PL83581B1 - - Google Patents
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- Publication number
- PL83581B1 PL83581B1 PL1972157842A PL15784272A PL83581B1 PL 83581 B1 PL83581 B1 PL 83581B1 PL 1972157842 A PL1972157842 A PL 1972157842A PL 15784272 A PL15784272 A PL 15784272A PL 83581 B1 PL83581 B1 PL 83581B1
- Authority
- PL
- Poland
- Prior art keywords
- methoxy
- ethyl
- acid
- hydrazide
- azide
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 9
- 150000001540 azides Chemical class 0.000 claims description 6
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Description
Uprawniony z patentu: Fratmann AG., Chene-Boygeries/Genewa (Szwaj¬ caria) Sposób wytwarzania N-/l-etylo-a-pirolidylometyIo/2-metoksy-5- -sulfamidobenzamidu Przedmiotem wynalazku jest sposób wytwarza¬ nia N-/1-etylo-a-pirolidylometylo/-2-metoksy-5- -sulfamidobenzamidu, stosowanego do leczenia* schorzen przewodu zoladkowo-jelitowego i jako srodek leczniczy w psychiatrii.Sposobem wedlug wynalazku N-/l-etylo-a-piroli- dylometylo/-2-metoksy-5-sulfamidobenzamid wy¬ twarza sie z kwasu 2-metoksy-5-sulfamidobenzoeso- wego, przeprowadzajac go najpierw w hydrazyd, a nastepnie w azydek, który z kolei poddaje sie re¬ akcji z l-etylo-2-aminometylopirolidyna. Reakcje wytwarzania hydrazydu i azydku kwasu 2-meto- ksy-5-sul£amidobenzoesowego mozna prowadzic w roztworze wodnym, natomiast reakcje z l-etylo-2- -aminometylopirolidyna prowadzi sie korzystnie w dioksanie. Proces wedlug wynalazku przebiega we¬ dlug schematu podanego na rysunku. We wzorze produktu wyjsciowego podanym w tym schemacie R oznacza rodnik alkilowy o 1—4 atomach wegla.Przyklad. a) W naczyniu reakcyjnym o pojemnosci 1 litra, wyposazonym w mieszadlo, chlodnice i termometr, umieszcza sie 355 g (7,1 mola) wodzianu hydrazyny i 60 ml wody, po czym dodaje malymi porcjami 100 g (0,39 mola) estru etylowego kwasu 2-metoksy- -5-sulfamidobenzoesowego. Mieszanine ogrzewa sie W temperaturze 60°C w ciagu 20 minut, po czym chlodzi, odsacza osad o barwie bialej, przemywa go woda i suszy w suszarce w temperaturze 50°C.Otrzymuje sie 82 g hydrazydu kwasu 2-metoksy-5- -sulfamidobenzoesowego o temperaturze topnienia 201°C. 10 15 Analiza produktu: %C VoH %N znaleziono 39,56 4,65 17,7 obliczono 39,18 4,49 17,14 30 b) W kolbie o pojemnosci 250 ml, wyposazonej w mieszadlo, termometr, chlodnice i wkraplacz u- mieszcza sie 4,9 g (0,02 mola) hydrazydu kwasu 2- -metoksy-5-sulfamidobenzoesowego i 72,4 ml wody, po czym chlodzac w kapieli wodnej dodaje stop¬ niowo 22,7 ml 36% kwasu solnego. Nastepnie chlo¬ dzi sie mieszanine do temperatury 0°C i utrzymu¬ jac temperature nizsza niz 5°C wkrapla roztwór 1,59 g (0,023 mola) azotynu sodowego w 22,8 ml wody.Po zakonczeniu wkraplania miesza sie w tempe¬ raturze 5°C w ciagu 15 minut, po czym odsacza o- trzymany azydek kwasu 2-metoksy-5-sulfamidoben- zoesowego, przemywa go woda i wilgotny produkt stosuje do dalszej reakcji. Wysuszona próbka tego zwiazku rozklada sie latwo w temperaturze 132°C na plytce Koflera. c) W kolbie o pojemnosci 250 ml, wyposazonej w mieszadlo, termometr i chlodnice polaczona ze skraplaczem, umieszcza sie 5,1 g (0,04 mola) N-ety- lo-a-aminometylopirolidyny i 100 ml dioksanu i 83 58183 Wt utrzymujac (temperature 10QC dodaje malymi porcja¬ mi azydek kwasu 2-metoksy-5-sulfamidobenzoeso- wego otrzymany w sposób opisany w ustepie b).Mieszanine pozostawia sie do ogrzania do tempe¬ ratury pokojowej, po czym ogrzewa i utrzymuje w stanie wrzenia pod chlodnica zwrotna w ciagu 1 godziny. Otrzymany roztwór o barwie pomaranczo¬ wej pozostawia sie na noc, po czym dodaje 4 ml 36°/o kwasu solnego, wytracajac chlorowodorek N- -/l-etylo-a-pirolidylometylo/-2-metoksy-5-sulfami- dobenzamidu.Mieszanine chlodzi sie lodem, odsacza krystali¬ czny produkt o barwie zóltej i suszy go w suszar¬ ce w temperaturze 50°C. Otrzymany produkt roz¬ puszcza sie w 70 ml wrzacej wody, wytraca wolna zasade za pomoca 30% roztworu wodorotlenku a- monu, chlodzi, odsacza osad i przemywa go woda.Wilgotny produkt przekrystalizowuje sie niezwlocz¬ nie z 20 ml bezwodnego etanolu, otrzymujac 2,9 g czystego N-/1 -etylo-a^pirolidylometylo/-2-metoksy- 10 15 20 -5-sulfamidobenzamidu o temperaturze topnienia 178°C.Analiza za pomoca kwasu nadchlorowego (99,49%) wykazuje, ze produkt zawiera 9,42% siarki, podczas gdy wedlug obliczen zawartosc siarki w tym zwiaz¬ ku wynosi 9,38%. PL PL
Claims (2)
1. Zastrzezenia patentowe 1. Sposób wytwarzania N-/l-etylo-a-pirolidylome- tylo/-2-metoksy-5-sulfamidobenzamidu, znamienny tym, ze kwas 2-metoksy-5-sulfamidobenzoesowy przeprowadza sie najpierw w hydrazyd, a nastep¬ nie w azydek, który z kolei poddaje sie reakcji z l-etylo-2-aminometylopirolidyna.
2. Sposób wedlug zastrz. 1, znamienny tym, ze proces przeprowadzania kwasu 2-metoksy-5-sulfa- midobenzoesowego w hydrazyd, a nastepnie w azy¬ dek prowadzi sie w roztworze wodnym, a reakcje z l-etylo-2-aminometylopirolidyna w srodowisku dioksanu. C00R t^N-N^O PONHNHg ArtJCH, S — HjNas-k^ HjNOgS^ C0N3 _rVCH* 3+ +NaN02 H2N02S^ C0NHCH, H2NCH2-C C2H5 Schemat Bltk 830/76 r. 110 egz. A4 Cena 10 z» PL PL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH881472A CH567466A5 (pl) | 1972-06-13 | 1972-06-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL83581B1 true PL83581B1 (pl) | 1975-12-31 |
Family
ID=4345038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972157842A PL83581B1 (pl) | 1972-06-13 | 1972-09-20 |
Country Status (31)
| Country | Link |
|---|---|
| JP (1) | JPS5612633B2 (pl) |
| KR (1) | KR780000068B1 (pl) |
| AR (1) | AR194967A1 (pl) |
| AT (1) | AT319931B (pl) |
| AU (1) | AU466331B2 (pl) |
| BE (1) | BE787794A (pl) |
| BG (1) | BG19591A3 (pl) |
| CA (1) | CA973187A (pl) |
| CH (1) | CH567466A5 (pl) |
| CS (1) | CS164788B2 (pl) |
| DD (1) | DD100250A5 (pl) |
| DE (1) | DE2246803A1 (pl) |
| EG (1) | EG10797A (pl) |
| ES (1) | ES407142A1 (pl) |
| FI (1) | FI58118C (pl) |
| FR (1) | FR2187781B1 (pl) |
| GB (1) | GB1353571A (pl) |
| HU (1) | HU166399B (pl) |
| IE (1) | IE36759B1 (pl) |
| IL (1) | IL40501A (pl) |
| IT (1) | IT1034030B (pl) |
| LU (1) | LU65946A1 (pl) |
| MC (1) | MC940A1 (pl) |
| NL (1) | NL7213129A (pl) |
| OA (1) | OA04180A (pl) |
| PL (1) | PL83581B1 (pl) |
| RO (1) | RO60561A (pl) |
| SE (1) | SE385696B (pl) |
| YU (1) | YU35118B (pl) |
| ZA (1) | ZA727086B (pl) |
| ZM (1) | ZM16972A1 (pl) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5223114A (en) * | 1975-08-15 | 1977-02-21 | Saito Shinroku | High pressure phase boron nitride polycrystal sintered bodies and manufacture |
| US4188194A (en) * | 1976-10-29 | 1980-02-12 | General Electric Company | Direct conversion process for making cubic boron nitride from pyrolytic boron nitride |
| JPS62278170A (ja) * | 1986-05-23 | 1987-12-03 | 株式会社豊田中央研究所 | 立方晶窒化硼素焼結体の製造法 |
| DE8911414U1 (de) * | 1989-09-25 | 1990-01-25 | Bostik-Tucker GmbH, 6370 Oberursel | Kabelbefestigung mit leiterartigem Gurt |
| JPH074934A (ja) * | 1993-02-12 | 1995-01-10 | General Electric Co <Ge> | 結晶性物体の分級・選別 |
| US6342195B1 (en) | 1993-10-01 | 2002-01-29 | The Penn State Research Foundation | Method for synthesizing solids such as diamond and products produced thereby |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA711710B (en) * | 1970-05-28 | 1971-12-29 | Squibb & Sons Inc | Amino derivatives of purazolo-pyridine carboxylic acids and esters |
-
0
- BE BE787794D patent/BE787794A/xx not_active IP Right Cessation
-
1972
- 1972-06-13 CH CH881472A patent/CH567466A5/xx not_active IP Right Cessation
- 1972-08-21 FR FR7229789A patent/FR2187781B1/fr not_active Expired
- 1972-08-23 LU LU65946A patent/LU65946A1/xx unknown
- 1972-08-30 IT IT28619/72A patent/IT1034030B/it active
- 1972-09-06 MC MC1009A patent/MC940A1/fr unknown
- 1972-09-15 SE SE7211913A patent/SE385696B/xx unknown
- 1972-09-19 HU HUFA922A patent/HU166399B/hu unknown
- 1972-09-20 PL PL1972157842A patent/PL83581B1/pl unknown
- 1972-09-20 YU YU2385/72A patent/YU35118B/xx unknown
- 1972-09-21 FI FI2596/72A patent/FI58118C/fi active
- 1972-09-21 AT AT812772A patent/AT319931B/de not_active IP Right Cessation
- 1972-09-23 DE DE19722246803 patent/DE2246803A1/de active Pending
- 1972-09-25 CS CS6510A patent/CS164788B2/cs unknown
- 1972-09-28 OA OA54702A patent/OA04180A/xx unknown
- 1972-09-28 AR AR244320A patent/AR194967A1/es active
- 1972-09-28 NL NL7213129A patent/NL7213129A/xx unknown
- 1972-09-29 ES ES407142A patent/ES407142A1/es not_active Expired
- 1972-09-29 DD DD165956A patent/DD100250A5/xx unknown
- 1972-09-29 GB GB4494572A patent/GB1353571A/en not_active Expired
- 1972-09-30 RO RO72380A patent/RO60561A/ro unknown
- 1972-10-03 CA CA153,126A patent/CA973187A/en not_active Expired
- 1972-10-03 ZA ZA727086A patent/ZA727086B/xx unknown
- 1972-10-04 IL IL40501A patent/IL40501A/xx unknown
- 1972-10-05 AU AU47461/72A patent/AU466331B2/en not_active Expired
- 1972-10-12 IE IE1388/72A patent/IE36759B1/xx unknown
- 1972-10-16 KR KR7201544A patent/KR780000068B1/ko not_active Expired
- 1972-10-27 ZM ZM169/72*UA patent/ZM16972A1/xx unknown
- 1972-12-24 EG EG537/72A patent/EG10797A/xx active
-
1973
- 1973-01-08 JP JP510973A patent/JPS5612633B2/ja not_active Expired
- 1973-02-02 BG BG022597A patent/BG19591A3/xx unknown
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