | |
| US2489881A (en) | Oxazoiiones and rbrocess for | |
| US4443621A (en) | p-Nitrophenyl 3-bromo-2,2-diethoxy-propionate and synthetic utility therefor | |
| SU645575A3 (ru) | Способ получени производных (5-алкилуреидо-1,3,4-тиадиазол2-ил-сульфонил) уксусной кислоты | |
| JPS5914461B2 (ja) | ５−メルカプト−１，２，３−トリアゾ−ルの製法 | |
| US2449038A (en) | Preparation of 3-substituted benzotetronic acid and salts thereof | |
| US4107179A (en) | Method for preparing ticrynafen | |
| US4107178A (en) | Thioprene or furan derivatives and process for preparation thereof | |
| US4051151A (en) | Thiophene derivatives and process for preparation thereof | |
| SU501670A3 (ru) | Способ получени производных циклопентено-хинолона | |
| US4565872A (en) | Process for 8-cyano-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acids and intermediates thereof | |
| SU455545A3 (ru) | Способ получени пироно-рифамицинов | |
| EP0146102A2 (en) | Process for preparing benzothiazine compounds | |
| SU561513A3 (ru) | Способ получени производных пиперазина или их солей | |
| US4153631A (en) | Process for processing silver halide developing agents | |
| PL98296B1 (pl) | Sposob otrzymywania estrow acetoksymetylowych cefalosporyn | |
| SU1482525A3 (ru) | Способ получени 4-окси-2-оксопирролидин-1-ил-ацетамида | |
| SU493964A3 (ru) | Способ производных изоиндолина или их солей |