CH509992A - Verfahren zur Herstellung von Sulfonamiden - Google Patents
Verfahren zur Herstellung von SulfonamidenInfo
- Publication number
- CH509992A CH509992A CH787569A CH787569A CH509992A CH 509992 A CH509992 A CH 509992A CH 787569 A CH787569 A CH 787569A CH 787569 A CH787569 A CH 787569A CH 509992 A CH509992 A CH 509992A
- Authority
- CH
- Switzerland
- Prior art keywords
- solution
- preparation
- water
- formula
- urea
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229940124530 sulfonamide Drugs 0.000 title description 2
- 150000003456 sulfonamides Chemical class 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 2
- MTGRWHDDDGKLLX-UHFFFAOYSA-N 1-(2-hydroxycyclohexyl)-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1C(O)CCCC1 MTGRWHDDDGKLLX-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- -1 acetaminophenyl Chemical group 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- MTGRWHDDDGKLLX-OLZOCXBDSA-N 1-[(1r,2s)-2-hydroxycyclohexyl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N[C@H]1[C@@H](O)CCCC1 MTGRWHDDDGKLLX-OLZOCXBDSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- LKKCSUHCVGCGFA-KGZKBUQUSA-N (1r,2r)-2-aminocyclohexan-1-ol;hydrochloride Chemical compound Cl.N[C@@H]1CCCC[C@H]1O LKKCSUHCVGCGFA-KGZKBUQUSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- NMTPEIYPRKMYFA-UHFFFAOYSA-N CC(C=C1)=CC=C1S(NC(NC(CCCC1)C1=O)=O)(=O)=O Chemical compound CC(C=C1)=CC=C1S(NC(NC(CCCC1)C1=O)=O)(=O)=O NMTPEIYPRKMYFA-UHFFFAOYSA-N 0.000 description 1
- NZFGOMANOWKERH-UHFFFAOYSA-N CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1C(CCC1)=O Chemical compound CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1C(CCC1)=O NZFGOMANOWKERH-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- VTLHPYXKUOESEM-UHFFFAOYSA-N sodium;(4-methylphenyl)sulfonylazanide Chemical compound [Na+].CC1=CC=C(S([NH-])(=O)=O)C=C1 VTLHPYXKUOESEM-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/64—Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/59—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
- C07D263/28—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH787269A CH510648A (de) | 1966-08-08 | 1966-08-08 | Verfahren zur Herstellung von Sulfonamiden |
| CH787569A CH509992A (de) | 1966-08-08 | 1966-08-08 | Verfahren zur Herstellung von Sulfonamiden |
| CH787469A CH509991A (de) | 1966-08-08 | 1966-08-08 | Verfahren zur Herstellung von Sulfonamiden |
| CH787169A CH510647A (de) | 1966-08-08 | 1966-08-08 | Verfahren zur Herstellung von Sulfonamiden |
| CH787369A CH509990A (de) | 1966-08-08 | 1967-07-07 | Verfahren zur Herstellung von Sulfonamiden |
| SE10481/67A SE334354B (forum.php) | 1966-08-08 | 1967-07-12 | |
| IL28401A IL28401A (en) | 1966-08-08 | 1967-07-26 | Arylsulfonyl ureas,their manufacture and pharmaceutical compositions containing them |
| DE1967H0063446 DE1668199B2 (de) | 1966-08-08 | 1967-07-29 | Benzolsulfonyl-3-(2-hydroxycyclohexyl)harnstoffe |
| NL6710676A NL6710676A (forum.php) | 1966-08-08 | 1967-08-02 | |
| GB50521/68A GB1147405A (en) | 1966-08-08 | 1967-08-04 | Novel oxazolidinone derivatives |
| BE702280D BE702280A (forum.php) | 1966-08-08 | 1967-08-04 | |
| GB50520/68A GB1147404A (en) | 1966-08-08 | 1967-08-04 | Novel sulphonamide derivatives |
| GB35845/67A GB1147403A (en) | 1966-08-08 | 1967-08-04 | Sulphonamides |
| DK401867AA DK122761B (da) | 1966-08-08 | 1967-08-07 | Analogifremgangsmåde til fremstilling af arylsulfonylurinstofderivater. |
| ES343910A ES343910A1 (es) | 1966-08-08 | 1967-08-07 | Un procedimiento para preparar nuevas sulfonamidas. |
| JP5054967A JPS5516575B1 (forum.php) | 1966-08-08 | 1967-08-08 | |
| FR117194A FR1546595A (fr) | 1966-08-08 | 1967-08-08 | Procédé pour la préparation de sulfamides |
| FR117192A FR7148M (forum.php) | 1966-08-08 | 1967-08-08 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH787469A CH509991A (de) | 1966-08-08 | 1966-08-08 | Verfahren zur Herstellung von Sulfonamiden |
| CH1136566A CH500176A (de) | 1966-08-08 | 1966-08-08 | Verfahren zur Herstellung von Sulfonamiden |
| CH787569A CH509992A (de) | 1966-08-08 | 1966-08-08 | Verfahren zur Herstellung von Sulfonamiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH509992A true CH509992A (de) | 1971-07-15 |
Family
ID=27175874
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH787469A CH509991A (de) | 1966-08-08 | 1966-08-08 | Verfahren zur Herstellung von Sulfonamiden |
| CH787569A CH509992A (de) | 1966-08-08 | 1966-08-08 | Verfahren zur Herstellung von Sulfonamiden |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH787469A CH509991A (de) | 1966-08-08 | 1966-08-08 | Verfahren zur Herstellung von Sulfonamiden |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5516575B1 (forum.php) |
| BE (1) | BE702280A (forum.php) |
| CH (2) | CH509991A (forum.php) |
| DE (1) | DE1668199B2 (forum.php) |
| DK (1) | DK122761B (forum.php) |
| ES (1) | ES343910A1 (forum.php) |
| FR (1) | FR7148M (forum.php) |
| GB (3) | GB1147405A (forum.php) |
| IL (1) | IL28401A (forum.php) |
| NL (1) | NL6710676A (forum.php) |
| SE (1) | SE334354B (forum.php) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2739356C2 (ru) | 2015-02-16 | 2020-12-23 | Дзе Юниверсити Оф Квинсленд | Сульфонилмочевины и родственные соединения и их применение |
| JP7072586B2 (ja) | 2017-05-24 | 2022-05-20 | ザ ユニバーシティ オブ クィーンズランド | 新規な化合物及び使用 |
| WO2019008025A1 (en) | 2017-07-07 | 2019-01-10 | Inflazome Limited | NOVEL CARBOXAMIDE SULFONAMIDE COMPOUNDS |
-
1966
- 1966-08-08 CH CH787469A patent/CH509991A/de not_active IP Right Cessation
- 1966-08-08 CH CH787569A patent/CH509992A/de not_active IP Right Cessation
-
1967
- 1967-07-12 SE SE10481/67A patent/SE334354B/xx unknown
- 1967-07-26 IL IL28401A patent/IL28401A/en unknown
- 1967-07-29 DE DE1967H0063446 patent/DE1668199B2/de active Granted
- 1967-08-02 NL NL6710676A patent/NL6710676A/xx unknown
- 1967-08-04 BE BE702280D patent/BE702280A/xx unknown
- 1967-08-04 GB GB50521/68A patent/GB1147405A/en not_active Expired
- 1967-08-04 GB GB50520/68A patent/GB1147404A/en not_active Expired
- 1967-08-04 GB GB35845/67A patent/GB1147403A/en not_active Expired
- 1967-08-07 DK DK401867AA patent/DK122761B/da unknown
- 1967-08-07 ES ES343910A patent/ES343910A1/es not_active Expired
- 1967-08-08 JP JP5054967A patent/JPS5516575B1/ja active Pending
- 1967-08-08 FR FR117192A patent/FR7148M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1668199A1 (de) | 1971-09-02 |
| ES343910A1 (es) | 1968-10-01 |
| JPS5516575B1 (forum.php) | 1980-05-02 |
| GB1147405A (en) | 1969-04-02 |
| FR7148M (forum.php) | 1969-08-04 |
| IL28401A (en) | 1971-04-28 |
| DK122761B (da) | 1972-04-10 |
| GB1147403A (en) | 1969-04-02 |
| GB1147404A (en) | 1969-04-02 |
| BE702280A (forum.php) | 1968-02-05 |
| DE1668199B2 (de) | 1976-06-24 |
| NL6710676A (forum.php) | 1968-02-09 |
| SE334354B (forum.php) | 1971-04-26 |
| CH509991A (de) | 1971-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |