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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1080272A CH565149A5 (US07696358-20100413-C00002.png) | 1972-07-19 | 1972-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL82470B1 true PL82470B1 (US07696358-20100413-C00002.png) | 1975-10-31 |
Family
ID=4367011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972159072A PL82470B1 (US07696358-20100413-C00002.png) | 1972-07-19 | 1972-11-24 |
Country Status (29)
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 (en) * | 1990-05-02 | 1991-11-14 | Yoshitomi Pharmaceutical Industries, Ltd. | Amide compound, pharmaceutical use thereof and novel 1-substituted pyrrolidinemethyl-amines |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4940459B1 (US07696358-20100413-C00002.png) * | 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 HU HURE521A patent/HU167514B/hu unknown
- 1972-11-24 PL PL1972159072A patent/PL82470B1/pl unknown
- 1972-11-24 DE DE2257624A patent/DE2257624A1/de active Pending
- 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 AT AT1038972A patent/AT319932B/de not_active IP Right Cessation
- 1972-12-06 CS CS8355A patent/CS174865B2/cs unknown
- 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/xx 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 active
- 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
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