PL82470B1 - - Google Patents
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- Publication number
- PL82470B1 PL82470B1 PL1972159072A PL15907272A PL82470B1 PL 82470 B1 PL82470 B1 PL 82470B1 PL 1972159072 A PL1972159072 A PL 1972159072A PL 15907272 A PL15907272 A PL 15907272A PL 82470 B1 PL82470 B1 PL 82470B1
- Authority
- PL
- Poland
- Prior art keywords
- ethyl
- formula
- methoxy
- pyridine
- solvent
- Prior art date
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- NBFYWQQYIJTQQV-UHFFFAOYSA-N 5-ethylsulfonyl-2-methoxybenzoic acid Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(C(O)=O)=C1 NBFYWQQYIJTQQV-UHFFFAOYSA-N 0.000 claims description 2
- UNRHXEPDKXPRTM-UHFFFAOYSA-N Sultopride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=CC=C1OC UNRHXEPDKXPRTM-UHFFFAOYSA-N 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 claims 1
- 235000011007 phosphoric acid Nutrition 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IGOWMQPOGQYFFM-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-5-ethylsulfonyl-2-methoxybenzamide;hydron;chloride Chemical compound [Cl-].CC[NH+]1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=CC=C1OC IGOWMQPOGQYFFM-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- -1 1-ethyl-2-pyrrolidylmethyl Chemical group 0.000 description 1
- AHYZXIUNHHXCHO-UHFFFAOYSA-N 2-ethylsulfonylbenzoic acid Chemical compound CCS(=O)(=O)C1=CC=CC=C1C(O)=O AHYZXIUNHHXCHO-UHFFFAOYSA-N 0.000 description 1
- RSENJWVCZBIONW-UHFFFAOYSA-N Cl.NP(N)(N)=O Chemical compound Cl.NP(N)(N)=O RSENJWVCZBIONW-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- SUZXWXGJCOCMHU-UHFFFAOYSA-N n-sulfonylbenzamide Chemical compound O=S(=O)=NC(=O)C1=CC=CC=C1 SUZXWXGJCOCMHU-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- VMPYTOIPVPQDNX-UHFFFAOYSA-N pyrrolidin-1-ylmethanamine Chemical compound NCN1CCCC1 VMPYTOIPVPQDNX-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/224—Phosphorus triamides
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Description
Sposób wytwarzania N-(l-etylo-2-pirolidylometylo)- -2-metoksy-5-etylosulfonylobenzamidu 10 15 Przedmiotem wynalazku jest sposób wytwarza¬ nia N-(l-etylo-2-pirolidylometylo)-2-metoksy-5-ety- losulfonylobenzamidu o wzorze 1 i jego soli addy¬ cyjnych z farmakologicznie dopuszczalnymi kwasa¬ mi nieorganicznymi lub organicznymi oraz jego czwartorzedowych soli amoniowych na drodze reak¬ cji benzamidu z alifatycznymi lub aromatycznymi srodkami alkilujacymi.Sposób wedlug wynalazku polega na tym, ze N-etylo-aminometylopirolidyne poddaje sie reakcji z tlenochlorkiem fosforu, po czym otrzymany N', N", N,//-(N-etylo-a-metylopirolidyno)-fosforamid o wzorze 2 kondensuje sie z kwasem 2-metoksy-5- -etylosulfonylobenzoesowym o wzorze 3. Otrzymany benzamid wykazuje cenne wlasciwosci farmakolo¬ giczne, zwlaszcza jako srodek przeciwwymiótny i psychotropowy.Sposób wedlug wynalazku zachodzi wedlug reak¬ cji podanych na schemacie przedstawionym na ry¬ sunku. Reakcje podane na schemacie prowadzic mozna w odpowiednich rozpuszczalnikach, takich jak dioksan, pirydyna lub im podobne, przy czym calosc ogrzewa sie do temperatury wrzenia pod chlodnica zwrotna. 25 Stosowanie pirydyny jako rozpuszczalnika sta¬ nowi te zalete, ze chlorowodorek fosforamidu nie musi byc wyodrebniony.Podane nizej przyklady objasniaja blizej prak¬ tyczne wykorzystanie sposobu wedlug wynalazku. 30 20 Przyklad I. Chlorowodorek N-(l-etylo-2-piro- lidylo-metylo(-2-metoksy-5-etylosulfonylobenzamidu.W naczyniu reakcyjnym o pojemnosci 1 litra roz¬ puszcza sie 27 g N-etylo-a-aminometylopirolidyny w 560 ml pirydyny. W temperaturze otoczenia do¬ daje sie roztwór 6,1 g tlenochlorku fosforu w 65 ml pirydyny i miesza sie mieszanine reakcyjna w cia¬ gu pól godziny. Do mieszaniny dodaje sie 15,6 g kwasu 2-metoksy-5-etylosulfonylobenzoesowego, po czym calosc ogrzewa sie w ciagu 4 godzin w tem¬ peraturze wrzenia pod chlodnica zwrotna.Po zakonczonej reakcji pirydyne odpedza sie pod próznia a pozostalosc ekstrahuje sie w 300 ml wody i 40 ml 36% kwasu solnego, w celu usuniecia ewentualnych resztek nieprzereagowanego kwasu.Roztwór alkalizuje sie lugiem i ekstrahuje chlor¬ kiem metylenu.Warstwe organiczna suszy sie, przesacza i za- teza pod próznia. Pozostalosc rozpuszcza sie w 20 ml acetonu, a chlorowodorek straca sie doda¬ tkiem kwasu solnego. Odsacza sie go, przemywa 10 ml etanolu i suszy w suszarce w temperaturze 50°C.Otrzymuje sie 16 g chlorowodorku tego benza¬ midu o temperaturze topnienia 188—189°C. Pro¬ dukt ten dwukrotnie przekrystalizowuje sie z eta¬ nolu, otrzymujac 10 g chlorowodorku N-(l-etylo-2- -pirolidylometylo)-2-metoksy-5-etylosulfonyloben- zamidu o temperaturze topnienia 190—192°C. Sto- 82 4703 82 470 4 pien czystosci wedlug oznaczenia za pomoca kwasu nadchlorowego wynosi 99,7%.Przyklad II. N', N", N"'-(N-etylo-a-metylo- pirolidyno)-fosforamid.Do naczynia reakcyjnego o pojemnosci 250 ml wprowadza sie roztwór 15,3 g N-etylo-a-aminome- tylopirolidyny w 60 ml toluenu. W temperaturze otoczenia do roztworu dodaje sie 6,1 g tlenochlorku fosforu, rozpuszczonego w 40 ml toluenu.Po mieszaniu w temperaturze otoczenia w ciagu 2 godzin wytracony osad odsacza sie, przemywa i suszy. Otrzymuje sie 20,3 g chlorowodorku N', N", N,/,-(N-etylo-a-metylopirolidyno)-fosforamidu o temperaturze topnienia 106—110°C.Tak otrzymany chlorowodorek rozpuszcza sie w 350 ml wody a roztwór alkalizuje sie lugiem. Ten roztwór nastepnie ekstrahuje sie chloroformem.Warstwe organiczna suszy sie nad weglanem pota¬ sowym i zateza pod próznia. Otrzymuje sie 10,5 g 10 15 N', N", N^-CN-etylo-a-metylopirolidynoJ-fosfora- midu. Stopien czystosci wedlug oznaczenia za po¬ moca kwasu nadchlorowego wynosi 98,2%. PL PL PL
Claims (2)
1. Zastrzezenia patentowe 1. Sposób wytwarzania N-(l-etylo-2-pirolidylome- tylo)-2-metoksy-5-etylosulfonylobenzamidu o wzo¬ rze 1 i jego soli addycyjnych z farmakologicznie dopuszczalnymi kwasami nieorganicznymi lub orga¬ nicznymi oraz jego czwartorzedowych soli amonio¬ wych, znamienny tym, ze N-etylo-a-aminometylo- pirolidyne poddaje sie reakcji z tlenochlorkiem fos¬ foru, po czym otrzymany amid kwasu fosforowego kondensuje sie z rozpuszczonym w rozpuszczalniku kwasem 2-metoksy-5-etylosulfonylobenzoesowym.
2. Sposób wedlug zastrz. 1, znamienny 20 ze jako rozpuszczalnik stosuje sie pirydyne. tym, o=p; ci ci Xl + 3 H2N-CH2 I C2H5 0=P -NH-CH, 3 I C2H5 3 HCl OH 0=P - NH-CH2-C I C2H5 Wzór 2 COOH +3 ^k-OCH, H5C20S^J - Wzór 3 CO-NH-CH ^C 3 ^yOCH3 C2H5 Wzor 1 + H3PO4 Schemat Druk WZKart. Zam. C-5086. Cena 10 zi PL PL PL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1080272A CH565149A5 (pl) | 1972-07-19 | 1972-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL82470B1 true PL82470B1 (pl) | 1975-10-31 |
Family
ID=4367011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972159072A PL82470B1 (pl) | 1972-07-19 | 1972-11-24 |
Country Status (29)
| Country | Link |
|---|---|
| JP (2) | JPS4935377A (pl) |
| KR (1) | KR780000089B1 (pl) |
| AR (1) | AR194145A1 (pl) |
| AT (1) | AT319932B (pl) |
| AU (1) | AU471164B2 (pl) |
| BE (1) | BE793871A (pl) |
| BG (1) | BG20347A3 (pl) |
| CA (1) | CA976974A (pl) |
| CH (1) | CH565149A5 (pl) |
| CS (1) | CS174865B2 (pl) |
| DD (1) | DD102380A5 (pl) |
| DE (1) | DE2257624A1 (pl) |
| EG (1) | EG11435A (pl) |
| ES (1) | ES409348A1 (pl) |
| FR (1) | FR2192820B1 (pl) |
| GB (1) | GB1394409A (pl) |
| HU (1) | HU167514B (pl) |
| IE (1) | IE37363B1 (pl) |
| IL (1) | IL41522A (pl) |
| LU (1) | LU66787A1 (pl) |
| MC (1) | MC961A1 (pl) |
| NL (1) | NL7215710A (pl) |
| OA (1) | OA04313A (pl) |
| PH (1) | PH9390A (pl) |
| PL (1) | PL82470B1 (pl) |
| RO (1) | RO62350A (pl) |
| YU (1) | YU36499B (pl) |
| ZA (1) | ZA73537B (pl) |
| ZM (1) | ZM1773A1 (pl) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1151533B (it) * | 1982-03-29 | 1986-12-24 | Ravizza Spa | Procedimento per la preparazione di p. clorofenossiacetil-piperonilpiperazina |
| WO1991017144A1 (fr) * | 1990-05-02 | 1991-11-14 | Yoshitomi Pharmaceutical Industries, Ltd. | Compose amide, utilisation pharmaceutique de ce compose et nouvelles pyrrolidinemethyl-amines 1-substituee |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4940459B1 (pl) * | 1970-12-21 | 1974-11-02 |
-
0
- BE BE793871D patent/BE793871A/xx not_active IP Right Cessation
-
1972
- 1972-07-19 CH CH1080272A patent/CH565149A5/xx not_active IP Right Cessation
- 1972-11-20 NL NL7215710A patent/NL7215710A/xx unknown
- 1972-11-22 AR AR245248A patent/AR194145A1/es active
- 1972-11-24 DE DE2257624A patent/DE2257624A1/de active Pending
- 1972-11-24 PL PL1972159072A patent/PL82470B1/pl unknown
- 1972-11-24 HU HURE521A patent/HU167514B/hu unknown
- 1972-11-30 BG BG022005A patent/BG20347A3/xx unknown
- 1972-12-01 RO RO73014A patent/RO62350A/ro unknown
- 1972-12-05 YU YU03015/72A patent/YU36499B/xx unknown
- 1972-12-06 CS CS8355A patent/CS174865B2/cs unknown
- 1972-12-06 AT AT1038972A patent/AT319932B/de not_active IP Right Cessation
- 1972-12-06 ES ES409348A patent/ES409348A1/es not_active Expired
- 1972-12-11 FR FR7244002A patent/FR2192820B1/fr not_active Expired
- 1972-12-15 MC MC1024A patent/MC961A1/fr unknown
- 1972-12-28 DD DD167945A patent/DD102380A5/xx unknown
-
1973
- 1973-01-03 LU LU66787A patent/LU66787A1/xx unknown
- 1973-01-12 OA OA54805A patent/OA04313A/xx unknown
- 1973-01-18 CA CA161,588A patent/CA976974A/en not_active Expired
- 1973-01-24 ZA ZA730537A patent/ZA73537B/xx unknown
- 1973-01-26 AU AU51514/73A patent/AU471164B2/en not_active Expired
- 1973-02-06 JP JP48014354A patent/JPS4935377A/ja active Pending
- 1973-02-12 ZM ZM17/73A patent/ZM1773A1/xx unknown
- 1973-02-13 IL IL41522A patent/IL41522A/en unknown
- 1973-02-14 KR KR7300264A patent/KR780000089B1/ko not_active Expired
- 1973-02-21 GB GB846873A patent/GB1394409A/en not_active Expired
- 1973-03-02 IE IE339/73A patent/IE37363B1/xx unknown
- 1973-04-03 JP JP3749673A patent/JPS5532704B2/ja not_active Expired
- 1973-04-23 PH PH14537*UA patent/PH9390A/en unknown
- 1973-07-15 EG EG277/73A patent/EG11435A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| ES409348A1 (es) | 1975-11-16 |
| FR2192820B1 (pl) | 1976-07-02 |
| JPS4943966A (pl) | 1974-04-25 |
| CS174865B2 (pl) | 1977-04-29 |
| NL7215710A (pl) | 1974-01-22 |
| EG11435A (en) | 1977-03-31 |
| JPS4935377A (pl) | 1974-04-01 |
| AR194145A1 (es) | 1973-06-22 |
| FR2192820A1 (pl) | 1974-02-15 |
| AU471164B2 (en) | 1976-04-08 |
| HU167514B (pl) | 1975-10-28 |
| OA04313A (fr) | 1980-01-15 |
| ZM1773A1 (en) | 1973-10-22 |
| LU66787A1 (pl) | 1973-03-19 |
| BE793871A (fr) | 1973-05-02 |
| DE2257624A1 (de) | 1974-02-07 |
| PH9390A (en) | 1975-10-22 |
| MC961A1 (fr) | 1973-12-07 |
| AU5151473A (en) | 1974-08-01 |
| AT319932B (de) | 1975-01-10 |
| IE37363B1 (en) | 1977-07-06 |
| CH565149A5 (pl) | 1975-08-15 |
| YU301572A (en) | 1982-02-25 |
| CA976974A (en) | 1975-10-28 |
| KR780000089B1 (en) | 1978-04-08 |
| ZA73537B (en) | 1973-10-31 |
| GB1394409A (en) | 1975-05-14 |
| BG20347A3 (bg) | 1975-11-05 |
| IE37363L (en) | 1974-01-19 |
| IL41522A0 (en) | 1973-04-30 |
| RO62350A (pl) | 1977-08-15 |
| DD102380A5 (pl) | 1973-12-12 |
| JPS5532704B2 (pl) | 1980-08-26 |
| YU36499B (en) | 1984-02-29 |
| IL41522A (en) | 1977-11-30 |
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